Home Vacation Condo Rentals By Owner In Siesta Key, FL

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Exceptional(2)

$259.87

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Rare Find - Perfection & Luxury on the Beach in Siesta Key Village! Walk to Shopping, Dining & Enter

Siesta Key, Florida, United States

Location, location, location with impeccable views! Rarely available, luxury three-bedroom, full three-bath ocean-front condo on Siesta Key Beach with 5 balconies featuring spectacular beach views and located in the exclusive Beach Terrace building!brbrThe location is second to none, directly on the beach with private beach access and just steps away from the heart of the Siesta Key village. Walk to all of the restaurants, boutiques, markets, spas, and night life located within two blocks of The Terrace.brbrThe unit features an open floorplan with plenty of room to relax, large updated kitchen with new appliances, and west-facing Gulf views from every room. Each bedroom has its own full bathroom, balcony, and ROKU television. Free cable TV is provided in the living room and primary bedroom. Free WiFi is provided. Gated and dedicated and assigned parking spot that is covered, and close to the entry door. All of your beach gear is provided (beach towels, beach chairs, coolers, etc.). The Terrace is a secure building with a locked lobby, and elevators are inside the lobby.brbrOnsite amenities include a fantastic pool; over-sized, extremely deep, heated, saltwater with full gulf-front views. An exercise space with new equipment and gulf views. A large lobby with kitchen facilities, dining area, and comfortable seating to gather with your friends and family. WiFi available in the lobby and at the pool. If you enjoy sunsets and walking the beach you have found paradise. The award-winning white sugar sand of Siesta Key, the finest white sand in America is at your doorstep.brbrRental Terms: 3 month minimum for Jan, Feb & March. 2 month minimum the rest of the year.
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$376.8

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Beachside Fun & Family Comfort, Just Steps from the Sand – Aloha Kai #16 - Roelens

Siesta Key, Florida, United States

Aloha Kai #16brbrA Siesta Key Beachside Bliss Awaits!brbrEscape to the sun-kissed shores of Siesta Key and immerse yourself in the laid-back luxury of Aloha Kai #16. This charming beach 2-bedroom house is your perfect retreat, where the soothing sounds of the Gulf of Mexico and the vibrant energy of Crescent Beach create an unforgettable vacation. Thoughtfully designed with two spacious bedrooms and a relaxing patio, this home is perfect for a family of four looking to unwind in comfort and style. Aloha Kai #16 invites you to kick off your shoes, sip morning coffee on your private patio, and dive into a world of relaxation and adventure. Here's what makes this home so special:brbrBedding Arrangement:br2 Bedrooms:brMaster Bedroom with King-size bed and Smart TVbrGuest Bedroom 1 with Two Twin-size beds and Smart TVbrTop Features:brSleeps 4brLargest Pool on Siesta Key: Dive into the expansive, sparkling pool surrounded by a large lounging deck with plenty of poolside lounges, tables, and chairs for ultimate relaxation.brDirect Beach Access: Steps away from the powdery white sands of Crescent Beach, rated the #1 beach in the U.S., with shaded pavilions and lounge chairs for your comfort.brFront Screened Porch: Sip coffee in the mornings in your screened porch or curl up with a good book.brCommunity Amenities: Enjoy shuffleboard, ping pong, and a poolside community room, plus complimentary beach toys and floats for fun in the sun.brPerfect Home Base Location: Plenty of things to do and unique places to visit. Stroll to nearby restaurants, ice cream parlors, and bars, or hop on the Siesta Key trolley for easy island exploration. There are plenty of activities for children of all ages, thrill seekers and those who want to experience the natural wonders of the region.brNestled within the gated, family-friendly Aloha Kai resort, Aloha Kai #16 places you in the heart of Siesta Key's Crescent Beach, famous for its dazzling quartz sand and emerald waters. Whether you're lounging under a shaded beach pavilion, taking a soul-soothing walk along the 3-mile shoreline, or marveling at breathtaking Gulf sunsets, this little gem offers the perfect blend of tranquility and convenience. With friendly staff, 24-hour support, and daily trash removal, your stay will be seamless and stress-free. Book your Siesta Key escape at Aloha Kai #16 today and create memories that will last a lifetime!brbrRoelens 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: br**10% deposit is due at time of booking, final payment is due 60 days out. Any reservations made within 60 days require full payment. No refunds will be given on deposits.**brThis home does not allow pets. brThis home has a minimum age requirement of 25 to book. Smoking is not allowed on the property.brEvery Villa has ONE designated parking space and parking pass. Additional vehicles and guests must register in the front office for a separate parking pass.
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Exceptional(26)

$413.35

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Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!

