Vacation Home Rentals By Owner In Siesta Key, FL

$397.59

Coastal Cottage - Direct Beach Access

Siesta Key, Florida, United States

Coastal Cottage by Tropical Sands Accommodations brbrEscape to Coastal Cottage, a delightful 3-bedroom, 2-bath retreat nestled along the iconic Beach Road, just steps from the vibrant heart of Siesta Key Village. This century old gem is one of the island’s oldest homes, offering direct access to the world famous Siesta Key Beach. With its unbeatable location, vintage charm, and modern comforts, it’s the perfect sanctuary for families, couples, or friends looking to soak up the island lifestyle just moments from the sand and local shops and restaurants. brbrHighlights: br• Direct access to Siesta Key Beach br• 3 Bedrooms / 2 Bathrooms br• Accommodates up to 6 guests with 2 kings and 1 queen bed br• Beach chairs and beach cart provided br• Washer and dryer br• Outdoor shower br• Electric grill br• Near Siesta Key Village shops and dining br• Parking for 2 vehicles br brEnjoy tranquil mornings on the porch with the soothing sound of waves just beyond your doorstep, then take a short stroll down your private path to enjoy the soft, quartz sand of Siesta Key Beach. After a fun day at the beach, rinse off in the outdoor shower before grilling fresh seafood on the electric grill. This charming home is equipped with beach chairs and a cart, making your beach days effortless, while the washer and dryer ensure your swimsuits and towels are fresh and ready for your next adventure. br brStep inside Coastal Cottage to find a cozy coastal design that beautifully blends old Florida character with modern updates. The living area features plush seating and a flat-screen TV, providing a relaxing retreat after your sun filled days. The fully equipped kitchen comes with an air fryer/convection oven/microwave combo, a full-size refrigerator, coffee maker, and ample cookware, making it easy to prepare delicious home-style meals. The dining area comfortably seats your entire group, perfect for shared breakfasts or sunset dinners. br brThe primary suite is a restful haven, featuring a king bed, an ensuite bathroom with a shower/tub combo, and plenty of storage space for your belongings. The second bedroom also offers a king bed, while the third bedroom features a comfortable queen bed. A shared hallway bathroom, equipped with a walk-in shower, ensures convenience for all guests, making this home ideal for families or groups. brbrRoom Details: br• Primary Bedroom: King bed, ensuite bathroom with shower/tub combo br• Second Bedroom: King bed br• Third Bedroom: Queen bedbr brBeyond the beach, enjoy everything Siesta Key has to offer with just a short walk to shops, cafes, and vibrant nightlife. With its historic charm, prime location, and thoughtful amenities, Coastal Cottage provides a true island experience. brbrMake your Siesta Key getaway unforgettable at Coastal Cottage by Tropical Sands Accommodations. Steps from the sand and moments from the Village, your slice of Florida history awaits. Book now and start counting down to your beach escape! br brbr- brThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Tropical Sands Accommodations Rental Policies for full details. brbr2 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrWe do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Tropical Sands Accommodations Rental Policies for full details. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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$634.5

/ Nightly

Private Vacation Home

The Shore House Private Dock Hot Tub

Siesta Key, Florida, United States

Welcome to your Siesta Key sanctuary — a beautifully designed 3-bedroom, 2-bath beach house tucked in a quiet neighborhood just a short stroll from the white sands of Siesta Beach and the vibrant Siesta Village.brbrThis home blends coastal charm with modern comfort, creating a relaxed, stylish retreat for families or friends.brbr The SpacebrStep inside an open-concept main floor designed for connection and comfort. Lounge on cozy seating, stream your favorite shows on the smart TV, or cook a fresh seafood dinner in the fully equipped kitchen stocked with all essentials.brbrTwo spacious king bedrooms with smart TVs and ceiling fans share a bright, updated bathroom with a tub/shower combo.brbrUpstairs, a private master suite awaits — featuring a king bed, walk-in closet, and a serene balcony with bistro seating. Enjoy your morning coffee or evening glass of wine under the palms. The suite also includes a convenient kitchenette and a spa-style bathroom with double sinks, a walk-in shower, and an oversized jetted tub.brbr☀️ Outdoor LivingbrRelax and recharge in multiple outdoor spaces: a large deck with lounge seating, a screened lanai for bug-free evenings, and a beautifully lit patio for dining under the stars. Fire up the grill, play lawn games, or unwind around the firelight.brbrThe private Grand Canal dock is perfect for fishing, sunbathing, or launching the included kayaks and paddleboards.brbr Easy Access & AmenitiesbrTwo complimentary beach cruisers make exploring Siesta Village and the beach a breeze. You’re just minutes from restaurants, live music, boutique shops, and the island’s best sunsets.brbr Why You’ll Love ItbrbrWalk or bike to Siesta Beach & Siesta VillagebrbrPrivate fishing & kayak dock on the Grand Canalbrbr3 king bedrooms with TVs + luxury master suitebrbrFully equipped kitchen + outdoor grillbrbrScreened lanai, deck, and patio for relaxing outdoor livingbrbr2 beach cruisers, kayaks, and paddleboards includedbrbrYour Siesta Key escape starts here — where coastal comfort meets effortless style.

