Vacation Rentals By Owner In Sarasota, FL

$271.61

Villa Paradiso - Private 3 Bed Pool Home by The Bay & Key Collection

Sarasota, Florida, United States

Escape to style and serenity in this beautifully designed 3-bedroom mid-century, modern contemporary home. Located in a quiet residential area, this modern retreat features sleek interiors, a large private pool and outside seating with BBQ setup perfect for alfresco dining. brbrKey Features:br3 Stylish Bedrooms – Colourful modern design with cozy comfortbrPrivate Pool & Yard – Perfect for lounging, swimming, and soaking up the Florida sunbrQuiet Residential Location – Peaceful setting just a short drive from downtown Sarasota and the beachesbrFully Equipped Kitchen – Ample appliances and everything you need to dine inbrOutdoor BBQ Area – Great for grilling and entertaining family or friendsbrContemporary Amenities – Thoughtfully designed interiors with comfort and style in mindbrIdeal for Families or Remote Work Getaways – Plenty of space and high-speed Wi-FibrClose to Local Attractions – Easy access to Siesta Key, shopping, dining, and parksbrbrConveniently located to everything Sarasota has to offer, you are close to Downtown and its restaurants, but also on the gateway to miles of beaches with fine sand and shallow waters, such as Siesta Key Beach, Lido Beach, or Anna Marie Island. If you feel like shopping, just take a convenient ride to the UTC Mall which houses Sacks Fifth Avenue, Crate & Barrel, and Macy's to name just a few of the stores, all undercover in an air-conditioned Mall. Nathan Benderson Park, with its world-class rowing facilities and sprawling outdoor sports opportunities, is close by too! So what are you waiting for Book now to experience the best of what the Sunshine State has to offer! Near the Legacy Trail (18.5-mile paved recreational trail that runs between Venice and Sarasota).brbrHome Owners desired minimum stay is 60-nights in season. brbrStart your journey on I‑75, then take Exit 207 to merge onto SR‑758 West (Bee Ridge Road). Continue straight for approximately 4.4 miles, passing through vibrant commercial areas before reaching a quieter residential stretch. Make a right turn onto S Tuttle Avenue and drive about 0.3 miles. Next, turn right onto Tanglewood Drive, and stay on it for roughly 0.2 miles. Finally, make a right turn onto Fair Oaks Place, and you’ll arrive at the property.brbrParking is available on site for a maximum of 2 cars in the driveway. The garage is also available to guests.brbrDiscover a seamless blend of sleek, modern design and Florida relaxation in this refined 3‑bedroom, 3‑bath single-family home, thoughtfully decorated and fully furnished for an effortless vacation getaway.brbrWith an open-concept layout and 1,685 sq ft of living space, the home invites you to unwind in style.n Step inside to a bright, airy living area featuring Smart TV and contemporary furnishings, a custom pantry—perfectly equipped with everything you need, from cookware and utensils to linens brbrOutside, the private oasis awaits: a sparkling screened pool, covered lanai with seating perfect for morning coffee or evening cocktails. Each of the three bedrooms offers comfort and privacy, while the three full baths provide convenience—ideal for families, friend groups, or remote work retreats. brbrStay stress-free with, landscaping, and pool maintenance covered under your stay. Parking is a breeze with a 2‑car garage, private circle driveway, and additional outdoor spots. Plus, enjoy thoughtful extras like in‑garage laundrybrbrIf you still have any questions concerning our homes, rates, availability calendar, amenities, policies, or otherwise, please contact our team and we will be happy to assist you. brbrGulf Coast Holiday Homes offer a wide range of services including: br- An any day arrival policy and length of stay requirements starting at just 7-nights.br- We have a professional property manager and maintenance systems meaning you’ll experience the service you deserve.br- Professional housekeeping pre-stay and during stay if requested. br- 'Guide Books' allowing you to be able to add experiences to your itinerary and see some of our recommendations. br- 'Preferred Vendors' meaning you can trust the company you use for rentals.brbrAll properties listed with Gulf Coast Holiday Homes benefit from an interactive 'Guide Book' which will be sent ahead of arrival and will include the house manual, check in instructions, preferred vendors and unique information about the home.brbrPrior to your stay, we require you to complete a pre-arrival form and sign & agree to our rental conditions. brbrAccidental Damage Insurance: Accidental Damage Insurance is included within all guest stays at The Bay & Key Collection. On this property, for stays greater than 29 nights, an additional $90 will be due as the current rates are for 29 nights or less. For additional blocks of 30 nights past 59 nights you, will be charged $71. brbrGuests must cancel at least 60 days before check-in to receive a full refund for all nights, minus a 10% processing fee.brGuests must cancel at least 30 days before check-in to receive a 50% refund for all nights.brIf a guest cancels less than 30 days before check-in, you’ll be charged 100% for all nights.brWe strongly recommend that you purchase your own travel insurance for your protection.

