Siesta Key Beach Florida Vacation Rentals, Hotels & Resorts

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We have partnered with a major provider of vacation rentals, 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 Siesta Key, FL. Browse hundreds of Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer.

Siesta Key condo

Siesta Beach House

Fabulous Siesta Beach House

Our place on the #1 Siesta Key beach is near to Siesta Key village, Downtown Sarasota, Lido Key, St Armand s circle and LongBoat Key. You’ll love our place because of the location, and the ambiance. LITERALLY a few steps to private Crescent beach ( ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Siesta Key, FL

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Siesta Key condo

FC 3BR

Beachfront Condo - 3 BR- Heated Pool - Free Boat Docks – Upscale – Siesta Key

Beachfront Condo - Three Bedroom - Heated Pool - Free Boat Docks - Upscale - Siesta KeyLocated Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstr ....

3 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key apartment

Island House Beach Resort 5N

Island House Beach Resort 5 North

Island House Beach Resort - Crescent Beach, Siesta Key. Gulf Front Unit, 3rd Floor, Panoramic Views. This luxury apartment is 1300 sq. ft. non-carpeted and is 2 bedrooms, 2 bathrooms. It has a large living area, dining area, fully equipped kitchen, ( ....

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

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Siesta Key house

SiestaKey, house- TopWorld Bch

ISLAND GLASS - HOUSE, AVAILABLE

THIS IS A HOUSE W/ GARAGE- PRIVATE POOL, W/ FREE ...KITCHEN, BATH, LAUNDRY CONDIMENTS.... BELOW MARKET... NOT A CONDO....Go to earthcam .com view siesta key beach for yourself. It is lovely outside today. WE HAVE THE BEST GUEST!.... PLEASE READ. ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 4
Siesta Key, FL

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Siesta Key condo

Chinaberry 423 at Midnight Cove Siesta Key, FL.

Chinaberry 423 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Pools, Fitness Center and Tennis Courts.

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 dec ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key condo

Beach front Condo

Direct Siesta Key Beachfront condo!

Our beautiful fully remodeled condo is located directly across the street from world famous Siesta Key Beach! Whether you would like to put your toes in the crystal white sands of the beach or enjoy our large heated pool you will be in paradise! Enjo ....

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

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Siesta Key apartment

SV 1BR

1BR - Garden Apartment of Siesta Key Townhouse - Heated Pool -Siesta Key Village

SEASIDE VILLAS - Deluxe Garden Apartment of Siesta Key Townhouse Vacation Rental - With Heated Pool Located in the Heart of Siesta Key Village, Sarasota, FL - Short Walk to Crescent Beach SEASIDE VILLAS: This Siesta Key one bedroom garden apartment ....

1 Bedroom(s) 1 Bath(s) Apartment
Siesta Key, FL

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Siesta Key apartment

Island House Beach Resort 9S

Island House Beach Resort - 9 South

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 twi ....

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

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Siesta Key condo

Siesta Heron 6 / Sunset Suite

Romantic Lakefront Two bedroom unit W/ access to Heated Pool and More

This is a spacious studio style two bedroom unit furnished with king-size bed and queen sleeper sofa downstairs and queen bed upstairs Accommodating up to 6 persons. The downstairs bathroom is equipped with tub/shower combo. While the upstairs offers ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key villa

Island House Beach Resort V7

Island House Beach Resort - Villa 7

Island House Beach Resort, Crescent Beach, Siesta Key Florida! Newly renovated 2 bedroom, 2 bath unit. The unit is approx. 1000 sq. ft. has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, covered parking, sc ....

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

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Siesta Key condo

FC 2BR

Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Turtle Beach

Siesta Key - Gulf-Front Retreat - 2 BR - Free Boat Docks Located Next to Turtle Beach on the Southern End of Siesta Key, Sarasota, FL Fisherman's Cove is a very rare Siesta Key condo where every unit has direct, unobstructed, full Gulf views. The b ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key studio

Large Private Studio Apartment

Large & Comfortable Private Studio with Separate Entrance - Walk to Village

Relax, get away and enjoy Siesta Key's laid back lifestyle! Surrounded by lush, tropical vegetation, and nestled in a quiet residential neighborhood, you’ll love this comfortable, 500 square foot, private Studio Apartment. The Studio accommodates 2 ....

1 Bedroom(s) 1 Bath(s) Studio - Sleeps 2
Siesta Key, FL

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Siesta Key house

Latitude Adjustment - 461

Latitude Adjustment - One of The Cottages on the Key

Welcome to Latitude Adjustment! This breathtaking 4 bedroom, 4 bathroom home is perfectly situated between America's #1 beach in the world and Siesta Key's famous North Village! You will not be able to ask for more as you drive up to this tropical oa ....

4 Bedroom(s) 4 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key house

Sea Shell Casita - 1121

Sea Shell Casita - One of The Cottages on the Key

The Sea Shell and Sea Wave are two separate units which can be uniquely configured to create Villa Brisa Marina, an absolutely beautiful and stunning private pool home. Please Note: These units [Sea Shell & Sea Wave] can be rented separately. Combi ....

2 Bedroom(s) 2 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key house

Sand Dollar Cottage - 910

Sand Dollar Cottage - One of The Cottages on the Key

Welcome to the completely remodeled, and newly furnished Sand Dollar Cottage! This lovely 3 bedroom, 2 bath home comfortably sleeps 6 in beds, with a soft ultra plush sofa sleeper in the living room for an extra 2. Enjoy the peacefulness of a large h ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key cottage

Siesta Key Beach Cottage

Siesta Key Beach Cottage Across The Street From #1 Beach In USA

The Siesta Key Beach Cottage is located right on Beach Rd directly across the street from the #1 Beach in the USA. Walk out the front door and walk across the street to beach access #7 and you are on the white powder Beach of Siesta Key. You can loo ....

