Vacation Home Rentals By Owner In Siesta Key, FL

$2135.02

Southern Exposure~2 Homes from Beach! Heated Pool!

Siesta Key, Florida, United States

Summary:brbrThis stunning six-bedroom, four-bath home on Siesta Key is an absolute must-see! Perfectly situated just steps from Siesta Key Village, you’ll have the island’s best shopping, dining, and entertainment right at your doorstep. Plus, it’s only minutes away from the powdery white sands of world-famous Siesta Key Beach—making this the ultimate coastal retreat for relaxation and fun in the sun.Kick back and relax in this calm, stylish space.brbrbrbrThe Space:brbr☀️ Southern Exposure | 2 Homes from Beach • Heated Pool ️brbr 91 Avenida Veneccia, Siesta KeybrbrbrbrWelcome to Southern Exposure, your coastal escape just two homes from the beach and steps from vibrant Siesta Key Village ️ With six bedrooms, four bathrooms, and a private heated pool, this bright and stylish retreat is perfect for families, friends, and sun-seekers looking to experience the best of island living.brbrbrbrSpend your mornings strolling to the beach for powder-soft white sand and turquoise Gulf waters . Walk to the Village for coffee, boutique shopping, fresh seafood, and live music—then come home to your private backyard paradise.brbrbrbrInside, the open-concept layout is filled with natural light and crisp coastal charm. The airy white interior, cozy living room with a white brick faux fireplace, and thoughtfully updated finishes create a warm and welcoming space. The kitchen features granite countertops, stainless steel appliances, and bar seating—perfect for gathering after beach days ️✨brbrbrbrStep outside to your private oasis where you’ll find a sparkling heated pool with in-water sun shelf, lush turf yard, lounge chairs, and an outdoor dining area with grill—ideal for soaking up the Florida sunshine and enjoying laid-back BBQ evenings ☀️brbrbrbrPet-friendly (dogs with approval & fee), so your furry family members can enjoy island life too brbrbrbr✨ Highlightsbrbr• ️ Only 2 homes from the beachbrbr• Steps to Siesta Key Villagebrbr• Private heated pool with sun shelfbrbr• Tropical backyard with turf yardbrbr• Outdoor dining area & BBQ grillbrbr• Dog-friendly (approval & fee required)brbr• ️ 6 Bedrooms / 4 Bathroomsbrbr• ☀️ Bright open-concept coastal designbrbrbrbr ️ BedroomsbrbrMain Level:brbr• Bedroom 1 – Twin over Full bunk bedbrbr• Bedroom 2 – Queen bedbrbr• Bedroom 3 – King bedbrbrbrbrUpper Level:brbr• Bedroom 4 – King bedbrbr• Bedroom 5 – King bedbrbr• Bedroom 6 – Two Full bedsbrbrbrbrPerfect layout for multiple families or large groups traveling together.brbrbrbrGuest Access:brbrGuests have full access to the entire home, including a private heated pool/spa and a fully fenced 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 4 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! ✨

5

Bed

4

Bath

13

Sleeps

$254.75

/ Nightly

Private Vacation Home

3-bedroom house in Siesta Key

Siesta Key, Florida, United States

Nestled in Siesta Key, this lovely and recently remodeling house offers a perfect retreat for guests seeking comfort and convenience. With three bedrooms featuring a king, queen, and 2 twin , there’s plenty of space for everyone to relax. Two bathrooms include refreshing showers to make mornings easy. Guests can enjoy a pleasant stay with air conditioning to keep things cool and an iron for any last-minute touch-ups. Kitchen with many cooking utensils .brEnjoy pool (not heated ) back yard .sofa ,outdoor dining table brWhether you’re unwinding indoors or exploring nearby spots, this home provides a welcoming base. Enjoy all that Siesta Key has to offer when you stay at our place.

3

Bed

2

Bath

6

Sleeps

$406.85

/ Nightly

Private Vacation Home

Siesta Key Beach Townhouse - Walk to Beach - 2BR - Pool & Parking

Siesta Key, Florida, United States

Stay, relax, and play—your Siesta Key escape starts here.brbrCreate lasting memories at this inviting townhouse just steps from the world-famous quartz sands of Crescent Beach. With private beach access and no roads to cross, enjoying the Gulf is safe, simple, and stress-free for the whole family.brbrUnwind in spacious, light-filled living areas, prepare meals in the fully equipped kitchen, and gather for games or movie nights after a day in the sun. This 2-bedroom retreat also features dedicated private parking and a prime beach location near local shops and dining. Hop on the free Siesta Key Breeze Trolley to explore the island with ease.brbrWhether you're here for beach days, sunsets, or laid-back island living, this is the perfect home base for your Siesta Key getaway.

