Vacation Rentals By Owner In Siesta Key, FL

Escape to paradise in this lovely upstairs beachfront retreat with a glassed-in balcony offering breathtaking views of the Gulf of Mexico! This spacious 2 bedroom, 2 bath condo features a king-sized bed in the main bedroom, perfect for a romantic getaway, and a queen and full beds in the second bedroom for friends or family. The condo has been newly updated with modern appliances and fresh furniture, ensuring a comfortable and stylish stay. And, plans are underway for a complete bathroom renovation in the near future! With an array of amenities at your fingertips, including shuffleboard, tennis/pickle ball, basketball, two swimming pools, 4 grills, and picnic areas, you'll never want to leave. Book your dream beach vacation today!

Casa Mar - Unit 37 ; 2 Bedroom 2 Bath Beach Front

Siesta Key, Florida, United States

2

Bed

2

Bath

6

Sleeps

$442.78

Escape to a tropical oasis in this beautifully renovated 2 bedroom, 1.5 bath condo on Siesta Key! This stylish retreat boasts a queen-sized bed in the master suite, and a double and single bed in the second bedroom, sleeping up to 5 guests comfortably. The modern kitchen features new stainless steel appliances, perfect for cooking up a storm after a day at the beach. With its prime location just steps from the beach, you'll have easy access to the Gulf's crystal-clear waters and soft white sand. Enjoy the resort's many amenities, including two sparkling pools, shuffleboard, tennis/pickle ball, basketball, and four grills and picnic areas. Book this serene retreat for your next Siesta Key vacation!

Casa Mar - Unit 33 ; 2 Bedroom 1.5 Bath Pool View

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$459.38

Dive into relaxation in this nautical-themed 2 bedroom, 1.5 bath vacation rental on Siesta Key! This charming retreat features a queen-sized bed in the master suite, perfect for a comfortable night's sleep after a day of sun and surf. The second bedroom boasts two single beds, ideal for kids or friends. Enjoy a refreshing soak in the tub after a day at the beach. With amenities galore, including 4 shuffleboard courts, a tennis/pickle ball court, basketball court, and two swimming pools, you'll never be bored! Fire up one of the 4 grills and enjoy a picnic with friends and family at one of the four picnic areas. Book this delightful retreat for your next Siesta Key getaway!

Casa Mar - Unit 31 ; 2 Bedroom 1.5 Bath Pool Side

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1456.39

Las VentanasbrResort-like setting with semi-private pool, rooftop deck, in-house elevator, and 5 terraces in heart of Siesta Village! Just 1-minute walk to Siesta's best Beach and the shopping dining and entertainment of the village! Spacious, bright, airy, and surrounded by palms. Experience Siesta Key's top attractions without sacrificing space and comfort. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiestabrbrWhat Guests Lovebr∙ Terraces and Rooftop –beautiful views from five balconies and rooftop terracebr∙ Semi-private Pool – heated pool and sun shelves shared with just one other unitbr∙ The Beaches – 1-minute to Siesta Key's top beaches with white sand and calm clear waterbr∙ Restaurants – 1-minute walk to the shopping dining and entertainment of the Siesta Villagebr∙ Gulf Breezes –Ventanas means “Windows” and 3000 ft.² of windows catch sea breezes day and nightbr∙ Relaxing – 5 baths and a balcony off every bedroombr∙ Sunsets –walk 1-minute to best sunsets or just enjoy from your rooftop deckbr∙ Activities – a few free bikes and paddleboards provided, but scooter and golf cart 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 – walk to all Siesta Key's top attractions and guaranteed fun for allbrbrThe BeachbrOur beach is the widest, has panoramic views of the gulf to the North-West-and-South, and is the top spot in North America for sunsets. You can swim or wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin sand-dollars and “occasionally” manatee and giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. You can go from the water to lunch or dinner and back to the sand without putting on your shoes.brbrThe LocationbrYou aren't planning one vacation, you're planning vacations for every individual in your party. Whether it's solitude or activities, this property will deliver what they need. It's just steps to the top attractions on the island including 4 beach accesses, and 20 bars and restaurants. Walk right 450ft to the best beaches in America or left 450ft to the world-famous shopping dining and entertainment of the Siesta Key Village. This area has - ice-cream, tide pools, daiquiris, dolphins, fresh oysters, white-quartz-sand, big breakfast, sunsets, amazing seafood, white lagoons, craft beer, sand dollars, live music, shopping, and gourmet donuts. Back at the house, you'll enjoy a semi private pool (shared with just one other unit), as well as private features including - four private gathering areas for your bonding enjoyment including a poolside swim-out room with wet bar, and a rooftop sundeck with ocean views and wet bar. When you'd prefer to relax, you'll find lots of bright and airy out the way rooms and terraces for quiet decompressing.brbrBedroom DetailsbrThis is a huge 4BR, you can sleep up to 13 family style. The master suite (large) has two queen beds with bath en-suite, a twin bed in the alcove and a large terrace. Bedroom #2 has a king bed and terrace. Bedroom #3 has a queen bed with bath en-suite and a terrace. Bedroom #4 is a swimout apt with a queen bed, living room, TV, full bath en suite, and private lanai poolside.brbrBeach 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 ProvidedbrWe provide 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 BringbrIt's 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. 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.

