Cottages in Siesta Key
Find the cottages that appeal to you the most
Cottages for every style
Find the right cottage for you in Siesta Key
The best cottages in Siesta Key
Check out our selection of great cottages in Siesta Key
Filter by:
Review score
Siesta Key Island Rentals
Siesta Key Island Rentals in Siesta Key provides accommodations with an indoor pool, a garden, and a tennis court. With pool views, this accommodation provides a swimming pool.
Beautiful property on Siesta Key
Providing an outdoor swimming pool, Beautiful property on Siesta Key features accommodations in Siesta Key. This villa provides air-conditioned accommodations with a patio.
Poolside Paradise Near Siesta Key Beach
Poolside Paradise Near Siesta Key Beach is located in Sarasota, just 13 miles from Sarasota International Convention Center and 8.3 miles from Marina Jack Restaurant And Marina.
2bed/2bath Condo next to Siesta Key ~A Hidden Gem
2bed/2bath Condo next to Siesta Key ~A Hidden Gem offers accommodations in Sarasota, a 19-minute walk from Crescent Beach and 10 miles from The John and Mable Ringling Museum of Art.
5min from the beach 8 min from Siesta Key
5min from the beach 8 min from Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.3 miles from Sarasota Opera.
Pool Home on Gulf Gate 5min away from Siesta Key
Offering a garden, Pool Home on Gulf Gate 5min away from Siesta Key provides accommodations in Sarasota. This property offers a private pool, free Wifi, and free private parking.
Tiny House Siesta
Tiny House Siesta offers self-catering tiny houses in Sarasota, Florida. Features include a kitchenette, TV, and free WiFi. Siesta Key is less than 1 km away and Siesta Key Beach is 1.6 km away.
Siesta Key Beachside Villas
Siesta Key Beachside Villas is located in the heart of Siesta Key. It features an outdoor pool and free WiFi. Beach access is a 2 minutes' walk from the property.
Siesta Key Beach Resort and Suites
Located just 1 minutes’ walk from the beach, this Siesta Key resort features a swimming pool. Guests can also enjoy access to free WiFi in common areas.
Sarasota Updated pool home, Near Siesta Key
Sarasota Updated pool home, Near Siesta Key is located in Sarasota, just 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable Ringling Museum of Art.
Looking for a cottage?
Most booked cottages in Siesta Key and surrounding area in the past month
Popular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 8.2Very Good - What previous guests thought, 53 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 8.8Excellent - What previous guests thought, 4 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 8.8Excellent - What previous guests thought, 23 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 9.6Exceptional - What previous guests thought, 8 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 9.0Wonderful - What previous guests thought, 14 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 8.6Excellent - What previous guests thought, 56 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 8.7Excellent - What previous guests thought, 109 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 7.9Good - What previous guests thought, 64 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 9.1Wonderful - What previous guests thought, 24 reviewsPopular with guests booking cottages in Siesta Key
Scored out of 10, guest rating 8.5Very Good - What previous guests thought, 205 reviews
These cottages in Siesta Key and nearby have options with free cancellation
Tiny House Siesta
SarasotaFree cancellation options availableScored out of 10, guest rating 8.3Very Good - What previous guests thought, 635 reviewsTiny House Siesta offers self-catering tiny houses in Sarasota, Florida. Features include a kitchenette, TV, and free WiFi. Siesta Key is less than 1 km away and Siesta Key Beach is 1.6 km away.
From $167.24 per nightCozy Getaway Home - near Siesta Key Beach
SarasotaFree cancellation options availableCozy Getaway Home - near Siesta Key Beach is located in Sarasota, just 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable Ringling Museum of Art.
From $338.66 per nightCoastal Retreat near Siesta Key Beach and Downtown
SarasotaFree cancellation options availableScored out of 10, guest rating 7.0Good - What previous guests thought, 3 reviewsOffering a private beach area, Coastal Retreat near Siesta Key Beach and Downtown provides accommodations in Sarasota. This vacation home offers free private parking and free Wifi.
From $543.99 per night5min from the beach 8 min from Siesta Key
SarasotaFree cancellation options availableScored out of 10, guest rating 9.0Wonderful - What previous guests thought, 20 reviews5min from the beach 8 min from Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.3 miles from Sarasota Opera.
From $352.09 per nightBernice 3bd2bth With Heated Pool Near Siesta Key!
SarasotaFree cancellation options availableScored out of 10, guest rating 8.6Excellent - What previous guests thought, 29 reviewsBernice 3bd2bth With Heated Pool Near Siesta Key! offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.7 miles from Sarasota Opera.
From $487.24 per nightLUX VILLAs on beautiful Palmer Ranch
VamoFree cancellation options availableScored out of 10, guest rating 7.8Good - What previous guests thought, 45 reviews13 miles from The John and Mable Ringling Museum of Art in Vamo, LUX VILLAs on beautiful Palmer Ranch features accommodations with access to a hot tub, fitness center, and open-air bath.