3

Bed

3

Bath

6

Sleeps

$480.62

/ Nightly

Condo

SK Condo on Beach - 2 Pools, Private Beach - Island Time T504 SSRC - sleeps 6

Sarasota, Florida, United States

Wake up just steps from the powder-white sands of Siesta Key Beach, consistently ranked among the best beaches in the United States. This beautifully furnished 2-bedroom, 2-bath condo at Sarasota Surf & Racquet Club offers resort-style living in the heart of Siesta Key with private beach access, heated pools, and stunning tropical surroundings.brbrLocated on the 5th floor of the Tower Building, this privately owned condo combines comfort and convenience with a spacious open layout, updated furnishings, and everything you need for a relaxing beach getaway.brbrWhether you're planning a family vacation, couples trip, or extended beach stay, this beachfront retreat provides the perfect place to unwind and enjoy the beauty of Florida’s Gulf Coast.brbrKITCHEN AND LIVING SPACEbrbrThe condo features a bright open living space designed for comfort and relaxation after a day at the beach. Guests can enjoy a large 70” TV, comfortable seating, and an inviting atmosphere for gathering with family or friends.brbrThe fully equipped kitchen offers plenty of space for cooking and entertaining, complete with a dining table for six and a dedicated coffee station stocked to kickstart your mornings right. The kitchen is fully furnished with cookware, dishes, and essentials for both short and extended stays.brbrSLEEPING ARRANGEMENTS brbrThis condo comfortably accommodates up to 6 guests across two spacious bedrooms. The primary suite features a king bed, dual vanities, a private toilet room, walk-in closet, and a large walk-in shower. The second bedroom offers two queen beds, a dresser, TV, and a large walk-in closet. A full bathroom with vanity, sink, and tub/shower combination is located just outside the second bedroom. Fresh linens, bath towels, and starter toiletries are provided for guest convenience.brbrAMMENETIESbr brGuests will find a dedicated beach closet near the entry stocked with Tommy Bahama beach chairs and an umbrella, making it easy to enjoy long days on Siesta Key Beach. The condo also includes six plush beach and pool towels for guest use.brbrLaundry facilities are conveniently located just across the hall and are operated via a prepaid card available through the onsite office.brbrSarasota Surf & Racquet Club also offers a full resort-style experience with beautifully maintained tropical grounds and amenities including:brbr- Two heated swimming poolsbr- Private beach accessbr- Tennis courts for guest usebr- On-site fitness centerbr- BBQ grilling areas near the beach and poolbr- Gated community with security entrancebr- Complimentary WiFibr- One reserved parking space per condobrbrLOCATIONbrbrThis condo is perfectly situated directly on Siesta Key Beach, famous for its powdery quartz sand and breathtaking Gulf sunsets. The property is located near the shops, restaurants, and vibrant atmosphere of Siesta Key Village, while still offering a peaceful beachfront retreat.brbrThis is your perfect Siesta Key beach escape awaits—just bring your swimsuit, sunglasses, and get ready to enjoy paradise.

Bed

Bath

Sleeps

$212.81

/ Nightly

Villa

Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

Sarasota, Florida, United States

Cottage style 2 bedroom 1 bath condo in Siesta Key is just a 2-3 min walk to the Pool, Beach, Restaurants and shops.br((Also see our other listing 1569277)brbrDo you prefer a single-story, ground floor cottage over a high-rise A garden patio over a balcony This might be your best Siesta Key vacation yet!brbrOur Cottage comes complete with comfortable, quality furniture, and top quality bedding and linens.brbrFully equipped, offering everything you need for a fun and relaxing vacation at the country's #1 beach. Crescent Beach on Siesta Key!brbrStep outside to the patio for your the perfect spot for your morning coffee or evening BBQ.brbrEverything is included at this cozy cottage from wireless internet to beach towels!brbrWe have a lovely large heated salt-water pool and our own private gated access to Crescent Beach. Both are just a 2-3 min walk from the cottage.brbrEverything is right here: Restaurants & Shops within easy walking distance. And Lively Siesta Key Village with its quaint shops and nightlife is just a quick drive up the road. Also there is a free trolley to take you up and down the Siesta Key so no need to drive.brbrA great vacation spot!!