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$230.87

E63 - 2Bd/2B - Directly on Siesta Key Intracoastal, Free Trolley To Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$387.15

Welcome to Gulf Villa — your renovated 2‑bedroom waterfront escape on Siesta Key. Enjoy peaceful Grand Canal views from your private porch, then walk just 3 minutes to world‑famous Siesta Key Beach or the Village for dining, shopping, and nightlife. Bright, stylish interiors and unbeatable location make this vacation rental ideal for couples, families, or friends seeking comfort and relaxation.brbr☀ Beach Accessbr☀ Private Dockbr☀ Poolbr☀ BBQ Grillbr☀ Patiobr☀ Pet Friendlybrbr :br : Private outdoor seating overlooking the scenic Grand Canal for morning coffee or evening sunsets.br : A leisurely 3‑minute walk to Siesta Key Beach and steps from Siesta Village shops and restaurants.br : Bright, open‑concept living and dining with modern finishes and comfortable furnishings.br : Two queen beds plus flexible living space—ideal for families or friends.br : Guest‑only heated in‑ground pool, pool deck with loungers, and a gas grill for outdoor meals.br : Private guest‑only boat/fishing dock on the Grand Canal for memorable waterfront moments.br : Beach wagon, chairs, and towels provided so you can head to the sand without the hassle.br : Smart TVs in living room and bedrooms, on‑site laundry, complimentary Wi‑Fi, and off‑street parking.brbrOpen, airy living areas flow into a fully equipped kitchen—perfect for family breakfasts or casual dinners. Two comfortable bedrooms offer restful nights, while the living room and porch expand your space for relaxing and entertaining. Thoughtful touches throughout make Gulf Villa a welcoming base for your Siesta Key getaway.brbr Guests have full access to the villa, the guest‑only heated pool and lounge areas, the private canal dock, and on‑site laundry. We supply beach essentials and parking to keep your stay easy and stress‑free.brbr brSet in the heart of Siesta Key, Gulf Villa places you minutes from powder‑white sand, waterfront dining, and local shops. Walk to the Village for fresh seafood, live music, and island vibes—no long drives required.brbr brbr☀ Waterfront tranquility with direct canal access.br☀ Renovated, comfortable interiors and resort‑style amenities.br☀ Walk everywhere: beach, Village, and local hotspots.br☀ Family‑friendly layout with practical beach gear and parking.brbr to enjoy a perfect blend of comfort, style, and convenience at Gulf Villa.brbr★ :br ☀ Sarasota Beach: 4 min walkbr ☀ Siesta Key Craft Festival: 7 min walkbr ☀ Sunset Beach: 10 min walkbr ☀ Point Of Rocks: 9 min drivebrbr★ :br ☀ Gilligan`s Island Bar & Grill: 5 min walkbr ☀Summer House Resturant: 5 min walkbr ☀ Lobster Pot Restaurant: 6 min walkbrbr★ :br ☀ CVS Pharmacy: 12 min drivebr ☀ Sarasota Memorial Hospital: 14 min drivebrbr★ :br ☀ Beach Rd @ Calle De La Siesta: 3 min walkbr ☀ Ocean Blvd @ Calle Miramar NB: 4 min walkbr ☀ Ocean Blvd @ Canal Rd SB: 6 min walkbrbr★ :br ☀ Sarasota Bradenton International Airport: 26 min drivebrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Thunder By The Bay Music & Motors Festival: Feb 13–15, 2026br☀ `Say I Do Again` Vow Renewal Ceremony: Saturday, Feb 14, 2026br☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N` Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026