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$905.98

/ Nightly

Private Vacation Home

Waterfront KEY home w/ Pool, HotTub, mins to beach

Siesta Key, Florida, United States

Minutes from the beach, marina, and village center, your tropical paradise awaits you at this bright, 5 bedroom 3 bathroom vacation rental house. This property boasts a private pool with jacuzzi tub. There’s even a putting green on site to polish your golf skills. Families can decide between enjoying the private pool, nearby beach, charter boats, eco tours, or shopping and dining. Challenge your guests to some friendly competition via the arcade Pac Man or Golden Tee Golf games located right in the lower level!brbrBRAND NEW 6 SEAT GOLF CART AVAILABLE FOR RENT!brStreet legal 6 seater cart with a 4+2 Seat cart configuration featuring Apple Car Play, rear camera, premium sound system, head/tail lights, turn signals, back seat folds down to hold beach chairs, groceries, etc. It has a 60-mile range and max speed of 25 mph.brbrRental rates are:br$700 /weekbr$1800 /monthbrPlease inquire to reserve for your stay!brbrUpstairs:brBedroom 1- King BedbrBedroom 2- King BedbrBedroom 3- Two Twin BedsbrDownstairs:brBedroom 4- King BedbrBedroom 5- Two Twin XL over Queen Bunk Bedsbr2 Living Rooms! (2 Rollaway single beds available for use)brbrWeather Disclaimer: Pool temperatures may not fully reach the temperature the heater is set to if the outside air temperature is below 70 degrees.brbrHouse is located blocks from the Out of Doors Academy. Approximately 1 mile from the village area of Siesta Key and about 1 mile from the closest beach access.brbrAs you step into this lovely home, you feel refreshed as you gaze up toward the open-air cathedral ceilings. Enter the living room to a plush new sofa and comfy loveseat set in front of a large flat-screen TV. For your viewing pleasure, watch your favorite movies, enjoy complimentary Youtube TV or local channel programming on Roku. Past the living area, you`ll find a beautifully appointed dining table with seating for 8 guests to enjoy a delicious meal.brbrThe fully equipped kitchen offers ample granite countertop space for preparing a home-cooked meal while your travel companions join you. Enjoy the feast at the nearby dining table, while taking in the views of the natural setting as you dine. The chef in your group will appreciate the newly updated stainless-steel appliances.brbrBask in the sun when you head out to the open and airy patio to take a refreshing swim in the sparkling, heated pool. Let your spa treatment continue as you progress into the soothing hot tub. Then dry off under the warm Florida sun as you soak up the rays on the plush chaise lounge chairs. Outdoor living at its best!brbrWhen hunger strikes, cookout on the gas grill and enjoy your lunch at the nearby patio table. Want a large family meal Make use of the Crock Pot Slow Cooker. Brew your morning coffee using the provided Keurig coffee maker.brbrAfter a fun-filled day, retreat to one of the cozy bedrooms for a peaceful slumber. The master has a king bed, second bedroom a king, third bedroom a king, fourth has two twin beds, and the fifth has 2 Twin XL over Queen Bunk Beds. Room for everybody! What’s more, two twin rollaway beds are also provided featuring super comfy memory foam!brbrYour family can tour the key on the 5 provided “Beach Cruiser” bicycles parked in the garage awaiting your adventure. Beach chairs, beach umbrella, beach toys, beach wagon, pool toys, etc. are also included.brbrPack lightly when you travel to this lovely home, as you`ll be able to refresh your laundry in the washer and dryer. No need to fumble with keys and lock boxes as this rental is equipped with quick & easy keyless entry.brbrOutside:brbrThe home is set back from the street with a deep, palm-filled front yard. Behind the house are a shady pool, hot tub, and putting green! The house is at the end of a private canal and driveway parking.brbrbrInside:brbrThe updated, top-of-the-line, windowed kitchen is fitted with stainless steel appliances, Keurig and all useful gadgets, and terrific cooking and eating counter space. The kitchen storage exceeds any renter`s needs!brbrThe kitchen is open to the dining/living room, with large dining area, TV, working fireplace, and pool views. The entire living room opens through sliding doors to the balcony above the patio with a lovely view of the canal, with another roomy dining table and separate seating area. Proximity to the living room is ideal for entertaining: opening the sliding door brings the outside into the whole living space, and island breezes fill the porch all evening. Off the porch, back stairs lead directly to the pool area.brbrThis newly renovated upper-level home has been meticulously updated and appointed to highlight its open layout and airy entertaining space. A vacation-ready Siesta Key pool & canal residence, the house is elevated on a corner waterfront lot in a prime, quiet neighborhood minute from the beach.brbrSiesta Beach continues to rank highly on the “Top Beach” lists curated by worldwide travelers and renowned coastal experts. Its nearly 100% quartz-crystal sand, dubbed the “world’s finest, whitest sand”, never gets hot under the Gulf Coast sun and tropical weather.brbrSiesta Key Beach named by TripAdvisor as the top beach in the U.S.!br$25 Pet fee per pet, per nightbrbrAdditional $200 per week or $500 per month to heat pool to the optimal and desired temperature of 88 degrees!brbr24-hour outdoor camera and remote security team monitoring not actively monitoredbrNoise detection sensors installed in property – These devices monitor decibel levels inside the property 24 hours a day and automatically notify us if noise levels are too high.

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$1947.38

/ Nightly

Private Vacation Home

Sugar Sand Cottage – Gulf-View Siesta Key Escape

Siesta Key, Florida, United States

Summary:brbrSugar Sand Cottage is a 5BR/3.5BA Siesta Key retreat directly across from the Gulf . Just a 2-minute walk to the beach and moments from Siesta Key Village, this home offers Gulf views, a private pool, and a wraparound patio perfect for sunset lounging. With a split floor plan, bunk rooms, and plenty of space to gather, it’s ideal for families and groups ☀️ ️.brbrbrbrThe Space:brbr ️ Sugar Sand Cottage – Gulf-View Siesta Key Escape brbrbrbrWelcome to Sugar Sand Cottage, a bright and breezy 5-bedroom, 3.5-bath coastal retreat directly across the street from the Gulf of Mexico . Just steps from the powdery white sands of Siesta Key Beach and moments from the lively Siesta Key Village, this home offers the perfect blend of location, comfort, and relaxation. Enjoy non-stop Gulf views, a private pool, and a stunning wraparound patio designed for soaking up the island sunshine ☀️.brbrbrbrSpend your days at the beach, then retreat to your peaceful backyard oasis to cool off in the sparkling pool or unwind on the deluxe outdoor seating with Gulf breezes and sunset views . With shops, restaurants, and nightlife just minutes away, you’ll have everything you need for an unforgettable island getaway.brbrbrbrInside, the open living space is warm and inviting, featuring cozy seating, a large TV, and coastal touches throughout . The gorgeous kitchen is a dream for entertaining, equipped with stainless steel appliances, stylish tile work, and plenty of storage. Gather around the dining table or bar-top seating for meals, game nights, or morning coffee.brbrbrbrDesigned with a split floor plan, Sugar Sand Cottage offers privacy and flexibility for families and groups. A second living area provides extra space to spread out, while sleeper sofas add even more sleeping options for guests.brbrbrbr✨ Highlights ✨brbrbrbr• ️ 2-minute walk to Siesta Key Beach (across the street)brbr• ️ 5 Bedrooms / 3.5 Bathroomsbrbr• Gulf views from wraparound patiobrbr• Private poolbrbr• ️ Walk to restaurants, shops & Siesta Key Villagebrbr• Washer & dryerbrbr• Spacious outdoor seating & entertaining areasbrbrbrbr Bedrooms brbrbrbr• Primary Bedroom: King bed, ensuite bathroom with walk-in showerbrbr• Second Bedroom: Queen bed, hall bathroom access with walk-in showerbrbr• Third Bedroom: Full-over-Full bunk with twin trundle, hall bathroom accessbrbr• Fourth Bedroom: King bed, Jack-and-Jill bath with tub/shower combobrbr• Fifth Bedroom: Full-over-Full bunk, Jack-and-Jill bath with tub/shower combobrbrbrbrAdditional sleeper sofas provide extra accommodations.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool and backyard—perfect for relaxing, entertaining, and enjoying your own secluded space.☀️brbrbrbrOther Things to Note:brbr ️ Beach-Ready Convenience brbrTo make your stay effortless, the home is fully stocked with beach chairs, a beach cart, and a beach umbrella, plus all bath towels, beach towels, and linens—just pack your bags and enjoy island time ☀️ brbrbrbr Parking InformationbrbrParking is available for up to 3 vehicles maximum. Please plan ahead and coordinate with your group accordingly.brbrbrbr Friendly Island ReminderbrbrThis home is located in a residential neighborhood. We kindly ask guests to be respectful of our neighbors by keeping noise at a considerate level day and night. Thank you for helping preserve the peaceful island atmosphere brbrbrbrInteraction with Guests:brbrIf you need anything during your stay, I’m always here to help! You can call or text me directly on my cell anytime. I’m available 24/7 to answer questions, share local tips ️, or assist with anything that comes up. Your comfort and peace of mind are my top priority! ✨

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$692.13

/ Nightly

Private Vacation Home

Island Paradise 3-bedroom canal house in Siesta Key AC, private heated pool

Siesta Key, Florida, United States

Located in Siesta Key village! Enjoy what this 3-bedroom canal house has to offer. Guests will find a fantastic mix of comfort with a king bed, queen bed, bunk bed, spread across the bedrooms. Two bathrooms provide convenience, each featuring a refreshing shower. The house stays comfortable year-round with heating and air conditioning. Whether relaxing indoors or planning your next adventure, this marvelous home creates an enjoyable retreat. 1/2 block to village. 5 minute walk to beach. House is located on the canal with a private heated pool. Plenty of room for parking and pet friendly.

