Home Vacation Rentals By Owner In Siesta Key, FL

Showing 1740 Of 2077 Vacation Rentals
Slider Thumb
Exceptional(37)

$465.19

/ Nightly
Apartment

Island House Beach Resort 2S

Siesta Key, Florida, United States

This beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a King-size bed, along with a guest bedroom offering two 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. The condo also features three large flat-screen televisions and central heating and air conditioning for year-round comfort. Step onto the lanai to enjoy gorgeous views of the Gulf of Mexico with truly spectacular scenery with magnificent sunsets that are a sight to behold.br 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!
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(4)

$247.47

/ Nightly
Condo

Steps to private Siesta Key Beach - Coastal Condo, 2 Pools- Unit 71 at Casa Mar

Siesta Key, Florida, United States

Welcome to Solace on Siesta at Casa Mar, your relaxing Siesta Key Beachside condo. Just steps from the world-famous private white quartz sand beach and stunning Gulf Coast sunsets (no roads to cross).brbrThis beautifully designed 1 bedroom/1 bathroom Siesta Key vacation rental is perfect for couples, small families, girls trip or anyone looking for a peaceful coastal escape with easy private beach access, modern comforts, and a true island vibe. Natural light and coastal décor create a space that instantly puts you in vacation mode. A king size bed in the bedroom, and sleeper sofa in the living room allows for up to 4 guests max. Enjoy the fully equipped kitchen for relaxing meals at home, sip your morning coffee or an evening glass of wine on the private patio located just outside the sliding glass doors of the enclosed lanai. brbrGuests at Casa Mar enjoy access to two heated swimming pools, private beach access with complimentary beach loungers, picnic and BBQ areas, and recreational amenities including tennis, pickleball, basketball and shuffleboard. Covered parking just outside the condo is included for convenience. Casa Mar is a gated resort for your added comfort and peace of mind.brbrConveniently located in the middle of the island, hop the trolley out front for easy access to the Siesta Key Village (restaurants, bars, shops). Enjoy a short walk to the shops/restaurants at the South Village or venture off the island just minutes to all that downtown Sarasota has to offer.brbrFor your convenience beach essentials are provided (including portable beach chairs, 2 beach umbrella, cooler, beach towels, beach wagon, small blue-tooth speaker). The condo is equipped with 3 Smart TV's (bedroom, living room and enclosed lanai), WIFI, Cable, Hair Dryer, Free Parking, Laundry Facilities, Gated Community. brbrThis isn’t just a place to stay—it’s a feeling.brSolace on Siesta = no stress, no rush, just beach life.brWake up slow.brFeel the gulf breeze.brStay out for sunset.brRepeat.brbr***Please note we are new to VRBO in 2026, but professionally hosted with five years of successful guest stays and vacation rental experience. We have chosen to switch to this platform to make your stay on Siesta Key more affordable. brbrBook Your StaybrPrime dates fill quickly—especially during peak season.brClick to save or reserve now to lock in your stay at Solace on Siesta at Casa Mar on Siesta Key.
Bed 1

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(29)

$294.6

/ Nightly
Condo

#1 Beach @ Siesta condo/best deal out there! Jamaica Royale Siesta Key Condo 109

Siesta Key, Florida, United States

Enjoy America’s #1 beach, take a short bike ride to the Siesta Key village rich in dining/shopping choices or soak up the sun on the private terrace at this newly renovated exclusive Siesta Key condominium. Fabulous location with direct access to the sparkling Gulf of Mexico, the world famous white sand Siesta Key beach and is convenient to all the cultural activities Sarasota has to offer. In addition to the easy access to both the beaches and village, the Community amenities include complimentary beachfront chairs, 3 pools, 2 BBQ areas, 2 covered gazebos for relaxing in the shade, shuffleboard and shaded parking at the door. Completely renovated 2/2 with wood plantation blinds that allow for both privacy & natural light and luxury vinyl plank flooring. Flawlessly appointed with all new chic coastal reclaimed driftwood furniture, new wood cabinets, new Samsung appliances, quartz countertop, hard to find in unit laundry with new full size Samsung washer and dryer and new distressed reclaimed driftwood dining room furniture and 8’ sunbrella sofa and comfy chair. This unit can easily accommodate 4 - 6 guests - Master bedroom has new pillow top king mattress & guest bedroom has 2 full beds with new pillow top mattresses both triple sheeted with new high thread counts sheets and bedding. There is a large screen high definition TV in both bedrooms and living room with complimentary WIFI being available throughout the community as well in the unit.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(18)