Siesta Key, Florida, United States

The Bayside UnitbrTop floor bayside Siesta Key vacation rental with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now!brbrWhat Guests Lovebr∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moorsbr∙ The Balcony – royal palm views from balcony connecting bedrooms and living areabr∙ The Grounds – fishing causeway, private bay and Siesta Key beach access, lined by royal palmsbr∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sandsbr∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainmentbr∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balconybr∙ Activities – scooter, golf cart, bike and kayak rentals nearby br∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – perfect fit for all with resort amenities and trolley to all top attractionsbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbr brbrThe BeachbrOur beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.brbrThe LocationbrWith so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool.brbrBedroom DetailsbrThis is a 3rd-floor (top) unit with an elevator. This two-bedroom unit has a king bedroom, a bedroom with two fulls, and a sofa in the living room. You can sleep up to 6. If you need more space, I can get an additional unit nearby. brbrBeach Gear ProvidedbrWe provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.brbrImportant Resort Limitsbr1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional emergency parking space is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available.brbrHousehold Items ProvidedbrThis vacation rental comes with bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.brbrWhat to BringbrSiesta Key is a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.brbrPost Booking SupportbrWe understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time. brbrTravel InsurancebrIf you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.brbrTermsbrPayments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.
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$285.64

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Gulf view, quiet and comfortable.

Siesta Key, Florida, United States

This beautiful waterfront condo offers a luxurious and tranquil living experience on the shores of the Gulf of Mexico and the Intercoastal waterway during the high season.brWith breathtaking views and a serene environment, this home is the perfect oasis for those seeking relaxation. Located on the sought-after shores of Siesta Key, this condo truly captures the essence of coastal living. Step onto a private balcony and immerse yourself in the panoramic vistas of the sparkling Gulf of Mexico. The mesmerizing dance of the sun and sea invites you to unwind and enjoy the natural beauty that surrounds you. Inside, the newly painted, meticulously maintained 2-bedroom, 2-bathroom condo exudes a sense of relaxation. The open-concept layout seamlessly blends indoor and outdoor living, providing ample space for both relaxation and entertainment. Large, hurricane-rated impact windows and sliding glass doors offer stunning views of the ever-changing waterscape. The updated kitchen is a culinary enthusiast's dream, featuring top-of-the-line appliances, granite countertops, and ample storage space. In addition to the stunning views, this condo offers an array of resort-style amenities. Take a dip in the waterfront pool, fish off the dock, or enjoy a BBQ with friends and family. Other amenities include picnic tables, a fitness center, recreational room, and bike storage. With these amenities, you can embrace an active lifestyle or simply relax by the pool with a good book. Situated just a 10-minute walk to Siesta Key village and a short distance away from local attractions, you'll never be far from entertainment, dining, shopping, and cultural experiences.brbrWith 24/7 security and resident access only, you can enjoy peace of mind in your waterfront retreat. Experience the charm and allure of Siesta Key, known for its white sandy beaches, vibrant community, and laid-back atmosphere. This condo perfectly captures the essence of coastal living at its finest. No Smoking, no pets. brNote: Pictures of condo are digitally enhanced.
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Exceptional(5)

$394.66

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Siesta Key bayfront condo - two pools - tennis and pickleball - beach access - GBB 1366

