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Below you will find our complete inventory regardless of travel dates, locations, or desired amenities. We understand that looking through hundreds of properties while planning your vacation is a daunting task. So, to narrow your search, please use the search bar to the right. As the number of properties may be limited during a certain period, such as peak season (February - April), we recommend starting with your travel dates, seeing what's available, and narrowing your search from there with area and amenities selections.

There are several additional options you can select to narrow your search if you find there are too many to choose from after applying your dates. For starters, you may want to select a single-family home for maximum privacy or a smaller condo or studio apartment when fewer travels require accommodations. Select the number of bedrooms and bathrooms required for your party to comfortably enjoy their stay. You may also like to select some essential amenities such as WiFi or pet friendly.

You may still find yourself falling in love with several different properties. Great news! Click the heart icon on any listings you would like to save as your favorites and review them later by clicking the “My Favorites” link. From the My Favorites page, you will be able to email yourself the list as well as anyone else who can assist you in choosing the right property for your vacation.

Below you will find our complete inventory regardless of travel dates, locations, or desired amenities. We understand that looking through hundreds of properties while planning your vacation is a daunting task. So, to narrow your search, please use the search bar to the right. As the number of properties may be limited during a certain period, such as peak season (February - April), we recommend starting with your travel dates, seeing what's available, and narrowing your search from there with...Read More
73 Properties Returned
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73 Properties Returned
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4 Bedrooms
3½ Baths
Sleeps 10

Type: Townhouse
Area: Siesta Key

Walk to Siesta Key beach from this large town home located at the center of Siesta Key. Offers heated pool and elevator access within the home.

2 Bedrooms
1 Bath
Sleeps 5

Type: Condominium
Area: Anna Maria Island

Don't just visit the beach, STAY at the beach in this beautiful cozy cottage located only steps away from the sands of Holmes Beach.

4 Bedrooms
2 Baths
Sleeps 8

Type: House
Area: Main Land

Exquisite spacious home with a pool in the renowned Gulf Gate Estates community of Sarasota, and only 3 miles from the #1 Siesta Key Beach

2 Bedrooms
2 Baths
Sleeps 6

Type: Condominium
Area: Siesta Key

Come and rejuvenate at Bay Oaks on Siesta Key. This complex offers heated pool, fishing pier, tennis court, club house and picnic area overlooking the waterway.

Studio
1 Bath
Sleeps 4

Type: Apartment
Area: Siesta Key

Perfect little beach side studio located at a stones throw to the white sands of Siesta Beach. Short distance to Siesta Village for restaurants and more.

2 Bedrooms
2 Baths
Sleeps 8

Type: Townhouse
Area: Siesta Key

Cozy 2 bedroom 2 bathroom town home less than 2 minutes walking distance to Siesta Beach and community heated swimming pool.

New Property
2 Bedrooms
1½ Baths
Sleeps 6

Type: House
Area: Main Land

Spacious vacation home located on and overlooking Philippi Creek in Sarasota, and only minutes from all the beaches on Siesta Key.

2 Bedrooms
2 Baths
Sleeps 6

Type: Condominium
Area: Siesta Key

Bring the whole family to this spacious condo just a short walk to the beach with heated pool. Walk or bicycle to restaurants, bars, grocery store, and more.

New Property
3 Bedrooms
2 Baths
Sleeps 6

Type: House
Area: Siesta Key

Discover Siesta Key at this private single family home with heated pool located in a central yet quiet neighborhood.

3 Bedrooms
2 Baths
Sleeps 6

Type: House
Area: Main Land

Sarasota water front home with dock and pool located minutes to shopping, restaurants, and beaches. Amazing sunsets included.

New Property
3 Bedrooms
2 Baths
Sleeps 8

Type: House
Area: Anna Maria Island

If you are planning your vacation to visit the beach then this is the perfect beach house for your stay. This 3 bedroom house is located on the soft white sands of Holmes Beach on Anna Maria Island with incredible ocean views.

2 Bedrooms
2½ Baths
Sleeps 6

Type: House
Area: Main Land

Enjoy this updated pool home nestled among tranquil tropical landscaping on a quiet street just minutes to Siesta Key, downtown Sarasota, and more.

2 Bedrooms
1 Bath
Sleeps 6

Type: Condominium
Area: Anna Maria Island

Stay at your own piece of tropical paradise by the beach and centrally located on Anna Maria Island. Surround by palm trees and lush vegetation and only a short walk to the soft sands of the Gulf Of Mexico. Your perfect beach vacation in paradise is here!

3 Bedrooms
2 Baths
Sleeps 6

Type: House
Area: Siesta Key

Hidden among topical landscape this lap pool home is located within a short walk to Shell Beach at the north end of the key offering easy access on and off the island.

 

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