Vacation Rentals By Owner In Siesta Key, FL

$179.24

Comfy and Cozy on Siesta Key

Siesta Key, Florida, United States

Enjoy remodeled 2 bedroom 2 bathrooms at 55 + community condo on the 4th floor with spectacular views and all amenities for enjoyable stay. 1 king size bed and two full size beds. Electronic recliners for evening relaxation after day on the beach or pool for movie nights. If you enjoy cooking, kitchen is equipped with all you need. Heated pool, hot tub, exercise room is just a few things on sight. Just cross the street (3 minutes walk) and you will enjoy the powdery sand of the beach. Wagon, beach chairs, towels all provided. Free trolley will take you to town to enjoy restaurants, cafes and shopping, and bring you back at the door. Just bring your swimsuit everything else is waiting for you. brSiesta Key offers water sports, sailboarding, fishing, snorkeling and parasailing.brDowntown Sarasota, less than eight miles north, is Florida's cultural center, offering attractions like the John Ringling Mansion and Art Museum, Monte Marine Aquarium as well as Marie Selby Botanical Gardens seven miles away. brPlease note: association requires background check 2 weeks prior to arrival by third party, $150 fee and government issued picture ID.

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$272.11

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Steps to 2025 #1 Rated Beach in USA Fun-n-Sun Modern 2+2 Condo Pool Pickleball

Siesta Key, Florida, United States

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$455.76

/ Nightly

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Welcome to Paradise! Welcome To Paradise!

Siesta Key, Florida, United States

pYou'll find bicycles, water sports equipment, and more on site at this beach condo. Siesta Key Beach is just steps away and Crescent Beach is within an easy 11-minute walk, so leave your car at the property, which offers covered onsite parking. /ppAfter you return to this 1290-sq-ft condo, you can unwind at the beach (enjoy the sun loungers!), chill by the communal pool, or sip a drink on the deck or patio; you may also like the BBQ grill. For a change of scenery, come inside and enjoy the free WiFi, cable/satellite TV, and DVD player. /ppThis 2-bedroom, 2-bathroom rental features a living room, air conditioning, and a printer. Bathroom amenities include a hair dryer, towels, and toilet paper. The kitchen is equipped with an oven, a stovetop, and a refrigerator, as well as a coffee maker, an ice maker, and a microwave. And you can even pack a bit lighter because there's a washer and dryer. /p

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$318.78

/ Nightly

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Spacious 2BR condo on Siesta Key with beach access - GBB 1272

Siesta Key, Florida, United States

Escape to this beautifully updated two-bedroom, two-bathroom vacation rental at the Gulf and Bay Club Bayside, Professionally managed by Gulf Coast Vacation Rentals, where comfort meets convenience in the heart of Siesta Key. With beach access just a stroll away, this inviting retreat is the perfect place to soak up the Florida sunshine and enjoy the island's world-famous white sands.brbrInside, the open-concept layout is enhanced by stylish tile flooring throughout, creating a clean, modern feel. The spacious master bedroom features a luxurious king-size bed, ensuring restful nights, while the guest room offers two double beds, making it ideal for families or groups. Recently redecorated and furnished with thoughtful amenities, this home-away-from-home provides everything you need for a relaxing stay.brbrLocated in the sought-after Gulf and Bay Club Bayside community, you'll have access to fantastic on-site amenities, including two heated pools, tennis and pickleball courts, and a well-equipped fitness center. Explore the vibrant Siesta Key Village just minutes away, where you'll find unique shops, fresh seafood restaurants, and lively entertainment.brbrWhether you're looking to relax by the pool, take morning walks on the beach, or explore the charm of Siesta Key, this vacation rental is the perfect base for creating unforgettable memories.brbrHouse Rules: No Motorcycles, golf carts, RVs, boats, or trailers allowed. No smoking. No burning candles inside of lodging. No parties. No Pets.

2

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2

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4

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$1259.78

/ Nightly

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True Gulf View Siesta Key Beach Condo Private Beach Access

Siesta Key, Florida, United States

Beachfront Siesta Key—full Gulf views + private beach access. Wake up to sparkling water views, sip coffee in the sunroom, then head straight down to Siesta Key Beach’s famous sand. This updated 2BR/2BA condo sleeps 6 and is inside a gated beachfront resort with 24/7 security—perfect for an easy “park it and relax” vacation. Guests love the beach chair service at our beach entrance: complimentary lounge chairs are delivered and set up in the morning by request. Umbrellas are $20/day and they’ll set those up too, and cabanas or cushioned loungers are available to rent by reservation if you’d like an upgraded setup. When the attendants aren't on duty, guest are welcome to grab the lounge chairs themselves. The beach team returns later to collect everything—so no hauling chairs back. Inside the condo, you’ll enjoy bright, clean modern coastal style and a comfortable place to recharge. On the resort grounds, enjoy amenities including 2 heated pools, tennis, pickleball, a fitness center, and BBQ grills/beach pavilion (reserve at the front office), along with on-site community laundry room + covered parking. Walkable to Point of Rocks—a local favorite for snorkeling. Wristbands are issued for registered guests (required on property/when entering from the beach). If you’re bringing a car, a parking pass is required (we’ll collect vehicle make & color for resort registration). Getting around without a car is easy: the Siesta Key Frog Hop runs ~9am–1am—call 844-Frog-Hop about 20 minutes ahead; there’s no ride fee (tips only), they pickup and drop-off wherever you are on Siesta Key. We’d love to host you—come unwind, wake up to breathtaking Gulf views, soak up the sunsets, and enjoy the best of Siesta Key right outside your door.