Siesta Key, Florida, United States

Welcome to luxury living at its finest in this exquisite 3-bedroom, 2-bathroom condo situated in the prestigious Gulf and Bay Club Bayside. Professionally managed by Gulf Coast Vacation Rentals.brbrPerched on the second story, this residence offers unparalleled bay-front views that will take your breath away. The open-concept living space seamlessly blends the living, dining, and kitchen areas, creating an inviting atmosphere bathed in natural light. The heart of the home, the screened-in lanai, which boasts bay views, and has ample seating for you to enjoy your morning cup of coffee to the view. brbrThe primary bedroom suite, located on the second floor, provides a private sanctuary with sweeping bay views from the balcony and has a king-size bed, attached is the spa-like bathroom featuring a luxurious dual vanity and a walk-in shower. On the first level there are the other two bedrooms. The second bedroom has a queen-size bed, plenty of closet space and a TV. The second bathroom has a large vanity with a shower/tub combo. The third bedroom has two full-size beds, which offers ample space to kick back and relax after a long day at the beach. brbrStep onto the private balcony to savor panoramic vistas of the bay, where you can unwind and enjoy spectacular sunsets. Gulf and Bay Club Bayside amenities, including pools, beach access, community grills, pickle-ball & tennis courts, and a fitness center, enhance the resort-style living experience.brbrThis condo epitomizes coastal elegance, inviting you to indulge in the beauty of Gulf and Bay Club Bayside and the captivating bay-front lifestyle it affords.brbrGulf & Bay Club Bayside offers resort-style amenities, including pools, tennis courts, and lush landscapes. With easy access to Siesta Key's renowned beaches, this condo epitomizes the pinnacle of coastal living, where luxury, comfort, and stunning bay vistas converge to create an unparalleled living experience.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.
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Exceptional(47)

$268.61

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COZY UNIT ON THE BEACH, ACCESS TO 3 POOLS. Very clean and newly remodeled!

Siesta Key, Florida, United States

PLEASE NOTE: ONE WEEK MINIMUM STAY REQUIRED DURING THE PRIME SEASON, AND 4 NIGHT MINIMUM STAY OFF SEASON.br*Banyan Tree Beach Resort requires a signed contract WITHIN ONE WEEK OF BOOKING to confirm.*brOn location, you can pick from the three pools, play shuffleboard, walk on the beach, or you may want to take a short walk to Siesta Key Public Beach Pavilion (by the beach or sidewalk) where there are Tennis courts, Pickleball courts, Volleyball and much more. You are less than a mile to the Village, where there are restaurants, banks, grocery stores, drug stores, gift shops, ice cream shops, bars, and nightclubs, banks, salons, coffee shops. You can rent bikes, Segways, boats, scooters, snorkel, fish, dive go parasailing, to name a few. We have several malls and outlet malls, movie theaters. You may also want to attend a play, musicals, fine dining, Sarasota Opera, The Players Theatre, Golden Apple Dinner Theater, Florida West Coast Symphony, Historic Spanish Point, Sarasota Jungle Gardens, John & Mable Ringling Museum, Mote Marine Laboratory, South Florida Museum Bishop Planetarium, Marie Selby Botanical Gardens, G-Wiz science museum, Van Wezel Performing Arts, Myakka River State Park, Oscar Scherer state park, Sarasota Ballet, Large fishing head boats or private charters, sailing, scuba diving, Golfing, or go to a professional ball game.brbrPlease note: Sleeper sofa will accommodate only one adult or two children.
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Exceptional(22)

$234.62

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Newly Renovated Siesta Key Waterfront Condo, Fishing Pier, Large Pool - Short Walk to Turtle Beach!