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Bath

Sleeps

$237.03

/ Nightly

Private Vacation Home

Leona Breeze: Long Term Perfection!

Siesta Key, Florida, United States

Leona Breeze by Tropical Sands AccommodationsbrbrWelcome to Leona Breeze, the perfect home for long-term renters seeking a relaxed, comfortable stay on Siesta Key. Designed for extended stays, this two-story residence offers four bedrooms and two and a half bathrooms, providing the ideal backdrop for families, professionals, or groups looking to settle into a peaceful, Florida retreat. Located at the end of a quiet cul-de-sac, the home offers privacy and stunning canal-front views, just five minutes from Siesta Key Village’s shopping and dining, and a 13-minute walk to the renowned #1 beach in America.brbrHighlightsbr• 30-night minimum staybr• Dog friendly with approval and additional feebr• 13-minute walk to the beachbr• Canal frontbr• Large kitchenbr• Snowbird friendlybr• Water viewsbr• Two living areasbr• Laundry roombr• BBQ grillbrbrOutside, enjoy the tranquil, private backyard, perfect for unwinding or hosting friends. Sip morning coffee beside the canal or gather in the evening around the pool, your personal tropical oasis. Fish from your own backyard or simply relax in your serene surroundings.brbrInside, terrazzo floors and water views create a welcoming, serene atmosphere. The open-concept kitchen features stainless steel appliances and a large island, perfect for meal prep or casual entertaining. With two living areas, everyone has space to relax and unwind.brbrThe four bedrooms are thoughtfully furnished for comfort. The primary suite includes a queen bed and an ensuite bathroom with a walk-in shower. The other three bedrooms include three queen beds and a full bed, sharing a spacious hallway bathroom with a shower/tub combo, and a half bath rounds out the first floor.brbrRoom Detailsbr-Primary Bedroom, 2nd floor: Queen bed and ensuite bathroom with walk-in showerbr-Second Bedroom, 2nd floor: Queen bedbr-Third Bedroom, 2nd floor: Queen bedbr-Fourth Bedroom, 2nd floor: Full bedbrbrIf you’re searching for a laid-back, long-term Florida escape, Leona Breeze offers the comfort, privacy, and slice of paradise you’ve been dreaming of. Book now and settle into your ultimate Siesta Key retreat!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.brbrbrWe 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.brbr4 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.brbrPlease Remember: You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property. *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.

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Bath

Sleeps

$2172.6

/ Nightly

Private Vacation Home

Gertrude's Siesta | Oceanview, 12-steps Beach, 4-min trolley to Village, tiki-bar, ping-pong!

Siesta Key, Florida, United States

The Oceanview 603 7BRbrOceanview Siesta Key vacation rental, 100% private, 12-steps to Siesta Key's best beach access! Listing includes three- units, two with stunning views and floor-to-ceiling “movable' glass walls. Just 3-min by trolley or bike to Siesta Village. Free bikes and paddle boards. Al-fresco lounging and dining, ping-pong, and Tiki bar. Perfect for large groups looking to relax, explore and repeat. Book your Siesta Key beach getaway now!brbrWhat Guests Lovebr∙ Separate Units – 3 units deliver space and privacy, perfect for large gatheringsbr∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or nightbr∙ Penthouse – best unit, top floor, no one above or next-door to youbr∙ Beaches – 12-steps to access for Siesta Key's best beach, white sand and calm clear waterbr∙ Relaxing – safe easy access to outside attractions and lots of plus-space on sitebr∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living roombr∙ Island Trolley –picks up out front, free of charge to all attractions and welcome's drinksbr∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby br∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the backbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ The Fun - nearby Siesta Village has live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donutsbr∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for allbr∙ Price - this Siesta Key vacation rental listing is direct with the manager and is the guaranteed lowest costbrbrThe BeachbrOur beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn't easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.brbrThe HomebrOcean view property includes second and third floor living and sleeping spaces and was remodeled in 2022. Units include two 3BR units and a 1BR unit (7BR total). The 3BR units each have floor-to-ceiling glass walls in master bedroom and living area to create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.brbrBedroom DetailsbrSleeping and living spaces are second and third floor. Units include two 3BR units and a 1BR unit. Each 3BR unit has one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. The 1BR unit is larger than most with a king bedroom and a queen sleeper sofa. Tempur-pedic rollaway beds are available with advance notice and you can sleep up to 23 family style. Need more space Ask about an additional unit nearby.brbrProperty TruthsbrThe unit is advertised as “100% private,” and in almost all cases it will be. On rare occasions, however, a brief staff visit may be necessary. These visits are unlikely and typically do not occur. If one is required, it will be limited to exterior or storage areas, take only a few minutes, and occur during daytime hours.brbrbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide snorkeling gear but this and anything you need can be rented or purchased nearby.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.brbrHistory – There's no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it's still the spot to fall in love or rekindle an old flame. 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. 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.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.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.