Gulf Villa | Beachfront Vibes & Dock | Pool | BBQ

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$577.65

Immerse yourself in a vibrant 3BR, pet friendly coastal retreat designed for bright, modern comfort and playful beachside charm. Just steps from Siesta Key Beach and the lively Village, this private first-floor oasis blends natural light, colorful décor, and spacious open-design living. From relaxing indoors to unwinding outdoors, every corner of this home is crafted to make your stay easy, memorable, and full of island warmth.brbr☀ Private Poolbr☀ Hot Tubbr☀ Game Consolebr☀ BBQbrbrBelow is a closer look at what this tropical escape offers.brbr★ PROPERTY HIGHLIGHTSbr☀ 3 Comfortable Bedrooms (Sleeps up to 12)br☀ Open-design living area with arcade tablebr☀ Smart TVs + Wi-Fibr☀ Fully equipped kitchenbr☀ Luxury Tiki hot tub + Private splash poolbr☀ Stunning mermaid mural (perfect for photos!)br☀ Fully fenced outdoor areabr☀ Parking includedbr☀ Steps from Siesta Key Beach & Villagebrbr★ LIVING ROOMbrRelax, gather, and enjoy a bright, artsy living area filled with natural light and cheerful décor.br☀ Two comfy sofas (convertible to queen beds)br☀ Smart TVbr☀ Coffee tables + reading lampsbr☀ Arcade game table for added funbrbr★ KITCHEN & DININGbrA fully equipped kitchen makes cooking effortless, whether you’re preparing breakfast or family dinners.br☀ Microwave, stove, oven, dishwasherbr☀ Coffee maker, toaster, blender, hot water kettlebr☀ Refrigerator/freezerbr☀ Pots, pans, dishes, glassware, utensilsbr☀ Kitchen bar seating for 10brbr★ BEDROOMSbrAll bedrooms are designed for comfort with soft décor and hotel-quality linens.br☀ Queen beds with premium memory-foam mattressesbr☀ Smart TVsbr☀ Closets with hangers and shelvingbr☀ Dressers + nightstands with reading lampsbr☀ Additional sleeping: 2 queen sofa beds in living roombrbrSleeping Layout:br• Master BR: Queen bed + Queen futonbr• BR 2: Queen bedbr• BR 3: Queen bedbrbr★ BATHROOMSbrBoth bathrooms include all essentials to ensure a carefree stay.br☀ Bathtub/shower combobr☀ Walk-in showerbr☀ Towelsbr☀ Shampoo, conditioner, body soap, shower gelbr☀ Vanity + mirrorbr☀ Hair dryerbrbr★ OUTDOOR AREAbrYour private tropical escape awaits outside.br☀ Luxury Tiki hot tubbr☀ Splash pool with waterfall vibesbr☀ Lounge seatingbr☀ String lightsbr☀ Outdoor showerbrbr☀ Fully fenced backyard for privacybr☆ Perfect for families, groups, beach lovers, and anyone looking for a colorful, fun, and private Siesta Key escape—book now and experience the magic of Siesta Key!brbr★☆ Guest Attractions nearby in Siesta Key Beachbr☀ Siesta Key Craft Festival – 4 min walkbr☀ Sarasota Beach – 8 min walkbr☀ Sunset Beach – 8 min walkbr☀ Point of Rocks – 11 min drivebr☀ Turtle Beach – 14 min drivebr☀ Sarasota Art Museum – 18 min drivebr☀ Bayfront Park – 20 min drivebr☀ TPC Prestancia (Golf Club) – 20 min drivebr☀ Ted Sperling Park Nature Trail – 27 min drivebr☀ Quick Point Nature Preserve – 28 min drivebr☀ South Lido County Park – 28 min drivebr☀ The John and Mable Ringling Museum of Art – 29 min drivebr☀ Ca' d'Zan (Historical Museum) – 30 min drivebr☀ South Lido Key Beach Park on the Gulf – 30 min