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$1081.05

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NEW LISTING! The Village Breeze (2 units) 4BR/4Bath Pool, Beach - Siesta Village Living!

Siesta Key, Florida, United States

The Village Breeze 4BR (REMODELED '25), a Gertrude Rentals property. No car required! Two side by side 2BR/2Bath units in an enviable location on quiet street, with heated Pool, near Beach, but just 250ft to the world famous Siesta Key Village. A true favorite of initiated guests, and sure to provide a combination of fun and rejuvenation you won't find in other getaways. *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!brbrWhat Guests Lovebr∙ The Village – 1-min walk to 25 restaurants in world famous Siesta Villagebr∙ The Fun – steps to live music, daiquiris, oysters, stone crab, craft beer, ice cream & donutsbr∙ Space - 2 separate private units (4BR total) perfect for larger groups who enjoy spacebr∙ Decor – beautifully remodeled thru-out in May 2025br∙ Sunsets – 8-min walk to best sunsets in America & 300-degree Gulf viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ Activities - kayak, bike, paddleboard, scooter, golf cart rentals nearby br∙ No Car Required - you're already where you want to be:)br∙ The Memories - one of a kind Siesta Key experience, the favorite of initiated visitorsbrbrProperty Truths - Our front is residential, but the back is alley access for stores. This is the heart of Siesta Village with many nearby shops restaurants stores and attractions. It won't be noisy, makes shopping and other activities convenient, but we want you to be aware.brbrbrThe Location – The possibilities are endless! Enjoy the best Beaches, Seafood, Drinks, Ice-Cream, Shopping, Oysters, Live-Entertainment, fresh-Donuts, Daiquiris, big-Breakfast, and the Coldest-Beer on the Island. Rare secluded street in the heart of Siesta Keys world famous Village. Just a short walk to two of the best beaches on the planet and only 250 feet to all the best of the Village. One of only four units in this building. The beaches at this location are the widest and have panoramic views of the gulf to the North-West-and-South and are the top spot in North America for viewing sunsets. You can swim or “often” wade to Sand Dollar Island, a naturally occurring white sand cay popular with dolphin's sand-dollars and “occasionally” giant-conch. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. This is the only Siesta neighborhood where you can go from the water to lunch or dinner and back to the sand without putting on your shirt and shoes. brbrPossible Itinerary - Wakeup, decide if you will wear shoes today, then head to Sun Garden Café for a Crab Cake Benedict. Theirs is the best and they serve breakfast til 12 so there's no rush. Eat there Al Fresco, return to the pool, or walk over to the beach and look for dolphins, swim, bike, or just or just go back to sleep. This is a special spot so exploring a little will be worth your while. I like wading out to the sand bar at low tide. Bike rides on the beach are also amazing. Bike south to check out Point of Rocks or north and east to Big Pass. I usually skip lunch and have a 3PM happy hour meal at SKOB or the Hub, after drinking my fill I grab a real dinner, then walk back down to the beach to watch the sunset and digest. The sunsets are amazing, it's what leaf season in the north would be like if it happened every day, and if they had dolphins and great weather there. Now it's dark and you can go out or go to bed, but you have to make a decision. While deciding consider my grandmothers advice “Life is a string of pearls and you never know how many you have left.”- GVLJbrbrBedroom DetailsbrThis is two side by side, ground floor 2BR units (4BR total, sleeps 12). Each unit has a king bedroom, a queen bedroom, and a queen sleeper sofa in the living room. If you need more space, I can get an additional unit nearby. brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, and usually have a few bikes and a paddleboard. 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 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.

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$1804.18

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Apartment

NEW LISTING! The Village Breeze 6BR with heated Pool, near Beach, 250ft to Siesta Key Village!