$855.98

/ Nightly
Private Vacation Home

Sweet Rae of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

Siesta Key, Florida, United States

Welcome to Sweet Rae of Sunshine, a newly updated coastal oasis in the heart of Siesta Key! This family-friendly, spacious home is just a few blocks from Siesta Key Village and the #1 rated white sand beaches in the country! A quiet neighborhood providing a serene stay, yet extremely convenient location to all Siesta Key has to offer! 4 bedrooms, 2.5 baths. Sleeps 11 guests. Heated pool/spa with private Lanai. Plus, a 6-seater ELECTRIC GOLF CART INCLUDED IN YOUR STAY!brbrThe moment you pull in to the paved driveway of our Sweet Rae of Sunshine, you will be WOWED by the beautiful scenery and Floridian charm. As you walk through the grand entryway, suitcases in hand and flipflops on, we hope you are instantly invited with the feel of that warm coastal aesthetic and consider this your new home away from home. Not only do you get a gem of a home in a highly desired location, you are also getting a fun, stylish ride to allow you to conveniently cruise all of Siesta Key, all while making great memories! The aqua blue SIX SEATER ELECTRIC GOLF CART IS INCLUDED IN YOUR RENTAL, making this home the ultimate package of everything you need and more!brbrA full kitchen with basic everyday dining and cooking needs to whip up some meals at home! Although we recommend all the delicious foods the gulf coast has to offer, we understand that convenience is key, hence why we made sure a large dining table that seats eight, plus island seating could accommodate all guests to gather and enjoy meals together. Not to mention, the double panoramic sliding doors provide indoor living to be brought outdoors to your backyard oasis with lanai. Just picture, splashing in the heated pool or spa, soaking in the sun or relaxing in the lounge chairs with a cold beverage from the mini fridge just taking in that fresh Florida air. The ultimate vacation while all being together in one large indoor/outdoor space. Other highlights during your stay include an outdoor shower, ideal for rinsing off your sandy feet and salty skin. Direct outdoor access to half bath. Private fenced yard. Lawn games, pool floats and water toys. For a day at the beach, sand toys, umbrellas, beach chairs and wagon will make your experience at the country’s #1 beach a seamless and fun day! ******WE APOLOGIZE, BUT OUTDOOR GRILL IS NO LONGER AVAILABLE TO GUESTS AS A SAFETY PRECAUTION, DUE TO MISUSE IN THE PAST.*******brbrThe second level is a private ensuite King bedroom designed with a calm, natural beauty where coastal meets relaxed tropical. Full bathroom with double sink and walk in shower. Large closet and dresser. Mounted TV, fan, and adjustable brightness bedside lamps with charging ports. A suite that every vacationer dreams of! brbrThe third level contains the remaining bedrooms, full bathroom with double vanity and shower/tub combination and washer and dryer. The first bedroom up the stairs has a twin daybed with twin trundle. A designated workspace for those needing to clock in some hours during your stay. A private balcony that overlooks the serene beauty of all the palms on the property and the sun setting at night. The perfect space to unwind or take a quick business call in peace and tranquility. The queen bedroom’s soft, airy, oceanic design is the ideal resting space after a long day in the sun. A mounted TV, fan, large closet and dresser are included in this room. The final bedroom, designed by our “Sweet Rae” herself, is the ultimate bunk room that can sleep six children on the full-full bunk with twin trundle, or adults can comfortably sleep below while two kids call “top bunk!” Tall dresser and closet as well, with extra storage on the side of the bunk as well. How ever you accommodate guests in this room, it’s the ultimate vibrant room with that perfect Florida charm we hope all will enjoy!brbrThose staying with littles, a highchair, two Pack N’ Plays (own crib sheet needed) and sound monitor is included. Please note, the home is not baby proofed.br brOther amenities: Queen air mattress available. Free Wi-Fi. Basic Xfinity Channels with access to log-in to your own Streaming Apps. Two Kayaks with oars. Lifejackets in assorted sizes not provided. Pedal bikes may have seen better days as past occupants did not take care of them correctly. But, if you would like to take one for a ride, they are there for you to use.brbrA 20minute walk to Siesta Key Village of cafes, restaurants and nightlife is also a desirable way to travel & enjoy the beautiful neighborhood while getting your steps in!
Bed 4

Bed

Bath 2

Bath

Sleep 11

Sleeps

Slider Thumb

$293.58

/ Nightly
Condo

Gulf and Bay Club - 410 - 3 Pools!