drivebr☀ Manatee Village Historical Park – 43 min drivebr☀ Palma Sola Botanical Park – 56 min drivebrbr★☆ Restaurants Nearby in Siesta Key Beachbr☀ Gilligan's Island Bar & Grill – 3 min walkbr☀ Lobster Pot Restaurant – 3 min walkbr☀ The Cottage – 3 min walkbr☀ Daiquiri Deck Siesta Key Village – 3 min walkbr☀ Summer House Resturant – 4 min walkbr☀ Siesta Key Oyster Bar – 4 min walkbr☀ Another Broken Egg Cafe – 4 min walkbr☀ Sun Garden Cafe – 4 min walkbr☀ Cafe Gabbiano – 5 min walkbr☀ The Old Salty Dog Siesta Key – 7 min walkbr☀ Clayton's Siesta Grille – 10 min drivebr☀ SPEARFISH GRILLE – 11 min drivebr☀ The Toasted Yolk Cafe – 14 min drivebr☀ Florence & The Spice Boys – 15 min drivebr☀ Casa Masa - The Landings – 17 min drivebrbr★☆ Airports in Siesta Key Beachbr☀ Sarasota Bradenton International Airport – 29 min drivebr☀ Hidden River Airport-22FA – 47 min drivebrbr★☆ Transportation Nearby Siesta Key Beachbr☀ Ocean Blvd @ Calle Miramar NB – 3 min walkbr☀ Ocean Blvd @ Avenida Madera – 4 min walkbr☀ Ocean Blvd @ Canal Rd SB – 4 min walkbrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N' Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026brbr☆ Free hop-on hop-off rides to top island attractions with two local services – 77 Siesta Islander and Bay Runner Trolleybrbr☆ The Breeze-local bus service – makes travel simple between Downtown Sarasota and Siesta Keybrbr★☆ Hospitals in Siesta Key Beachbr☀ SMH Urgent Care Center at Stickney Point Rd – 11 min drivebr☀ Sarasota Memorial Hospital – 14 min drivebr☀ HCA Florida Sarasota Doctors Hospital – 23 min drivebrbrGuest accessbrThe duplex unit and its private outdoor spaces are reserved entirely for you throughout your stay—offering uninterrupted comfort so you can relax, unwind, and feel right at home.brbrOther things to notebr★ Additional Accommodation OptionsbrTraveling with a larger group or finding your preferred dates unavailable We offer an additional unit within the duplex, as well as other listings in the area. Please visit our host profile to view all available properties.br★ Pet-Friendly HomebrPets are welcome on this property. Please note that an additional cleaning fee may apply if excessive pet hair, stains, or odors are detected after checkout.br★ Rentals, Activities & ToursbrA list of Preferred Vendors is provided for convenient rentals, activities, and tours. Options include:br✔ Golf Carts br✔ Mopeds br✔ Mini Carsbr✔ Umbrellas br✔ Bikes (Daily/Weekly)br✔ Kayaks br✔ Paddleboardsbr✔ Fishing Chartersbr✔ Adventure Toursbr✔ Sunset Cruises br✔ Eco-ToursbrGuests receive 10% off all listed prices using a special code provided before check-in.br★ Cleaning & SanitizationbrYour safety is our priority. Our team follows a detailed cleaning and sanitization process after every checkout to ensure a spotless, hygienic stay.br★ No Smoking IndoorsbrSmoking inside the home is strictly prohibited. Evidence of indoor smoking will result in an additional fee for odor removal and deep cleaning.br★ No Parties or EventsbrTo maintain a peaceful environment and protect the home’s condition, parties and large events are not permitted.brThank you for your understanding and cooperation.