Siesta Key, Florida, United States

The Village Breeze 6BR (REMODELED '25). No car required! Two side by side 2BR/2Bath Siesta Key vacation rentals in an enviable location on quiet street, with heated Pool, near Beach, but just 250ft to the world famous Siesta Village. A true favorite of initiated guests, and sure to provide a combination of fun and rejuvenation you won't find in other Siesta Key getaways. *NEW LISTING!! Please read the other Gertrude Rentals reviews. We are very proud of them!brbrWhat Guests Lovebr∙ The Siesta Village – 1-min walk to 25 restaurants in world famous Siesta Villagebr∙ The Patios – two separate private patios, only two other units in the complex have thisbr∙ The Fun – steps to live music, daiquiris, oysters, stone crab, craft beer, ice cream & donutsbr∙ Decor – beautifully remodeled thru-out in May 2025br∙ Privacy – three units for the price of one large unit means being together and having room to relaxbr∙ Sunsets – 8-min walk to best sunsets on Siesta Key & 300-degree Gulf viewsbr∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conchbr∙ Activities - kayak, bike, paddleboard, scooter, golf cart rentals nearby br∙ No Car Required - you're already where you want to be:)br∙ The Memories - one of a kind Siesta Key experience, the favorite of initiated visitorsbrbrProperty TruthsbrOur front is residential, but the back is alley access for stores. This is the heart of Siesta Village with many nearby shops restaurants stores and attractions. It won't be noisy, makes shopping and other activities convenient, but we want you to be aware.brbrThe BeachbrOur part of Siesta Key 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 HomebrExperience all Siesta Key's top attractions without sacrificing comfort and amenities. Beautifully remodeled thru-out in May 2025 with a heated pool. Perfect for couples and small families looking for the ease and relaxation of beach village living. Just 1-minute walk to the heart of the Village and shopping dining and live entertainment at 30 establishments!brbrBedroom DetailsbrThree units, each unit has one king bedroom, one queen bedroom, then there is a queen sleeper sofa in the living room. You can sleep 18 people total. Need more space Ask for a neighboring unit!brbrPossible Siesta Key ItinerarybrWakeup, decide if you will wear shoes today, then head to Sun Garden Café for a Crab Cake Benedict. Theirs is the best and they serve breakfast till 12 so there's no rush. Eat there Al Fresco, return to the pool, or walk over to the beach and look for dolphins, swim, bike, or just or just go back to sleep. This is a special spot so exploring a little will be worth your while. I like wading out to the sand bar at low tide. Bike rides on the beach are also amazing. Bike south to check out Point of Rocks or north and east to Big Pass. I usually skip lunch and have a 3PM happy hour meal at SKOB or the Hub, after drinking my fill I grab a real dinner, then walk back down to the beach to watch the sunset and digest. The sunsets are amazing, it's what leaf season in the north would be like if it was warm and happened every day.brbrBeach Gear ProvidedbrWe provide beach towels, chairs, carts, umbrellas, and usually have a few bikes and a paddleboard. 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 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.

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$624.78

/ Nightly

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2BR Penthouse - Stunning Beach Views on Siesta Key, Access to 3 pools

Siesta Key, Florida, United States

The stunning vistas of The Jamaica Royale Penthouse welcome you to your dream condo located on the 8th floor, overlooking the magnificent Siesta Key Beach. This fully remodeled and elegantly furnished 2-bedroom, 2-bathroom condo is the perfect getaway for anyone looking to enjoy the beauty of the Gulf Coast.brbrAs soon as you step into the condo, you'll be struck by the stunning views of the beach, which can be enjoyed from every corner of the unit. The floor-to-ceiling windows flood the condo with natural light, creating a warm and inviting atmosphere, allowing you to soak in the breathtaking sunsets and the sparkling waters of the Gulf of Mexico. With a large wrap-around balcony, you can enjoy the breathtaking views from every angle, savoring the warm sun and gentle sea breeze.brbrThe living room boasts comfortable living room furniture and a large flat-screen TV, perfect for entertaining or relaxing with loved ones. The dining area is adjacent to the living room and seats six people comfortably. The kitchen is fully equipped with modern appliances, granite countertops, and all the cookware and utensils you'll need to whip up a delicious meal.brbrThe master bedroom is a true oasis of relaxation, boasting a comfortable king-size bed, luxurious linens, and an ensuite bathroom with a walk-in shower. The guest bedroom has two full-size beds and a flat-screen TV. Both bedrooms are tastefully decorated and have ample closet space. This condo also includes all the modern amenities you need for a comfortable stay, including air conditioning, high-speed internet, cable TV, and a washer and dryer.brbrThe Jamaica Royale complex features a range of amenities, including three heated pools, tennis courts, direct beach access, and beach amenities including chairs, umbrellas, and coolers.brbrLocated just minutes away from Siesta Key Village, you'll have easy access to restaurants, cafes, and shops. Whether you're looking to relax on the beach or explore the local area, this condo has everything you need for an unforgettable vacation. Book your stay today and experience the beauty of Siesta Key!brbr**Cancellation Policy**brBookings canceled at least 30 days before the start of the stay will receive a 100% refund minus Cancellation Fee's ($100 plus 6% Credit Card Processing Fee). Bookings canceled at least 14 days before the start of the stay will receive a 50% refund Minus Cancellation Fee's. Bookings canceled within the 14-day window are non-refundable. brbrReservations of 15 nights or more may be canceled at least 90 days before the start of the stay will receive a 100% refund minus Cancellation Fee's ($100 plus 6% Credit Card Processing Fee). Cancellations within 45 days of the check-in date and are refundable up to 50% minus Cancellation Fee's.brbrShould a refund be issued, a credit to the original credit card in the amount of the reservation minus the cost of the cancellation fees will be issued within 5 to 7 business days. brbrWhat's provided for your stay: Have fun at the beach with chairs, coolers, umbrellas, toys and more, pre-stocked into the villa prior to your arrival. Each residence has their own Property Liaison to ensure any problems or concerns will be resolved in an effective and timely manner.