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$1282.5

/ Nightly

Private Vacation Home

Pelicans Place | Your Family Beach Getaway Steps from Siesta Key Beach & Village

Siesta Key, Florida, United States

Welcome to Pelican's Place — Your Family's Ideal Beach EscapebrNestled just steps from the world-famous Siesta Key Beach, Pelican's Place offers the perfect family retreat in the heart of Siesta Key Village. This charming 2-bedroom, 2-bath invites families to experience the best of island living with unbeatable proximity to the shimmering Gulf shores and vibrant local attractions. Whether you're here for beach days, sunset strolls, or exploring the village's unique shops and dining, Pelican's Place has everything you need for an unforgettable getaway.brbrBeachside Comfort Meets Family FunbrStep inside and feel at home in this welcoming vacation haven. The spacious living area is perfect for family gatherings, featuring free WiFi and HDTVs for entertainment after a fun-filled day on the sand. With 2 bedrooms (1 King, 2 Full beds), a full sleeper sofa, and the ability to comfortably accommodate up to 8 guests, there's plenty of room for everyone to relax. Whether you're lounging together or creating meals in the fully-equipped kitchen, this cozy home provides everything your family needs to unwind and connect. The kitchen is stocked with essential amenities, including a regular and Keurig coffee maker, dishwasher, and everything you need to whip up your favorite meals. Your furry family member (dog) is also welcome, up to 25 lbs., with an additional fee.brbrConvenience and Thoughtful Details for a Perfect StaybrYour comfort and convenience are our top priority. We've thought of everything so you can relax and enjoy your stay from the moment you arrive. A starter pack of toiletries and home essentials is provided, and for your beachside adventures, we've included beach towels, chairs, a cooler, and a caddy to make your time by the water even easier. Our CottageClean Team ensures enhanced cleaning protocols, so you can enjoy a pristine and safe space throughout your stay.brbrExperience the Best of Siesta KeybrStep out the door, and you'll be just moments away from the breathtaking Siesta Key Beach, known for its powdery white sands and crystal-clear waters. Spend your mornings beachcombing or swimming, afternoons basking under the sun, and evenings strolling through the charming Siesta Key Village, where family-friendly restaurants, unique boutiques, and lively local events await. Don't miss the chance to explore Downtown Sarasota with its art, culture, and shopping—just a short drive away. And with island shuttle services available, getting around is a breeze.brbrYour Family's Beachside Adventure AwaitsbrPelican's Place is not just a place to stay—it's the gateway to a memorable beach vacation. From the relaxed pace of Siesta Key to the vibrant activities in the Village, every moment is filled with opportunity for adventure, relaxation, and family bonding.brbrBook Your Stay TodaybrDon't wait—secure your family's beachside retreat at Pelican's Place today and start creating lasting memories just steps from the beauty of Siesta Key's Gulf Coast!brbrExclusive Amenities Include:br• Located In Siesta Key Villagebr• 1/2 Block to Siesta Key Beachbr• 2 Bedrooms, 2 Full Bathsbr• 1 King Bed, 2 Full Beds, 1 Full Sleeper Sofa (Sleeps 8) with linens providedbr• Free WiFi & HDTV'sbr• Regular & Keurig Coffee Maker, Dishwasher, Washer & Dryer, and Kitchen Essentials Providedbr• Starter Pack of Toiletry Essentials Included - Shampoo, Conditioner, Hand / Face Soap, Body Lotion, & Makeup Wipesbr• Starter Pack of Home Essentials Included - Dish Soap, Dish Sponge, Dishwasher Tablets, Laundry Tablets, & Cleaning Wipesbr• Beach Towels, Chairs, Cooler, & Caddy Providedbr• Enhanced cleaning protocols provided by our CottageClean Teambr• Island Shuttle Transportation Availablebr• Shared Gas Grillbr• Dog friendly, up to 25 lbs., with a feebrbrPelicans Place can accommodate up to 8 guests with a bedding configuration as follows:brbr• Bedroom # 1: King Bed (1) - Sleeps: 2br• Bedroom # 2: Double Beds (2) - Sleeps: 4br• Living Room: Sleeper Sofa (1) - Sleeps: 2brbrWe go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol within our CottageClean Program. After our six hour in-depth cleaning of your home, we complete a 35 point property inspection to ensure that you feel tremendously safe and happy with this amazing home. This allows you to vacation worry free regarding the cleanliness of your home and truly relax as soon as you arrive. Our goal is to have you feel like you are walking into a brand new vacation home that no one has ever stayed at before!

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Sleeps

$296.92

/ Nightly

Private Vacation Home

301 Avenida Madera A- Siesta Key Village House with Roof Top Deck

Siesta Key, Florida, United States

Siesta Key Main Village Location - No Car Needed for this fantastic, waterfront location with Heated Salt Water Pool... Generously Appointed with all the things that make a Good Siesta Key Guest Stay a GREAT Siesta Key Guest Stay... brbrIf you are looking for the perfect location for your next vacation, then your search is over! This 2 bedroom, 2 bath property features a prime location within The Village of Siesta Key and is 3.5 blocks to the beach. Beautifully updated, this home is decorated in a coastal theme and features a fully updated kitchen with solid surface counter tops, stainless appliances, and a breakfast nook. The primary bedroom has a king bed, an en suite bathroom featuring a walk in shower and best of all........a rooftop deck complete with outdoor furniture, and a stainless steel grill. At night, sit and enjoy watching the sunset over the #1 rated Siesta Key beach as you enjoy the tropical breezes and plan your next days adventures. During the day, take advantage of being within walking distance to the beach and all the shopping and dining that Siesta Key Village offers or take the short drive over the bridge into Sarasota for even more activities during your vacation. This Pet friendly home is the perfect place for your next family gathering. If the rest of the family is coming, you can also rent Unit B (VRBO# 1064659) which features another 2 bedrooms and 2 bathrooms. NOTE: There is a $250 fee for up to 2 dogs. Must state you are bringing a pet at time of inquiry/booking. An additional $100 will be charged if not notified about pet. The canal and pool area is a shared space with the other Unit. The Units are attached, but have separate private entrances, and are private! There are no shared walls to any rooms of the Units. For guest safety, there are outside security cameras, including the pool area. This Unit is smoke free. No smoking is permitted inside the Unit. Enjoy your stay!! :-)brbrNote: The pool temperature is dependent and subject to the outside temperature during the cooler months in Florida. When the temperature dips into the low 60’s and below during the evening, the pool may not get up to a comfortable temperature during the day.