Bed

Bath

Sleeps

$1467.21

/ Nightly

Private Vacation Home

Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!

Siesta Key, Florida, United States

Mainsail by Siesta Key Luxury Rental Properties brbrMainsail by Siesta Key Luxury Rental Properties is a breathtaking 4 bedroom, 3 and a half bath waterfront luxury home with a bonus room, private dock, and spectacular Intracoastal Waterway views. Nestled at the end of a quiet street and just a 10-minute walk to Crescent Beach, this upscale retreat offers a refined yet relaxed coastal lifestyle perfect for large families and groups. With a private pool, in-ground spa, multiple outdoor lounges, and seamless indoor and outdoor living. Mainsail sets the stage for an unforgettable Siesta Key luxury rental experience near South Siesta Key Village. brbrHighlights br• 10-minute walk to Crescent Beach br• 4 Bedrooms / 3.5 Bathrooms br• 1 King, 4 Queens br• Private dock (18 ft) br• Private heated pool and in-ground spa br• 2 kayaks included br• Outdoor bar and outdoor kitchen br• Covered outdoor dining and lounge areas br• Wet bar and wine fridge br• 5 parking spaces brbrDesigned for waterfront relaxation, Mainsail features a private heated pool, a spa, and wide poolside terraces capturing panoramic waterway views. Enjoy evening cocktails at the outdoor bar, prepare meals in the covered outdoor kitchen, or gather for sunset dining on the balcony overlooking the Intracoastal. With two kayaks included, guests can explore the calm waterway right from the private dock. Every outdoor space is crafted for comfort, inviting you to unwind in a true tropical outdoor oasis. brbrInside, Mainsail offers a bright and expansive open concept layout with designer inspired coastal interiors. Floor to ceiling windows frame sparkling water views throughout the living and dining areas, while the gourmet kitchen features high end appliances, generous counter space, and island seating ideal for group gatherings. The dining table seats nine comfortably for shared meals, and an additional wet bar with a wine fridge enhances the luxury entertaining experience. Multiple lounge areas, and beautiful hardwood floors throughout, create a warm, elevated atmosphere. brbrRetreat to the luxurious second-floor primary suite, complete with a king bed, ensuite bathroom, double vanity, walk-in shower, and walk-in closet, plus a convenient mini refrigerator. On the main floor, two guest suites offer queen beds and private ensuite bathrooms, one with a shower/tub combination and one with a walk-in shower. A fourth bedroom includes two queen beds, making it ideal for families or additional guests. The bonus room features a twin daybed, offering a space for relaxing or flexible use. All rooms are designed with calming coastal finishes to ensure a restful stay. brbrRoom Details br-Primary Bedroom (2nd floor): King bed, ensuite bathroom with double vanity + walk-in shower br-Second Bedroom (1st floor): Queen bed, ensuite bathroom with shower/tub combo br-Third Bedroom (1st floor): Queen bed, ensuite bathroom with walk-in shower br-Fourth Bedroom (1st floor): Two Queen beds brbrThis home includes a private dock, kayaks, outdoor bar, outdoor kitchen, multiple waterfront terraces, balcony seating, covered lounges, wet bar, and extensive space for up to five vehicles. Located near South Siesta Key Village, guests are close to shops, nightlife, restaurants, and beautiful Siesta Key Beach. brbrMainsail by Siesta Key Luxury Rental Properties is a rare blend of waterfront elegance, luxury amenities, and prime island location. From its private dock and expansive outdoor spaces to refined interiors and incredible waterway views, this home offers the perfect setting for a memorable Siesta Key escape. brbrBook your stay at Mainsail today and experience the best of waterfront luxury on Siesta Key! brbr- brThis home is managed by Siesta Key Luxury Rental Properties. brbrThis property does not allow pets of any kind. brbrThis property has active video surveillance on the exterior public approach areas and the pool equipment. brbr5 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 Siesta Key Luxury Rental Properties 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.

