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Vacation Rentals by Owner in Siesta Key
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Condo
4.9 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Siesta Key - Beachfront Condo - 2 BR – Free Boat Docks - Upscale - Renovated
Private Vacation Home
5.0 Star Review
Siesta Key, Florida
4 Bedrooms
6 Bath(s) Sleeps 8
Luxurious Waterfront Retreat minutes from Beach, bay front with city views.
Condo
5.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
4th Floor Crescent Beach Condo Offering Full Unobstructed Gulf Views.
Condo
5.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Firethorn 611 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Pool...
Condo
4.8 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Luxury on Crescent Beach - Great Location!
Apartment
4.9 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 5
Walk To Siesta Village And Beach/Private Pool & Hot Tub
Condo
4.9 Star Review
Siesta Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 8
BEACHFRONT CONDO - THREE BEDROOM - HEATED POOL - FREE BOAT DOCKS - RENOVATED
Condo
3.9 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Ground Floor at Bay Oaks in Siesta Key - Watch Dolphin in the Bay - Fish from the Pier. Unit E81
Condo
4.5 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Sprinkle of Irish charm, beautifully updated, Siesta Dunes 8-205
Condo
5.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 5
1st Floor Gulf View, Convenient Walk Out to Pool w/ 3 Porches!
Apartment
5.0 Star Review
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 9
Stunning 3 Bedroom Home with Roof-Top Pool on Siesta Key!
Private Vacation Home
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 8
Stunning 3 bed/ 2.5 bath Townhouse Steps From Siesta Key Beach!
Condo
4.3 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Beautiful 2Bed/2Bath at Crystal Sands, Steps from Pool and Siesta Key Beach!!
Apartment
5.0 Star Review
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 9
Beautiful 3 Bed/2.5 bath With Roof Top Pool on Siesta Key!
Private Vacation Home
4.9 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Prime Location! 200 feet to the beach. 2 blocks to shopping and restaurants
Private Vacation Home
Siesta Key, Florida
4 Bedrooms
3 Bath(s) Sleeps 8
NEW! Luxury 4/3 Home on Siesta Key w. Heated Pool & Water View!
Condo
5.0 Star Review
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 8
Modern 3 Bed/2.5 bath Gulf Side Condo Steps from Siesta Key Village and Beach!!
Condo
3.7 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 5
Updated Top Floor Siesta Key Vacation Rental at Bay Oaks
Condo
5.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 8
Beautifully Updated Ground Floor at Gulf & Bay Club. Gulf Front Living at it's Finest!
Condo
4.8 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 5
Bay Oaks, End Unit, Walk to Beach, WiFi, Updated, Pool, Tennis, Complex Fishing Pier
Condo
4.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
New Listing! Ground floor, easy access to the pool and beach! Siesta Dunes 2-104
Private Vacation Home
4.8 Star Review
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 6
Perfect Siesta Village Pool Home! Walk to the beach and hang out in the Village!
Condo
5.0 Star Review
Siesta Key, Florida
Studio
1 Bath(s) Sleeps 2
Cozy Siesta Key studio 5 minute walk to Village
Condo
4.9 Star Review
Siesta Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
Cozy Romantic Siesta Key Beachfront Condo-full beach view. 50 steps to the beach
Cottage
4.8 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Prem 2Bed/2Bath Gate House Cottage with private beach access!
Private Vacation Home
5.0 Star Review
Siesta Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 8
3 bedroom house+ Private pool + huge yard. 12min walk to beach. Pet friendly.
Condo
4.8 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Bay, Pool, Tennis Court Views, 2 Master Suites, Stainless Kitchen, Tile Floors, 3 TV's
Condo
4.8 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
NEWLY REMODELED! On World Famous Crescent Beach
Condo
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Stunning Siesta Key Beach Views from 2 Bedroom Condo!!
Private Vacation Home
2.5 Star Review
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 8
Spacious 3 Bedroom Gulf Side Townhome with Rooftop Sun Deck On Siesta Key!!
Condo
4.6 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
SIESTA KEY! MIDNIGHT COVE 2/2 GULFRONT! BOOKING FOR SUMMER/FALL 2023 NOW!
Apartment
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
2 Bedroom Single_family (427377) by Houzlet
Private Vacation Home
3.0 Star Review
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 6
Beautiful 3 Bedroom Home With Rooftop Sun Deck & Views of Siesta Key Beach!
Condo
5.0 Star Review
Siesta Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
Buttonwood 447 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
NEW LISTING! Spend your winter in this condo just steps from Siesta Village!
Private Vacation Home
Siesta Key, Florida
4 Bedrooms
4 Bath(s) Sleeps 12
Beautiful 4 Bedroom/ 4 Bath Beach House-Directly on Beach!
Condo
3.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Chinaberry 413 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
Siesta Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
Buttonwood 940 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
5.0 Star Review
Siesta Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
Buttonwood 472 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
5.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Chinaberry 414 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
Siesta Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
Buttonwood 950 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
4.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Chinaberry 423 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
4.9 Star Review
Siesta Key, Florida
1 Bedrooms
1 Bath(s) Sleeps 4
NOV and DEC AVAILABLE!! 1 bedroom 1 bathroom with access to private beach
Private Vacation Home
4.8 Star Review
Siesta Key, Florida
3 Bedrooms
3 Bath(s) Sleeps 8
Grand Canal Front 3BR/3bath, Pool/Hot Tub, Walk to Beach & Siesta Village
Condo
4.7 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Chinaberry 456 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
5.0 Star Review
Siesta Key, Florida
3 Bedrooms
2 Bath(s) Sleeps 6
Buttonwood 417 - 3 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
5.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 6
Chinaberry 913 - 2 Bedroom Condo with Private Beach with lounge chairs & umbrella provided, 2 Poo...
Condo
5.0 Star Review
Siesta Key, Florida
2 Bedrooms
2 Bath(s) Sleeps 4
Peppertree Bay Gulf Beach!- Steps from your private beach
Find the Top Vacation Rentals in Siesta Key, Sarasota Florida.
We have 2,3 or 4 Bedroom beachfront Siesta Key Vacation Rentals with ocean view or a Beach House for the entire family. Book Direct Here!
Siesta Key Beach consistently ranked in the top spot as the most beautiful beach in the United States, Siesta Key is the ultimate beach escape. Located close to Sarasota, an eight-mile barrier island with stunning natural beauty, this award-winning beach is known for its pristine sugary white sand that is often described as the finest in the world. Vacation Rentals near Siesta Beach, Turtle Beach and Crescent Beach area are the most popular along the barrier island, offering tranquil waters that provide a safe spot for swimming and snorkeling.