Siesta Key, Florida


Properties Available 103 properties available
CONTACT US TO GET AN ADDITIONAL 10% OF DATES IN FEBRUARY 2023!Welcome to Blu Sky Cottage! This 3 bedroom 2 bathroom home is perfect for an extended stay on Siesta Key. Not only does it include a spacious heated luxury pool and spa, but it also sits directly on the canal. Whether you choose to catch up on your favorite book poolside, kayak out on th
Blu Sky Cottage - 5037 (281547)
Siesta Key, FL
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Welcome to Island Escape, where you're able to escape from reality into the tropical island of Siesta Key! This beautiful 4 bedroom / 2.5 bathroom home features a newly renovated kitchen & master bathroom, private heated saltwater pool, gourmet outdoor kitchen, cabana room, and several other exciting amenities to make your vacation nothing less tha
Island Escape - 638 (281489)
Siesta Key, FL
House
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 12 guests
Welcome to Admirals Watch, also known as a little slice of paradise! Load up your luggage on the private elevator, head upstairs to your gorgeous vacation rental on Siesta Key, and enjoy the panoramic views of the # 1 Beach in America! This home is located directly across the street from Beach Access #11 and less than a mile from Siesta Key Village
Admirals Watch - 673 (281474)
Siesta Key, FL
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Welcome to Baydream Bungalow! This quaint 3 bedroom 2 bathroom vacation rental home located on Siesta Key's north end is perfect the ultimate Florida vacation. Here, you're able to catch up on your latest reads by the private heated screened-in pool, catch some rays at the beach, or grill out with the family! Not only is this home located less than
Baydream Bungalow - 3472 (281477)
Siesta Key, FL
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
"This adorable 2 bedroom/2 bathroom home is a unique combination of 4 units that can be rented separately or together. Combined with its sister unit Vinca, both units make up Mandevilla. All four units combined make up The Hummingbird. This home is located less than 5 minutes from Siesta Key beach, voted the # 1 beach in the USA! Reserve Plumbago n
Plumbago - 5251C (281535)
Siesta Key, FL
House
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Welcome to Sandy Seahorse Cottage, a unique configuration of two units: “Sandy Cabana” and “Seahorse Cabana.” Each unit offers their own kitchen, living areas and lanai areas. This charming beach cottage has been recently updated with brand new furnishings throughout. This home is perfect for families and beachcombers alike!Tucked between the quiet
Sandy Seahorse Cottage (281498)
Siesta Key, FL
House Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rest from your beachside adventures in this casual condo situated less than seven miles from Bayfront Park. Perfect for families and groups that want to keep things simple, this condo is outfitted with everything guests need during their vacation, plus some bonuses like a screenedin balcony! Each bedroom features a ceiling fan and central air con
Blue Palm (259438)
Siesta Key, FL
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
This adorable 1 bedroom/1 bathroom home is a unique combination of 4 units that can be rented separately or together. Combined with its sister unit Lantana, both units make up Honeysuckle. All four units combined make up The Hummingbird. This home is located less than 5 minutes from Siesta Key beach, voted the # 1 beach in the USA! Reserve Mimosa n
Mimosa - 5251B (281533)
Siesta Key, FL
House Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
This tranquil oasis has everything need for your most perfect beach getaway at an absolutely UNBEATABLE location in Crescent Village and just minutes away from world famous Siesta Beach, voted the #1 beach in the USA! Serenity Cottage is the ideal vacation home for family get-togethers and small groups. Your Siesta Key adventure awaits you…Cross th
Serenity Cottage - 1028 (281502)
Siesta Key, FL
House
Bedrooms 3 bedrooms
Bathrooms 4 baths
Guests 8 guests
Welcome to Sea Angel! This private unit is perfect for small families, with the ability to accommodate up to 4 guests, with 1 bedrooms and 1 bathrooms.Cross the drawbridge from Sarasota to enter the serene island escape of Siesta Key, Florida! With clear blue gulf waters and powdery white sand, Siesta Key's world-renowned beaches are the perfect sp
Sea Angel - 274 (281566)
Siesta Key, FL
House Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
"This adorable 2 bedroom/2 bathroom home has all of the amenities for your perfect beach vacation at an unbeatable location! Combined with its sister property Mimosa, both units make up Honeysuckle. All four units combined make up The Hummingbird. Lantana is perfectly located less than five minutes from world famous Siesta Key beach, voted the # 1
Lantana - 5251A (281532)
Siesta Key, FL
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
This private tropical oasis has all the amenities for your most memorable beach vacation at an absolutely UNBEATABLE location, just a short walk to Beach Access 5 or 7 and close to The Siesta Key Village! Along with its sister property Villa Fiesta, both units make up Casa De Siesta.Cross the drawbridge from Sarasota to enter the serene island esca
Villa Margarita - 314L (281484)
Siesta Key, FL
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests

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