Bed

Bath

Sleeps

$840.8

/ Nightly

Private Vacation Home

Spacious 4 bedroom home with dock access on the canal on Siesta Key!

Siesta Key, Florida, United States

Experience beautiful Siesta Key living on a spectacular scale at this light and spacious 4-bedroom, 3.5-bathroom home spans between 4 floors and can Sleep up to 8. On the ground floor, you will find a private entry, an oversized garage with a ping pong table, table shuffle board and two kayaks. The second level features a stunning chef-like kitchen with deluxe appliances, breakfast bar, spacious living room and dining room with a large screened in balcony. The third level has two guest bedrooms with a shared bathroom in the hallway and master bedroom with an en-suite bath with separate his-and-hers sinks, spa tub, separate shower, and walk-in closets. The top level is a bedroom with three large twin day beds. Also included is a boat dock on the canal that is available to the owners of Siesta Villas and heated community pool, only shared between the 4 homes in the community. Capture your piece of paradise with this fabulous Siesta Key townhome where you can soon be enjoying notable coastal comforts!br*This property is stairs only; all guest must have the ability to climb stairs.br*No garage parking. Driveway parking only.brbrMaster - KingbrBedroom 2 - KingbrBedroom 3 - QueenbrBedroom 4 - 3 Twin Day BedsbrUnit Size - 2,756 Sq. Ft.brbrAdded 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: $1,500

Bed

Bath

Sleeps

$621.82

/ Nightly

Private Vacation Home

Siesta Sunrise II-Between the Beach and Village

Siesta Key, Florida, United States

One of the best locations on Siesta! Located between the beach and the village this 2 bedroom 2.5 bath townhouse is great for couples and families. There is a shared pool with one other unit. Walking distance to everything. The masterbedroom has a new thomasville bedroom set with king bed, long dresser, and wardrobe cabinet. The second bedroom has two queen beds. In the bonus room there is a queen size murphy bed as well. Saturday to Saturday bookings during season.

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Bath

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$1308.45

/ Nightly

Private Vacation Home

Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!

Siesta Key, Florida, United States

Island Escape | Heated Saltwater Pool + 2 Min Walk to Siesta Beachbrbr Why You'll Love This HomebrStep into Island Escape, where freshly completed renovations meet the charm of Siesta Key's coastal lifestyle. With a heated saltwater pool, gourmet indoor and outdoor kitchens, and two spacious balconies, this single-family retreat blends modern luxury with island ease—just steps from the powder-soft sands of Siesta Key Beach.brbr ‍ ‍ Perfect ForbrFamilies, friend groups, and beach lovers seeking an upscale, walk-to-everything home with indoor/outdoor living and private resort-style amenities.brbr Imagine ThisbrWake up to gentle Gulf breezes, brew coffee in the sunlit kitchen, then step onto your balcony for a poolside view. Spend the morning at the beach—only a 2-minute stroll away—before returning for a grill-side lunch in the shaded outdoor kitchen. Cool off in the heated pool, lounge in the cabana room for ping pong or TV time, then gather on the balcony for sunset. Evenings are for strolling to Siesta Key Village's shops and dining, just 0.7 miles away.brbr Where You ll Sleepbr• Bedroom 1 – Main Level: Queen Bed, Adjacent Half Bath, TVbr• Bedroom 2 – Upper Level (Primary): King Bed, Ensuite Bath, TVbr• Bedroom 3 – Upper Level: King Bed, Shares Hall Bath, TVbr• Bedroom 4 – Upper Level: Two Queen Beds, Shares Hall Bath, TVbr• Living Room: Queen Sleeper Sofabrbr Explore the Areabr• 0.1 Miles / 2-Minute Walk to Siesta Key Beachbr• 0.7 Miles to Siesta Key Village for Dining, Shops, and Nightlifebr• Easy Access to Water Sports, Fishing Charters, and Coastal Parksbrbr⌛ Don't Miss Out - This home books quickly—your stay includes our CottageClean™ program: a 6-hour deep clean and 35-point inspection so you arrive to a home that feels brand new. brbrNeed To Know - The pool is heated from November 15th to April 15th. There are stairs in this home leading to the upstairs bedroom; if any guest has difficulty with stairs, please contact us for alternative accommodations. Starter packs of kitchen and toiletry essentials are provided for a seamless first couple of nights.