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$268.52

/ Nightly

Private Vacation Home

Tropical Siesta Key Townhouse at Bay Oaks - Watch Dolphin in the Bay! G12

Siesta Key, Florida, United States

You are sure to appreciate the tropical surroundings and professionally landscaped grounds at Bay Oaks. Enjoy the large BBQ/Picnic area and piers on the bay as you watch for dolphin in the bay waters!brbrThis beautifully remodeled townhouse offers 2 floors of living space complete with 2 lanais and a porch. Downstairs is the comfortable and spacious living room with views of tropical landscaping and mature trees. Off of the living room is a screened in lanai with table and chairs. The full size kitchen includes a dishwasher, microwave, oven/stove, full size side by side refrigerator and granite counters. There is a nice dining area with views, and also additional seating at the kitchen bar/counter. A full size washer & dryer are provided in the laundry room. There is also a half-bath downstairs.brbrUpstairs are the 2 bedrooms with ensuite bathrooms in both. The master bedroom is tastefully decorated in a Tommy Bahama decor with a queen size bed, walk in closet, a private deck, and a jetted tub in the bathroom. The bright and cheerful guest bedroom offers bunk beds with a twin/full combination and an additional twin bed. There is also an additional deck located between the two bedrooms for more outside space. TV’s and DVD players are provided in the living room as well as both bedrooms, and the unit also offers free cable and WiFi.brbrThe townhouse is equipped with everything you need for fun at the beach including beach chairs, beach towels, 'boogie boards', sand buckets & shovels and beach umbrella. All you need is suntan lotion and your bathing suit!br brAlso provided for your enjoyment on-site are a heated pool, tennis courts, sauna, showers, recreation room with pool table and a lounge where various social gatherings are scheduled. Bike racks are convenient to your doorstep. Free WiFi access is also available in the clubhouse and at the pool. Walk 4 blocks to Beach Access #12, or hop on the free Siesta Key Breeze Trolley right in front of the resort and ride to the public beach pavilion (concession stand, restrooms), Siesta Key Village and Turtle Beach.brbrRENTAL POLICIES: Weekly rentals are Saturday to Saturday. Monthly rentals are the first day of the month to the last day of the month during Jan, Feb, and March.

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$279.08

/ Nightly

Private Vacation Home

Beachside home with pool and beach access

Siesta Key, Florida, United States

The beauty of Siesta Key is renowned throughout the world and the charms found in our Siesta Beach House, Cottage B, reflect the spirit of the Key. Offering 3 bedrooms, 2 baths, and enough room for 8 visitors to happily cohabitate, its proximity to white sand beaches and a heated pool shared by other cottages in this community make it extra special! Shaded by palm trees and offering the traditional Florida vibe, Cottage B is destined to be the one you temporarily make your own.brbrEntering through the front door, the open concept floor plan of Cottage B harbors no secrets and as you step into the living room, you will feel your stresses and troubles instantly melt away. Sea-themed art adorns the walls, swimming across blue hued walls that complement the soft sofa and variety of chairs that the room provides. A flat screen television hangs on the wall opposite the sofa, providing entertainment during quiet times.brbrThe cozy confines of Cottage B somehow seem larger due to high ceilings and plenty of natural light and the dining room, centered between the living area and the fully equipped kitchen, is destined to be the most used spot in the home. A glass table is surrounded by cushioned wicker chairs and a modern light fixture ensures that everyone will be able to read the words on the cards of the games being played with the family.brbrThe kitchen anchors the open concept floor plan, offering all the appliance necessities to create a meal and includes a coffee maker to ensure guests are fully caffeinated. The blue walls continue into this space, creating a cool contrast to the crisp white painted cabinets.brbrThe first of the guest rooms provides sleeping space for 4 in its two queen beds topped with sea themed quilts. A flat screen television rests on the bureau opposite the beds allowing for a little mindless entertainment before occupants fall into deep and dreamless sleep. This room shares access to the main bath with the second guest room, in which you will find a standup shower and a single vanity.brbrThe queen bed that anchors the second of the guest rooms is topped with the same sea themed quilt above which hangs a colorful swordfish, reminding visitors of their proximity to the sea. This room also offers its own flat screen television, this one hanging from a mount on the blue wall.brbrThe same quilt that was in the first two rooms will be found on the King bed in the master suite. Also offering a flat screen television that hangs on the wall directly opposite the bed, this room has its own master en suite. A walk-in shower, single porcelain sink, and tiled walls add a traditional Florida charm to the space.brbrLocated just a ¼ mile from Siesta Key's breathtaking public beach, guests have the choice of swimming in the gulf or sticking closer to home and practicing their cannonballs in the community pool that is heated during the cooler winter months! Also offering a barbecue grill for that makes your catch of the day taste absolutely delicious, plenty of onsite parking, and a traditional Florida experience that will make guests wish the good times never had to end. Book this special property today!

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$1218.78

/ Nightly

Private Vacation Home

Holiday Sunshine Savings: Luxurious Waterfront Retreat minutes from beach

Siesta Key, Florida, United States

Villa Siesta sits poetically in a walled, gated garden on deep, azure-colored Hansen Bayou with views of Sarasota Bay & City skyline. This architecturally unique 5400 sf villa is built around a spacious tower with winding 3 story staircase opening to each living level.brbrThe romantic residence is located just a few blocks from Shell Beach, less than 3 mi from award-winning Siesta Beach & short distance (less than 4 mi) to downtown Sarasota where restaurants, shops & cultural activities abound.brbrVilla Siesta is registered with the City of Sarasota under vacation rental certificate registration #VR22-00060.brbrThe villa opens to outdoor living areas with terraces on each level for enjoying the beautiful environs. Recently renovated and professionally-decorated, Villa Siesta offers exquisite living spaces featuring 4/5 bedrooms, 5 and a half baths, a bright open floor plan on second floor with chef's kitchen with eat-in island, dining area overlooking canal, bar with lounge seating and large family room area also overlooking canal. Want to dine al fresco Open the French doors and enjoy the additional outdoor terraced dining area overlooking bay and city views. You won't want to leave this enchanting property with the added graciousness of a spacious living room with fireplace, library and master bedroom suite on third floor, all with open views of bay and city. Bedrooms boast private baths to add to privacy and relaxation. A three stop elevator allows for easy access to any of the many spaces and features including bumper pool/poker table and ping pong table on first floor. brbrbrThe private dock offers some of the finest boating water in the entire area: very deep and protected, clear and clean due to the proximity to Sarasota Bay, Big Pass and Gulf of Mexico. Dolphins play at the water's edge. Heated pool, multiple outdoor areas for sun worshippers, and lush gardens (including private garden with swing) will complete your most memorable holiday experience.brbrEnjoy a first time-offered 10% discount for the Holiday Season 2024. Luxury and savings- what could be better!

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$209.45

/ Nightly

Private Vacation Home

Newly Refurnished Tropical Townhouse - Watch Dolphin in the Bay, Fish from the Docks! Unit B62

Siesta Key, Florida, United States

Newly Refurnished Tropical Townhouse at Bay Oaks - Enjoy the large waterfront BBQ/Picnic area and fishing piers on the bay as you watch for dolphin in the bay waters!brbrNewly refurnished unit offers 2 floors of living space featuring 2 patios and a screened in lanai for plenty of outside space. New flooring, no carpet. Downstairs is the spacious living room with comfortable new furnishings including a queen sleeper sofa & views of tropical landscaping and mature trees. Adjoining the living room is a screened in lanai.. The dining area has nice views, and additional seating is provided at the kitchen bar/counter. A full size washer & dryer are provided in the laundry room. There is also a half-bath downstairs. brbrUpstairs are the 2 bedrooms with ensuite bathrooms in both. The master bedroom has a comfortable queen size bed, walk in closet, TV, and a private balcony. The guest bedroom has 2 queen beds.. An additional deck located between the two bedrooms for more outside space. TV’s are provided in the living room as well as both bedrooms. The unit also offers free WiFi and free YouTube streaming service. Everything you need for a fun time at the beach is provided including beach chairs, beach umbrella, beach towels, and beach toys.brbrWatch dolphin from the beautiful waterfront area on the Bay where you can BBQ, picnic, or fish from the piers! Also provided for your on-site enjoyment are a heated pool, tennis courts, fishing piers, recreation room with pool table and a lounge where various social gatherings are scheduled. Bike racks are convenient to your doorstep. Free WiFi access is also available in the clubhouse and at the pool. Walk 4 blocks to Beach Access #12, or hop on the free Siesta Key Breeze Trolley right in front of the resort and ride to the public beach pavilion (concession stand, restrooms), Siesta Key Village and Turtle Beach.