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$321.34

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Spacious 2BR Siesta Key condo with beach access - GBB 1241

Siesta Key, Florida, United States

Discover the perfect retreat for your next vacation in this spacious two-bedroom, two-bathroom vacation rental. Professionally managed by Gulf Coast Vacation Rentals, this turnkey furnished condo offers everything you need for a comfortable and enjoyable stay, including a washer and dryer for added convenience, and a private garage for secure parking.brbrNestled in the heart of Siesta Key, guests staying here are just a leisurely stroll away from the #1 beach in America. Siesta Key is renowned for its world-famous, powdery white sandy beaches that stretch along the mesmerizing Gulf of Mexico. With this prime location, you can immerse yourself in the sheer beauty and tranquility of Siesta Key's coastal landscape.brbrThe condo's open and inviting layout creates a welcoming ambiance where you can relax and unwind. The well-appointed kitchen is fully equipped, allowing you to prepare delicious meals and snacks at your leisure. The living area provides a cozy space for lounging after a day of sun and surf, with ample seating and entertainment options for your enjoyment.brbrEach of the two bedrooms is designed with your comfort in mind, promising restful nights of sleep. Step out onto your private balcony to soak in the warm Siesta Key sun and take in the breathtaking views that stretch before you. Whether you're sipping your morning coffee or savoring a glass of wine at sunset, this outdoor space is a true oasis.brbrBeyond the comforts of your vacation home, Siesta Key offers a wealth of activities and attractions to explore. Delight in the island's vibrant dining scene, browse local boutiques, or engage in thrilling water sports adventures. The warm, sunny Siesta Key weather provides the perfect backdrop for outdoor fun and relaxation.brbrAs the day comes to a close, be sure to head to the beach for one of Siesta Key's spectacular sunsets, a sight that is nothing short of magical. The soft hues of orange and pink painting the sky as the sun dips below the horizon are truly unforgettable.brbrIn summary, our vacation rental on Siesta Key invites you to experience the ultimate beachfront getaway. With its spacious accommodations, unbeatable location, and modern amenities, it's the perfect home base for your Siesta Key adventure. So, why wait Come stay with us and enjoy the warm, sunny paradise that is Siesta Key, where memories are made and relaxation is a way of life. Book your stay today and start counting down the days until your beachfront escape!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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$226.38

/ Nightly

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Spacious condo on Siesta Key with beach access - GBB 1200

Siesta Key, Florida, United States

Welcome to your spacious one-bedroom, one-bathroom vacation rental home at the Gulf and Bay Club Bayside, professionally managed by Gulf Coast Vacation Rentals, an idyllic retreat on the beautiful Siesta Key, just off the coast of Sarasota, Florida. Set amidst the natural splendor of this island paradise, our rental home promises an unforgettable beachfront experience like no other.brbrAs you step into our charming vacation rental, you'll immediately feel the coastal ambiance that permeates every corner of the space. The open and airy layout invites you to unwind and relax, creating a perfect home away from home. With a full kitchen, dining area, and a comfortable living space, you'll have all the conveniences needed to prepare meals, dine, and lounge in comfort.brbrThe bedroom offers a cozy haven for a restful night's sleep. These breathtaking vistas are a constant reminder that you're in a tropical paradise.brbrBut the true gem of this vacation rental is its location. Private access to Crescent Beach on the Gulf of Mexico is just a few steps away, allowing you to easily transition from the comfort of your vacation home to the powdery white sands and crystal-clear waters. Spend your days sunbathing, building sandcastles, or taking long walks along the shoreline. And don't forget to relish in the incredible sunsets that Siesta Key is renowned for – each one a masterpiece painted across the evening sky.brbrBack inside the rental, you'll find modern amenities to enhance your stay. Stay connected with a free high-speed internet connection, perfect for sharing your beachfront adventures with friends and family or catching up on work if needed. Additionally, the convenience of a garage adds to the ease of your stay, ensuring your vehicle remains secure and protected from the elements.brbrSiesta Key itself offers a myriad of attractions and activities to explore during your stay. Beyond the beach, you can discover the island's vibrant dining scene, indulge in watersports, explore local shops, or simply bask in the island's laid-back atmosphere. With its mix of natural beauty and cultural charm, Siesta Key has something for everyone.brbrSo, whether you seek relaxation, adventure, or a little bit of both, our vacation rental at Gulf and Bay Club Bayside is your gateway to an extraordinary coastal getaway. Book your stay today and start creating memories that will last a lifetime in this tropical paradise.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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$322.31

/ Nightly

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Relaxing Siesta Key condo - pickleball - 2 heated pools - beach access - GBB 1344

