Vacation Rentals By Owner In Siesta Key, FL

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2-bedroom, 2-bathroom villa offers comfort, style, and privacy just steps from the beach. The primary ensuite features a king-size bed, while the guest bedroom includes 2 twin beds and a sleeper sofa in the living area, making it ideal for families or friends traveling together.brbrEnjoy the spacious living and dining areas, a fully equipped kitchen with updated countertops, modern appliances, and a private screened lanai perfect for relaxing after a day in the sun.brbrFor your convenience, the villa includes three large flat-screen TVs, central heating and air conditioning, and all the amenities you need for a comfortable stay.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Villa

Island House Beach Resort V32

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$365.69

Directly across from Siesta Key Beach and Pavilion! Enjoy sunsets on the beach and walk to Village shopping and dining. This well-maintained 2-bedroom, 2-full bathroom unit includes a spacious kitchen, breakfast nook and separate dining area, spacious living area with full sliders to a private patio. Bedrooms include a king bed and twin beds that can be converted to a king, each with a private full bathroom. Convenient, dedicated covered parking is adjacent to the unit. Complex has private, heated pool, grills, and laundry rooms. brbrBeach chairs, umbrella, and cooler are provided for your convenience. brbrThis is a monthly rental only.

2 Bed Condo Across from Siesta Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$338.34

Welcome to The Palm Bay Club on Siesta Key BeachbrEnjoy sunrise to sunset from our great resort that has private bay to beach access . Updated 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C .brResort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

The Palm Bay club Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$407.93

You will love this sun filled, ground floor unit with wonderfully appointed accommodations. Located directly across from Beach Access 10 and an easy walk to town for a little music or something to eat. All the beach equipment and a sturdy beach appropriate wagon to get you there! Newly renovated one bedroom apartment with screened outdoor patio and outdoor space. The unit is approximately 1200 SF and was fully renovated. There is a king bed with closet, dresser and nightstands as well as luggage racks. In addition, there is a twin rollaway in the unit that can be easily moved to the living room. The bathroom has a beautifully renovated step-in shower with single vanity and comfort toilet. All the linens are provided. The kitchen table can be configured to seat 6 comfortably or the bench can be used to pull up to work at the desk. The kitchen is fully equipped for long or shorter stays for couples or a family. The living room has a sectional couch, seating area with a view of the Gulf and a nice reading chair. The outside area has an eating area as well as seating area and lounge chairs.

Across from beach, no stairs, spacious renovated one bedroom with outdoor space!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$397.59

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.

Coastal Cottage - Direct Beach Access

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$421.22

Island House Beach Resort – Siesta Key, Florida (Crescent Beach)brbrThis beautifully appointed 2 bedroom, 2 bathroom villa features a spacious primary ensuite with a king bed, while the guest room offers one double bed and one twin bed. The villa includes a large living area, a dedicated dining space, and a fully equipped kitchen with all major appliances. A private screened lanai is perfect for relaxing after a day in the sun. For your comfort and entertainment, the villa is equipped with three large flat-screen TVs as well as central heating and air conditioning.brbrExperience the privacy and ease of your own standalone villa, while being part of the beautiful Island House Beach Resort community. Just a short walk through the resort brings you to the powdery white sands and turquoise waters of the Gulf of Mexico—perfect for relaxing in the sun, sand, and surf.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Villa

Steps to the beach! Island House Beach Resort V19

Siesta Key, Florida, United States

Bed

1

Bath

4

Sleeps

$326.73

We invite you to stay in our spacious 1,250 square foot 2 bedroom 2 bathroom condominium at The Anchorage Yacht and Tennis Club which is ideally situated across the street from the #1 rated Siesta Key Crescent Beach. The Anchorage Yacht and Tennis Club offers all the amenities of a resort and all the comforts of a private residential condominium/community in one convenient location.brbrAbsolutely gorgeous views of the Gulf of Mexico from the balconies are just one of the many features ...you will enjoy staying in this vacation home. Sitting in the living areas of this home you are overlooking the sights of Siesta Key. The openness of the floor plan allows for entertaining, family dinners and a sense of togetherness. The sliding gass doors open to create an indoor/outdoor living space where you can relax with picturesque views of the Intercoastal Waterway and the Gulf of Mexico. Prepare your favorite meals in the fully stocked kitchen connected to the living space. The large master suite boasts an ensuite bathroom with separate dressing area, walk-in closet and balcony access. The spacious guest bedroom also has a walk-in closet and balcony access. Complementary Wi-Fi is provided in the condo and through out The Anchorage complex.brbrThe Anchorage is known for its amenities which include private gated beach access (across the street), heated Olympic-sized pool, lighted tennis and shuffleboard courts, BBQ grills, exercise room and free boat docking. The Anchorage complex backs up to the Intercoastal Waterway with a serene park-like setting where you can grill, picnic, fish or just relax and watch the boats go by.brbrEvery imaginable beach vacation option can be found within walking distance of The Anchorage including restaurants (many with live entertainment), shops, a market, charter boats, rental of fishing equipment, jet ski, kayak/paddleboard, para-sailing and bike rentals. You can also hitch a free trolley ride to Siesta Key Village to explore other shopping, dining and entertainment options.brbrBook your stay today and experience the magic of the Anchorage Yacht and Tennis Club and Siesta Key!brbrAmenities Include:brbr- Coin operated washer dryer: Yesbrbr- TUB/SHOWER: Yesbrbr- Balcony: Yesbrbr- BBQ Grill: Yesbrbr- Beach Access: Privatebrbr- Bed Size 1st/Master: KINGbrbr- Bed Size 2nd Rm: QUEEN & TWINbrbr- Elevator: Yesbrbr- Exercise Facility: Yesbrbr- Floor No.: 5thbrbr- Internet Access: WIFIbrbr- Parking: Yesbrbr- Parking Space Type: 54brbr- Electric Stove: Yesbrbr- View: Yesbrbr- PICKLEBALL: Yesbrbr- Gulf View: Yesbrbr- Tennis Courts: Yesbrbr- Pool: Yesbrbr