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$574.82

/ Nightly

Private Vacation Home

Stylish Siesta Key Canal Home w/ Private Pool & Boat Dock - Pet Friendly

Siesta Key, Florida, United States

Welcome to your freshly reimagined Siesta Key retreat — a beautifully remodeled waterfront home on the Grand Canal, completely updated with extensive top-to-bottom renovations and ready to welcome guests in style.brbrThis spacious, light-filled home features all-new furniture, a brand-new kitchen, and fully renovated bathrooms, blending modern comfort with relaxed coastal elegance. The layout includes a comfortable living room, a formal dining area, and a separate den, offering multiple spaces to gather, relax, or spread out.brbrThe home comfortably sleeps up to 7 guests. The primary suite features a king bed, direct access to the lanai, and a private, spa-inspired bathroom. One guest bedroom offers a queen bed, while the second guest room includes a queen bed plus a twin—ideal for families or groups.brbrA private office provides a quiet, dedicated workspace, and a full laundry room adds everyday convenience—especially for longer stays.brbrStep outside to the large screened lanai with a private pool, accessible directly from the living room, den, and primary bedroom—creating seamless indoor-outdoor living. The lanai overlooks the Grand Canal and is perfect for morning coffee, afternoon swims, and relaxing evenings.brbrFlorida’s warm climate typically keeps the pool comfortable during the summer months without additional heat. For guests visiting during cooler times of year, optional pool heating is available for a flat fee of $400 per month.brbrOne of the home’s standout features is the private boat dock on the Grand Canal, ideal for guests bringing a boat or simply enjoying the peaceful waterfront setting.brbrLocated in a quiet residential neighborhood just minutes from world-famous Siesta Key Beach, dining, shopping, and local attractions, this home offers the perfect balance of privacy and convenience.brbrRENTAL POLICY: A one-month minimum is required January - April. Weekly rentals are accepted May - December.brbrPOOL HEATING POLICY: Optional pool heat is available for a flat fee of $400 per month and heats the pool to approximately 85 degrees. The full monthly fee applies regardless of length of stay and must be requested prior to arrival. The pool heating fee will not be reflected in the online price quote, but will be added to your total prior to finalizing your reservation.brbrPET POLICY: Small dogs will be considered with a $200 non-refundable pet fee but we must be notified before your reservation can be confirmed. The pet fee will not be reflected in the online price quote, but will be added to your total prior to finalizing your reservation.

Bed

Bath

Sleeps

$539.17

/ Nightly

Private Vacation Home

Boutique Hotel Style Home is Just Steps From The Fully Recovered Siesta Beach!

Siesta Key, Florida, United States

SK Beach is #1 again! And we're offering a 10% discount for weekly bookings, including July 4th! Our reviews tell the story. You will not be disappointed!!brbrWelcome to the Good Life - your Siesta Key private home just a 5-minute walk from the Siesta public beach pavilion, and a 7-minute bicycle ride to Siesta Village, the heart of Siesta Key's restaurant, shopping & nightlife district. The home's decor is designed to capture the feel of a boutique hotel - both inside & out. Not only is this home absolutely beautiful, but we have also tried to provide you with everything you will need to enjoy a truly memorable beach vacation, including bikes, beach chairs, a cooler, and beach cart for easily transporting everything.brbrEverything is new, including the kitchen, dining room, and an outdoor patio, all of which provide an opportunity for great meals and even better conversation. The home has everything you will need for an amazing vacation, including a private enclosed saltwater pool and large covered outdoor area with a new propane grill and outdoor shower - perfect for gathering everyone after a great day at the beach! brbrThe home has Wifi throughout, a large television with a Sonos surround sound system in the family room, as well as flat-screen televisions in all 3 bedrooms. brbrCheck-in & start relaxing - that's our only goal. We've thought of everything, so you can focus on unwinding and creating memories! We can't wait to host you.brbrNote that the homeowners will provide a comprehensive rental guide, and will also require a signed separate rental agreement as a final step in the booking process.

3

Bed

2

Bath

6

Sleeps

$311.33

/ Nightly

Private Vacation Home

Our House at the Beach C-114

Siesta Key, Florida, United States

Our House at the Beach C-114 by Tropical Sands AccommodationsbrbrWelcome to Our House at the Beach C-114, a comfortable two bedroom, two bathroom townhouse style vacation rental located directly across from the world famous Crescent Beach on Siesta Key. Situated within the well loved Our House at the Beach community, this inviting condo offers a relaxed island setting just steps from the sand and a short drive to Siesta Key Village for dining, shopping, and nightlife. Perfect for families or small groups, this home provides everything you need for an easy beach getaway.brbrHighlightsbr• Across the street from Crescent Beachbr• 2 Bedrooms / 2 Bathroomsbr• 1 King, 2 Twins, Sleeper Sofabr• Sleeps up to 6 guestsbr• Community heated poolbr• Tennis courtsbr• Beach chairs and beach cart providedbr• Washer and dryer in unitbr• Private screened patiobr• 7 night minimum stay br• Convenient location near dining and shoppingbrbrGuests staying at Our House at the Beach enjoy access to the community’s heated pool and tennis courts, along with beautifully maintained grounds that make relaxing outdoors easy. The beach access is located directly across the street at Crescent Beach, known for its powder soft white sand and breathtaking Gulf sunsets. Beach chairs and a beach cart are provided in the unit to make your beach days simple and enjoyable.brbrInside, the condo offers a comfortable living space designed for easy vacation living. The living room features cozy seating and a television, with a sleeper sofa available for additional guests. Sliding glass doors lead to a screened patio, providing a peaceful spot to enjoy your morning coffee or relax after a day at the beach. The kitchen includes essential appliances and cookware needed for preparing meals during your stay, while the nearby dining area offers a welcoming place to gather for breakfast before heading out for the day.brbrThe primary bedroom features a comfortable king bed, ample storage, and easy access to a bathroom. The second bedroom includes two twin beds, making it a great option for children or additional guests. The sleeper sofa in the living room allows the condo to comfortably accommodate up to six guests. Bathrooms in the home have been updated with modern finishes and offer either a walk in shower or a shower and tub combination for added convenience.brbrRoom Detailsbr-Primary Bedroom: King bedbr-Second Bedroom: Two Twin bedsbr-Living Room: Sleeper sofabrbrAdditional amenities include in unit washer and dryer, beach chairs, and a beach cart, making it easy to enjoy long days at the beach. The central Siesta Key location provides quick access to Crescent Beach, local restaurants, grocery stores, and the lively atmosphere of Siesta Key Village.brbrWhether you are planning a relaxing beach vacation or a fun filled getaway on Siesta Key, Our House at the Beach C-114 by Tropical Sands Accommodations offers a comfortable and convenient home base just steps from Crescent Beach. Book your stay today and experience the beauty of Siesta Key’s famous white sand beaches.