From $427.84 per nightPoolside Paradise Near Siesta Key Beach
SarasotaFree cancellation options availableScored out of 10, guest rating 9.4Wonderful - What previous guests thought, 5 reviewsPoolside Paradise Near Siesta Key Beach is located in Sarasota, just 13 miles from Sarasota International Convention Center and 8.3 miles from Marina Jack Restaurant And Marina.
From $542.15 per nightCute 3/2 Siesta home steps from Siesta waters
SarasotaFree cancellation options availableScored out of 10, guest rating 10.0Exceptional - What previous guests thought, 1 reviewOffering a garden, Cute 3/2 Siesta home steps from Siesta waters offers accommodations in Sarasota. Both Wifi and private parking are accessible at the vacation home free of charge.
From $517.54 per night
Traveling by car? These cottages in Siesta Key and nearby offer free parking
Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bailey HallFree parkingSea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bailey HallFree parkingSea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Sea Angel - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Bailey HallFree parkingSea Angel - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta on Lee - SRQ Pool Home Near Top Beaches! is located in Sarasota, just 7.9 miles from John and Mable Ringling Museum of Art and 8 miles from The John and Mable Ringling Museum of Art.
From $563.34 per nightA recently renovated vacation home, Siesta Beach Getaway - Minutes to Beach, Shops, Dining offers accommodations in Sarasota.
From $360.68 per night- Scored out of 10, guest rating 8.9Excellent - What previous guests thought, 10 reviews
Sarasota Updated pool home, Near Siesta Key is located in Sarasota, just 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable Ringling Museum of Art.
From $618.30 per night Coastal Getaway minutes from Siesta Key Beach offers accommodations in Sarasota, 9 miles from John and Mable Ringling Museum of Art and 9 miles from The John and Mable Ringling Museum of Art.
From $483.76 per nightHouse by Siesta Key
SarasotaFree parkingScored out of 10, guest rating 9.1Wonderful - What previous guests thought, 8 reviewsHouse by Siesta Key offers accommodations in Sarasota, 11 miles from The John and Mable Ringling Museum of Art and 7.1 miles from Sarasota Opera.
From $321.17 per night
Enjoy breakfast in Siesta Key and nearby
The Sun Dial - 827
Siesta KeyBreakfast optionsThe Sun Dial - 827 offers accommodations in Siesta Key, 1.1 miles from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.
Sand Dollar Cottage - 910
Siesta KeyBreakfast optionsSand Dollar Cottage - 910 offers accommodations in Siesta Key, a 15-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.
Oasis on Siesta Key
SarasotaBreakfast optionsA 6-minute walk from Siesta Key Beach in Sarasota, Oasis on Siesta Key features accommodations with access to a fitness room.
Villa Champagne - 5322
Siesta KeyBreakfast optionsScored out of 10, guest rating 10.0Exceptional - What previous guests thought, 1 reviewVilla Champagne - 5322 is located in Siesta Key, just a 9-minute walk from Siesta Key Beach and 11 miles from The John and Mable Ringling Museum of Art.
Beach Palm Villa - 5533
Siesta KeyBreakfast optionsBeach Palm Villa - 5533 is located in Siesta Key, just a 11-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.
La Contento Casa - 5560
Siesta KeyBreakfast optionsScored out of 10, guest rating 8.0Very Good - What previous guests thought, 1 reviewLa Contento Casa - 5560 is located in Siesta Key, just a 15-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.
Siesta Key Paradise, Vacation Pool Home, Near Beach, Restaurants and More offers accommodations in Sarasota, 10 miles from John and Mable Ringling Museum of Art and 10 miles from The John and Mable...
Isla Amor - 86
Siesta KeyBreakfast optionsScored out of 10, guest rating 9.0Wonderful - What previous guests thought, 1 reviewIsla Amor - 86 is located in Siesta Key, just a 7-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.
FAQ about cottages in Siesta Key
Cottages That Guests Love in Siesta Key
- Scored out of 10, guest rating 8.2Very Good - What previous guests thought, 53 reviewsBeautiful location and close to the beach. Pretty and comfortable bungalow.Guest review byHollyFamily with young children
- Scored out of 10, guest rating 9.5Exceptional - What previous guests thought, 4 reviewsAmazing location of a beautifuly and well equiped cozy house. Will definitely come backGuest review byAgustinTravelers with friends
- Scored out of 10, guest rating 9.0Wonderful - What previous guests thought, 5 reviewsEverything! Location is wonderful, home is as nice or nicer than pics show. Cottages on the Key was great to work with, very attentive to service and making sure we had what we needed for a fabulous week in Siesta Key. Thanks and we hope to be back soon!Guest review byJenniferFamily with young children
- Scored out of 10, guest rating 8.2Very Good - What previous guests thought, 53 reviewsSpacious house with all amenities you could wish, tucked away in a gated neighborhood, we felt very safe and cozy. All useful information has been provided by Mira in advance as well as a Key for Beach access. Parking for the whole day after checkout was possible.Guest review byElias HummelYoung couple
