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Siesta Key Vacation Rentals, Condos & Apartment Rentals.

Book Your Siesta Key Florida Vacation Rental Homes Here and Save! Many to choose from!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer in Siesta Key, Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals in Siesta Key to choose from, we now have the selection and value to offer our visitors going to Florida.

Listings

Vacation Rental

Stunning Siesta Key-2B/2B Full Bayfront Condo

Experience spectacular intracoastal bay views in this FULL BAYFRONT condo. Relax while watching the parade of boats in the bay through the custom trifold sliding doors on the lanai or walk outside to the private patio equipped with brand new dining table and four outdoor chairs. This unit is directly on the path to the new private fishing pier. Fi.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Condo Rental

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Vacation Rental

Sunset Royale - 204- Close to Beach and Siesta Village

Fantastic Beach and Gulf views await you with this beautifully decorated one bedroom condo directly across the street from Beach Access 11 on Siesta Key Beach featuring the world-famous crystal white sands. Located on the second level, the open floor plan boasts views of the Gulf, white sands, and magnificent sunsets. Enjoy morning coffee or pre di.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Siesta Key Apartment Rental

Details


Vacation Rental

Our House at the Beach E-704 Best view of the Gulf!

Just across the street from the acclaimed #1 Beach in the US. This beautiful two bedroom/ 2 bath condo has all the comforts of home! This condo offers a fully equipped kitchen, spacious living room, dining area, washer and dryer and balconies off of both the living room and dining room. Linens and towels are also provided. The facilities includ.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Condo Rental

Details


Vacation Rental

Sunsets Abound in this stunning 2 bedroom right across from Siesta Key Beach,

Location, location, location. Bright and beachy open floor plan beachfront condo right across the street from the famed white sands of Siesta Key and a mile from Siesta Key Village.From the moment you walk through the door, this elegant third floor condo has everything you need for your stay in Paradise. The views alone will leave you coming back .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Apartment Rental

Details


Vacation Rental

Aloha Kai - Unit 31- close to the beach!

Fully furnished villa offering living room, dining area, fully equipped kitchen, two bedrooms and one bathroom. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offer a private parking space directly outside your front door. .......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Siesta Key Cottage Rental

Details


Vacation Rental

Aloha Kai - 2 beautful unit and close to pool!

Fully furnished villa offers living room, dining area, fully equipped kitchen, two bedrooms and 2 bathrooms. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and offers a private parking space directly outside your front door. T.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Cottage Rental

Details


Vacation Rental

Siesta Dunes 5-303, Come enjoy our little piece of Paradise!

Nicely appointed and spacious. Beautiful gulf and pool views. Updated, well-equipped kitchen. Bright Master Bedroom with a King bed and plantation shutters. Tiled baths. Updated dining and living room furnishings including a double Murphy bed on the Lanai. Two large wall-mounted flat-screen HDTV's! BlueRay & standard DVDs. iPod/iPhone dock with spe.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


Vacation Rental

Private Beach, Full Gulf Views, Wifi/Cable, Heated Swimming Pool Overlooking Ocean, Walk to Village

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! Hands down, best location with the best views! This home away from home 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.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Condo Rental

Details


Vacation Rental

Island House Beach Resort V27

Island House Beach Resort, Siesta Key Florida- Crescent Beach - This large 2 bedrooms, 2 bath villa is non-carpeted and approx. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, screened lanai, covered parking, central ac/heat, free wi-fi in unit! The unit has a king size bed, 2 twins, sleeper sofa. The u.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Villa Rental

Details


Vacation Rental

Tivoli by the Sea-Unit 503 - 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 4 with a king in the master, and two twin size .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Apartment Rental

Details


Vacation Rental

Our House at the Beach W-301 Stunning panoramic beach views

Looking for an amazing location with access to the most beautiful beach? Look no further! This 2-bedroom, 2 bath condo (sleeps 6) on Siesta Key sits right across from the Siesta Key Beach, voted #1 Beach in USA. This large condo is light and bright with two large wrap around balconies, 50' of floor to ceiling windows, and has a great view the ocean.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


Vacation Rental

Contemporary Garden View, Ground Floor Unit, Short Walk to Pool/Beach

Ground floor unit. Kitchen and flooring renovated in 2015. Brand new contemporary kitchen and high-end stainless steel appliances. Bathrooms fully renovated in 2017. Contemporary tiles and finishes give the unit a bright and clean feeling. Private outdoor patio connected to the lanai and master bedroom. Very quiet and peaceful location only a short.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Condo Rental

Details


Vacation Rental

Dog-Friendly Siesta Key Bungalow, Wifi, Adorable Cottage Close to Siesta Key Beach w/Private Yard

Totally renovated adorable Siesta Key bungalow nestled on a shaded street just minutes from Siesta Key beach and the village of Siesta Key with a variety of shops, restaurants and nightlife. Drive into the circular driveway and park your car under the covered parking to be away from the 10 minute typical afternoon showers which freshen the air and.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key House Rental

Details


Vacation Rental

Island House Beach Resort 9S

Island House Beach Resort! Siesta Key Florida, Crescent Beach. Ground floor unit. This 2 bedroom, 2 bath condo is 1300 sq. ft., non-carpeted and has a large living area, dining area, fully equipped kitchen, all appliances, lanai. It has a king, 2 twins, Central heat/ac. Free Wi-Fi in unit. This beautifully maintained complex is located on the wides.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Apartment Rental

Details


Vacation Rental

Chinaberry 423 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...