Bed

Bath

Sleeps

$468.41

/ Nightly

Private Vacation Home

Stunning 2 Bedroom/ 1 Bath in Siesta Key, Quick Walk to Beach and Pool!

Siesta Key, Florida, United States

Sun and Sea, 2-bedroom, 1-bath, is a stunning remodel. Featuring a queen bed in the master, and two twins in the second bedroom, this lovely home can sleep up to 4. Inside, you’ll find top of the line stainless appliances, granite counter tops, cabinets and kitchen drawers, full-size washer and dryer in each unit. Sun and Sea is a Siesta Key duplex with private and gated Beach Access, just steps away to the beautiful crystal sands and community pool located at Calini Beach Club, directly in the heart of the vibrant South Siesta Key Village. You won't need a car, with such easy and close access to the beach and across from the Village which features numerous restaurants, including the Daiquiri Deck, bars, pharmacy, full-service grocery and much more - this is the epitome of your dream island vacation property!brbrBedroom 1- QueenbrBedroom 2- 2 TwinbrLiving Room - Sleeper SofabrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles,brWifi,brParking,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool Access,brAccess to Siesta Beach Pickleball Courts,brFree-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 25br*To book a Beachside Managed Property Between February 1st and April 15th, the booker must be 27 years old or older. br*Security Authorization Hold taken upon check-in. Amount: $500

Bed

Bath

Sleeps

$377.45

/ Nightly

Private Vacation Home

REMODELED, Heated Pool and Spa, POOL Table, games, bikes included!

Siesta Key, Florida, United States

Brisas Del Mar by Siesta Key Luxury Rental Properties brVacation Rental License #VR22-00121brbrWelcome to Brisas Del Mar, a modern coastal retreat featuring four bedrooms and three bathrooms split between a main house and a private guest house, perfect for families or groups of friends traveling together. Located 2 miles to Siesta Key Beach and just a quick bike or trolley ride to Siesta Key Village, this inviting home offers a private pool, outdoor kitchen, and stylish interiors for an elevated island getaway on Florida’s Gulf Coast. brbrHighlights br• 2 miles to Siesta Key Beach br• 4 Bedrooms, 3 Bathrooms br• 2 Kings, 3 Queens, Sleeper Sofa br• Private Pool with Waterfall Feature and Hot Tub br• Guest House with Separate Living Space br• Outdoor Kitchen and Dining Area br• Outdoor Showerr br• Pool Table and Bicycles br• 4 Parking Spaces brbrDesigned for seamless indoor outdoor living, Brisas Del Mar offers a private tropical oasis perfect for entertainment and relaxation. The sparkling pool features a tranquil waterfall, in-ground spa, and cozy loungers ideal for reading, sunbathing, or enjoying an afternoon siesta. A covered patio with an outdoor TV sets the stage for casual lounging, while the full outdoor kitchen and dining table invite guests to share meals in the warm Gulf breeze. This home also includes a guest house, providing added privacy for extended families, couples, or friends. Bicycles, a pool table, and spacious indoor living areas ensure guests of all ages stay entertained throughout their Siesta Key vacation. brbrInside the main house, guests are welcomed by a bright and open living room featuring a large sectional and TV for movie nights. A separate den offers a pool table and additional lounging space. The modern kitchen is equipped with stainless steel appliances, cooking essentials, and sweeping granite countertops with bar seating. A dining table sits just off the kitchen, creating a perfect place for shared meals. An additional living area with a sleeper sofa and TV provides extra room for games, relaxation, or accommodating larger groups comfortably. brbrThe primary suite offers chic decor, a desk for those needing a quiet workspace, and private doors opening directly to the pool area. Its ensuite bathroom features a double vanity and a floor to ceiling tiled walk-in shower. Two additional bedrooms in the main house, a king room and a queen room, are designed with comfort in mind; featuring built-in closet storage and TVs for late-night entertainment. The shared hall bathroom also provides convenient pool access. The guest house, accessible from the screened-in pool area, includes two queen beds and a private ensuite bathroom with a walk-in shower, making it ideal for guests seeking more privacy or their own retreat. brbrRoom Details br-Primary Bedroom (Main House): King bed, ensuite bathroom with double vanity and walk-in shower br-Second Bedroom (Main House): King bed br-Third Bedroom (Main House): Queen bed br-Fourth Bedroom (Guest House): Two Queen beds, ensuite bathroom with walk-in shower br-Additional Sleeping Sleeper Sofa in extra living area brbrBrisas Del Mar includes a private guest house, outdoor kitchen, bicycles, pool table, and a gorgeous screened-in pool area designed for year round enjoyment. Located close to Siesta Key Village, guests can enjoy boutique shopping, dining, ice cream shops, coffee cafes, and live entertainment; all just a quick ride away. brbrWith its private pool, outdoor kitchen, guest house, and prime location near both Siesta Key Beach and Siesta Key Village, Brisas Del Mar by Siesta Key Luxury Rental Properties offers the ideal setting for unforgettable coastal memories. brbrBook your stay at Brisas Del Mar today and experience the best of Siesta Key! brbr- brNo Pets Allowed brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest. brbrIn accordance with the City of Sarasota's Rental Ordinance, this property requires a minimum rental period of 7 nights. The maximum occupancy for this home is 10 adults; however, children under 6 years of age are not included in the City’s occupancy limit. Siesta Key Luxury Rental Properties enforces a total occupancy limit of 12 persons, including both adults and children under 6. Should you have any questions regarding the City’s occupancy restrictions, alternative homes without such restrictions, or details about our rates, amenities, or policies, please feel free to reach out.

Bed

Bath

Sleeps

$1144.11

/ Nightly

Private Vacation Home

NEW LISTING! | Ocean-views, Walk 1-Min Beach & Village, Private Balconies Hot-tub Deck & Elevator!

