72,107 properties available

Located in Siesta Key, Florida, United States. Beautiful 3 Bed/2.5 bath With Roof Top Pool on Siesta Key! SIESTA KEY BEACH RESIDENCE: This must-see, rare, and beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 2nd floor above the garage, has 3 bedroom, 2/5 bathrooms and can sleep up to 9 guests. This home is perfectly located 0.1 miles from beach access #11, offering quick access to the #1 rated Siesta Beach! Enjoy the breathtaking view from the incredible rooftop pool and relax knowing your vacation home awaits!*This property is stairs only; all guest must have the ability to climb stairs.*No garage parking. Driveway parking only.Bedroom 1: King Bedroom 2: KingBedroom 3: Full and Twin BedLiving room: Queen Sleeper SofaIncluded in your stay:Complimentary Bicycles,Wifi,Parking,Beach Chairs,Beach Towels,Beach Wagon,Beach Cooler,Free-Rides Around Siesta Key,A 7-day week, Beachside Management office for your convenience and guest needs!*Minimum age requirement from February

Located in Siesta Key, Florida, United States. Live the Dream in this 2 Bed/1 Bath Home Steps from Siesta Key Beach! Experience the Gulf of Mexico breeze and partial gulf views with this lovely 2-bedrom, 1-bathroom home directly across from our world-famous Siesta Key Beach! Beautifully decorated, this home features a king bed in the master, a queen in the second bedroom, and a queen sleeper sofa in the living room, accommodating up to 6 guests. This unit, located on the second floor, is right outside of the Siesta Key Village, making it a breeze to walk to many of the restaurants, shops, and live entertainment the island has to offer. Relax in the sugary white sand or swim in the crystal-clear waters. Enjoy the brilliant colors of sunset at this beautiful vacation home that will have you coming back year after year!*Stairs only. All guests must have the ability to climb stairs.*No garage parking.Sleeps 6 GuestsBedroom 1: KingBedroom 2: QueenLiving Area: Queen Sofa SleeperIncluded in your stay:Complimentary Bicycles,Wifi,Parking,Be

Located in Siesta Key, Florida, United States. Casa Van Lopik(Jardin)- Tiki-Bar, Balcony, Tropical Patio, 250 steps to Beach and Village! This is Casa Van Lopik, a Gertrude Rentals property! Leave the car behind! Large 3BR home perfectly located steps to the best beaches, shopping, dining, and entertainment on Siesta Key. Out-door dining and grilling (shared), open floor plan perfect for bigger groups, surrounded by palms with king beds in both master bedrooms. Sure to provide a combination of fun and relaxation you can't get in other getaways.CASA VAN LOPIK “AT A GLANCE” - Large 3BR/2Bath (sleeps 11)- In the World-famous Siesta Key Village.- Award Winning Beaches, 20 Bar Restaurants, Walk to everything!- Live Music, Daiquiris, Oysters, stone crab, ice cream, fresh donuts.- Walk to Siesta Key Beaches and clear calm Azure Water & pure quartz White Sand. - Tide Pools & Sand Bars for lounging, sleeping, relaxing, or water sports.- Perfect house for large gatherings vaulted ceilings & Great Room flows onto Balcony.- Garden-patio (

Located in Siesta Key, Florida, United States. 7 minute walk to Siesta Key beach. Large heated pool/spa. Very private.1/2 acre Welcome to Lagoon House Siesta Key beach. A uniquely private, dog friendly (up to 25 lbs), one story house with guest house (and a six person golf cart available for an extra rental fee). This property is situated within a 7 minute walk to the Number 1 beach in America, Siesta Key Beach. It is also just a short 3 minute golf cart ride (or bike ride) to Siesta Key Village where you can enjoy many restaurants, shops and live music.The Lagoon house sits on a half-acre property that has a huge new heated pool and large 6’x9’ hot tub that will accommodate 8 people. The separate guest house (Flamingo cottage) is all newly remodeled and contains it’s own full bath, refrigerator/freezer and sitting area along with a California King bed and it’s own separate heating and cooling units and Nespresso coffee maker and 55” TV.The main house has three bedrooms and two full baths and many separate gathering areas inclu