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Bath

Sleeps

$361.93

/ Nightly

Private Vacation Home

Tropical Green Cottage – Siesta Key, Just Cross the Street! Unit B

Siesta Key, Florida, United States

Worth every penny — this is Siesta Key’s best value, just steps from the Gulf. 100 Feet to the Beach! Max 4 Guests & 1 CarbrbrThis is the best value you’ll find in Siesta Key — the perfect location and real beach house vibe.brJust across the street from the #1 beach in the USA, with restaurants, bars, shops, and live music all within easy walking distance. No car needed — but if you bring one, you have free parking on the lot!brbrIt’s great to be able to pop back to the cottage for a quick break from the sun, grab a snack, or refill the cooler.brThis cozy spot is ideal for couples, small families, or even wedding guests — with nightlife, shopping, sports and dining all right around the corner in the Village.brbr Direct beach access — just cross the street!br Safe, quiet, easy neighborhood.br Everything is walkable, no car necessary.brbrBedroom 1: King Bed (Sleeps 2)brBedroom 2: Queen Bed (Sleeps 2)brbrGot questions Just ask — I’m happy to help you plan your perfect Siesta Key beach getaway!

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Sleeps

$294.25

/ Nightly

Private Vacation Home

SIESTA KEY, BLUE ROMANTIC DREAM! 100 FEET TO THE BEACH!

Siesta Key, Florida, United States

Perfect for Couples! Max 2 Guests + 1 CarbrbrWorth every penny — this is Siesta Key’s best value, just steps from the Gulf.brbrLooking for the perfect romantic getaway brThis cozy beach cottage is all about location and value — just across the street from the #1 beach in the USA and within easy walking distance to restaurants, bars, shops and live music in the Village.brNo car needed — everything is right here, but free parking is available if you bring one!brbrIt’s perfect to pop back to the cottage for a quick break from the sun, grab a snack or refill your cooler. The safe, quiet neighborhood makes it extra relaxing — ideal for couples or honeymooners.brbr- Direct beach access — just cross the street!br- Romantic, cozy and freshly renovated.br- Walk everywhere — no car needed.brbrBedroom: Queen Bed (Sleeps 2)brLiving Room: Sofa brbrGot questions Just ask — I’m happy to help you plan a perfect stay in Siesta Key!

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Sleeps

$524.66

/ Nightly

Private Vacation Home

Beach Front and Walking Distance to Village

Siesta Key, Florida, United States

This 3 story unit is a 3 Bedroom / 3.5 Bathroom house with spectacular views from every bedroom and private beach access. The house is located a short 2 minute drive to Siesta Key Village, which has the best dining and shopping options on the island. Although you won't have to go any farther than your own backyard to get to Siesta Beach, the #1 rated beach in the USA. This 99.9% pure quartz white sand beach is why people come from all over the world to Siesta Key.brbrThere is a one car garage on the main floor, and a nice covered private stairway taking you up to the first floor of the unit. When you enter the house you immediately step into the open concept living room. With plenty of seating, a large television, and million dollar ocean views, this is where you'll probably spend most of your time in the house.brbrThe fully equipped kitchen is adjacent to the family room. There is a 4 seat dining table in the kitchen, a screened in balcony right off the kitchen with seating for 2, and a large formal dining table on the other side of the family room with incredible ocean views. With plenty of dining areas, you'll look forward to relaxing and taking in the views while you eat.brbrAt the base of the stairway on the main floor there is a 1/2 bathroom which gives access to those in the kitchen and dining areas. When you go up to the second floor you'll find 2 bedrooms. The Master bedroom with a king size bed, walk in closet, and huge sunroom balcony with sliding glass doors and epic ocean views. The en suite Master bathroom is equipped with a double vanity, shower, and large bathtub. brbrThe second bedroom on this floor has a vaulted ceiling, and two twin beds with another covered balcony with views out the front of the house. Just outside this bedroom in the hallway is a full bathroom with shower/tub combination. With your own washer and dyer on this floor doing the laundry is as convenient as possible.brbrAs you go up to the third floor you'll find a huge guest bedroom with 2 Queen beds, more closet space, another TV, and yet another spectacular view from the balcony looking over Siesta Beach. This bedroom offers another full en suite bathroom for convenience.brbrAnd to make this house even more incredible you've got a private BBQ outside on the ground floor with seating, countertops, and plenty of food prep area. The beach access trail is accessible from here, and an outdoor shower right around the corner make this vacation a great indoor/outdoor living experience.