Bed

Bath

Sleeps

$429.48

/ Nightly

Private Vacation Home

Charming Beach Cottage on Lido Beach....walk to the beach and St Armand's Circle

Sarasota, Florida, United States

Slow down enjoy this Cozy Beach Cottage steps from Lido Beach and St Armand's Circle.brbrThis comfortably decorated home has just been updated with new linens, cookware, 55' Smart Bluetooth TV, BBQ grill and more. The backyard has a fun tiki bar, outdoor dining set, fire ring, hammock and is fenced for dogs.brbrBeach towels, rolling cooler and chairs are provided for a day at the beach accessed by the adjacent path. Someone said it takes less time to walk from the house to the sand than it does to walk from the beginning of the sand to the waterbrYep....you are that close!brThe beach access is next to the side yard. Walk out....turn left....cross the street and you are on the sand :)brCruiser bikes are provided for touring around Lido key!!brbrBoth the living room and family room are great for conversation and the dining table comfortably seats 6.brbrThis home is 3 bedrooms / 2 bathsbrThe master bedroom has a luxurious Beauty-Rest Black Series king bed while the second bedroom is a queen. Both share the Jack and Jill bath. brThe kitchen is fully stocked with everything you could need. A laundry room / office space completes the home.brbrThe 3rd bedroom is wonderfully private with bath, queen bed, sitting area including a couch, chair and TV. There is also an office with a work space desk, counter top with coffee station, bar sink and mini fridge. The suite can be accessed either through the main home off the living room or through an exterior door.. brIt perfect for family, guests or friends that need a little extra space and privacy.brOur family loves the setup!!brbrThe back yard of the suite is under the shade of a large tree and has an outdoor shower, and table & chairs for morning coffee or afternoon wine :)brbrParking for up to 3 cars in tandem is available on the left side of the driveway.brbrThe beach access is adjacent to the side yard. Walk out....turn left....cross the street and you are on the sand :)brbrPets are allowed with owner approval. Dogs only...unfortunately no cats.brbrIf an entire week is not in your vacation schedule please email me.......I can accommodate nights needed then block the calendar for a total of 7 nights to comply with Lido Beach rules!brbrThere is a completely independent unit upstairs that is also on VRBO #2389948. It would be a perfect addition rented together with the cottage for a larger family that needs 4 bedrooms and a little extra room.brbrCharming Cottage VR 22-00125

Bed

Bath

Sleeps

$394.84

/ Nightly

Villa

Newly Remodeled Luxury Beach Villa! Nearest Stand-Alone Villa on Siesta Key!

Sarasota, Florida, United States

The newly remodeled 2 bedroom / 2 bath Villa sleeps up to 6 people. The Master bedroom features a king-size bed with an attached bathroom and high definition TV and entertainment system. The Guest Bedroom features one twin size bed, a bunk bed with a full-size bottom bed, and a high definition TV. The comfortable living room is furnished with plenty of seating, a high definition flat screen with 5.1 Dolby surround sound system and bar area. The gourmet kitchen is loaded with anything you will need for cooking and entertaining! The owners love to entertain so you'll never need extra glasses or cookware. The Villa also features a garage conversion we call the ‘MAN CAVE’ with a high definition TV and electric fireplace perfect for relaxing, watching sports or movies and enjoying the fun atmosphere with the garage door open or closed. The patio features outdoor seating and a grill ready for you to enjoy a meal al fresco. Truly a gorgeous place for out of towners or Floridians looking for a “staycation”.brbrThe Villa is located in a gated community of Crescent Arms, right on Siesta Key Beach, just north of the Stickney Point bridge. The grounds feature a heated swimming pool, clubhouse, private beach with beach lounge chairs provided. Our villa also provides beach chairs, a cooler, swimming toys, Bluetooth radio, and a beach wagon to haul it all to the sand! This is a great spot to relax and spend time with the family!brbrThe Villa is available for 7 nights or more. Cleaning fee of $150 is waived if you stay with us for multiple weeks, in a row. Rates vary throughout the year. All guests must be 25 years of age or accompanied by an adult or legal guardian. brbrPlease contact us with any questions. We are more than happy to help you plan the perfect trip to Siesta Key and Villa 7.br

2

Bed

2

Bath

6

Sleeps

$168.49

/ Nightly

Condo

Tranquil Sarasota Retreat Near Beaches, Pool & Nature Escape - Timberwood Villa #183 - Roelens