Located in Siesta Key, Florida, United States. Slice of Beach Paradise | Private Wraparound Balcony with Amazing Gulf Views Beach Road Condo Unit 2Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Perched by the shoreline, this 3BR/2BA townhome is a slice of beach paradise. With the Gulf just a 2-minute walk away, enjoy the stretches of sugar-white sand and turquoise waters in your backyard! Buzzing Ocean Boulevard is also a short stroll from your door.Entertaining is a breeze with the townhome’s spacious and open floor plan; high-end touches and remodeled interiors make for a sophisticated getaway. Take in unparalleled views on the private balcony.LIVING AREAExpansive wraparound glass doors flood the living room with natural light. There’s comfortable seating for nine and a 60” flat-screen TV with DVD player.KITCHEN & DININGWhip up fresh recipes in the gorgeous kitchen, detailed with gleaming granite countertops, ample cabinet space, and stainles

Located in Siesta Key, Florida, United States. Beach Road Condo - Private Deck - Siesta Key Village & Beach Walkable! Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.One of the closest rentals to the beach in Siesta Key Dream’s portfolio features a bright, airy 2 bedroom space on the second floor of the building. You’ll experience a spacious floor plan connecting a welcoming living room, a dining room that seats 6, and kitchen. Your dining room contains a large sliding door to a private front porch that and Beach Road. Siesta Key Dreams is happy to provide free, high-speed internet & Wi-Fi, an HD Television equ

Located in Siesta Key, Florida, United States. Isla Amor | Waterfront Home on Siesta Key w/ Private Heated Pool, Fire Pit, Walk to Beach! Welcome to Isla Amor, a tropical paradise nestled in the prestigious neighborhood of Palm Island on Siesta Key. This luxurious vacation home offers the perfect blend of romance and relaxation, providing an unforgettable retreat for your tropical getaway. With its resort style private heated pool, waterfront location, and enchanting ambiance, Isla Amor feels like your own private resort.As you enter the home, you'll find that the interior is thoughtfully designed, showcasing modern and airy furnishings. Featuring 5 bedrooms and 3.5 bathrooms, this spacious retreat comfortably accommodates up to 11 guests. The sleeping arrangements include 3 king beds and 5 twin beds, all adorned with luxurious linens for your ultimate comfort.In the kitchen, take advantage of the indoor bar space complete with a wine cooler and sink, setting the stage for unforgettable evenings of relaxation and indulgence. Enjoy

Located in Siesta Key, Florida, United States. Townhome with Pool, Steps from Siesta Key Beach & Shops! - Tarpon Villa Tarpon Villa by Siesta Key Luxury Rental Properties Home in Siesta Key, Florida Welcome to Tarpon Villa, a beautiful family-friendly 4-bedroom, 2.5-bathroom townhome just a quick 4-minute walk from Siesta Key Beach and steps from Siesta Key Village. This vacation home offers a variety of sleeping accommodations, making it the ideal destination for memorable family adventures. Highlight • 4-minute walk to the beach • Private heated pool• Fenced yard for added privacy • Outdoor seating and BBQ grill • Beach chairs and wagon provided • Smart TVs in living areas and bedrooms Bask in the sun by your private heated pool, or relax on the covered patio with dining and lounge seating. The spacious ground level features a bright open great room, including a fully equipped kitchen, a dining area that seats six, and a cozy living area with an HDTV. Large sliding glass doors provide access to the tranquil pool area and ample

Located in Siesta Key, Florida, United States. Spacious 3 Bedroom Gulf Side Townhome with Rooftop Sun Deck On Siesta Key! Welcome to Surfside! Where you will experience beautiful Siesta Key Living! This 3-Bedroom, 2.5-bathroom home sleeps up to 6. Relax on the spacious rooftop sun deck and take in the amazing sweeping views of our world-famous beach, Siesta Key. Inside, on the first living level, you will find a large, open living area, a half bathroom, a nice sized balcony for enjoying that island breeze, and a large kitchen with plenty of space to cook in. The second living level has 3 bedrooms, 2 full baths, a washer and dryer, and another balcony off the bedrooms. Up one more flight of stairs is the large rooftop sun deck, perfect for watching gorgeous sunsets all year round. This home is equipped with 2 parking spaces: 1 in the drive way and 1 carport space is in the rear. For your convenience, there is an onsite beach access path that will lead you to the sugary sands and crystal-clear waters. This home is just a short stroll