Siesta Key, Florida, United States

Beautifully renovated 2 bedroom, 2.5 bath waterfront townhouse on Blind Pass Lagoon in Siesta Key just a short 3-5 minute walk from Turtle Beach. Relax and enjoy peaceful surroundings, fish from the docks, take a dip in the pool and watch kayaks paddling past on the waterway. Bring your boat, or rent one from nearby Turtles Marina (docking is free for residents).brbrRecent renovations include a new kitchen with custom cabinetry, granite counters, appliances, and the entire townhouse was repainted. On the first level is the large living room, large updated kitchen, dining area and half bathroom. Living room leads out to the main balcony. 2 bedrooms and 2 bathrooms are on the second level, and another balcony is accessible from the master bedroom. Sleeps 6 with a king in the master & 2 full beds in the guest bedroom plus new queen sleeper sofa in the living room. Full size Maytag washer & dryer are in the unit. TV's are in the living room & both bedrooms. Free WiFi & cable, plus all of your beach gear is provided. Covered, assigned parking garage.brbrThe Cozy Cove community located on the quieter southern end of Siesta Key and is comprised of six intimate units. It is the perfect spot for a relaxing tropical experience.brbrTurtle Beach is a just short walk with Picnic areas, playground, and volleyball court. Several restaurants, including Turtle's Restaurant and Ophelia's on the Bay, are both within a 5 minute walk and you can dine on the water. Turtle Beach Marina is nearby if you want to rent a boat or kayak. Free trolley service is provided from one end of the island to the other, which is a great option to explore Siesta Key Village and Crescent Beach.
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$296.11

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Harbor Towers 628 - Tropical Sands Accommodations

Siesta Key, Florida, United States

Harbor Towers 628 by Tropical Sands AccommodationsbrbrWelcome to Harbor Towers 628, a beautifully appointed three-bedroom, three-bathroom Siesta Key vacation rental located on Midnight Pass Road. Perfect for extended stay guests with a 13-night minimum, this spacious condo offers comfortable coastal living just minutes from world famous Siesta Key Beach and Siesta Key Village. With serene views, generous living space, and access to one of the most amenity rich communities on the island, this residence is ideal for seasonal stays, remote work escapes, or long term coastal retreats.brbrHighlightsbr• 3 Bedrooms / 3 Bathroomsbr• 1 King, 1 Queen, 2 Twinsbr• 13-night minimum stay communitybr• Located on Midnight Pass Rdbr• Short drive to Siesta Key Beachbr• Two heated community poolsbr• Three Har-Tru tennis courtsbr• 40-slip marinabr• Gated waterfront communitybr• In-unit washer and dryerbrbrHarbor Towers is one of Siesta Key’s most desirable gated waterfront communities. Guests enjoy access to two heated pools surrounded by tropical landscaping, three tennis courts, and a private 40-slip marina. The beautifully maintained grounds and waterfront setting create a peaceful atmosphere perfect for extended stays. Whether you are enjoying a morning swim, an afternoon tennis match, or simply relaxing by the water, this community elevates your Siesta Key experience.brbrThe open living and dining area is bright and welcoming, with comfortable seating and large windows that allow natural light to fill the space. The layout flows seamlessly into the fully equipped kitchen, featuring granite countertops, modern appliances, and ample cabinet space. A breakfast bar provides additional seating, while the dining table offers the perfect setting for shared meals, remote work, or evening gatherings after a day at the beach.brbrThe primary bedroom serves as a peaceful retreat with a king-sized bed and an ensuite bathroom designed for comfort and privacy. Natural light and coastal tones create a calm, relaxing atmosphere ideal for restful nights. The second bedroom features a queen bed and convenient access to a nearby bathroom. The third bedroom offers two twin beds, making it perfect for guests or visiting family members. A shared hallway bathroom provides additional convenience for the home. Each bedroom is thoughtfully arranged to ensure comfort for longer stays.brbrRoom Detailsbr• Primary Bedroom: King bed with ensuite bathroombr• Second Bedroom: Queen bedbr• Third Bedroom: Two twin bedsbr• Shared hallway bathroombrbrThis Siesta Key condo includes an in unit washer and dryer, central air conditioning, elevator access within the building, and secure gated entry. The 14-night minimum stay requirement makes this residence especially well suited for snowbirds, seasonal visitors, and extended coastal escapes.brbrIf you are searching for a spacious, amenity rich Siesta Key vacation rental designed for longer stays, Harbor Towers 628 offers the perfect blend of comfort, location, and community features. Secure your dates and experience waterfront living at Harbor Towers on Siesta Key today.
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Exceptional(4)

$247.47

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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.
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Home Most popular vacation rentals in Siesta Key