Sarasota, Florida, United States

Timberwood Villa #183brbrYour Tranquil Sarasota Retreat Awaits!brbrWelcome to Timberwood Villa, a peaceful hideaway nestled in a lush, resort-style community where nature, comfort, and convenience come together. Village Des Pins is a charming neighborhood set in a peaceful, park-like environment surrounded by lakes and pine trees. The community features an oversized heated pool, Jacuzzi, two lighted tennis courts, a basketball court, shuffleboard, a putting green, and a picnic area with grills. Whether you're planning beach days, cultural adventures, or simply relaxing in a serene setting, Timberwood Villa offers an inviting home base close to Sarasota's most loved attractions. Here's what makes this home so special:brbrBedding Arrangement:br2 Bedrooms:brMaster Suite: King-size bed, Smart TV, Direct Lanai Access, Ensuite BathroombrGuest Bedroom: Two Twin-size bedsbrTop Features:brSleeps 4brResort-Style Community Pool & Spa: Enjoy sunny Florida days at the oversized heated pool or unwind in the soothing community spa surrounded by tropical landscaping.brPeaceful, Nature-Filled Community: Wander through tranquil walking paths, enjoy scenic ponds, and spot local wildlife right outside your door.brPrivate Patio Retreat: Start your mornings with coffee or end your evenings with a glass of wine on your own private patio, perfect for quiet relaxation.brBright, Single-Level Living: Skylights and an open layout fill the living space with natural light, creating a warm and welcoming atmosphere throughout. Large 2 bedrooms and 2 bathrooms.brTennis & Recreation Amenities: Stay active with access to community tennis courts, shuffleboard, putting green, and a clubhouse with a pool table and library.brPrime Sarasota Location: Just minutes from Siesta Key Beach, Lido Beach, Venice Beach, shopping, dining, golf courses, and top attractions like The Ringling and MOTE Marine Laboratory.brTimberwood Villa offers the perfect blend of peaceful living and easy access to Sarasota's beaches, culture, and dining. Whether you're here for sun-soaked adventures or laid-back leisure, this charming villa invites you to feel right at home. Book your stay today and experience the relaxed beauty of Timberwood living.brbrSome of our Favorites:brGrocery:brPublix- 8-minute drivebrCostco - 3 minute drivebrSprouts Farmer's Market - 5 minute drivebrWalmart neighborhood market - 13-minute drivebrSam's Club- 23 minute drivebrRestaurant's: brMillie's - Landmark American Breakfast & LunchbrGecko's Grill & Pub - Casual pub with a broad menu and multiple TV's for sports fansbrOak & Stone - Super cool place with self serve craft beer taps and great foodbr83 Tavern - Great local spot with a laid back classy atmospherebrBeckham's Sarasota Restaurant on the Trail - Another local favorite spot - just wonderful all round!brSahara Cafe & Mediterranean Foods - Fresh & authentic Mediterranean food in a casual atmospherebrSmoke & Fire BBQ - A vibrant eatery that specializes in mouth-watering smoked meats and bold barbeque flavors. Great casual atmosphere.brCasey Fish House - Fresh seafood, dockside dining and tropical tiki vibes. Flavorful dishes in a relaxed waterfront setting.brBeaches:brSiesta Beach - 5 minute drivebrCrescent Beach - 15 minute drivebrVenice Beach - 25 minute drivebrTurtle Beach - 20 minute drivebrNokomis Beach - 20 minute drivebrbrRoelens Vacations is proud to partner with the city to promote recycling and make our community more sustainable and greener. Thank you for your cooperation and for being part of a more sustainable future!brbrDISCLAIMERS:brThis unit is a 7 night minimum staybrThis home does not allow pets.brPlease note: This home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.

Bed

Bath

Sleeps

$458.11

/ Nightly

Condo

Condo on the beach! Footsteps to water. Spacious unit with a view.

Sarasota, Florida, United States

The Sea Shell Condo 505, a spacious 2 bedrooms-2 baths en-suite, a completely renovated unit. Sleep 6 with an additional upgraded memory foam queen sofa bed. It has a lovely beach decor design with a great beach and gulf view from the living room, patio, and partial from bedrooms. Beach-themed decor with tiled floors and ceiling fans throughout the unit. Well supplied, bright newer kitchen with updated appliances including Keurig and drip coffee systems. Pass through window from the kitchen to the dining room. Dining room table seats 6 people, plus additional leaf. There is also a coffee table that rises to a table. All new bedding throughout with a king bed in the master bedroom, a queen, and a full bed in the guest room. There is a large TV and DVD player in the Living room and TVs in both of the bedrooms. Plantation shutters are throughout the entire unit. Free Wi-Fi and local telephone in the unit.brbrNo need to worry about parking, your unit and parking are on the beach! Sea Shell Condos is on the free trolley stop if you prefer downtown shops or enjoy the convenient south village right across the street, including a grocery store, pharmacy, post office, bars, shopping, breakfast/lunch spots, bike and boat rentals. Sea Shell has its own private beach with free beach chairs already on the beach just waiting for you. For a small free you can have your umbrella and chairs set up and waiting for you. White soft sands await.

Bed

Bath

Sleeps

$236.17

/ Nightly

Condo

Condo WITH PRIVATE BEACH adjacent to Siesta keys public beach - parking - pool

Sarasota, Florida, United States

With a secluded private Beach of our own, Right next to the world famous siesta key public beach, with access to private beach area, tennis court, pool, parking, separate entrances very convenient to all.brenjoy the tranquility of our very own private beach or enjoy the crown at the public beach right next to it. Since you stay at at the unit with private beach, the guests have exclusive access to the private and the public beach.

Bed

Bath

Sleeps

$459.65

/ Nightly

Condo

Stunning 3 bedroom Condo w/ Ocean view and Pool!

Sarasota, Florida, United States

Enjoy stunning views from this 3 bedroom, 2 bath condo on Siesta Key! This beautiful home offers an open floorplan with room for up to six guests. Enjoy beautiful views of the gulf from the open-air balcony, or relax on the beach and enjoy the peaceful tropic breeze. This complex also offers a small workout-room for your use. With 13 public beach access points, wonderful shops and restaurants, Siesta Key promises great experiences for everyone who visits. Take advantage of the tranquil waters, soft sand, and warm sun as you explore all the island has to offer and unwind at the end of a fantastic day in this beautiful home.brbrBedroom 1 - King,brBedroom 2 - Queen,brBedroom 3 - QueenbrbrAdded 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