Located in Siesta Key, Florida, United States. Great Family Retreat with Pool, Spa, Putting Green & Game Room - Paradise Cove Paradise Cove by Siesta Key Luxury Rental PropertiesHome in Siesta Key, FLWelcome to Paradise Cove! This beautiful five-bedroom, five-bathroom vacation rental in Siesta Key is perfect for families. Just a short stroll from stunning beaches, enjoy swimming, kayaking, and exploring nature trails. Siesta Key Village is also a five-minute walk away, featuring charming shops, dining, and ice cream parlors for all ages! Highlights • 4-minute walk to the beach • 5-minute walk to shopping and dining • Private Pool with In-ground Spa • Putting green, Ping Pong, and Foosball table • BBQ grill and covered patio for outdoor dining • Dog friendly with approval and additional fee • Screened-in lanai Jump into the luxurious private pool featuring a relaxing in-ground spa and fun in-pool planters. The outdoor space feels like your personal resort, with plush lounge chairs, a putting green, and a grill for barbecues. Enjoy c

Located in Siesta Key, Florida, United States. Bright and Beachy 3 Bedroom/2 Bath - Short Walk to Siesta Key Beach & Village 3 Bedroom/2 Bathroom 1st floor unit in a great location on Siesta Key! This bright and open floor plan, no stairs, beachy rental is a spot that's hard to beat. Sleeps 6 people, great for families, couples or close friends. Steps away from beautiful white sands of Siesta Key beach! Beach access #8 is across the street. Short walk to the Siesta Key Village for shops, restaurants and nightlife! Central location, close to everything!!!Fully equipped kitchen, one bathroom with walk-in shower and a second bathroom with a bathtub. Spacious backyard and patio is shared with the second floor apartment.Guests will have access to the first floor unit of this property. The parking, backyard, backyard patio furniture, outdoor shower/foot wash and grill are shared by guests in both the upper and lower rental units. The second floor deck is for second floor unit guests only.Weekly 7 Day Rentals Only - Saturday Check in to

Located in Siesta Key, Florida, United States. Casa De Siesta | Pet Friendly Home In Siesta Village, Private Pool and Hot Tub, Walk to the Beach! Welcome to Casa De Siesta, your ultimate island retreat nestled in the heart of Siesta Key Village. This stunning property offers a flexible rental option, allowing you to book the entire duplex as Casa De Siesta or choose to rent Villa Fiesta or Villa Margarita separately. Whether you're seeking a spacious getaway for a large group or a more intimate stay, Casa De Siesta has the perfect accommodations for you.This unit features four bedrooms, two full baths, and two half baths, providing ample space and comfort for up to 12 guests. The sleeping arrangements include two king beds, two queen beds, and two queen sleeper sofas, all furnished with high-quality linens for a restful stay.Casa De Siesta's unbeatable location places you directly in Siesta Key Village, ensuring easy access to an array of shops, restaurants, and entertainment options. Siesta Key Beach, known for its powdery white s

Located in Siesta Key, Florida, United States. Tivoli by the Sea-Unit 502 - Beautiful unit with a beautiful view Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea!!! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!!! This unit sleeps 5 with a king in the master, a full and twin bed in the guest bedroom. 1 week minimum rental.

Located in Siesta Key, Florida, United States. Beach Dream | Home w/ Ocean Views, 2 Private Pools, & Rooftop Lookout! Steps to Siesta Key Beach Welcome to Beach Dream, the ultimate vacation rental duplex for those who want to indulge in luxury and relaxation, while being just steps away from the crystal-clear waters at Siesta Key Beach. This duplex is the perfect place to escape the hustle and bustle of everyday life and immerse yourself in the tranquility of the Florida Gulf Coast!Upon entering the units, you'll be greeted by the bright and airy living areas, complete with comfortable seating and large windows that let in plenty of natural light. The open-concept design flows seamlessly into the dining area, perfect for gathering with family and friends for a meal.The open living areas are elegantly decorated in a modern style, with chic, comfortable furnishings and high-end finishes. Both all-white kitchens feature stainless steel appliances, including a large fridge, oven, microwave, and dishwasher, and are fully equipped with a