Siesta Key, Florida, United States

Welcome to Gulf & Bay Club Bayside Unit 1344 on Siesta Key, proudly managed by Gulf Coast Vacation Rentals. This inviting two-bedroom condo is designed to make your stay memorable and relaxing. The spacious primary bedroom features a plush king bed, while the guest room is furnished with a comfortable queen bed—making it perfect for families or couples traveling together.brbrYou'll love the open-concept living area, which leads to a beautiful tiled lanai surrounded by sliding windows and doors. Whether you want to bask in the morning sunlight over breakfast or enjoy the evening breeze with a glass of wine, this space offers flexibility to enjoy the outdoors however you like.brbrThis fully furnished condo provides all the comforts of home, including a washer and dryer, a fully stocked kitchen, and even a private garage for your convenience. Step outside and you're just a short walk to the beach access, where the world-famous white sands of Siesta Key and the sparkling Gulf of Mexico await.brbrAs a guest at Gulf & Bay Club Bayside, you'll also have access to two heated pools—perfect for a relaxing swim any time of year—and pickleball courts for a bit of friendly competition. The resort-style amenities don't stop there: there's a fitness center, tennis courts, and a fishing dock for you to enjoy during your stay.brbrPlus, you're just a short distance from the vibrant Siesta Key Village, where you'll find a fantastic selection of shops, local restaurants, and cafes to explore. Whether you're in the mood for fresh seafood, unique boutiques, or a lively beachside atmosphere, it's all close by.brbrBook your stay at Gulf & Bay Club Bayside Unit 1344 and experience the perfect blend of comfort, convenience, and the coastal lifestyle that makes Siesta Key such a beloved destination. Let Gulf Coast Vacation Rentals make your getaway easy, relaxing, and unforgettable.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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$411.31

/ Nightly

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Serene Siesta Key bayfront condo - 2 pools - pickleball - tennis - beach access - GBB1368

Siesta Key, Florida, United States

Embark on a remarkable vacation experience on Siesta Key within the luxurious confines of our generously proportioned three-bedroom, two-bathroom vacation rental, Professionally managed by Gulf Coast Vacation Rentals, nestled within the prestigious Gulf and Bay - Bayside community. This beautifully appointed condo promises an extraordinary retreat, boasting not only ample space but also a plethora of conveniences that will elevate your stay to the pinnacle of comfort and relaxation.brbrUpon entering this spacious haven, you'll be immediately struck by the welcoming ambiance that permeates every corner. The expansive living area invites you to unwind in style, with plush seating arrangements and a chic decor that exude both comfort and sophistication. Whether you're curling up with a good book, catching up on your favorite shows, or simply savoring the tranquil atmosphere, this living space is designed for maximum enjoyment.brbrThe adjacent dining area provides an elegant setting for memorable meals with your loved ones. The open layout seamlessly connects the dining space with the fully equipped kitchen, ensuring that preparing and sharing meals is a delightful experience. The kitchen is outfitted with modern appliances, ample counter space, and all the culinary essentials you might need during your stay.brbrRetreat to the serene bedrooms for a restful night's sleep. The master suite offers a luxurious king-sized bed and an en-suite bathroom, providing a private sanctuary for relaxation. The additional bedrooms are thoughtfully designed and tastefully decorated, ensuring that everyone in your group enjoys their own personal haven.brIn addition to the comfortable interiors, this condo also features a range of amenities for your convenience and enjoyment. You'll find a washer and dryer within the unit, allowing you to keep your beachwear fresh and ready for your next adventure. A private garage provides secure parking for your vehicle, ensuring peace of mind throughout your stay.brbrOne of the standout features of this vacation rental is its proximity to Siesta Key's world-renowned white sandy beach on the Gulf of Mexico. Guests have the privilege of being within walking distance of a beach access, where they can soak up the sun, swim in the crystal-clear waters, and witness breathtaking sunsets over the Gulf. Whether you're a beach enthusiast, a water sports aficionado, or simply someone who appreciates the beauty of nature, Siesta Key's beach offers an array of activities and sights to savor.brbrIn conclusion, our spacious three-bedroom, two-bathroom vacation rental in Gulf and Bay - Bayside on Siesta Key is the epitome of luxury and comfort. With its generously appointed living spaces, modern amenities, and proximity to the world-famous beach, it offers an idyllic retreat for those seeking warm and sunny Siesta Key experiences. We invite you to come stay with us and discover the perfect blend of relaxation and adventure in this tropical paradise. Book your unforgettable Siesta Key getaway today!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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$334.79

/ Nightly

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Relaxing 2BR Siesta Key condo with beach access - GBB 1365