Siesta Key, Florida, United States

Gulf and Bay Club Unit B410 by Tropical Sands AccommodationsbrbrbrWelcome to Gulf and Bay Club Unit B410, a 2-bedroom, 2-bathroom coastal retreat located in the heart of Siesta Key, FL, just steps from the world-famous Siesta Beach. Nestled within the sought-after Gulf and Bay Club community, this 28-night minimum rental is perfect for snowbirds, extended vacationers, or remote workers looking to soak in Florida sunshine with the comfort of home and the amenities of a resort.brbrbrHighlightsbr• Private Beach with Secured Access br• 3 Shared Heated Pools br• Shared Tennis, Pickleball, Racquetball, Basketball, and Shuffleboard courts br• Shared Fitness Center br• Community Electric Vehicle Chargers br• 1 assigned Covered Parking Spot br• Shared BBQ areas brbrbrEnjoy the very best of Siesta Key vacation living with access to Gulf and Bay Club’s luxury community amenities. Start your day with a stroll along the sugar-soft sands of Siesta Beach, then unwind in one of three sparkling shared pools or soak in the hot tub. Keep active with the on-site fitness center or challenge your group to a friendly match at the tennis or pickleball courts. With shuffleboard, cornhole, and a welcoming clubhouse for socializing, there’s always something to enjoy.brbrThe condo's inviting living room offers cozy seating, a flat-screen TV, and access to natural light, perfect for relaxing after a day in the sun. The fully equipped kitchen features everything needed for home-cooked meals, including a refrigerator, stove, oven, microwave, dishwasher, drip coffeemaker, and toaster. A dining area nearby makes it easy to gather for breakfast or dinner before heading out to explore Siesta Key Village or nearby Sarasota.brbrThe primary bedroom offers a king-sized bed, and a private ensuite bathroom complete with dual vanity sinks and a walk-in shower, the perfect space to unwind in comfort. The second bedroom is spacious with two queen beds, making it ideal for families or guests, and has easy access to a hallway bathroom with a shower/tub combo and single vanity sink.brbrbrRoom Detailsbr• Primary Bedroom: King Bed, ensuite bath, dual vanity sinksbr• Bedroom 2: Two Queen Beds. Access to shared hallway bathbrbrbrGulf and Bay Club Unit B410 also includes a private washer and dryer, covered parking, and complimentary beach chairs for guest use. Located mid-island on Siesta Key, the property offers easy access to local dining, shopping, and activities, including kayaking in Sarasota Bay, exploring Point of Rocks, or enjoying a sunset at Siesta Key Beach Pavilion.brbrWhether you're planning a long beach escape, working remotely from paradise, or simply enjoying island life, Gulf and Bay Club Unit B410 by Tropical Sands Accommodations offers comfort, convenience, and a premier location near one of the most beautiful beaches in the U.S. Book your extended stay today and experience the best of Siesta Key, Florida!brbr-brbrThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(1)

$293.58

/ Nightly
Condo

Gulf and Bay Club - B308 - Beachfront Resort Amenities Included!

Siesta Key, Florida, United States

Gulf and Bay Club Unit B308 by Tropical Sands AccommodationsbrbrWelcome to Gulf and Bay Club Unit B308, a beautifully appointed 2-bedroom, 2-bath condo nestled in the heart of Siesta Key. Located within the highly sought-after Gulf and Bay Club community, this vacation getaway offers the perfect blend of comfort, convenience, and coastal charm. Just a 5-minute stroll from the world-renowned Siesta Beach. This 28-night minimum rental is perfect for snowbirds, extended vacationers, or remote workers looking to soak in Florida sunshine with the comfort of home and the amenities of a resort.brbrHighlights br• Private Beach with Secured Access br• 3 Shared Heated Pools br• Shared Tennis, Pickleball, Racquetball, Basketball, and Shuffleboard courts br• Shared Fitness Center br• Community Electric Vehicle Chargers br• 1 assigned Covered Parking Spot br• Shared BBQ areas brbrbrAs a guest of Gulf and Bay Club Unit B308, you'll enjoy access to an array of resort-style amenities. Lounge by one of three sparkling shared pools, unwind in the hot tub, or challenge your companions to a game of tennis, pickleball, or shuffleboard. The community also offers a modern fitness center, cornhole, and beautifully maintained grounds. After a sun-soaked beach day, rinse off and relax in comfort back at your stylish retreat.brbrThe open concept living area features cozy seating and a large flat-screen TV, perfect for a laid-back movie night. The adjacent dining area flows into a fully equipped kitchen with all the essentials: a full-size refrigerator, stove, oven, microwave, dishwasher, drip coffeemaker, toaster, and more. Whether you're preparing a beach picnic or a full dinner, you'll feel right at home.brbrThe spacious primary suite boasts a king-sized bed, with an ensuite bathroom that offers dual vanities for added convenience. The second bedroom includes two queen beds, making it ideal for families or visiting friends. A second full bathroom with a shower/tub combo is located off the hallway and easily accessible from all living areas.brbrRoom Detailsbr• Primary Bedroom: King bed, ensuite bathroom, dual vanitiesbr• Second Bedroom: Two queen beds, access to hallway bathroombrbrEnjoy the convenience of a covered parking space and in-unit washer and dryer, making long stays easy and comfortable. With beach chairs provided and Siesta Key’s top-rated beaches just minutes away, every day can be a beach day. You'll also be just a short drive or bike ride from local restaurants, boutique shops, and vibrant coastal attractions.brbrReady to unwind in paradise Gulf and Bay Club Unit B308 by Tropical Sands Accommodations is your perfect home base for a long-term escape on Siesta Key, a barrier island renowned for its powdery quartz sand, turquoise waters, and laid-back coastal charm. Spend your days lounging on Siesta Beach, consistently ranked among the best beaches in the U.S., explore the vibrant shops and dining in Siesta Key Village, or kayak through nearby mangrove tunnels teeming with wildlife. Book your stay now and experience the relaxed elegance and natural beauty of Florida’s Gulf Coast.brbr-brbrThis home is managed by Tropical Sands Accommodations, a Siesta Key and Sarasota property management company. brbrThis property does not allow pets of any kind.
Bed 2