3

Bed

2

Bath

6

Sleeps

$365.32

/ Nightly

Condo

On Siesta Key Beach, View, pool, 2 Bed 2 Ba, plus pull out Queen,

Sarasota, Florida, United States

Our Beach is Beautiful & PERFECT LOCATION, NEW UV AIR PURIFICATION SYSTEM. Contact us if you don't see your dates available so we can help. You will know you are at the beach as soon as you walk in to this Beautiful top floor penthouse 2 Bedroom, 2 Bath 5th floor condo. New hurricane doors and windows. New 5x4 shower with double sinks and granite tops in master. Use the Request to book tab for immediate confirmation of your trip within minutes. Each bedroom offers its own on suite bath. Flat screen TVs in both bedrooms and family room. The Kitchen has all new stainless steel appliances, 2 icemakers in refrigerator and is stocked with plenty of cooking and dishware including spices ,trash bags, soap pods for dishwasher as well as dish and hand soaps. We provide Shampoo, and Body wash in each bathroom as well as blow dryers , and curling irons. The family room has books and games as well as a DVD player and many DVD movies..Family room has a Lazy Boy couch and love seat as well as 2 leather recliners. There is also a Queen Murphy bed in Family room in case you have an occasional overnight guest or child.The Dinning room seats 6 and we offer a booster seat and pac n play in case you have a small child. The View from the Balcony is just as pictured.. Great view of Beach and Ocean. The quiet 5 th floor location means you do not have anyone above you.. and quick walk to restaurants shops etc, Our condo has beach towels, beach chairs that you can take with you to offsite locations, also coolers ,noodles, boogie board, umbrellas, and 2 sets of snorkel gear, even Sunscreen! There is off beach snorkeling at Point of Rocks area just south of the condo. We offer FREE Beach Chaise lounges on the beach ! There is also a new Tiki on the beach with picnic tables and 2 gas grills and heated pool and restrooms with showers located at the office end of the building. Nice shower to rinse off at the beach before heading back to the condo.. Nice place to read a book in the shade if you prefer. The Beach and water are clean and clear.. wonderful for kids and parents alike. Very shallow for safe swimming.. The location is awesome, South Village is just across the street Grocery Store,. 8 restaurants, Sniki Tiki with nightly music, many Shops, Beauty Salon, Drug Store, 7/11 store, Marina, Boat, Bike and Kayak rentals, Ice cream store with Bakery items, Nice place for an easy stroll . You will love the location! easy on and off the Key via Stickney Point Bridge. brYou will have Parking on ground floor under building in your personal parking space. The 2 Elevators are conveniently located in the middle of the building. Coin Laundry areas located on each floor near elevators .There are luggage carriers and grocery carts located on the ground floor for ease of taking items to the condo via the elevator from you car. Free Chaise lounges on the beach for SeaShell guests. This is a place I'm sure you will want to return Year after year! Owners Ron and Carol are easily accessible by phone or text if you have any questions before during, or after your trip. Condo is on the beach side with the south village across the street.brWe only take Sat to Sat bookings .

Bed

Bath

Sleeps

$107.38

/ Nightly

Apartment

Private Studio · Near Siesta Key · Pet Friendly

Sarasota, Florida, United States

pLocated in Sarasota, this welcoming apartment lets you experience it all. With the property's convenient onsite parking, you'll be ready to make the quick 4-minute drive to The Landings or the 3-minute drive to Bee Ridge Park./ppAfter you return, unwind in the garden and enjoy the outdoor furniture. As for the great indoors, you can come inside and enjoy the free WiFi and TV. /ppThis 1-bedroom, 1-bathroom rental features air conditioning and a desk. Bathroom amenities include towels, toilet paper, and soap. The kitchenette is equipped with a refrigerator, as well as a coffee maker, a microwave, and cookware. /p

Bed

Bath

Sleeps

$136.4

/ Nightly

Condo

Resort-like setting a short drive to beaches and downtown, new vinyl plank floor

Sarasota, Florida, United States

Enjoy the tennis court, 24-hour fitness center, walks around the complex and, of course, the fabulous heated pool. If you choose to venture off your lounge chair, enjoy nearby shopping, 5-star restaurants, the country's #1 ranked beach, and activities including golfing, boating, and fishing (all within a 10 mile radius).

Bed

Bath

Sleeps

$159.3

/ Nightly

Apartment

Private Siesta Key In-law Aprtment

Sarasota, Florida, United States

Serene In-Law Suite Steps from the Beach – Siesta KeybrWelcome to your private oasis on the south end of Siesta Key—just a leisurely 15 minute stroll to the Gulf of Mexico and Point of Rocks, one of the best snorkeling spots on the island. With no busy streets to cross, beach access is safe and simple.brbrYou'll love the casual, beachy vibe of the neighborhood, filled with local restaurants, ice cream shops, boutiques, bike rentals, and everything you need for a perfect coastal getaway. There’s even a village grocery/deli and drugstore nearby, and larger supermarkets are just off the Key for weekly essentials.brbrYour upstairs In-Law apartment is a quiet and private retreat, featuring:brbrA King-size bed with soft, fluffy bedding for restful sleepbrA fully equipped private kitchen to cook your own meals (or explore one of the great breakfast spots down the street)brA private entrance with no shared spacesbrIn-unit washer and dryer (detergent provided)brBeach towels and chairs includedbrOne dedicated parking spacebrPlease note: the backyard and pool area are not accessible to guest. brbrThis unit is perfect for travelers seeking both adventure and relaxation. Live like a local with the comforts of home and the beauty of Siesta Key.