Bed

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$663.62

/ Nightly

Private Vacation Home

*** FULLY UPDATED *** On the Beach, Walk to Village, Watch the Sunsets from Balcony

Siesta Key, Florida, United States

*** FULLY UPDATED December 2025*** This 3 story unit is a 3 Bedroom / 3.5 Bathroom house with spectacular views from every bedroom and private beach access. The house is located a short 2 minute drive to Siesta Key Village, which has the best dining and shopping options on the island. Although you won't have to go any farther than your own backyard to get to Siesta Beach, the #1 rated beach in the USA. This 99.9% pure quartz white sand beach is why people come from all over the world to Siesta Key.brbrThere is a one car garage on the main floor, and a nice covered private stairway taking you up to the first floor of the unit. When you enter the house you immediately step into the open concept living room. With plenty of seating, a large television, and million dollar ocean views, this is where you'll probably spend most of your time in the house.brbrThe fully equipped kitchen is adjacent to the family room. There is a 2 seat dining table in the kitchen, a screened in balcony right off the kitchen with seating for 2, and a large formal dining table on the other side of the family room with incredible ocean views. With plenty of dining areas, you'll look forward to relaxing and taking in the views while you eat.brbrAt the base of the stairway on the main floor there is a 1/2 bathroom which gives access to those in the kitchen and dining areas. When you go up to the second floor you'll find 2 bedrooms. The Master bedroom with a king size bed, walk in closet, and huge sunroom balcony with sliding glass doors and epic ocean views. The en suite Master bathroom is equipped with a double vanity, shower, and large bathtub. brbrThe second bedroom on this floor has a vaulted ceiling, one twin bed, and one double bed with another covered balcony with views out the front of the house. Just outside this bedroom in the hallway is a full bathroom with shower/tub combination. With your own washer and dyer on this floor doing the laundry is as convenient as possible.brbrAs you go up to the third floor you'll find a huge guest bedroom with one twin bed, and one double bed with even more closet space, another TV, and yet another spectacular view from the balcony looking over Siesta Beach. This bedroom offers another full en suite bathroom for convenience.brbrAnd to make this house even more incredible you've got a private BBQ outside on the ground floor with seating, countertops, and plenty of food prep area. The beach access trail is accessible from here, and an outdoor shower right around the corner make this vacation a great indoor/outdoor living experience.

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$720.7

/ Nightly

Private Vacation Home

High Tide - 170 “Siesta Key”

Siesta Key, 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!!brbrPremier local manager, Destination Paradise welcomes you to “High Tide”… a cozy 5 bedroom 4 bath vacation home with an awesome outdoor lounge area! This ranch style home sleeps up to 11. It is located in the heart of Siesta Key and is just minutes from world famous Siesta Key Beach and Siesta Key Village.brbr“High Tide” is less than 500 yards to secluded Shell Beach! When you don’t have your toes buried in the fine white sand sun bathing with friends and family, relax on the large private pool patio. Plenty of room for everyone to relax under the lush tropical palm landscape or take a swim into the heated pool and spa. Kick back in the evenings around the propane fire-pit and enjoy cooking on the grill. This home features 3 master bedrooms with attached full bathrooms. Both of which have direct access to outdoor patio. A fourth bedroom has a private outdoor sitting area accessed through a sliding glass door. All bedrooms (except bunk bed room) are fitted with large smart TVs. Have fun cooking and eating in the updated kitchen with plenty of space for everyone. The kitchen is stocked with all the tools needed to prepare a gourmet meal. Wake up with a hot cup of coffee brewed from the combo coffee maker. Enjoy your coffee and breakfast sitting at the outdoor dining table while you admire the morning sun shine through the Florida palm trees. Your paradise is closer than you think, we look forward to having you as a guest.brbrwww.vacationDP .(c o m)brbr“High Tide” can accommodate up to 10 guests with a bedding configuration as follows:br• Bedroom #1, King Bed (1) - Sleeps: 2br• Bedroom #2, King Bed (1) - Sleeps: 2br• Bedroom #3, Queen Bed (1) - Sleeps: 2br• Bedroom #4, Bunk/Trundle Bed (2) - Sleeps: 2br• Bedroom #5, King Bed (1) - Sleeps 2brbrbr***PLEASE NOTE***brbrCOFFEE MAKER: Combo Coffee maker (both drip and K-cups)brbrPOOL HEATER RULES:brPool heat temp is set at 83º and runs each day from 7 AM until 7 PM from October 15-April 15. Outside of these dates, the Florida weather should naturally heat the pool. Pool temps are not guaranteed. This pool is heated by a heat pump and is only capable of heating to around 20-25 degrees warmer than the ambient temperature. (If the high for the day is 55, the pool may only be able to reach 75).brThe spa has a timer of 3 hours, once turned on and can be run at any time and will heat to 100ºbrbrPET POLICY: This home has a $20/pet/day fee. Aggressive/Large breeds (ie. pitbulls, etc) will need to be approved by management prior to your stay. Unclaimed pets will result in a minimum fine of $500/pet. By making this reservation, you agree to this policy. DOGS ONLY. CATS ARE NOT ALLOWED.brbrSecurity Camera Notice: The driveway and front of the home has cameras for security and safety measures.brbrA SIGNED DESTINATION PARADISE RENTAL AGREEMENT AND ID WILL BE REQUIRED FOR ALL RESERVATIONS.brbrVR Certificate # VR22-00134

