Search Siesta Key Cottage Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Siesta Key

The Inn On Siesta Key
Balcony view
The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (164)
"Such a beautiful week maintained property with every thing you could possibly need or want to enjoy the area. ♥️"
The Inn On Siesta Key
Retreat Half-mile to Beach/siesta Key Village
TV, books
Retreat Half-mile to Beach/siesta Key Village
3.0 star property
Retreat Half-mile to Beach/siesta Key Village
Siesta Key Village Home < Half Mi to Beach!
Private kitchen
Siesta Key Village Home < Half Mi to Beach!
3.0 star property
Siesta Key Village Home < Half Mi to Beach!
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!
Private kitchen
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!
2.5 star property
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!
Siesta Key Couple's Escape - Walk to Beaches!
Interior
Siesta Key Couple's Escape - Walk to Beaches!
3.0 star property
Siesta Key Couple's Escape - Walk to Beaches!
Flip Flop Cottages
Outdoor pool
Flip Flop Cottages
3.0 star property
7.6 out of 10, Good, (6)
"Very cute. Pool was a bit small"
Flip Flop Cottages
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!
Exterior
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!
3.0 star property
Siesta Key Oasis w/ Outdoor Pool + Screened Lanai!
Sarasota Vacation Rental w/ Pool & Game Room!
Outdoor dining
Sarasota Vacation Rental w/ Pool & Game Room!
3.0 star property
Sarasota Vacation Rental w/ Pool & Game Room!
Luxe Bayfront Sarasota Home Rental: Pool, Lanai!
Outdoor pool
Luxe Bayfront Sarasota Home Rental: Pool, Lanai!
3.0 star property
Luxe Bayfront Sarasota Home Rental: Pool, Lanai!
Modern Siesta Key Getaway w/ Private Pool!
Outdoor dining
Modern Siesta Key Getaway w/ Private Pool!
3.0 star property
Modern Siesta Key Getaway w/ Private Pool!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Siesta Key
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Siesta Key

Tropical Beach Resorts
Property amenity
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts
Captiva Beach Resort
Private kitchen
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1057)
"Nice and quiet place, close to the beach and dining places."
Captiva Beach Resort
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sports facility
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (208)
"Excellent property, I’ve been there twice this year and planning on definitely coming back."
The price is S$728
includes taxes & fees
19 Nov - 20 Nov
The Residences at Siesta Key Beach by Hyatt Vacation Club
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Why book your cottage in Siesta Key with Expedia?
We think that holidays should be a piece of cake, so if you’re searching for cottages in Siesta Key at a competitive rate, Expedia can help. Save cash and check in to a low-cost option far away from the downtown buzz, or splurge on an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Siesta Key?
The simplest way to compare cheap cottages in Siesta Key is with Expedia’s convenient filter tool. Narrow down your search by amenities, star rating and budget to nab unbeatable deals in just a few clicks.