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 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 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 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

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 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 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 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 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 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

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

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 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 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

SIESTA BEACH 3 BEDROOM

Beautiful Apartment with Ocean Views, Includes beach towels and chairs!

Check out my other amazing VRBO property reviews: Vrbo.com/4802815 ! Location, location, location! This beautiful apartment has been decorated to a home cozy feel. Newly done oversize balcony has most spectacular view on the Gulf and Beach, so you ....

3 Bedroom(s) 2 Bath(s) Apartment - 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

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 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

LaSiesta Condominiums Beach RD

Inquire about discounts! Just steps to the #1 Siesta Key Beach, Renovated 2017

This Completely renovated in 2017 Two Bedroom, One Bath condo with a view of the beach is just steps to the white, powdered-sugar sand of Siesta Key . Here at La Siesta Condominiums you also have easy access to Siesta Village and it's numerous resta ....

2 Bedroom(s) 1 Bath(s) Condo - Sleeps 5
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

Midnight Cove II Bldg 6

Private Beach Access, Gulf Views, Wifi/Cable, Pool, Renovated Condo With Amenities, Tennis

Enjoy your vacation in this beautifully renovated two bedroom 1.5 bath condo that sleeps 6. Step into the unit and immediately notice the warm open feel, the beautifully tiled floors and the sweeping panoramic views of an inlet off of the intra ....

2 Bedroom(s) 2 Bath(s) Condo
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

Casa De Mariposa

Casa De Mariposa - One of The Cottages on the Key

Welcome to Casa de Mariposa! This gorgeous property is comprised of two units, Monarch and Peacock Villa which are both mirror images of one another. Each unite features a 3 bedroom, 3 bathroom configuration with their very own common space to includ ....

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

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Siesta Key condo

Siesta Harbor Condominium

Siesta Key Condo....Relax, enjoy and feel at home......

Come vacation in this beautiful one bedroom, two bath, third floor condo. Siesta Harbor is an over 55+ community located directly across the street from America's #1 beach. Deeded access to Crescent Beach makes this super convenient. The condo also h ....

1 Bedroom(s) 2 Bath(s) Condo - 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

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

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

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 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

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

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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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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