Anchorage 503

Siesta Key, Florida, United States

Bed

Bath

6

Sleeps

$188.94

White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.brPlease note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.brOur condominium is privately owned and decorated, unique and beautifully maintained. Check out the amenities and photos!brOur unit has an assigned carport. brWhy just go to Florida when you can visit the #1 Beach in the USA! White Sands Village is a short 0.3 mile from Siesta Public Beach. No need to worry about Beach Parking while staying here at White Sands Village.brbrSiesta Beach: Rated 2021 #1 beach in Florida by Holidu https://www.bizjournals.com/tampabay/news/2021/06/23/siesta-key-beach-named-no-1-beach-in-the-state.html, 2020 Tripadvisor #1 beach in the USA https://www.sarasotamagazine.com/news-and-profiles/2020/08/siesta-key-beach-named-no-1-in-the-country-again-tripadvisor , Dr Beach 2017 #1 beach in the USA https://www.drbeach.org/2017-siesta-beach-sarasota-floridabrbrSORRY, NO PETS.brbrThe condo is NOT ADA ACCESSIBLE. NO SMOKING.brbrThe first sign that White Sands Village is the right place for you are the grounds, seven acres beautifully landscaped with palm trees, live oaks, flowering shrubs and tropical flowers.brOur pool is heated year-round to a warm 86º, so you can enjoy a swim even during the cooler months. Catch a bit of sun on a lounge chair, or sit in the shade and enjoy a bit of vacation reading.brPublic tennis/pickleball courts are just across the street.brFour lighted gas grills, on the White Sands property, are available for your use.brOne covered parking space is provided for each unit, with additional parking available.brLaundry facilities are available at four locations.brLinens are supplied and kitchens are fully equipped in each of our one- and two-bedroom rental units.brSit by the peaceful lagoon connected to the Intracoastal Waterway.brIn addition to the stunning Siesta Key Public Beach, there are two additional Gulf of Mexico beaches on Siesta Key, as well as great little shops and restaurants. You’ve got easy access to boat rentals, jet ski rentals, parasailing…recreation awaits you!brCrescent Beach, just south of the public beach, is a quieter and more private beach, with only one public access road. Its southern tip is the Point of Rocks, a great snorkeling and diving area with coral reefs that often harbor abundant marine life.brTurtle Beach, south of Crescent Beach, is a great family play area, with a playground, horseshoe pit, boat launch, volleyball court and picnic tables. It’s also a good place for finding shells and perhaps some shark teeth. Here you can launch your boat, fish in Blind Pass Lagoon, or eat in a nearby restaurant.brSiesta Key Village is full of shops and restaurants. You can buy just about everything you need to enjoy your beach vacation, including beachwear, sun products, and toys. There are also little boutique shops where you can indulge your love of unique clothing, jewelry, flowers and scented lotions. Several local restaurants offer patio dining, which you can enjoy from breakfast spots to dinner and evening entertainment.

Ground Floor Upgraded 2 Bed 2 Bath, Washer/Dryer, Short Walk to #1 Siesta Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$338.67

This completely renovated unit in the Sunset Royale is the perfect place to relax and enjoy the world famous sands of Siesta Beach. From the moment you walk through the door, you are greeted with sweeping, unobstructed 180 degree views of Siesta Key Beach and the blue-green waters of the Gulf of Mexico. The sand of Siesta Key beach is less than 50 feet from the front entrance of this recently renovated building. A fully stocked gourmet kitchen with stainless steel appliances and granite countertops is provided to prepare your beachfront view meals. For those who prefer their meals out, the restaurants and nightlife of Siesta Key village are less than a mile walk away. The free Siesta Breeze Trolley gives you access to the village and the entire island from the convenient stop right in front of the building. Boat, jet ski, parasailing and paddle board rentals are also close by. Beach chairs, umbrella, sand toys, beach towels, a cooler, and a cart to carry them in are also provided for your trips to the beach. Just bring your swimsuit and sandals, and enjoy this little piece of paradise. When choosing accommodations for your Siesta Key holiday, do not settle for no views, long walks to the beach, or crowded parking lots. We have been coming to Siesta Key for 20 years, and have not found a better overall location or view of Siesta Beach than you will have from Sunset Royale 312!