Bed

Bath 2

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(8)

$432.95

/ Nightly
Condo

Luxurous Island Living at Excelsior Beach to Bay, Siesta Key, America's #1 Beach

Siesta Key, Florida, United States

Deluxe Condo in a Tropical Courtyard Setting steps from the Beach. Our home features two bedrooms, pull-our couch with an aero bed mattress, two bathrooms, dressing room with sink and vanity, and it's own enclosed terrace lanai. On the bayside, enjoy Little Sarasota Bay, heated swimming pool, outdoor showers with hot water, whirlpool, lighted tennis and pickle ball courts (equipment available), exercise room, or relax at the shaded fishing and picnic area. On the beach side, enjoy America's #1 beach on the Gulf of Mexico, heated swimming pool, ourtdoor showers with hot water, whirlpool, and shaded picnic area. Several barbecues are located throughout the grounds. Both gulf and bayside residents enjoy easy access to the beach and all beachside amenities including beach lounge chairs. Indoor activities include playing games, doing puzzles, or finding a book in our community library. The social committee has various activities and events planned each month during season. Our unit has washer, dryer, refrigerator, dishwasher, stove/oven with built in microwave, fully controllable air conditioning/heat, cable TV with Prime Video, Netflix, DVR, On Demand, WiFi/INTERNET, and covered parking. You'll definitely feel at home in the friendly tropical Excelsior community. Excelsior's location is second to none. Enjoy a wonderful collection of shops and restaurants right on Siesta Key. We have quick access to I-75 for trips to Tampa. Orlando, Miami, and the Keys. There are many attractions in area. Bush Gardens, Legoland, Disney World, Mote Aquarium, Ringling Museums, Myakka State Park, Marie Selby Botanical Gardens, Deep Sea Fishing, Asolo Repertory Theatre, Historic Spanish Point, St Armand's Circle. Spring Training Parks, Tampa's Lowry Park Zoo, Universal Studios Orlando, Sarasota Jungle Gardens to name a few. brMinimum rental: Two Weeks.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Very Good(1)

$430.3

/ Nightly
Private Vacation Home

Firethorn 212 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Pool...

Siesta Key, Florida, United States

Under new ownership and just completed a partial remodel in January 2019. This owner takes pride in their rental property and has plans to make even more updates in Fall 2019!!! Just converted into a 2-bedroom, 2-full bathroom! This unit has tile flooring throughout the condo and now comfortably sleeps a maximum of 6 people; with a queen bed in the master bedroom, 2 twin beds in the guest bedroom and a sleeper sofa in the living room. Fully equipped kitchen with ample cabinet space for storage. The enclosed lanai has recently been tiled with updated wood plank tile flooring and has a modern outdoor bistro table so you can dine outdoors while you enjoy the tropical breeze. Bedrooms and living room have been updated with new furniture, window treatments, ceiling fans and new flat screen TV’s in the living room and master bedroom. Guest bathroom has been fully remodeled with a walk-in shower and modern glass doors. Brand new, full sized washer and dryer install in 2019. This condo in located on the Gulf Side of the property in building 2 on the ground floor and is just steps away to the pool and our private beach and just a short walk across the street to our club house, fitness center and main office. Stay connected with free wireless internet, phone and cable services. Book your stay in Firethorn 212 today and enjoy our complimentary beach service with lounge chairs and umbrellas on our private beach!
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Home Most popular vacation rentals in Siesta Key