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 townhome

Updated Bayside Townhouse

Updated Townhouse! Private access to Beach. Enjoy Tennis, Heated Pools, Fishing

Across the street is our Private Access to one of the BEST beaches - Siesta Key Beach with the world renowned white sands - rated one of the top ten in the US! Gulf & Bay Club Bayside is a gated resort community of Key West style Town Homes all with ....

2 Bedroom(s) 2 Bath(s) Townhome - Sleeps 6
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 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 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

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 cottage

Mermaid's Retreat

Mermaid's Retreat on Siesta Key, #1 beach in the US!

This newly renovated studio cottage is on canal water and a casual walk to famous USA #1 Siesta Beach. It comfortably accommodates two guests with a futon option for a third. Mermaid's Retreat is the perfect location for your Florida Vacation. You ....

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

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Siesta Key house

Casita Sol - 1137W

Casita Sol - One of The Cottages on the Key

Welcome to Casita Sol of Sol y Mar. This COMPLETELY RENOVATED, single level (2 Bedroom / 1 Bathroom - 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 setti ....

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

LuLu's Key House Green 1/1 Upstairs

LuLu Green Brand New 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 ....

1 Bedroom(s) 1 Bath(s) Condo
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 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 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 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

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 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 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 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 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 townhome

Beach Cove

Walk to the #1 Beach in America, Offers Heated community Pool, Free Wi-Fi

Siesta Key has been named America's #1 beach time and time again. Experience fun in the sun like never before at this two-story townhome style condo located just a few hundred feet from the private access beach. Towards the front of the community gue ....

2 Bedroom(s) 3 Bath(s) Townhome
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 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 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 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 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 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

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

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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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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