Unique & Artsy Beach Getaway: Pool ~ Hot Tub ~ Pkg

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$452.49

Experience Siesta Key like a local in this 3-Bedroom, 3 Bathroom house. With 2 king beds and 1 queen bed, this wonderful property offers a serene escape for guests. Enjoy the gorgeous surroundings and modern amenities like WiFi, AC, and a washer/dryer. The master bathroom even comes equipped with a bidet for added comfort. Fall in love with Siesta Key and enjoy the magic the island has to offer.

Waterfront Siesta Key House Within Walking Distance of the SK Village and Beach

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$393.44

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

Villa

Island House Beach Resort V15

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$1008.19

Mandevilla | 2 Balconies + 3 King Suites | 0.2 Miles to Siesta Key Beachbrbr Why You'll Love This HomebrMandevilla combines two top-floor retreats into one seamless haven—complete with 3 private king bedrooms, 2 balconies, dual kitchens, and easy access to both Siesta Key Beach and the Village's vibrant energy.brbr ‍ ‍ Perfect ForbrLarge families, friend groups, or multi-generational travelers looking for spacious living, walkability, and tropical charm.brbr ️ Imagine ThisbrWake up to sunlight streaming through balcony doors and sip your morning coffee overlooking the palm-lined streets below. Walk just 0.2 miles to Siesta Key Beach for a day of sand and surf, then come home for a mid-afternoon dip in the shared heated pool. Prepare group meals in one of two fully equipped kitchens, dine together on the balcony, and wind down in your private bedroom suites—each with a king bed and plush linens. At Mandevilla, every space is designed for connection, comfort, and a breezy island rhythm.brbr Where You'll Sleepbr- Bedroom 1 (Plumbago): King Bed, Ensuite Bath, Second Floor, TVbr- Bedroom 2 (Plumbago): King Bed, Shared Bath, Second Floor, TVbr- Living Room (Plumbago): Queen Sleeper Sofabr- Bedroom 3 (Vinca): King Bed, Shared Bath, Second Floorbr- Living Room (Vinca): Queen Sleeper Sofabrbr Explore the Areabr- 0.2 miles to Siesta Key Beachbr- 0.1 miles to Siesta Key Villagebr- Walk to beachfront cafés, boutiques, and barsbr- Enjoy a car-free lifestyle with bike rentals nearbybrbr Don't wait—this home books fast. Every reservation is covered by our CottageClean™ Program, including a 6-hour deep clean and 35-point inspection to ensure total peace of mind upon arrival.brbr Need to Know: Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. This home is part of a duplex-style structure with shared walls, floors/ceilings, and outdoor amenities. Located on the second floor with stair access at both front and rear of the property. Heated pool available from November 15 – April 15. If any guest has difficulty with stairs, please contact us for alternative accommodations.

