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Siesta Key Vacation Rentals, Condos & Apartment Rentals.

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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 Rentals - Siesta Key Condo

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. First floor means there are no steps to climb. Condo has been professionally remodeled and impeccably .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Details


Sunset Royale - 204- Close to Beach and Siesta Village - Siesta Key Apartment

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 dinner cocktails from the Sunroom. The condo features a fully equipped kitchen, King size bed, smart .......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Apartment Rentals

Details


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

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 include a heated pool, tennis courts and a covered pavilion with grilling area........read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Details


Sunset Royale - 314- Sunsets Abound in this stunning 2 bedroom r - Siesta Key Apartment

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 year after year. The kitchen features white Corian countertops and is fully equipped for all your ne.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Apartment Rentals

Details


Aloha Kai - Unit 31- close to the beach! - Siesta Key Cottage

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. The kitchen in each villa is fully equipped with appliances, pots, pans, utensils, and dishes for al.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 4 Cottage Rentals

Details


Aloha Kai - Unit 2 Beautful unit and close to pool! - Siesta Key Cottage

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. The kitchen in each villa is fully equipped with appliances, pots, pans, utensils, and dishes for all.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Cottage Rentals

Details


5-303 - Siesta Key Condo

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 speakers. Wireless internet and printer. Free long distance to US & Canada. Keurig Coffee maker availab.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


Terrace on Ocean - 3 - Siesta Key Condo

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 and in Siesta Key Village with gulf views, bay views, city light views, Big Pass Lido Key Beach vie.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Details


Tivoli by the Sea-Unit 503 - Beautiful view - Siesta Key Apartment

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 beds in the guest bedroom. 1 week minimum rental........read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Apartment Rentals

Details


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

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. It's stylish and recently renovated with everything you need for a restful and memorable vacation........read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


1-104 - Siesta Key Condo

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 walk from the beach, pool and grill area. Enjoy sitting in the back patio overlooking the garden af.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Details


Winding Way Siesta Key - Siesta Key House

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 quickly lead back to a wonderfully sunny summer day here at the beach. The yard is green and canop.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 House Rentals

Details


Bay Oaks, 4th Floor Corner - Elevator - Siesta Key Condo

Walk to Beach, Heated Pool, Tennis, Fishing Pier, Distant Gulf View from Master, Elevator Bldg. WiFi

Come vacation in this beautiful two bedroom, two bath condo with lots of amenities at your fingertips in a relaxing atmosphere. Bay Oaks condominium complex on Siesta Key, Fl is set among tropical foliage and beautiful walkways throughout. Enjoy a stroll along the coconut palm trees and tall shade oaks that line the brick pathways throughout Bay Oaks. You will have access to the complexes private fishing pier, the tennis courts, pool table in t.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Details


Chinaberry 423 at Midnight Cove Siesta Key, FL. - Siesta Key Condo

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 updated kitchen with an open floor plan. The colors of the unit are off white and pale blue. Beautiful.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


Siesta Beach House #106 Beautiful Updated Unit - Siesta Key Condo

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 beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorg.......read more

2 Bedroom(s)
1 Bath(s) - Sleeps 2 Condo Rentals

Details


Tivoli by the Sea-Unit 606 - Amazing full Gulf view! - Siesta Key Apartment

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 bed in the guest bedroom. 1 week minimum rental........read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Apartment Rentals

Details


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

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. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dress.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


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

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 offers a private parking space directly outside your front door. The kitchen in each villa is fully equ.......read more

1 Bedroom(s)
1 Bath(s) - Sleeps 4 Cottage Rentals

Details


6536 South Village Pool Home - Siesta Key Apartment

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 renowned Siesta Key Beach just a short walk away. This beautiful home is pet friendly- so leave no love.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 Apartment Rentals

Details


ANC506 - Siesta Key Condo

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 master and guest bedrooms have walk in closets and are filled with natural light making the spaces feel .......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


Our House at the Beach C-102- Townhouse Near Beach and Pool! - Siesta Key Condo

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. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dress.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


Our House at the Beach C-122 Updated First Floor - Siesta Key Condo

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. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dr.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


2-300 - Siesta Key Condo

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 you enjoy the tropical breeze. Of course the perfect condo would not be complete without ocean view.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 4 Condo Rentals

Details


Harbor Towers 2 Bedroom Bay View - Siesta Key Condo

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 smaller wading pool for children are waiting for you. Considered one of Siesta Key's nicest pools, the.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Condo Rentals

Details


Home Away From Home on Siesta - Siesta Key House

2BR/2BA House Just Steps to Siesta Village & Siesta Key Beach

This charming tropical 1,320 2 bedroom 2 bath home is located within the heart of Siesta Key Village and a block away from the famous Siesta Key Beach. This private beach home will have you relaxed from the moment you kick off your flip flops. The home is equipped with 3 4K smart TVs and a ton of beach toys, chairs to keep traveling easy. .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 House Rentals

Details


Vacation Rentals - Siesta Key House

5 bedroom Mid Century home, steps from Siesta Key Beach

Filled with art and light, this one floor home is sprawling, yet comfy... with three separate bedroom wings and plenty of outdoor and indoor gathering spots. Tropical, this home has a private backyard with jacuzzi, a fish pond (with no fish) and a pier with snook and sometimes, manatees! Perfect for family and friend gatherings, making memories and enjoying life on this heart shaped island. The home is user friendly, with a large eat-in kitchen, .......read more

5 Bedroom(s)
4 Bath(s) - Sleeps 10 House Rentals

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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