1

Bed

1

Bath

2

Sleeps

$978.64

/ Nightly

Private Vacation Home

Casa De Siesta - 312 “Siesta Key”

Sarasota, Florida, United States

KEEP READING BELOW. THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME. THERE IS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!brbrCasa De Siesta | Private Heated Pool + Walk to Siesta Key VillagebrbrWhy You’ll Love This HomebrStep into tropical elegance just steps from the village. You’ll enjoy sunlit interiors, a private heated pool & hot tub, and seamless indoor‑outdoor living designed for connection and rejuvenation.brbr‍‍ Perfect ForbrFamily groups, multi‑gen travel, or couples seeking privacy with shared amenities.brbr️ Imagine ThisbrWake up to golden light filtering through palms, hit the pool for a morning dip, then wander down the block to sip coffee at a café in Siesta Key Village. Midday, stretch out on the sand at Siesta Key Beach (a quick 0.3 mile stroll), then return for a BBQ by the pool. As evening falls, gather with friends in the hot tub, and enjoy the sunset. You’ll feel relaxed, refreshed, and like you're exactly where you want to be.brbrFind us at: www.vactionDP .(c o m)brbrWhere You’ll SleepbrVilla Fiesta:br• Bedroom 1: King Bed, Ensuite Full Bath, First Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, First Floor, TVbr• Living Room: Queen Sleeper SofabrbrVilla Margarita:br• Bedroom 3: King Bed, Ensuite Full Bath, Second Floor, TVbr• Bedroom 4: Queen Bed, Shared Bath, Second Floor, TVbr• Living Room: Queen Sleeper SofabrbrExplore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, NightlifebrbrThis home is a combination of 2 units - Villa Fiesta - 312R and Villa Margarita - 314L that are accessed by different entrances and do not share common space indoors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. brbrPET POLICY: This home has a $15/pet/day fee. Aggressive breeds (ie. pitbulls, etc) may not be allowed and will need to be approved by management prior to your stay. If you bring your pet without claiming them on the reservation or by trying to avoid paying the pet fee, a minimum fine of $500/pet will be collected. By making this reservation, you agree to this policy. DOGS ONLY. CATS ARE NOT ALLOWEDbrbrA SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.

6

Bed

4

Bath

12

Sleeps

$554.78

/ Nightly

Private Vacation Home

Villa Margarita - 314 “Siesta Key”

Sarasota, Florida, United States

KEEP READING BELOW. THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME. THERE IS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!brbrVilla Margarita | Pet Friendly Home In Siesta Village, Heated Pool and Hot Tub, Walk to the Beach!brbrWhy You’ll Love This HomebrTucked above the lively village streets, Villa Margarita offers a breezy, light-filled retreat with elevated privacy, designer comfort, and shared access to a heated pool and spa—just 0.3 miles from world-famous Siesta Key Beach.brbr‍‍ Perfect ForbrCouples, small families, or beach lovers craving a stylish escape with village convenience.brbr️ Imagine ThisbrWake to a soft breeze drifting through upstairs windows. Get the day going by brewing coffee in the bright kitchen, step onto the balcony, and watch the village below slowly wake up. By late morning, you're walking to the beach—cooler packed, flip-flops on. After a sun-soaked afternoon, it’s back to the villa to dip into the shared hot tub, grill fresh seafood, and toast to another unforgettable day on the Key.brbrFind us at: www.vactionDP .(c o m)brbrWhere You’ll Sleepbr• Bedroom 1: King Bed, Shared Bath, Second Floor, TVbr• Bedroom 2: Queen Bed, Shared Bath, Second Floor, TVbr• Bonus Room: Queen Sleeper Sofa – Main Living AreabrbrExplore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, NightlifebrWhether you crave barefoot luxury or spontaneous adventure, Villa Margarita places you in the perfect spot to enjoy it all.brbrThis home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the backyard pool area along with the right side of the building which includes the second and third floors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. This home has stairs, if you or someone in your party has trouble with stairs, please contact us for more details.brbrPET POLICY: This home has a $15/pet/day fee. Aggressive breeds (ie. pitbulls, etc) may not be allowed and will need to be approved by management prior to your stay. If you bring your pet without claiming them on the reservation or by trying to avoid paying the pet fee, a minimum fine of $500/pet will be collected. By making this reservation, you agree to this policy. DOGS ONLY. CATS ARE NOT ALLOWEDbrbrA SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.