Siesta Key, Florida, United States

Serious Leisure is a new listing by Gertrude RentalsbrbrNEW LISTING! Serious Leisure is an ocean-view unit just 1-min walk to all Siesta's top attractions! Large 3BR boasts 4 balconies, ocean-views, elevator, and 100% private outdoor areas including swim-spa, deck and alfresco dining area. In heart of Siesta Village. Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Spacious, bright, airy, and surrounded by palms. Experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests LovebrSERIOUS LEISURE “AT A GLANCE”br∙ Wonderful new listing! Gertrude Rentals Siesta Key has thousands of 5-star reviews! br∙ Private Balconies and Deck – beautiful views from 4 balconies plus deck in the palmsbr∙ Private Swim-spa – large outdoor heated swim-spa and deckbr∙ The Beaches – 1-minute to Siesta Key's top beaches with white sand and calm clear waterbr∙ Restaurants – 1-minute walk to the shopping dining and entertainment of the Siesta Villagebr∙ Gulf Breezes – 5 balconies and westerly windows means catching sea breezes day and nightbr∙ Relaxing – 3 baths, elevator, and a balcony off every bedroom and kitchenbr∙ Sunsets –walk 1-minute to best sunsets or just enjoy from private deck or balconiesbr∙ Alfresco Dining – large kitchen, 2 grill areas and 2 private al-fresco dining areasbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – walk to all siesta key is top attractions and guaranteed fun for allbrbrbrThe BeachbrOur beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.brbrbrThe LocationbrYou aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities, this property will deliver what they need. It's just steps to the top attractions on the island including 4 beach accesses, and 20 bars and restaurants. Walk right 450ft to the best beaches in America or left 450ft to the world-famous shopping dining and entertainment of the Siesta Key Village. This area has - ice-cream, tide pools, daiquiris, dolphins, fresh oysters, white-quartz-sand, big breakfast, sunsets, amazing seafood, white lagoons, craft beer, sand dollars, live music, shopping, and gourmet donuts. Back at the house, you'll enjoy private swim-spa, two alfresco, dining areas, four balconies, and a sundeck. When you'd prefer to relax, you'll find lots of bright and airy out the way rooms and terraces for quiet decompressing.brbrbrBedroom DetailsbrThis is a huge 3BR, you can sleep up to 11 family style. The master suite (huge) has a ocean-views, King bed, balcony, en-suite bath with shower and spa-tub, comfy chaise lounger, and enough room for pack-n-plays and rollaway beds. *Note master bedroom has ocean views are from the balcony, bathroom, and bedroom windows! Bedroom #2 has two full beds and balcony with obstructed ocean-views. Bedroom #3 has two twin beds and balcony with westerly exposure and a sliver of an ocean view. The living area has large sectional sofa big enough for two children:) If you need additional space we can offer more bedrooms nearby.brbrbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrbrHousehold Items ProvidedbrWe provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrbrWhat to BringbrIt's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.brbrbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.

Bed

Bath

Sleeps

$1168.08

/ Nightly

Private Vacation Home

Perfect for Families! Private Back Yard & Heated Pool - Bahama Mama

Siesta Key, Florida, United States

Bahama Mama by Siesta Key Luxury Rental Properties brHome in Siesta Key, Florida brbrSiesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key! brbrWelcome to Bahama Mama, a stunning vacation home boasting five bedrooms and five bathrooms, located just a five-minute walk away from the picturesque Gulf of Mexico beaches! The backyard of this home is a true tropical paradise, featuring a sparkling pool with a spa, comfortable loungers, and a charming covered patio that includes an outdoor dining table, a television, and a BBQ grill. We can't wait to welcome you to this unforgettable retreat! brbrAt A Glance br• 5-minute walk to the beachbr• Near restaurants and boutiquesbr• Pool with in-ground spabr• BBQbr• Outdoor showerbrbrThe modern living space is adorned with coastal touches and a cozy seating area with a large TV. The fully equipped kitchen has stainless steel appliances, a spacious kitchen island that serves as an ideal spot for preparing large meals, seating for six guests to keep the cook company, and a unique banquette-style table that adds character to the dining area. brbrWhat makes this home's bedrooms so delightful and unique is that each one has an ensuite bathroom! You'll appreciate the thoughtful design that prioritizes both comfort and elegance, along with convenient amenities like televisions and plenty of storage space. The King and Queen rooms boast walk-in showers, while the bunk room features a shower and tub combo. brbrRoom Details br-Primary Bedroom: King bed and ensuite bathroom with walk-in shower br-Second Bedroom: King bed, pool access, and ensuite bathroom with walk-in shower br-Third Bedroom: King bed, pool access, and ensuite bathroom with walk-in shower br-Fourth Bedroom: Queen bed and ensuite bathroom with walk-in shower br-Fifth Bedroom: Full over full bunk bed and ensuite bathroom with shower and tub combo. br-Bonus: Queen sleeper sofabrbrThis lovely home is in the heart of Siesta Key Village, just one block from Ocean Boulevard's fabulous boutiques and restaurants and Siesta Key Beach, famous for its shimmering white sand and warm waters. brbr- brWith host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment only. brbrThis property participates in our Professional Linen Program. This ensures high-quality linens and towels are always included in your stay. These are professionally laundered at a commercial facility for every guest.brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