Mandevilla | Pet Friendly Home Located in Siesta Key Village w/ Heated Pool, Walk to Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$404.21

Vinca | Top-Floor Hideaway + Balcony | 0.2 Miles to Siesta Key Beachbrbr Why You'll Love This HomebrTucked just above Siesta Key Village, Vinca offers a peaceful second-floor perch with a private balcony, a shared heated pool, and all the charm of coastal living—just a short stroll from sugar-white sands.brbr ‍ ‍ Perfect ForbrCouples, solo travelers, or small families seeking a quiet yet walkable island escape near the beach.brbr ️ Imagine ThisbrGreet the morning sun with coffee on your private balcony, just moments before heading to Siesta Key Beach—only 0.2 miles away. Stroll the shops of the Village or grab lunch at a local café before cooling off in the shared heated pool. Come evening, relax on the screened-in lanai with a good book, or enjoy dinner in the fully stocked kitchen. Whether it's your first visit or your fifth, Vinca offers cozy simplicity with just the right island touch.brbr Where You'll Sleepbr- Bedroom 1: King Bed, Shared Bath, Second Floor, TVbr- Living Room: Queen Sleeper Sofabrbr Explore the Areabr- 0.2 miles to Siesta Key Beachbr- 0.1 miles to Siesta Key Villagebr- Walk to ice cream shops, beach bars, and boutiquesbr- Enjoy a laid-back, walk-everywhere lifestylebrbr Don't wait—this home books fast. Your stay includes our CottageClean™ Program, a 6-hour deep clean and 35-point inspection before arrival—so you can start relaxing the moment you arrive.brbr Need to Know - Starter packs of kitchen and toiletry essentials provided for a seamless first couple of nights. This home is part of a duplex and may share walls, floor/ceiling, or outdoor spaces. Located on the second floor with rear-facing stair access. Heated pool available November 15 – April 15. If any guest has difficulty with stairs, please contact us for alternative accommodations.

Vinca | Great Location in Siesta Key Village w/ Heated Pool, Walk to Beach!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$628.28

Unwind in Siesta Key at this lovely house. With 4 bedrooms including 1 king bed, 4 twin beds, and a crib, guests will find ample space to relax. The 4 bathrooms feature a bathtub, jetted bathtub, and shower for ultimate comfort. House includes a pool and spa as well as lounge chairs and table on deck for al fresco dining. AC, WiFi, heating, grill, and a washing machine and dryer are available for convenience. Experience the magic of Siesta Key at our house. Located on a quiet tree-lined street one mile away from the Siesta Key Village. Note the room with the crib will have two twin beds. The crib will be available for interested families.

4-bedroom, 3.5 bath house w/Pool, AC, WiFi in Siesta Key; 1 mile from Village

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$407.84

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

Villa

Island House Beach Resort V8

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$603.18

Under new ownership, this exceptional unit has been thoughtfully upgraded throughout. All-new premium windows and doors invite the beautiful Siesta Key “beach feel” indoors, while the brand-new, heavily insulated exterior lanai enclosure allows the interior sliding doors to be removed—creating a wide-open, airy layout that feels as though the Gulf breeze is drifting right into your living space. Enjoy the soothing sound of the surf day or night, just steps from the sand.brbrA brand-new HVAC system provides reliable comfort around the clock. This apartment is uniquely positioned with no shared common walls, offering rare sound privacy. You’ll also enjoy two close, easy-access VIP parking spaces.brbrForget the hassle—this ground-floor unit requires no stairs, no elevator, and no FOB for entry, ensuring effortless access for groceries, luggage, and everyday convenience. A free washer and dryer are located just a few steps from the front door.brbrInside, this beautifully appointed 2-bedroom, 2-bathroom condo features a spacious primary ensuite with a king-size bed, a guest bedroom with two twin beds, and a sleeper sofa in the living area. The home offers a large living room, dedicated dining area, and a fully equipped kitchen with full-size appliances and granite countertops. You’ll also find three large flat-screen televisions and central heating and air conditioning for year-round comfort.brbrStep onto the lanai and take in the gorgeous views of the Gulf of Mexico—truly spectacular scenery with magnificent nightly sunsets you’ll never forget.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!