Brand New to the Rental Program! Absolutely GORGEOUS 2 bedroom 2 full bath unit on the 2nd floor in the main tower on the Gulf Side. Overlooking the beautiful tropical grounds, pool and the famous, white sugary sands of Crescent Beach! Tastefully decorated in a very light and bright, modern beach-theme, leather furniture in the living room, very up.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


Vacation Rental

Siesta Beach House #106 Beautiful Updated Unit

Modern decor, new bedding this is a great 1 bedroom unit at the Siesta Beach House. This unit sleeps 4 and is equipped with a King bed and a sofa bed. If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 2 Siesta Key Condo Rental

Details


Vacation Rental

Tivoli by the Sea-Unit 606 - Tivoli by the Sea-Unit 606 - Amazing full Gulf 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 and a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets!! This unit sleeps 4 with a king bed in the master, and a king.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Apartment Rental

Details


Vacation Rental

Our House at the Beach C-217 A MUST SEE!!!!!!

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. Th.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


Vacation Rental

Aloha Kai - Unit 14A-close to beach and pool!

Nicely renovated and Fully furnished villas offer living room, dining area, fully equipped kitchens, 1 bedroom/ 1 bathroom. Screened porch. Short walk to the beach or pool. ALOHA KAI is a five acre vacation retreat hosting 68 private villas and apartments, nestled on the powdery-white sands of the Gulf of Mexico. Villas are at ground level, and off.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Siesta Key Cottage Rental

Details


Vacation Rental

6536 South Village Pool Home

Fantastic 3 bedroom, 2 bath pool home on a Natural Lagoon located in the South Crescent Shopping area! Enjoy lounging in the small, heated pool, or sitting on the dock by the lagoon. Just a short walk to many fantastic restaurants and great Beach shopping for everyone! Enjoy having The Crescent Grocery at the end of your street and our world reno.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 Siesta Key Apartment Rental

Details


Vacation Rental

Tropical Oasis w Balcony, minutes to Beach

Warm natural light fills this home making it the vacation oasis you have always dreamed about! With 2 bedrooms and 2 bathrooms, everyone has plenty of space to call their own on your tropical vacation. In just a few short minutes, you can also be at the beach soaking up the warm Florida sun. Enter this home and enter into pure bliss. Both the mast.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


Vacation Rental

Our House at the Beach C-102- Near Beach and Pool!

Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. Th.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


Vacation Rental

Our House at the Beach C-122 Updated First Floor

Lake house offers a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances, including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the grounds........read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


Vacation Rental

Updated 2 Bedroom, 2 Bath Gulf View with 2 Lanais!

OCEAN VIEWS and ON THE BEACH!! This newly furnished and redecorated 3rd floor end unit, with 2 lanais, is perfectly situated, overlooking the Gulf of Mexico, the pool area, and of course Siesta Key’s incredible beach. Relax on the enclosed lanai or the end balcony with a glass of wine, a good book or just take in the spectacular ocean views as .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Siesta Key Condo Rental

Details


Vacation Rental

Harbor Towers Bay View, New Flooring, Pools, Tennis, Gated Complex, WiFi, Smart TV, Assigned Parking

Harbor Towers sits directly on the bay where you can enjoy spectacular morning sunrises! This is a premier property with all the amenities you could want or need and located conveniently on Siesta Key close to the beach! Fabulous powdery white sands of Siesta Key Beach are just a short bike ride or Trolley ride away. A heated pool and a smal.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Siesta Key Condo Rental

Details


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Find the Top Vacation Rentals in Siesta Key, Sarasota Florida.

We have 2,3 or 4 Bedroom beachfront Condo Rentals with ocean view or a Beach House for the entire family. Book Direct Here!

Siesta Key Beach consistently ranked in the top spot as the most beautiful beach in the United States, Siesta Key is the ultimate beach escape. Located close to Sarasota, an eight-mile barrier island with stunning natural beauty, this award-winning beach is known for its pristine sugary white sand that is often described as the finest in the world. Vacation Rentals near Siesta Beach, Turtle Beach and Crescent Beach area are the most popular along the barrier island, offering tranquil waters that provide a safe spot for swimming and snorkeling.

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