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Florida Vacation Rentals, Homes & Condos

Siesta Key Beach Vacation Rentals in Sarasota

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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 Vacation Places To Stay. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida.


Siesta Key Condo

Vacation Home - 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. Fi....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key House

Casita Sun Star - 1135 - Siesta Key House

Casita Sun Star - Ask About $99 Down!. This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer! We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have im....

4 Bedrooms 3 Baths - Sleeps 10
Siesta Key, FL

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Siesta Key House

Casita Sol - 1137W - Siesta Key House

Casita Sol - Ask About $99 Down!. This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer! We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have im....

2 Bedrooms 1 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Apartment

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

Sunset Royale - 204- Close to Beach and Siesta Village. Enjoy watching the beautiful sunsets every night from your own private lanai/patio in this one bedroom, one bathroom condo. Located at Siesta Beach with Siesta Key's famed "Village" a short walk away. This condo has everything you are looking for. Amenities include: beach access, BBQ, picnic tables (at the beach), Gulf view, western sunsets, family....

2 Bedrooms 1 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Condo

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 includ....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key House

Casita Morning Star - 6920 - Siesta Key House

Casita Morning Star - Ask About $99 Down!. This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer! We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have im....

4 Bedrooms 3 Baths - Sleeps 10
Siesta Key, FL

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Siesta Key Apartment

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,. Enjoy watching the beautiful sunsets every night from your own private lanai/patio in this two bedroom, two bathroom condo. Located at Siesta Beach with Siesta Key's famed "Village" a short walk away. This condo has everything you are looking for. Amenities include: beach access, BBQ, picnic tables (at the beach), Gulf view, western sunsets, family....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Apartment

Tivoli by the Sea-Unit 202- Nicely updated! - Siesta Key Apartment

Tivoli by the Sea-Unit 202- Nicely 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 and a gorgeous view of the Gulf of Mexico. Sit on your 26 ft open balcony and watch our spectacular sunsets! This unit sleeps 6 with at king in the master a queen in the g....

3 Bedrooms 2 Baths - Sleeps 6
Siesta Key, FL

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Siesta Key House

Casa De Mariposa - Siesta Key House

Casa De Mariposa - Ask About $99 Down!. This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer! We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have im....

7 Bedrooms 6 Baths - Sleeps 16
Siesta Key, FL

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Siesta Key House

Turtles Watch - 6925 - Siesta Key House

Turtles Watch - Ask About $99 Down!. This home could qualify for our BookCareFree promotion for 2020 and 2021 arrivals This includes: • Lenient Cancellation Policies • Deferred Payments • Adjusted Deposit Amounts Ask us about how you can qualify for this special offer! We go above and beyond the industry standard for cleanings with our multi-tiered cleaning protocol. We have im....

4 Bedrooms 5 Baths - Sleeps 8
Siesta Key, FL

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Siesta Key Condo

Siesta Beach House - 204 - Siesta Key Condo

Beachside Vacation Rental Condo on Siesta Key with Pool Access. *** NEW *** If you are looking for some Florida beach relaxation, Look no further than this 2 bedroom Siesta Key Beachside vacation rental condo. Located within a beachside vacation rental community, this unit offers direct beach access to a semi-private portion of Siesta Key Beach just a few short steps away. The community also offers free access....

2 Bedrooms 1 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Condo

LuLu's Key House Green 1/1 Upstairs - Siesta Key Condo

LuLu Green Right in the heart of Siesta Key Village, 4 minute walk to beach, Pool, Washer/dryer. Got Paradise!? Well now you do..... This oasis on Siesta Key is just that. The condo is only a couple of blocks away from the beach and rests in Siesta Key Village where you will find lots of great dining, amazing shops, coffee houses and more, all a short walk away. With everything you could want and need at your fingertips; I assure you that ....

1 Bedrooms 1 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Apartment

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

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. ....

2 Bedrooms 1 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Apartment

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

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....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Condo

Crescent Arms Unit 402S - Siesta Key Condo

Beachfront Condo - 2-Bedroom - Luxury - Directly on Crescent Beach. CRESCENT ARMS - Siesta Key Beachfront Vacation Condos on Crescent Beach (Two Bedroom Beachfront Unit for Rent) Located Directly on Crescent Beach on the middle of Siesta Key, Sarasota, FL Crescent Arms Condominium Complex: Located directly on world famous Crescent Beach these Siesta Key beachfront condos are walking distance to South Village. Cr....

3 Bedrooms 2 Baths - Sleeps 6
Siesta Key, FL

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Siesta Key House

Windward - Siesta Key House

Waterfront Luxury Home W/ Heated Pool, Dock, Jet Ski lifts. 3/4 mile to Siesta Village. Reside at this elegant retreat for your extended stay on beautiful Siesta Key. Enjoy the islands' miles of #1 rated beaches and laidback lifestyle of Siesta Key Village within walking distance or a quick bike ride. This single story 4 bedroom 3 1/2 bathroom canal front home features a large swimming pool with plenty of sun lounging area around in....

4 Bedrooms 4 Baths - Sleeps 8
Siesta Key, FL

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Siesta Key Villa

Island House Beach Resort V37 - Siesta Key Villa

Island House Beach Resort V37. Island House Beach Resort- Siesta Key Florida, Crescent Beach - The lovely villa is located on the widest part of Crescent Beach. It is approx. 1000 sq. ft. and is 2 bedrooms, 2 baths. The villa has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, screened lanai, covered parking, 3 tvs, dvd, free wi-fi in u....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, Fl

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Siesta Key Condo

Siesta Dunes 5-303 - Siesta Key Condo

Siesta Dunes 5-303, Come enjoy our little piece of Paradise!. Enjoy your beachfront vacation condo here in Siesta Key, with perfect sandy beaches right out your door. Siesta Key is a barrier island along the southwestern coast of Florida and is considered by beach experts to be one of the most beautiful beaches in Florida. When you stay with us at Siesta Dunes Condominiums, you stay in style and comfort, just....

2 Bedrooms 2 Baths - Sleeps 6
Siesta Key, FL

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Siesta Key Condo

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....

3 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Villa

Island House Beach Resort V27 - Siesta Key Villa

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....

2 Bedrooms 2 Baths - Sleeps 6
Siesta Key, Fl

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Siesta Key Apartment

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 ....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key Condo

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....

2 Bedrooms 2 Baths - Sleeps 6
Siesta Key, FL

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Siesta Key Condo

Siesta Dunes 1-104 - Siesta Key Condo

Contemporary Garden View, Ground Floor Unit, Short Walk to Pool/Beach. Ground floor unit, garden view 2 Bedroom, 2 Bathroom Unit. Updates through out which include new tile flooring as well as bathrooms and a new kitchen with stainless steel appliances. Contemporary tiles and finishes give the unit a bright and clean feeling. Enjoy sitting in the back patio overlooking the garden which is accessible through the master....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Siesta Key House

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....

2 Bedrooms 2 Baths - Sleeps 4
Siesta Key, FL

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Consistently ranked in the top spot as the most beautiful beach in the United States, Siesta Key is the ultimate beach escape. 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. Siesta Beach, Turtle Beach and Crescent Beach are the most popular along the barrier island, offering tranquil waters that provide a safe spot for swimming and snorkeling.

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