Siesta Key, Florida, United States

Immerse yourself in the peaceful charm of Siesta Key at this beautifully appointed vacation rental in Gulf & Bay Club Bayside, professionally manage by Gulf Coast Vacation Rentals. Situated directly along the intercoastal waterway, this spacious two-bedroom, two-bath residence offers a front-row seat to the natural beauty of Florida's Gulf Coast. From the comfort of your private lanai, you can relax as dolphins glide by and manatees surface in the calm waters—an unforgettable experience that captures the essence of island living.brbrInside, the home is newly furnished and thoughtfully designed for both comfort and style. Large windows fill the open-concept living and dining areas with natural light, while offering sweeping views of the harbor and surrounding tropical landscape. The fully equipped kitchen provides everything needed for your stay, and the in-unit washer and dryer add extra convenience.brbrBoth bedrooms are generously sized, providing ample space for families or couples traveling together. The primary suite features a comfortable king bed and an en-suite bath, while the second bedroom offers flexible sleeping arrangements and access to a full guest bathroom. A private garage is included for secure parking and easy storage of your beach gear.brbrLocated in the sought-after Gulf & Bay Club Bayside community, this property offers access to resort-style amenities including two heated pools, tennis and pickleball courts, a fitness center, and beach access just a short walk away. Enjoy a stroll through the gated, tropically landscaped grounds or head over to nearby Siesta Key Village for shopping, dining, and live entertainment.brbrWhether you're seeking a quiet retreat or an active beachside getaway, this vacation home provides the perfect blend of privacy, comfort, and convenience on one of Florida's most beautiful barrier islands.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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$287.2

/ Nightly

Condo

Beach & Pool Open! Beachfront View Every Room

Siesta Key, Florida, United States

Summary:brbrAmazing Gulf views from every room of this 3rd floor condo. Crescent Arms is a quiet, beach front, high rise condominium building that is ideally located for maximum fun and relaxation. Right on the beach with lounge chairs provided. We can comfortably accommodate 6 people. There are 2 double beds in one room and 1 King in the other. Our condo is on the side corner of the building with a view into the Gulf. From late fall to early spring, you can enjoy lavish sunsets right from the lanai.brbrbrbrThe Space:brbrAs close as you can get to the Gulf without being in the water!brbrbrbrEach bedroom has it's own flat-screen cable TV & ceiling fan.brbrbrbrThe unit also features a fully-equipped, modern kitchen and dining area.brbrbrbrHeated pool, covered parking. All the comforts of home. brbrbrbrPlenty of coin-operated laundry facilities are on-sitebrbrbrbrComputer is available in the clubhouse for guests to use during office hours. A printer is provided for airline boarding pass printing.brbrbrbrFree WiFibrbrbrbrGuest Access:brbrYou have full run of the entire condo.brbrbrbrThe Neighborhood:brbr-Nearby Sarasota has all the social and cultural attractions you could desire: Marie Selby Botanical Gardens, Mote Marine Aquarium, and The Ringling Brothers Museum of Art are all minutes away. brbrbrbr-A few miles north is St. Armand's Circle with its trendy shopping. brbrbrbr-Only one hour from Busch Gardens in Tampa. Two hours from Islands of Adventure, Epcot, Disney, and Universal Studios.brbrbrbrGetting Around:brbrIt’s easy to get around Siesta Key via the free trolley or multiple free ride services.brbrbrbrOther Things to Note:brbrWalking distance from shopping, restaurants, and stores.brbrbrbrPlenty of opportunities for shopping, golf, boating, fishing and much more.brbrbrbrInteraction with Guests:brbrWe are available 24/7 via text, email, or phone. And of course Airbnb messaging. We prefer to stay in contact and help you with any needs. We live just 10 minutes away so are able to stop by in case you need anything!

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$1838.17

/ Nightly

Private Vacation Home

High Tide - Beautiful pool with waterslide, 2 min walk to the beach

Siesta Key, Florida, United States

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$314.9

/ Nightly

Condo

Renovated Condo with Siesta Key-Beach Access!

Siesta Key, Florida, United States

This lovely, 1-bedroom, 1-bathroom features a queen bed, offering sleeping space for 2. This vacation home is located at a waterfront community on Siesta Key. It features a stunning space with a full kitchen, and living room. Enjoy Wi-Fi, a flat screen TV in the bedroom and living room and coin operated laundry facilities on the premises. The condo is located on the 2st floor, and allows easy access to and from the water at your leisure. Located between the bay and the beach, this unit offers easy access to a fishing pier with cleaning station, boat access, a heated pool and outdoor grill facilities on-site. Just walk across Midnight Pass to your dedicated beach access to our world-famous Siesta Key Beach, ranked #1 in US, and just one mile from Siesta Village, for enjoying the many restaurants, shops, and live entrainment the island has to offer!br*Located on the second floor. Stairs only. Guests must be able to use stairs.brbrBedroom 1- QueenbrbrAdded Amenities Included in Your Stay:brComplimentary Bicycles Rentals,brOne Complimentary Parking Space,brWifi,brBeach Chairs,brBeach Towels,brBeach Wagon,brBeach Cooler,brPartner Property Pool/Hot tub Access,brAccess to Siesta Beach Pickleball Courts,brSiesta Key Trolley - Free-Rides Around Siesta Key,brA 7-day week, Beachside Management office for your convenience and guest needs!brbr*Minimum Age to Book: 21br*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: $500