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$845.58

/ Nightly

Private Vacation Home

112 Columbus Blvd in the Village of Siesta Key

Siesta Key, Florida, United States

Summary:brbr3 bedroom, two and a half-bath home in the heart of SK Village. The living room and 2 bathrooms exude sophistication with their Italian Travertine flooring, while the den and kitchen offer durable and stylish floor tiling. Stay entertained with our 3 TVs, perfect for cozy movie nights. Please note that small dogs are warmly welcomed with a pet fee. ($300) The accommodation is thoughtfully designed to comfortably host your group with one king bed, one queen bed, two twin beds, and one aero bed,brbrbrbrThe Space:brbrYou will receive Check in and Check out instructions prior to your arrival. Please check your email.brbrbrbrGuest Access:brbrPrivate entrance and garage.brbrbrbrThe Neighborhood:brbrWalking distance to the village and to the beach.brbrbrbrGetting Around:brbrOpen air free cabs. Frog Hops, rentable golf carts via Zoom-around with Siesta 4 Rent discount.brbrbrbrOther Things to Note:brbrPlease note that a comprehensive Siesta 4 Rent Home Guide Book detailing home operations and island resources, is readily available for your convenience. We kindly request that you familiarize yourself with this guide upon arrival. If you note any additions you think should be included, please do let us know, and we will be happy to include them for you and our next guests. Thank you for being a guest of Siesta 4 Rent.brbrbrbrInteraction with Guests:brbrWe are available to assist you during your stay. Our office hours are Monday to Friday, 9 AM to 4 PM, and Saturday, 9 AM to 3 PM. For any urgent matters, we're reachable 24/7. The best way to reach us is via the platform's messaging system, where we aim to respond promptly. We're here to ensure your stay at our Siesta Key home is seamless and enjoyable.

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Sleeps

$5730.72

/ Nightly

Private Vacation Home

Siesta Key Oceanfront Palace with Private Beach

Siesta Key, Florida, United States

This direct beachfront palace sits beyond private gates on just under an acre of pure luxury, where you can enjoy sunsets from your own private beach or a terrace on one of three levels. Put your toes in world class sand & turquoise waters, in your own backyard, where boats go by via Big Pass between Siesta and Lido Key. With over 9,000 sq ft of space to entertain, you can enjoy privacy even with a family of 10. Have a cookout at the outdoor kitchen while enjoying a dream pool with hot tub, water slide and grotto. The outdoor patio is inviting with vines crawling up the side of the home and the water views peeking through magical landscaping. Also notable is game room with pool and foosball tables, roof top patio with bar, and gym - it doesn't get better than this. Located at the North end of the key, this provides for fighting the least amount of traffic - take a golf cart taxi to The Village, or drive/bike over the North bridge to key places like Southside Village, Selby Gardens and downtown. Ring doorbell camera at front door.

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$544.97

/ Nightly

Private Vacation Home

Family friendly Siesta Key home with heated pool. 5 minutes drive to beach.

Siesta Key, Florida, United States

You will be close to everything when you stay at this centrally-located house. It's a 2 min drive Siesta Key village restaurants and shops. A 5 min drive or 20 min walk to the #1 beach in US. Supermarket, gas station and pharmacy within 5 min drive. Stocked with beach chairs, umbrellas, cooler, and floats. The pool area has a bbq, full size bar, TV and dining set for 8. The home has a high chair, pack and play, puzzles, books and toys. Trolley stop around the corner that takes you to the beaches, the village and downtown Sarasota. You will certainly enjoy your stay here! Only one booking allowed per 30 day period.