5

Bed

5

Bath

12

Sleeps

$538.42

/ Nightly

Private Vacation Home

Siesta Key Waterfront Oasis - Game Room & Dock

Siesta Key, Florida, United States

This Siesta Key home sits on a rare wide, intersecting canal with about 110 feet of waterfront, so instead of staring into a neighbor’s backyard you look straight down a long, open waterway. The backyard faces south, so you get sunrise to the left of the dock, sunset to the right, and sparkling light on the water most of the day. It feels more like a quiet lake than a typical canal and has a very peaceful, private vibe.brbrThis home is set up to give you two vacations in one. In “Relaxing Coastal Retreat” mode, you’ll enjoy calm, uncluttered rooms, soft coastal colors, sun all day over the water, and quiet mornings with coffee by the pool or on the dock. In “Private Resort & Game Lounge” mode, you can roll out the games and turn the home into an entertainment hub with a pool table, ping pong, 200+ classic arcade games, darts, ring toss, giant Connect Four, cornhole, and pool basketball. You decide the vibe—keep everything tucked away and it feels like a spa-like waterfront escape; bring the games out and it’s a private resort you don’t have to share.brbrThe property sits on a rare wide, intersecting canal with ~110 feet of waterfront. Instead of looking straight into a neighbor’s lanai, you look down a long “runway” of water with no houses directly behind you. The backyard faces south, so you get sunrise to the left of the dock and sunset to the right, with light on the water all day long. This is a 30-day minimum stay (local rules), ideal for snowbirds, remote workers, medical professionals, relocations, and long, relaxing getaways.brbrEvery sleeping area in the house looks out over the water—all three bedrooms plus the Luonto king sleeper. The Primary Bedroom features a king bed with a water view, plus a dedicated desk and swivel chair overlooking the canal that makes an excellent work-from-home setup. You’ll also have a closet and dresser, and an ensuite bath with a double vanity. Bedroom 2 includes a king bed with water views and easy access to the guest bath. Bedroom 3 includes a queen bed with water views and a bright, quiet, cozy feel. In the living room, the high-end Luonto Hampton king sleeper has a memory-foam mattress and no center bar, so it sleeps like a real bed, and it faces the water through the sliding glass doors.brSleep quality is a priority throughout the home. We use encasements, waterproof pads, 600-thread-count Pima cotton sateen sheets, and comfortable pillows and blankets to help you truly rest during a longer stay.brbrWhen you want a quieter stay, the home works beautifully as a low-clutter retreat. The open-concept great room has leather seating, two brown swivel recliners, a smart TV, and large sliders that frame the pool and canal. The dining room includes a white table, woven-leather chairs, a bench, and a navy rug that anchors the space and keeps it feeling polished. The kitchen is chef-friendly with stainless appliances, plenty of counter space, and a coffee bar with labeled jars for coffee, decaf, and tea (drip coffee maker; no pods). Soft coastal blue walls (more pronounced in person) with crisp white trim complete the feel. You can keep games tucked away in the game room and garage and enjoy an uncluttered, peaceful living space.brbrWhen it’s time to play, you can flip into Entertainment Mode in minutes. The game room includes a pro-style pool table with gray felt and saddle pockets, a surfboard-style light over the table with bar seating, and a sit-down commercial arcade with 200+ classic games including Galaga, Pac-Man, Donkey Kong, Space Invaders, and more. You’ll also have darts and ring toss, plus room to hang out between games. In the garage, there’s a high-quality ping-pong table that wheels out and sets up quickly. Outdoors, you can bring out a 5-foot-tall Connect Four, cornhole for the dock area, ring toss, darts, and pool basketball in the saltwater pool. You can roll everything out for high-energy family fun, then tuck it away again when you want the house to feel calm and open.brbrOutdoor living is a major highlight, especially for longer stays. The screened saltwater pool (not heated) includes seating and loungers, and café-style string lights around the pool cage reflect off the water at night for a resort feel. There’s a covered lanai dining area under the cage that’s perfect for evening dinners in the breeze. A waterfront firepit with Adirondack seating makes a great spot for sunset drinks or late-night conversations, and the private dock includes seating directly on the wide canal.brbrThe home sits at a wide, intersecting “T” in the canal system where the water is deeper and curves around the property, making it a natural route and feeding area for wildlife. It’s common to see dolphins cruising through and occasionally pushing fish along the curved seawall, and manatees gliding by in calmer periods. On some days it genuinely feels like your own private dolphin show, right from the dock, pool deck, or even the kitchen window.brbrFor work-from-home and longer stays, you’ll have the dedicated desk and office chair in the primary bedroom with a water view, fast Wi-Fi for video calls and streaming, and a full laundry room with washer and dryer—an especially helpful feature for monthly bookings. There’s also plenty of storage and surfaces so it feels like a home, not a hotel room.brbrYou’ll have a private dock directly behind the house that’s perfect for fishing, lounging by the water, pickup and drop-off from local boat and fishing charter companies, and kayaks or paddleboards delivered right to the dock. Nearby independent providers (subject to their availability and policies) include Reel Tight Fishing Charters for inshore and nearshore fishing with dock pick-up, Siesta Key Bike & Kayak for bikes, e-bikes, kayaks and paddleboards with delivery options, and Safe Harbor Siesta Key for boat rentals with a range of sizes and engines. Important: all rentals and activities (boats, kayaks, paddleboards, bikes, charters, etc.) are booked directly by guests with third-party companies and are used entirely at guests’ own risk. The owner/host does not supervise, operate, or insure these activities and assumes no responsibility or liability for them.brbrGuest accessbrbrGuests have full access to the entire home, the saltwater pool and screened lanai, the dock and waterfront seating areas, the game room and garage ping-pong, and driveway parking. Self check-in is available.brbrNeighborhoodbrbrThe home is in a quiet, established Siesta Key waterfront neighborhood with easy access to Siesta Key Beach and Siesta Key Village. It’s a short drive to St. Armands Circle and downtown Sarasota, and it’s conveniently close to Sarasota Memorial Hospital—ideal for travel nurses and medical professionals. You get the convenience of being close to everything, but come home to a peaceful, private waterfront setting.brbrOther things to notebrbrMinimum stay is 30 consecutive nights per local rules. The pool is saltwater and not heated. No smoking is allowed inside the home. Children are welcome, but constant supervision is required near the pool and dock. Utilities, lawn care, and pool service are included with reasonable usage. A security deposit and simple lease/ID verification may be required for monthly stays, and optional mid-stay cleaning is available for longer bookings.

Bed

Bath

Sleeps

$1478.33

/ Nightly

Private Vacation Home

Prime Location with Pool, Spa, and Fun Waterslide - Summer House

Siesta Key, Florida, United States

Summer House by Siesta Key Luxury Rental Properties brbrWelcome to Summer House, a six-bedroom, six-bathroom Siesta Key pool home ideally located just a three-minute walk to Siesta Key Beach and a two-minute walk to Siesta Key Village. This ground level vacation home is designed for family fun and relaxed island living, featuring a private pool with spa and waterslide, spacious outdoor living areas, and walkable access to the island’s most popular restaurants, shops, and attractions. With room for the whole group and parking for four vehicles, Summer House is the perfect setting for a classic Sarasota beach vacation. brbrHighlights br- 3-minute walk to Siesta Key Beach br- 2-minute walk to Siesta Key Village br- 6 bedrooms / 6 bathrooms br- 2 kings, 2 queens, 6 full beds (bunk beds) br- Private pool with spa and rock waterslide br- Outdoor living space and BBQ grill br- Outdoor shower br- Washer and dryer br- 4 parking spaces br- Dog friendly with host approval and fee brbrThe backyard at Summer House is built for memorable vacations. Guests can enjoy a private pool complete with a waterslide, and spa; perfect for both kids and adults. Multiple outdoor seating areas allow the group to spread out, including a covered porch with comfortable seating and a second entertaining area with an outdoor TV and bar top seating. Whether grilling, relaxing poolside, or unwinding after a beach day, this outdoor space elevates every stay. brbrInside, the home offers a bright and welcoming open layout with coastal decor throughout. The living area features comfortable seating and a large TV for movie nights or downtime between island adventures. The fully equipped kitchen includes stainless steel appliances, ample counter space, and everything needed to prepare meals for the group. Guests can enjoy casual seating at the kitchen island or gather around the breakfast nook style dining table and bar-top seating area. brbrEach of the six bedrooms is designed with comfort and privacy in mind and includes its own ensuite bathroom and television. The primary suite is the largest and features a king bed, beach design, generous space, and a spa like bathroom with a double vanity and walk-in shower. An additional king bedroom, as well as two queen bedrooms, provide relaxing retreats for adults, while two bunk rooms are perfect for kids or teens, offering fun sleeping arrangements without sacrificing comfort. brbrRoom Details br- Primary Bedroom: King bed and ensuite bathroom with double vanity and walk-in shower br- Second Bedroom: King bed and ensuite bathroom with walk-in shower br- Third Bedroom: Queen bed and ensuite bathroom with double vanity and walk-in shower br- Fourth Bedroom: King bed, porch access, and ensuite bathroom with walk-in shower br- Fifth Bedroom: Two full-over-full bunk beds and ensuite bathroom with walk-in shower br- Sixth Bedroom: Full-over-full bunk bed and ensuite bathroom with shower and tub combination brbrSummer House is centrally located near Siesta Key Village, placing guests within walking distance of dining, shopping, coffee shops, and ice cream stops. Siesta Key Beach is just minutes away, offering world-famous powdery white sand and stunning Gulf Coast sunsets. The home also includes a washer and dryer, professionally laundered linens, and exterior security monitoring for added peace of mind. brbrWith its unbeatable location near Siesta Key Beach, private pool with waterslide, and spacious layout designed for families and groups, Summer House by Siesta Key Luxury Rental Properties delivers the perfect balance of comfort, fun, and island convenience. Book your stay today and experience the best of Siesta Key living! brbr- brThis property participates in our Professional Linen Program. This ensures high quality linens and towels are Always included for your stay. These are professionally laundered at a commercial facility for every guest. brbrThis property has an active Ring doorbell and additional video surveillance on the pool equipment. brbrThis property allows dogs with host approval prior to arrival. Please note there will be an additional pet fee associated, see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles. brbrPlease see our Siesta Key Luxury Rental Properties Rental Policies for full details. brbrThis home is managed by Siesta Key Luxury Rental Properties. We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

6

Bed

6

Bath

22

Sleeps

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