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$308.82

/ Nightly

Condo

Siesta Key-Siesta Dunes-Beautiful Condo with a View of the Gulf of America

Siesta Key, Florida, United States

This property sits on beautiful Crescent Beach and the Gulf of America. The grounds offer tremendous landscaping and green space. Amenities include a salt water heated pool, hot tub, tennis/pickleball court and oversized deck with gazebo and gas grills. Stay here for private beachfront access and walk right out to the beautiful white quartz sands of Crescent Beach & Siesta Key Public Beach. Voted #1 Beach in the United States numerous times by Travel Channel's Top 10 US Beaches! Sunsets are magnificent! Maximum 4 guests. Property has elevator nearby to make moving in and out easy. Building 1, Top Floor, Unit 405. ******Condo recently renovated. Remodeled Kitchen and Baths - New cabinets and countertops, appliances, sinks, faucets, window treatments, mirrors and lighting.brbr

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$118.38

/ Nightly

Condo

Harbor Towers & Yacht Club racket and

Siesta Key, Florida, United States

Harbor Towers Yacht and Racquet Club is located on the inter-coastal waterway on Siesta Key in Sarasota, Florida. From the marina you can fish or relax and read a good book while you watch the boat traffic go by from your comfortable seat in the gazebo or bench at water's edge. The beautiful gulf beaches are conveniently located right across the street.brbrHarbor Towers features beautiful tropical landscaped grounds, a deep-water harbor that can accommodate boats up to 50 feet in length, and two gorgeous swimming pools (adult and children). Tennis is played on our three Har-Tru courts right next to the Inter-coastal Waterway. If you like a brisk workout you will enjoy our exercise room with state-of-the-art exercise equipment.brbrMy unit is one of the best views in the building. It is located on the 4th floor overlooking the ocean.brbrHarbor Towers is a secure building requiring entry at all doors with special fob's given out only to owners and guests. Night time security is provided and automatic entry gates secure the grounds at all times.brbrAfter one visit to Harbor Towers Yacht and Racquet Club you will want to come back every year!brbr2 weeks (14 day) minimal- rules of the condo association.