Apartment

Island House Beach Resort 1S

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$475.84

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

Apartment

Island House Beach Resort 3N

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$313.16

Beachfront Condo Complex, Partial Gulfview, AMAZING location!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$228.57

This 2 bedroom, 2 bath unit has an expansive, open floor plan with beautiful décor, light and bright, flat screen TV, washer/dryer, and a beautiful kitchen with granite counter tops and stainless steel appliances. The screened in balcony off the living room has a lovely view of the pool and grounds. Newly appointed with lovely furnishings and beautiful wood laminate flooring.brbrThe Bay Oaks complex is a Siesta Key island development which is a stone’s throw away from the shores of Sarasota Bay and the Gulf of Mexico. The facilities and amenities inside the Bay Oaks community include a fishing pier, dock, a fabulous clubhouse, a resort-style swimming pool, sauna, tennis courts and BBQ area. Close proximity to the South Bridge. Convenient access to in-town attractions, including Ringling Museum of Arts, St. Armand’s Circle, Van Wezel and the Burns Square. Also close proximity to Siesta Village Restaurants, Shopping and the #1 Beach, Siesta Beach. You will love it here!brbrStarter Supplies ProvidedbrbrTo help you get settled, we provide a limited supply of essential starter items upon arrival. These are intended to get you through the first few days and may not last for the duration of your stay,.brbrKitchen & LaundrybrPaper towelsbrDishwashing liquidbrAll-purpose cleaning spraybrDishwasher tablets (if a dishwasher is available)brTrash bags (a few provided in each trash can)brLaundry detergent for one load (if the property has a washer)brbrBathroomsbrToilet paperbrSmall bottle of shampoo & ConditionerbrBar soap at each sinkbrbrGuests are responsible for purchasing any additional supplies needed during their stay.brbrSTARTER SUPPLIES PROVIDED INTENDEDbrTo Buy Time Before Purchase Quantitybr-----------------------------------------------------------brKitchen and Laundrybr• (1) Roll of paper towelsbr• (1) Small bottle dish washing liquidbr• (1) Small bottle cleaning liquidbr• (1) Scouring padbr• (2) Dishwasher tabletsbr• (2) Plastic trash bags in each trash canbr• Plastic trash bagsbr• (1) Load washer detergent IF property has washerbrbrBathroomsbr• (2) Rolls of toilet paperbr• (1) Small bottle of shampoobr• (1) Small bar of soap at each sinkbr• (1) Hair dryerbr• Bath towels, hand towels and washclothsbr• Guests are expected to wash all towels prior tobr• Departure in properties that have washing machinebr• Bedroomsbr• All Linens: Sheets, pillowcases and pillows, blanketsbr• Our cleaning company strips beds and launders linensbr• Beach Relatedbr• Beach towelsbr• Small coolerbrbr--------------------------------------------------brClosest Airports to Siesta Keybr--------------------------------------------------br• (SRQ) Sarasota - (20) Minutesbr• (PIE) St. Petersburg - (50) Minutesbr• (PGD) Punta Gorda- (55) Minutes br• (TPA) Tampa - (60) Minutesbr• (RSW) Ft. Myers - (90) Minutesbr• (MCO) Orlando - (2) Hoursbr• (SFB) Sanford/Orlando - (2) Hoursbrbr• Allegiant Airlines currently is the most cost-effective and flies direct from many Midwest airports to SRQ, PIE and PGDbr• Frontier Airlines sometimes offers unbelievable airfare deals and just began flying into Sarasotabr• Note - TPA and PIE are NOT THE SAME AIRPORT even though both are often listed as TAMPA / St. Petebr• Note - MCO and SFB are NOT THE SAME AIRPORT even though both are in Orlando

Bay Oaks - Amazing Siesta Key Condo on Intracoastal Waterway!

