Siesta Key Beach Florida Vacation Rentals, Hotels & Resorts

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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 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

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 house

Sandy Cabana - 1104N

Sandy Cabana - One of The Cottages on the Key

Welcome to the Sandy Cabana! Please Note: Sleeps 8- K, K, Q, QAB These units [Sandy Cabana & Seahorse Cabana] can be rented separately. Combined, these units are called: Sandy Seahorse Cottage (Sleeps 16) If one unit is not availabl ....

3 Bedroom(s) 3 Bath(s) Vacation Rental
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 condo

Sunset Royale - #208

Sunset Royale Luxury Condo #208 in Siesta Key

SIESTA KEY BEACH - RANKED 2011 #1 US BEACH BY DR. BEACH Sunset Royale Luxury Condo #208 is located on Siesta Key, an eight-mile long barrier Island connected to Sarsota and the mainland by two bridges. Along the island's west side, you'll ....

1 Bedroom(s) 1 Bath(s) Condo
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 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

Casita Playa - 1139W

Casita Playa - One of The Cottages on the Key

Welcome to Casita Playa of Playa y Blanca. This single level (2 BR/1BA - Master BR/1 Queen & 2nd BR/2 twins -sleeps 4) vacation home features private, gated beach access, a sparkling clean hot tub in a private, lush setting, a communal heated swimmin ....

2 Bedroom(s) 1 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

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 apartment

Island House Beach Resort 6N

Island House Beach Resort 6 North

Island House Beach Resort!! Siesta Key Florida. This 2 bedrooms, 2 bath unit is 1300 sq. ft. and is located on one the finest beaches in Florida. It has a large living area, dining area, 2 lanais, central heat/ac, fully equipped kitchen, ( all applia ....

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

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Siesta Key condo

Bay Oaks, 4th floor corner - elevator

Gulf View w/ Short Walk to Beach, Fishing Pier and Tennis

Bay Oaks, 2 Bedroom, 2 Bath, Sleeps 4. Enjoy this beautiful updated two bedroom, two bath condo which has all of the amenities you are looking for in a luxurious and relaxing atmosphere. Bay Oaks is set among tropical foliage and beautiful wal ....

2 Bedroom(s) 2 Bath(s) Condo
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 house

324 Avenida Madera, Siesta Key

Island Home in Paradise!!

Newly remodeled, single family home, 3 bedrooms, 2 baths, enclosed screened-in 27 x 13 heated outside pool(set to 82 degrees) with sunshelf...have dinner/cocktails outside in pool on sunshelf!! Short walking distance to 15 great restaurants, 12 bars, ....

3 Bedroom(s) 2 Bath(s) Vacation Rental - Sleeps 8
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 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 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 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 house

Sea Esta - 5319 (L)

Sea Esta - One of The Cottages on the Key

This private 3BR/2BA home is the perfect beach getaway to relax, unwind & take in everything Siesta Key has to offer. The best part? Siesta Salt Life is just 1 minute (seriously!) away from Siesta Key Beach, voted the # 1 beach in the U.S! Sea Esta o ....

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

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Siesta Key apartment

SIESTA BEACH APARTMENT

Prime location on Siesta Beach, Includes beach towels and chairs!

This apartment has been decorated to make feel like home with very cozy atmosphere. Has beautiful over sized closed in lanai. You can enjoy morning coffee and breakfast or just relax a in the afternoon or evening breathing fresh air. Ideal locatio ....

2 Bedroom(s) 2 Bath(s) Apartment - Sleeps 5
Siesta Key, FL

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Siesta Key house

536 Canal Road

Luxurious Vacation Home, Salt Water & Heated Pool, Partial Ocean Views

Welcome to Paraiso de Siesta, newly built in 2013 and one of the most Magnificent Vacation homes on Siesta Key. From the moment you walk into the the entry way, your eyes span the openness of the well designed space that leads to the balcony looking ....

4 Bedroom(s) 4 Bath(s) Vacation Rental - Sleeps 11
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 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 condo

Minorga On the Key

Heart of Siesta Key Village, Walk to Gulf/beach, WiFi, Heated Community Pool & Two Master Bedrooms

Location, location, location! Calle Minorga complex lies in the heart of Siesta Key Village with a heated pool. Restaurants, shops and nightlight are all only steps away - about a 1 minute walk from Sun Garden Cafe, Solorzarno's Pizza is 3 min ....

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

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SIESTA KEY condo

Beach Condo,The Calm @ Siesta!

Siesta PREMIER LOCATION and View just can't be beat!!!

This new vacation rental is the 'Calm of Siesta', as you enter with a full view of the Gulf of Mexico and Siesta Key Beach. The property has just been newly transformed to accommodate our guests best welcome to Siesta. The property is equipped with a ....

2 Bedroom(s) 2 Bath(s) Condo - Sleeps 5
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 condo

Harbor Towers

Newly Renovated & Modern, Wifi, Gulf Facing Harbor Towers, 3 bedroom with den

Newly remodeled, modern and beautiful 3 bedrooms, plus a den, 3 full bath condo right on Siesta Key, in a complex overlooking the intracoastal waterway and close to the beach!! Fabulous powdery white sands of Siesta Key Beach are just a short s ....

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

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Siesta Key condo

Siesta Heron 4 / Sand Dollar

Hidden Paradise on Lakefront Property Among Tropical Landscape on Siesta Key

This is a one bedroom one bathroom unit furnished with king-size bed in the private bedroom and queen-size sleeper sofa in the living room accommodating up to four persons. The living room is furnished with a 40" flatscreen TV with HD programing. The ....

1 Bedroom(s) 1 Bath(s) Condo
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 cottage

Honey Mango Cabana - 1144E

Honey Mango Cabana - One of The Cottages on the Key

Welcome to the Honey Mango Cabana! This beautiful and vibrant 2 bedroom, 1 bathroom vacation home accommodates up to 6 people. This property is very unique as it is one half of "Mango Manor," which is comprised of the two separate cabanas, Honey and ....

2 Bedroom(s) 1 Bath(s) Cottage
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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