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$210.84

/ Nightly

Apartment

Cute Siesta Key Condo Close To Beach Restaurants

Siesta Key, Florida, United States

Summary:brbrHave the Siesta Key vacation of your dreams at the charming 2BR 2Bath in the Harbor Towers Yacht & Racquet Club resort-style community, a few steps away from the sun-soaked Siesta Beach! Explore the nearby Village and its exciting restaurants, shops, attractions, and landmarks.brbrbrbrThe stylish design and rich amenity list will leave you in awe.brbrbrbr✔ 2 Comfy BRsbrbr✔ Open Design Livingbrbr✔ Full Kitchenbrbr✔ Balconybrbr✔ High-Speed Wi-Fibrbr✔ Community (Pools, Sports, Lounges, Parking)brbrbrbrSee more below!brbrbrbrThe Space:brbrAs soon as you step foot in the lovely tropical condo, you're welcomed by a very stylish yet highly comfortable open-plan living area. It is designed and decorated in an elegant manner that compliments the fantastic beachfront setting of the dreamy Siesta Key.brbrbrbrThe fully equipped kitchen and adjacent dining area open onto the entertaining living room, setting the stage for memorable evenings. Plenty of natural light comes through the large windows and balcony doors, making the home very bright during the day and enhancing the soothing ambiance.brbrbrbrRetreat to two comfortable bedrooms, which feature 5☆-resort comforts that allow you to rest after an exciting day at the beach and the bustling Siesta Village.brbrbrbrBut wait! The best is yet to come! Step out to the private balcony, where you can soak up the sun and the intercoastal waterway without leaving the condo.brbrbrbr★ LIVING ROOM ★brbrIt immediately feels like home. Find your place on the comfy sofa and chairs, get your favorite drinks and snacks and enjoy a fantastic night with your family and friends.brbrbrbr✔ Couch and chairs with Pillowsbrbr✔ Smart TVbrbr✔ Coffee Tablebrbr✔ Reading Lampsbrbr✔ Access to the Balconybrbrbrbr★ KITCHEN & DINING ★brbrIt is fully equipped with modern cooking appliances that make it suitable for preparing any meal, whether a simple breakfast, a quick snack, or a three-course gourmet dinner. Spacious countertops provide plenty of room for you to work your MasterChef magic.brbrbrbr✔ Microwavebrbr✔ Stovebrbr✔ Ovenbrbr✔ Blenderbrbr✔ Keurig Coffee Makerbrbr✔ Hot Water Kettlebrbr✔ Refrigerator/Freezerbrbr✔ Dishwasherbrbr✔ Sink - Hot & Cold Waterbrbr✔ Traysbrbr✔ Glassesbrbr✔ Silverwarebrbr✔ Pots & PansbrbrbrbrHave a few drinks on the balcony while the food is getting ready. Once it's done, serve it on the inviting dining table and enjoy a tasty meal with your loved ones.brbrbrbr✔ Dining Table with Seating for 4brbrbrbr★ SLEEPING ARRANGEMENTS – 2 BEDROOMS ★brbrAfter an exciting day of adventuring throughout Siesta Key, you will be looking to rest for an equally entertaining tomorrow. Once you are ready to relax, please make your way to these comfortable bedrooms. brbrbrbr♛ Master Bedroom: King-Size Bedbrbr♛ Bedroom 2: Two Single BedsbrbrbrbrBoth bedrooms are equipped with a similar set of amenities.brbrbrbr✔ Ensuite Bathroombrbr✔ Premium Pillows, Linens, and Sheetsbrbr✔ Smart TVsbrbr✔ Dressers with Spacious Drawersbrbr✔ Night Stands with Reading Lightsbrbrbrbr★ BATHROOMS ★brbrBoth bedrooms have ensuite bathrooms stocked with fresh towels and essential toiletries, so you don't have to overpack for your trip. brbrbrbr✔ Walk-In Showerbrbr✔ Bathtub with a Showerbrbr✔ Vanitybrbr✔ Mirrorbrbr✔ Toiletbrbr✔ Towelsbrbr✔ Essential Toiletriesbrbrbrbr★ BALCONY ★brbrA beachfront oasis would not shine in its best light if it did not have a private outdoor space where you can relax, catch a breath of fresh beach air and unwind after a day of sightseeing. brbrbrbr✔ Comfy Seating Area with table and chairs to enjoy a meal or coffee outside while watching the boats go bybrbrbrbrWe look forward to hosting you!brbrbrbrGuest Access:brbrThe condo is exclusively yours, without interruption during your stay, so relax, unwind, and make yourself home. brbrbrbrOther than the already mentioned amenities, our home also comes with the following:brbrbrbr✔ High-Speed Wi-Fibrbr✔ Self Check-In (Smart Lock)brbr✔ Air Conditioningbrbr✔ Heatingbrbr✔ Iron/Boardbrbr✔ Laundry Room On Floor (App controlled)brbrbrbrThe Neighborhood:brbrThe condo is nestled in the tropical Bayside community located directly on the Gulf Coast Intracoastal Waterway, featuring some of the most beautifully landscaped grounds on the island, including the notable Harbor Towers Waterfall, which is recognized as a Siesta Key landmark.brbrbrbrStaying at Harbor Towers can be as active or relaxing as you want to make it. We are close to The Village for wonderful restaurants and people watching …and have our expansive seawall on the ICW for those quieter times, fishing or watching the boats go by.brbrbrbrHere are some places of interest you'll surely be looking to visit during your stay.brbrbrbr✔ PARASAIL SIESTA (3 min away)brbr✔ Siesta Key Beach (3 min away)brbr✔ Crescent Beach (3 min away)brbr✔ Siesta Key Watersports (4 min away)brbr✔ Siesta Key Village (5 min away)brbr✔ Marie Selby Botanical Gardens (15 min away)brbr✔ Sarasota Jungle Gardens (25 min away)brbr✔ Mote Marine Laboratory & Aquarium (28 min away)brbr✔ South Lido County Park (28 min away)brbr✔ Lido Key Beach (28 min away)brbr✔ St. Petersburg (55 min away)brbr✔ Tampa (1h 10 min away)brbr✔ Fort Myers (1h 25 min away)brbrbrbr***Distance times are calculated if traveling by car.brbrbrbrGetting Around:brbrIf you arrive by car, you will be happy to know that we offer free parking. However, if you would like to avoid odriving during your stay, there are many convenient, easily accessible transportation options close to our home.brbrbrbr✔ Siesta Key Breeze Trolleybrbr✔ Taxibrbr✔ Lyft & UberbrbrbrbrOther Things to Note:brbrBooking party must be age 25+, and must be present at the home for the duration of the stay.brbrNo one under the age of 21 will be permitted on the property without their parent or legal guardian unless previously agreed upon in writing.brbrViolation is grounds for removal from property without refund. brbrbrbr★ ADDITIONAL ACCOMMODATION ★brbrTraveling in a larger group, or your preferred dates are already taken You'll be happy to know that we offer additional accommodation in the area. Please browse our host profile for the complete list of gorgeous propertiesbrbrbrbr★ NO PETS ALLOWED ★brbrWe love those little (and not so little) furry bundles of joy. Sadly, our home is not suitable to accommodate them.brbrbrbr★ NO SMOKING INSIDE ★brbrPlease refrain from smoking inside the home! Any smoking evidence will result in a fee for odor removal and furniture cleaning.brbrbrbr★ NO PARTIES/EVENTS ★brbrWe kindly ask you to treat our home as your own to preserve its pristine condition for future guests and your return visitbrbrbrbrThank you very much for your understanding.brbrbrbrInteraction with Guests:brbrWe will be accessible 24/7 for our guests via phone, text, or the Airbnb app. brbrExpect a quick and prompt response. We give our guests space but are available for every inquiry. brbrbrbrContact us now so we can begin arranging your perfect vacation!

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$1074.69

/ Nightly

Private Vacation Home

Oasis with Heated Pool

Siesta Key, Florida, United States

Make some memories at this unique and family-friendly place. Enjoy this lush and tropical pool area that will almost make you forget that a highly rated sometimes rated #1 Beach is just steps away! Provided for you are all the necessary beach items like beach towels and chairs and more! This is a very spacious house and cottage that make up the total of 4 bedrooms and 4 baths. The house and cottage are on the same property.

4

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4

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10

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