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$327.71

Experience the perfect Siesta Key getaway in this ultimate 1BR villa, located just steps from the world-famous beach and a short walk to village dining and nightlife. Unwind by the shared pool, relax on sun loungers or enjoy outdoor meals with the BBQ grill. Inside, a fully stocked kitchen makes home-cooked meals easy and convenient. Pet-friendly and ideal for couples, solo travelers or small families, this cozy villa offers comfort, location and relaxation. Book your Florida beach escape today.brbr☀ Siesta key beach br☀ Private Dockbr☀ Poolbr☀ BBQ Grillbr☀ Patiobr☀ Pet FriendlybrbrDesigned for effortless island living, this bright retreat pairs a private patio and exclusive guest‑only heated pool with modern comforts and easy access to Siesta Key Beach and the Village.brbr :brbr ‑ : Year‑round relaxation in a lush, lounge‑ready setting.br ‑ : Wagon, chairs, and towels provided so you can hit the sand in minutes.br : Secluded outdoor spot for morning coffee or evening sunsets.br : Fully equipped kitchen, high‑speed Wi‑Fi, and Smart HDTV for streaming.br : Off‑street parking included for stress‑free arrivals.br : Minutes from Siesta Key’s powder‑white quartz sand and steps from Village restaurants and boutiques.brbrBright, well‑appointed living area with an open flow to your private patio. Comfortable bedroom and thoughtful touches throughout—granite countertops, modern appliances, and cozy seating make this a perfect base for couples or solo travelers seeking tranquility and convenience.brbr brGuests have full access to the heated pool, outdoor lounge and BBQ area. We supply beach gear and an outdoor shower so you can rinse off after a day on the sand.brbr brSet just minutes from Siesta Key Beach, you’re close enough for sunrise walks and sunset cocktails in the Village—no long drives required.brbr brbr☀ Hassle‑free beach days with provided gear.br☀ Relaxing pool and private outdoor space.br☀ Modern amenities and easy walkability to dining and nightlife.br☀ Ideal for couples or solo travelers wanting a peaceful coastal escape.brbr to enjoy a relaxed, poolside Siesta Key getaway—comfort, convenience, and coastal charm all in one place.brbr★ :br ☀ Sarasota Beach: 4 min walkbr ☀ Siesta Key Craft Festival: 7 min walkbr ☀ Sunset Beach: 10 min walkbr ☀ Point Of Rocks: 9 min drivebrbr★ :br ☀ Gilligan`s Island Bar & Grill: 5 min walkbr ☀Summer House Resturant: 5 min walkbr ☀ Lobster Pot Restaurant: 6 min walkbrbr★ :br ☀ CVS Pharmacy: 12 min drivebr ☀ Sarasota Memorial Hospital: 14 min drivebrbr★ :br ☀ Beach Rd @ Calle De La Siesta: 3 min walkbr ☀ Ocean Blvd @ Calle Miramar NB: 4 min walkbrbr★ :br ☀ Sarasota Bradenton International Airport: 26 min drivebrbrb ★☆ Upcoming Events in Siesta Key Beach:/bbr☀ Thunder By The Bay Music & Motors Festival: Feb 13–15, 2026br☀ `Say I Do Again` Vow Renewal Ceremony: Saturday, Feb 14, 2026br☀ Elton John Tribute Concert: Feb 27, 2026br☀ Guns N` Roses Tribute Concert: Feb 28, 2026br☀ Sarasota Jazz Festival: Mar 9–14br☀ Sarasota County Fair: Mar 13–22br☀ Spring Break Season: All Monthbr☀ Siesta Key Drum Circle: March, 2026 Every Sunday in br☀ Siesta Key Farmers Market: March 2026, Every Sunday (9:00 AM – 1:00 PM) br☀ Embracing Our Differences (Outdoor Art Exhibit)—till April 13, 2026

Newly Renovated Beach-Side 1BR villa • Pool • BBQ

Siesta Key, Florida, United States

Bed

Bath

Sleeps

$303.87