3

Bed

2

Bath

6

Sleeps

$566.15

/ Nightly

Private Vacation Home

Villa Fiesta - 312 “Siesta Key”

Sarasota, Florida, United States

KEEP READING BELOW. THIS IS NOT JUST A BASIC DESCRIPTION OF THE HOME. THERE IS VERY USEFUL INFORMATION THAT YOU WON’T WANT TO MISS!!brbrVilla Fiesta | Pet Friendly Home In Siesta Village, Shared Heated Pool and Hot Tub, Walk to the Beach!brbrWhy You’ll Love This HomebrLive like a local in the heart of Siesta Key Village, just a 5-minute walk to the island’s world-famous beach. Villa Fiesta blends vibrant charm with relaxed coastal style—complete with a shared heated pool, dog-friendly policy, and the freedom to walk to everything. This colorful island retreat is made for morning strolls, beach days, and sunset BBQs.brbr‍‍ Perfect ForbrSmall families, couples, or friend groups looking for a lively, walkable Siesta Key experience—plus one well-behaved pup (under 25 lbs) is welcome too!brbr️ Imagine ThisbrThe village is alive with energy as you arrive—bike bells, café chatter, and the scent of coconut sunscreen in the air. You step inside Villa Fiesta and instantly feel at ease. The coastal-inspired living room invites you to kick off your flip-flops and stretch out on the sofa. Upstairs, sun-drenched bedrooms await, each designed for rest and recharge. After a lazy afternoon on Siesta Key’s powder-white beach—just 0.3 miles away—you return to the shared backyard oasis. The grill sizzles, the hot tub bubbles, and laughter echoes as the sun dips below the palms. Every moment here feels light, bright, and unforgettable.brbrFind us at: www.vactionDP .(c o m)brbrWhere You’ll Sleepbr• Bedroom 1: King Bed, Shared Full Bath, Second Floor, TVbr• Bedroom 2: Queen Bed, Shared Full Bath, Third Floor, TVbr• Living Room: Queen Sleeper Sofa – Main Living Area, Half Bath NearbybrbrExplore the Areabr• 0.3 Miles to Siesta Key Beach – Walk To The #1 Rated Beach in The U.S.br• 0.1 Miles to Siesta Key Village – Boutique Shops, Beach Bars, Seafood Shacks & Live Musicbr• 1.8 Miles to Siesta Key Marina – Boat Rentals and Dolphin Cruisesbr• 7 Miles to Downtown Sarasota – Art, Dining, NightlifebrWhether you crave barefoot luxury or spontaneous adventure, Villa Fiesta places you in the perfect spot to enjoy it all.brbrThis home is a part of a duplex unit, meaning that it could share a dividing wall, floor, ceiling, outdoor space, and/or amenities with another unit(s). When renting this unit, you will have access to the backyard pool area along with the right side of the building which includes the second and third floors. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather. This home has stairs, if you or someone in your party has trouble with stairs, please contact us for more details.brbrPET POLICY: This home has a $15/pet/day fee. Aggressive breeds (ie. pitbulls, etc) may not be allowed and will need to be approved by management prior to your stay. If you bring your pet without claiming them on the reservation or by trying to avoid paying the pet fee, a minimum fine of $500/pet will be collected. By making this reservation, you agree to this policy. DOGS ONLY. CATS ARE NOT ALLOWEDbrbrA SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.

Bed

Bath

Sleeps

$284.82

/ Nightly

Private Vacation Home

Siesta Key Paradise for 12

Sarasota, Florida, United States

Indulge in the allure of coastal living at the spectacular Siesta Key Paradise. Our expansive 3-bedroom, 2-bath home, enveloped with a secure, fenced-in yard, is splendidly designed to host up to 12 guests comfortably. Enriched with a king bed, two queen beds, two twin bunk beds and a queen sleeper sofa in the living room, every guest is guaranteed a snug retreat. For your satisfaction, we've included a private workspace, a pack ’n play travel crib, delightful board games, and beach essentials for a fun day out.brbrNestled in a serene neighborhood of Sarasota, our residency boasts a delightful balance between tranquillity, accessibility, and enthralling coastal adventure. Relish the beauty of the renowned Siesta Key Beach, famous for its powdery white quartz sand and soothing turquoise Gulf waters, located a mere 8 minutes away.brbrAdditionally, immerse yourself in the lively, charming atmosphere of Siesta Key Village, housed with locally-owned restaurants, beach bars, unique boutique shops, and live music. Downtown Sarasota is comfortably nearby, alluring with art galleries, theaters, and waterfront dining along the bayfront.brbrThe home is a mecca for outdoor enthusiasts, with kayaking at Turtle Beach, biking along the Legacy Trail, or exploring Myakka River State Park. Families can revel in the spectacular Marie Selby Botanical Gardens or Mote Marine Laboratory & Aquarium, both just a few miles away. Conveniently located grocery stores, coffee shops, and restaurants make your stay hassle-free.brbrWe offer an array of added amenities including a hot tub, garage parking, and an EV Charger. If interested, kindly message us ahead of time for a seamless arrangement.brbrExperience the quintessential Sarasota lifestyle of sun, sand and coastal charm at our Siesta Key Paradise. Embark upon an unforgettable vacation filled with beach days, family fun, or a soothing escape. Get ready to create timeless memories!