Located in Siesta Key, Florida, United States. Private Canal Home , short Walk to Siesta Key Beach Just made available for Christmas 2024. .One opening remaining in May. Very limited availability in 2025. Discounted monthly rates beginning at $21,420.Located in the exclusive Palm Island enclave 2.5 blocks from world renown Siesta Key Beach on a highly private oversize lot, Siesta Key Heritage House is tucked away in a secure and quiet residential neighborhood, yet close to popular village and beach attractions. This property affords modern luxuries in a home built reminiscent of the early Sarasota Bayfront hotels. Enjoy secluded canal and foliage views from the waterfront pool, jacuzzi and porches. Fish or launch complimentary stand-up paddle boards from your own private dock. Walk to the village or make use of the chef's kitchen stocked with comprehensive cookware and tableware service for 20. Amenities include: Bluetooth speakers inside and out, Flat screen TV, wireless internet, ceiling fans, Five Star professional 6 bur

Located in Siesta Key, Florida, United States. The Village Breeze (2 units) 4BR/4Bath Pool, Beach - Siesta Village Living! The Village Breeze 4BR, 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. THE VILLAGE BREEZE “AT A GLANCE” - TWO SIDE X SIDE 2BR/2BATH UNITS.- Steps to Oysters, Craft Beer, Ice Cream, Daiquiris, Live Music, Huge Breakfast, Stone Crab! - Award Winning Beaches, 20 Bar/Restaurants! - Walk to Siesta Key Beaches and clear calm Azure Water & pure quartz White Sand. - Tide Pools & Sand Bars for lounging, sleeping, relaxing, or water sports.- Best Sunsets in North America with 300-degree views of the Gulf. - Kayak, bike, paddleboard, scooter, golf cart rentals. - Free island Trolley & every activity imaginable. - A one of a Kind Isl

Located in Siesta Key, Florida, United States. Tivoli by the Sea-Unit 307 - Recently Updated Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen & a gorgeous view of the Gulf of Mexico. Sit on your 26ft open balcony & watch our spectacular sunsets! This unit sleeps 6 with a king in the master, a twin trundle & 2 full beds in the guest bedroom. 1 week minimum rental

Located in Siesta Key, Florida, United States. 5 Star LUXURY RETREAT on BEACH ROAD, SIESTA KEY BEACH, New POOL One of the nicest private homes on Siesta Key Beach. We have the highest 5 star rating on Siesta Key. See Vrbo 802548 for more reviews of this home - . Stunning and spacious on Beach Road right across the street from Beach Access 10 (ranked number one Beach in US.) Please note that our vacation home consists of two units. This listing's pricing is to rent one 3-bedroom unit. Please contact me about availability. Both units are beautifully furnished. They can also be rented together as one large property with 6 bedrooms and 4.5 baths. Our stunning home comes with all the amenities: beach chairs, beach caddies, umbrellas, beach toys, fine linens, beach towels, and so much more. 555 Beach is the perfect vacation home. It's larger, more spacious, and offers more room for entertaining than the majority of homes on Siesta Key. The backyard and resort pool area are new with new outdoor decor and dining areas. The he

Located in Siesta Key, Florida, United States. Tropical Hideaway Bungalow - Walk to Siesta Beach and Village SHORT WALK TO FAMOUS SIESTA WHITE SAND BEACH & QUAINT ISLAND VILLAGE. Situated in the quiet and welcoming neighborhood of Palm Island, the heart of Siesta Key. This beautiful private bungalow sits back from the street and is set in gorgeously secluded tropical gardens. The fabulous surprise of a two-story massive flagstone lanai is awaiting behind the zen gate. This home is comfortable and is made for entertaining from its open floor plan in the main living area to the outside summer kitchen and dining area under the covered porch with leads onto the lanai. The master bedroom has a walk-in California closet for ample storage. The second bedroom has a custom home office with a built-in desk, storage, filing, closet, and a full-sized murphy bed for your guests. There is a laundry room with a washer and dryer and a pantry with plenty of storage. The powder room is located off of the kitchen. This property has all the ameniti