Breathtaking Full Gulf Views Steps From The White Sands Of Siesta Key Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$203.13

Welcome to your dream condo at Harbor Towers in sunny Siesta Key! This beautiful one-bedroom, one-bath condo offers a relaxing escape with access to a refreshing pool, gym, bbq grills, billiards, and tennis courts. Enjoy the peaceful atmosphere and stunning views from the lanai, while living just steps from Siesta Key’s beautiful beaches. Perfect for a getaway, this condo provides everything you need for comfort and relaxation in paradise.

Fabulous 1-BR condo in resort-like setting steps from the beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$206.99

Summary:brbrEscape to paradise at this beautifully remodeled 2-bedroom, 2-bath condo in a tranquil bayside complex on Siesta Key! This third-floor unit boasts a stylish open kitchen with granite countertops and stainless steel appliances, perfect for preparing meals. Enjoy comfortable living with tile flooring in the main areas, carpeted bedrooms and a leather sofa. Amenities include a refreshing pool, tennis courts, a community room and a small pier for leisurely moments. With the in-unit laundry, you'll have everything you need for a relaxing getaway. Sleeps 6 (King, Queen, sleeper sofa). 1-week minimum.

Bay Oaks Siesta Key E43

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$634.5

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.

The Shore House Private Dock Hot Tub

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$905.98

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.

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

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1947.38

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! ✨

Sugar Sand Cottage – Gulf-View Siesta Key Escape

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$624.73

Experience the best Siesta Key Sunsets! Just 300 feet of powder white sand separate this unit from the crystal blue waters of the Gulf! This lovely, 2-bedroom 2-bathroom unit offers sleeping accommodations for 7. Inside, you will find a chef's kitchen with plenty of space to cook while being open to entertain guests as well. Relax on one of your private outdoor balconies or sit on the beach voted #1 in the USA! The unit is located in the tower, steps from one of the complex’s two heated pools and are closest to the private beach. All guests have access to the Crystal Sands private beach area located on Crescent Beach. Crescent Beach is one of three beaches located on Siesta Key and is known for being just as beautiful with fewer crowds than the more popular Siesta Key Public Beach. Pools are open from dawn till dusk daily. The beach access point is past the pool and guests will find beach chaises and chairs overlooking the crystal blue waters and soft white sand. brbrBedroom 1 – King brBedroom 2 – 2 QueensbrLiving Room - Twin Murphy BedbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbrPlease Note: Golf-Carts are NOT allowed on property grounds.brbr*Minimum Age to Book: 27 br*Security Authorization Hold taken upon check-in. Amount: $1,000

Stunning Sunsets! 2 Bed, 2 Bath Condo on Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$324.6

This 2-bedroom, 2-bathroom condo is the perfect place to take your next vacation! With a queen bed in the Master bedroom, two twins beds in the second bedroom, and a sleeper sofa, this condo can comfortably sleep up to 6 guests. You will be amazed by the breathtaking Siesta Key sunsets from the large balcony! This unit is on the 2nd floor, accessible by stairs or elevator. This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis/pickleball courts and a covered pavilion with grilling area. Right across the street is our world-famous Siesta Beach, and just minutes away is Siesta Key Village, offering endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! brbrBedroom 1- QueenbrBedroom 2- Two twinsbrLiving Room – Sleeper sofabrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-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: $1,000

Stunning Sunsets! 2 Bed, 2 Bath Condo on Siesta Key!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$692.13

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.

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

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1282.5

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!

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

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$586.08

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king bed, along with a guest bedroom offering 2 queen size beds. The unit includes a large living area, a dedicated dining space, and a fully equipped kitchen with all appliances and granite countertops. For your comfort and convenience, the condo offers three large flat-screen televisions and central heating and air conditioning. Step out onto the lanai to enjoy gorgeous views of the Gulf of Mexico and truly spectacular scenery with magnificent sunsets that are a breathtaking sight to behold.brbrIsland House Beach Resort boasts a range of attractive features including:brbr*A scenic beachfront courtyard with shuffleboard, cornhole, gas grills, and shaded seating areas—ideal for enjoying Siesta Key’s famous spectacular sunsetsbr*2 beach cabanas and beach chairs for your conveniencebr*A large, heated swimming poolbr*A recreation room with ping pong, air hockey and other gamesbrbrHop on the Siesta Key Trolley to visit the vibrant Siesta Village offering a plethora of dining and shopping options.brFeeling adventurous Explore nearby Myakka River State Park, rent a bicycle to tour the island, or kayak and paddleboard through the mangroves and the newly reopened Midnight Pass on the south end of Siesta Key. Explore nearby Sarasota for its golf courses, gardens, museums, and World Renowned Mote Marine Aquarium. With Tampa Bay just an hour away and Disney World and other Orlando attractions a quick 2.5-hour drive, you have the perfect base for a memorable vacation.brbrPack your bags and let Island House Beach Resort make your stay unforgettable!brbrWe look forward to welcoming you to Island House Beach Resort—your perfect getaway on Siesta Key!

Apartment

Island House Beach Resort 4N

Siesta Key, Florida, United States

Bed