1

Bed

2

Bath

12

Sleeps

$373.97

/ Nightly

Apartment

Luxury 2-Bedroom Sarasota Residence with Resort-Style Amenities

Sarasota, Florida, United States

Welcome to your Sarasota retreat.brbrThis beautifully furnished 2-bedroom residence offers the comfort of home with the ease of resort-style living. Whether you are visiting Sarasota for an extended stay, seasonal escape, relocation, or simply want a peaceful place to enjoy the Gulf Coast lifestyle, this apartment provides the space, amenities, and convenience you need.brbrInside, you will find a thoughtfully appointed layout with comfortable living areas, a full kitchen, private bedrooms, and everything needed for a relaxed stay. The home is designed to feel welcoming, clean, and easy to settle into, whether you are staying for a few weeks or a longer visit.brbrGuests also enjoy access to community amenities that create a true lifestyle experience, including beautiful gathering spaces, a resort-style pool, fitness center, outdoor areas, and opportunities to enjoy the community atmosphere.brbrLocated in Sarasota, this residence places you close to dining, shopping, arts, beaches, medical facilities, and the everyday conveniences that make longer stays simple and enjoyable.brbrWhether you are here for sunshine, relaxation, relocation, or a seasonal stay, this furnished 2-bedroom residence offers a comfortable place to land and enjoy Sarasota living.

2

Bed

2

Bath

4

Sleeps

$310.39

/ Nightly

Private Vacation Home

Spacious Family Friendly 4BR Home in Enchanting Sarasota with Hot Tub

Sarasota, Florida, United States

Modern Sarasota Retreat – Newly Renovated with Private Hot Tub!brWelcome to your stylish home base in the heart of Sarasota! This newly renovated 4-bedroom, 2-bath gem perfectly blends modern luxury with family-friendly comfort. Whether you’re here for the world-class beaches or the vibrant downtown scene, you’ll find everything you need for a seamless Florida getaway.brbrThe SpacebrInside, you’ll find a bright, open-concept living area with brand-new furnishings and high-end finishes.brSleeping: Two spacious King bedrooms, one Queen, and a fun Kids Oasis featuring a bunk bed and trundle.brKitchen & Bath: A fully equipped gourmet kitchen with new appliances and spa-like bathrooms with designer fixtures.brOutdoor Living: Step outside to a private, fenced backyard with professional hardscaping, lush turf, and a private hot tub—the ultimate spot to unwind after a day of exploring.brbrThe LocationbrYou are minutes away from the best of Sarasota:brBeaches: A short 15-minute drive to the famous white sands of Siesta Key.brDowntown: 10 minutes to top-tier dining, boutiques, and nightlife.brThe Legacy Trail: Just around the corner for biking and scenic walks.brbrPack your bags and experience Sarasota in style!

4

Bed

2

Bath

10

Sleeps

$196.66

/ Nightly

Hotel

Serene Lakefront Getaway Double Queen Gym & Pool

Sarasota, Florida, United States

Welcome to your cozy suite in Sarasota! Nestled near Lake Osprey, this modern stay offers a relaxing atmosphere with wellness-focused comfort and essentials.brbrEnjoy these fantastic perks:br• Daily breakfast available $8–$14br• Poolbr• Gymbr• HousekeepingbrbrWhether you're here to enjoy Florida’s sunshine, nearby beaches, or a productive business trip, we have you covered. Come experience the calm, coastal vibe of Sarasota!brbrSuite Highlights: Your Home Away From HomebrbrSleep & Relaxationbr• King-size bed with premium linensbr• Blackout curtains for uninterrupted restbrbrWork & Entertainmentbr• Fast WiFi (in-suite + public areas)br• Spacious workstation for productivitybr• TV with premium channels (HBO, CNN, ESPN)br• Kitchen & Diningbr• Refrigeratorbr• Coffee machine with unlimited tea/coffeebrbrFull Bathbr• Full bathroom with shower + bathtubbr• Daily restocked toiletries (no hassle!)brbrParking & Transportationbr• Free self-parking on sitebrbrAmenity Highlightsbr• 24-hour fitness center (stay on track)br• Outdoor pool (Pool access: 8:00 AM – 10:00 PM)br• Dog-friendly property (dogs only)br• Up to 2 pets totalbr• Fee: USD 100 per accommodation, per staybr• Service animals are welcome and exempt from feesbrbrFood & Beverage Optionsbr• Cooked-to-order breakfast available for a fee (Approximately USD 8–14 per person)br• Daily Housekeepingbr• Beds made + towels refreshed (opt-out with Do Not Disturb)br• Toiletries, paper towels, TP restocked dailybr• Self-serve Laundry availablebrbrPrime Location – Everything’s Close!brbrWhat's Nearbybr• Mall at University Town Center – 15 min walk (1.3 km)br• Main Street at Lakewood Ranch – 15 min walk (1.3 km)br• Nathan Benderson Park – 1 min drive (1.1 km)br• Premier Sports Campus at Lakewood Ranch – 12 min drive (12.2 km)br• Ed Smith Stadium – 14 min drive (13.5 km)brbrGetting Aroundbr• Sarasota–Bradenton Intl. Airport (SRQ) – 18 min drive

1

Bed

1

Bath

4

Sleeps

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