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$892.89

/ Nightly

Private Vacation Home

Beach Palm Villa | Private Heated Pool, Fire Pit, Putting Green, & Spacious Outdoor Lounging Area

Siesta Key, Florida, United States

Beach Palm Villa | Heated Pool + Walk to Siesta Key Beachbrbr Why You'll Love This HomebrImmerse yourself in coastal luxury at Beach Palm Villa, a private Siesta Key retreat just a short stroll from world-famous Siesta Key Beach. Designed for effortless comfort and style, this 4-bedroom oasis combines resort-level amenities with the relaxed rhythm of island living. From poolside lounging to family dinners under the stars, every moment here feels like a treasured memory in the making.brbr ‍ ‍ Perfect ForbrMulti-generational families, friend groups, or couples seeking a luxurious island escape within walking distance to the beach.brbr ️ Imagine ThisbrYou wake to the sound of rustling palms and the promise of another sun-filled day. Brew a cup of coffee in the gourmet kitchen and step outside to your private heated pool, where the morning light dances across the water. Spend your day soaking in the sun, strolling to Siesta Key Beach just 10 minutes away, or perfecting your short game on the outdoor putting green. As evening falls, laughter fills the air around the fire pit while the sky glows in shades of coral and gold. Here, every detail invites you to relax, reconnect, and make lifelong memories. The heart of Beach Palm Villa is its modern, fully equipped kitchen, perfect for culinary creativity and casual gatherings alike. Enjoy regular and Keurig coffee makers, a dishwasher, stainless-steel appliances, and a water purification system that ensures every sip and ingredient is as refreshing as the Gulf breeze. With plenty of prep space and elegant design, cooking here feels effortless and inspiring.brbr Where You'll Sleepbr• Bedroom 1: King Bed, Ensuite Bath, TVbr• Bedroom 2: King Bed, Shared Bath, TVbr• Bedroom 3: Queen Bed, Shared Bath, TVbr• Bedroom 4: Two Twin Bunk Beds with Trundles, Shared Bath, TVbrbr Explore the Areabr• 0.5 Miles (10-Minute Walk) to Siesta Key Beachbr• 0.7 Miles to Siesta Key Village – Dining, Shopping, and Nightlifebr• 7.0 Miles to Downtown Sarasota – Arts, Culture, and Entertainmentbr• 9.6 Miles to St. Armands Circle – Upscale Boutiques and Restaurantsbr• 11.5 Miles to Sarasota-Bradenton International Airport (SRQ)brbr⌛ Don't wait—this home books fast. Your reservation includes peace of mind with our CottageClean™ program: a 6-hour deep clean and 35-point inspection.brbr Need to Know: There is a 1 rental per 30 day period, per Sarasota, FL ordinance, contact us for more information. Reservation must follow under the accordance of the Sarasota County code regulations. The pool is heated from November 15th to April 15th. While the heater works to maintain comfortable temperatures, performance can vary during colder weather.

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Sleeps

$307.93

/ Nightly

Private Vacation Home

[escape to paradise] siesta key beach getaway

Siesta Key, Florida, United States

Walk to siesta beach from this stylish village house. Perfect for couples and group trips. The home is in a central location on Siesta key. Walking distance to Siesta Key village and beach access 7 (less than 1/2 mile).Enjoy the oversized private patio and with garden views or hop on a bike to siesta beach in less than 5 minutes. Both Siesta Key village and Beach access 7 are less than 1/2 mile from the home. Bikes available onsite ($40 per bike per stay by ven.)Unique and newly redesigned ground level unit. Lovely wood floors and a kitchen with an electric stove, microwave and full size refrigerator. Accommodates 2-5 guests with 2 bedrooms & 1 bath, and a couch bed. It is located on the ground level of the home with slider doors that open to a spacious patio and backyard. Please note there is a separate rental unit above, with a separate entrance . There is a washer and dryer at the entrance located in the garage that is shared and available for use from 3-8 pm daily. **Beach Gear items include only towels at this time.** beach cruiser rental please give 24 hour notice. Bikes are located onsite and a waiver and fee will be required.20 minute drive to Sarasota/Bradenton airport.All spaces are private, laundry is shared and available from 4-9 pm dailyBy air Bnb messengerSiesta keys village,

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$5188.47

/ Nightly

Private Vacation Home

Walk to Siesta Key Beach!

Siesta Key, Florida, United States

Your cozy getaway awaits in Siesta Key at this beatiful vacation rental. With 7 bedrooms, 2 kitchen, game room, theater room, 5 bathrooms and 2 family room. brPrivate pool and 2 minutes walking to Siesta key beach. This tranquil retreat is perfect for guests looking to unwind. Kickback, relax, and enjoy everything Siesta has to offer.

7

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5

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20

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