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 villa

Island House Beach Resort V24

Island House Beach Resort - Villa 24

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

2 Bedroom(s) 2 Bath(s) Villa - Sleeps 6
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 condo

Siesta Heron 3 / Captiva

Hidden Paradise Among Tropical Landscape on Lakefront Property 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 house

Coconut Grove

Coconut Grove - One of The Cottages on the Key

Welcome to Coconut Grove! A private home nestled right in the heart of the Siesta Village with the style, elegance and charm of Siesta Key. Enjoy a family home that sleeps 16, a private heated pool, and quite literally in the heart of Siesta Village! ....

6 Bedroom(s) 6 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 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 V37

Island House Beach Resort - Villa 37

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 ki ....

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

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Siesta Key condo

Our House at (Siesta) Beach

Direct Access to Splendid White Sands at Siesta Beach, Rated Best Beach in USA

Enjoy nature and culture at its best! Light-filled, two bedroom, two bath, corner unit condo has 2 walls of glass sliders that open onto two large furnished balconies. You will be just steps from Siesta Beach - rated one of the best beaches in the wo ....

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

Casita Blanca 1139E

Casita Blanca - One of The Cottages on the Key

Welcome to Casita Playa of Playa y Blanca. This COMPLETELY RENOVATED, 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 c ....

2 Bedroom(s) 1 Bath(s) Vacation Rental
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

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

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 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 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

Siesta Heron 5 / Key Lime

Small and Quiet Lakefront Resort on Siesta Key W/ Heated Pool and Kayaks

This is a two bedroom two bathroom unit furnished with king-size bed in one private bedroom, two twin-size beds in the other private bedroom, and sleeper sofa in the living room accommodating up to 6 persons. There are two bathrooms one with shower o ....

2 Bedroom(s) 2 Bath(s) Condo
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 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 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

Casita Sun Star - 1135

Casita Sun Star - One of The Cottages on the Key

Welcome to Casita Sun Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 8] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decadent ba ....

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

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

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 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 condo

Siesta Dunes 1-406

SIESTA DUNES 1-406 LUXURY CONDO WITH A GREAT VIEW!

Located on American’s #1 white sand Crescent Beach, this condo has a great ocean view from the top floor of Building 1! This fourth floor, non-smoking unit has cathedral ceilings and is beautifully decorated. An elevator and laundry room are just s ....

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

Casita Morning Star - 6920

Casita Morning Star - One of The Cottages on the Key

Welcome to Casita Morning Star! Our newly renovated luxury cottage (completion date of June 2017) has all the amenities your family [up to 10] can fathom. Inside you’ll enjoy contemporary porcelain wood style flooring throughout gorgeous and decade ....

3 Bedroom(s) 3 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 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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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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