1 Bedroom(s) 1 Bath(s) Cottage - Sleeps 2
Siesta Key, FL

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Siesta Key condo

The Terrace

Penthouse with Extraordinary Island Views, Directly on the Beach, Heated Pool

Siesta Key has come to be known around the world for is top rated beaches. One of the reasons it is continually rated #1 beach in America is of course it's extraordinarily soft white sands. Another main component which makes Siesta Key and its beache ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key house

Seagrove

NEW Private Siesta Key Vacation Rental Home W/ Heated Pool on Quiet Street

Discover Siesta Key at this three bedroom two bathroom vacation rental home located in the heart of Siesta Key tucked away in a quiet neighborhood. Hire one of the many free ride services on the key for a quick trip to visit Siesta Key village where ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key house

Vacation Home

Siesta Waterfront Retreat

Beautiful, spacious home away from home awaits for you. Water front house, right on the canal, only one bridge away from the ocean, it is located in a very quiet dead end road, which makes it very private and peaceful. Here, you are minutes away to ....

4 Bedroom(s) 3 Bath(s) Vacation Rental - Sleeps 12
Siesta Key, FL

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Siesta Key villa

Island House Beach Resort V25

Island House Beach Resort - Villa 25

Island House Beach Resort - Siesta Key Florida, Crescent Beach - This large 2 bedrooms, 2 bath villa is appox. 1000 sq. ft. It has a large living area, dining area, fully equipped kitchen, all appliances, central ac/heat, covered parking, screened la ....

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

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Siesta Key condo

CA 2BR Front Corner

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 ....

2 Bedroom(s) 2 Bath(s) Condo
Siesta Key, FL

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Siesta Key villa

Vacation Home

Beach Goers Paradise! Siesta Key 2/2 Condo

This charming villa allows you to enjoy all that beautiful Siesta Key has to offer. The white sands of Crescent Beach are just across the street. You may enjoy swimming in the Olympic size pool at Aloha Kai. Spend the evenings relaxing in your privat ....

2 Bedroom(s) 2 Bath(s) Villa - Sleeps 4
Siesta Key, FL

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Siesta Key apartment

Island House Beach Resort 17S

Island House Beach Resort 17 South

Island House Beach Resort!! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in central florida. This condo offers views of palm trees, white sand, and the crystal blue w ....

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

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Siesta Key villa

Island House Beach Resort V27

Island House Beach Resort - Villa 27

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 park ....

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

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Siesta Key condo

Sweet Siesta Condo at Beach

CONDO ON SIESTA KEY, 2 QUEEN BEDS, WALK OVER TO #1Beach in America, Only $75

This renovated Condo is right on Siesta Key, which is located in Sarasota Florida. Don't just stay in Sarasota or "near Siesta Key", stay right on Siesta Key, where you can Walk right over to Siesta Key Main Beach, again rated the #1 Beach in Americ ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 4
Siesta Key, FL

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Siesta Key house

Home Away From Home on Siesta

Stay in Siesta Key Village and Walk to the 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. Newly renovated and with all new furniture this private beach home will have you relaxed from the ....

2 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 6
Siesta Key, FL

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Siesta Key apartment

Island House Beach Resort 14S

Island House Beach Resort 14 South

Island House Beach Resort! Crescent Beach, Siesta Key Florida. This beautifully maintained complex is located on the widest part of one of the best beaches in Florida. This condos offers a view of the palm trees, white sand and turquoise waters of th ....

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

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Siesta Key house

Seahorse Cabana - 1106

Seahorse Cabana - One of The Cottages on the Key

Welcome to the Seahorse Cabana! Please Note: Sleeps 8: K, K, 2T, QAB (queen air bed) These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If on ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key house

Pura Vida Oasis - 350

Pura Vida Oasis - One of The Cottages on the Key

This spectacular bright cheerful, canal front cottage with a heated pool & spa has 5 bedrooms and 3 baths and it can sleep a total of 13. As you enter Pura Vida Oasis, you will notice an eclectic wine storage rack and desk area awaiting on your right ....

5 Bedroom(s) 3 Bath(s) Vacation Rental
Siesta Key, FL

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Siesta Key house

Garden House

Coastal Siesta Key Vacation Rental Home W/ Heated Pool and Beach Access

Never miss a sunset over the Gulf of Mexico from this island retreat. Located just a short walk to the beach, this two story home with private heated pool can accommodate you and up to 5 of your guests with comfort. Step into the home through the fro ....

3 Bedroom(s) 2 Bath(s) Vacation Rental
Siesta Key, FL

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Find Affordable Siesta Key Beach Hotels & Vacation Rentals

Plan your Siesta Key Florida Vacation here and get the best value possible for the trip! Find affordable Resort Hotels with oceanfront condo rentals, pool and much more. We have a great selection of 2,3 or 4 bedroom villas, condos or cottages that offer you the best available places to stay in Siesta Key, Florida. Our Vacation Rentals, including Pet Friendly Rentals, let you get the most from your vacation in Tampa Bay Area.


Vacation Rentals Nearby Tampa Bay Destinations

Find nearby vacation rentals and some of the Best Hotels with cheap rates in Siesta Key, FL for you visit to the area, all a short drive to Siesta Key, Florida. Spend quality time with your family and friends with cheap hotel rates you can afford, visit the nearby beaches for nightlife, entertainment and a wide variety of beach activities. Hundreds of properties to choose from, search for availability, photos, descriptions and best price.

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