Located in Siesta Key, Florida, United States. Beachfront, Full Ocean Views, Private Beach, Pool Experience the most amazing #1 rated Siesta Key beach views on the Gulf of Mexico from the 15th floor of the Terrace Building in Siesta Key Village! This gorgeous 2 bedroom 2 bath condo with almost 1,187 sq. ft. being almost 1/4 of the entire 15th floor is located right on Siesta Key Beach and in Siesta Key Village with gulf, bay, city lights, and Big Pass Lido Key Beach views. The Terrace Building includes a heated swimming pool overlooking the ocean, game & gym room, community room, assigned covered parking, and 24 hour locked entry.The 17-story condominium towers above the beach in lively Siesta Key Village with private beach side unobstructed views of the Gulf of Mexico, views of the bay, downtown Sarasota city lights, Lido and Longboat Key. There are plentiful nearby restaurants from casual to fine dining, all types of shopping to meet all your needs and nightly entertainment right outside your door. The Terrace building is saf

Located in Siesta Key, Florida, United States. Private Pool, Hot Tub, Siesta Key, Caribbean Dream Welcome to Caribbean Dream! Discover the epitome of island-style luxury as you step into this stunning retreat, nestled just moments away from the pristine shores of Siesta Key Beach. Renowned for its velvety, cool sands that beckon travelers from far and wide, this slice of paradise offers an unparalleled escape from the ordinary.Unveiling a tropical ambiance that seamlessly blends with the coastal surroundings, this magnificent residence boasts 5 -bedrooms and 4-bathrooms, ensuring ample space and comfort for you and your family. Each corner of this haven has been meticulously curated to evoke a sense of relaxation and indulgence.Enter the heart of the home, where a breathtaking kitchen awaits, ready to inspire culinary delights and unforgettable feasts. With all the appliances you could imagine, ample counter space, and stylish finishes, this culinary haven sets the stage for memorable gatherings with family and friends. The living

Located in Siesta Key, Florida, United States. Tivoli by the Sea-Unit 204 - Beautifully Renovated Your Ultimate Vacation Getaway Awaits you here at Tivoli by the Sea! This beautifully decorated 2 bedroom, 2 bath condo has all the comforts of home with a fully stocked kitchen and a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony & watch our spectacular sunsets! This unit sleeps 7, having a king in the master, 2 fulls in the guest bedroom & a sleep sofa. 1 week minimum rental

Located in Siesta Key, Florida, United States. Siesta Key Beachfront Suites Compound: 6 Bdrm Beachfront Beachfront Suites Compound: Surfside, Serenity, and Dreamview Condos on Siesta KeyWelcome to your ultimate beachfront retreat on Siesta Key, where the serene beauty of the Gulf of Mexico meets unparalleled comfort in our exclusive Beachfront Suites compound. Comprising three distinct condos - Surfside, Serenity, and Dreamview - each offering unique features and amenities, this stand-alone triplex delivers a personalized beach getaway experience directly on the world-famous Siesta Key Beach. Whether you seek a family adventure, a tranquil escape, or a romantic rendezvous, our Beachfront Suites cater to every desire.Property Features:-Surfside Condo (1st Floor): A family-friendly 3-bedroom haven with immediate beach access, a newly renovated bathroom, and a private patio. It's perfect for beach days or relaxing with a book in the large shared backyard.• Primary Bedroom: King Bed• Guest Bedroom 1: Queen Bed• Guest Bedroom 2

Located in Siesta Key, Florida, United States. Bright and Beachy 2 Bedroom/1 Bath - Short Walk to Beach & SK Village Bright and beachy 2 Bed/1 Bath 2nd floor duplex unit in the best location on Siesta Key! Great for small families, romantic getaways, or just some close friends. Steps away from beautiful white sand Siesta Key beach! Beach access #8 is just across Beach Rd. Short walk to the Siesta Key Village for shops, restaurants and nightlife! Central location, close to everything!!!Fully equipped kitchen, bathroom with walk-in shower. There is free stackable laundry inside the unit. Private second floor deck and a spacious backyard shared with the lower apartment. Guests will have access to the second floor unit of this property. The parking, backyard, backyard patio furniture, outdoor shower/foot wash and grill are shared by guests in both the upper and lower rental units.Property is located across Beach Road from public beach access #8. It is about a 5-minute walk on a sandy foot path through beach grasses right to the whit