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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

Looking for a cottage?

Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Siesta Key and surrounding area in the past month

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Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 23 reviews

Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Popular with guests booking cottages in Siesta Key

Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 17 reviews

Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 108 reviews

Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 8.7
Excellent - What previous guests thought, 58 reviews

Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 188 reviews

Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 66 reviews

Popular with guests booking cottages in Siesta Key

Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 55 reviews

These cottages in Siesta Key and nearby have options with free cancellation

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 4 reviews

Offering a bar, MERMAID HOUSE WITH POOL JACUZZI STEPS to SIESTA KEY BEACH offers accommodations in Sarasota. This beachfront property offers access to a terrace, free private parking, and free Wifi.

From $653.34 per night

Cozy Getaway Home - near Siesta Key Beach

Sarasota
Free cancellation options available

Cozy 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 $352.48 per night

Midcentury Modern Beach Home - 8 min to the beach offers accommodations in Sarasota, 11 miles from John and Mable Ringling Museum of Art and 11 miles from The John and Mable Ringling Museum of Art.

From $526.70 per night
Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 30 reviews

Bernice 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 night

Poolside Paradise Near Siesta Key Beach

Sarasota
Free cancellation options available
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 5 reviews

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.

From $542.15 per night

Comfortable Stay Near Golf Attractions Rm3 shared home is located in Sarasota, just 5.4 miles from Sarasota International Convention Center and 2.2 miles from Sarasota County Visitor Information...

From $125.48 per night

The Sun Dial - 827

Siesta Key
Free cancellation options available

The 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 Key
Free cancellation options available

Sand 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.

Enjoy breakfast in Siesta Key and nearby

A 6-minute walk from Siesta Key Beach in Sarasota, Oasis on Siesta Key features accommodations with access to a fitness room.

Siesta Dreamin'

Siesta Key
Breakfast options

Siesta Dreamin' offers accommodations in Siesta Key, a 15-minute walk from Siesta Key Beach and 10 miles from John and Mable Ringling Museum of Art.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Villa 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 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.

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review

La 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.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Avenida Sanctuary is located in Siesta Key, just a 4-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art. Guests can go for a swim in the private pool.

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...

Bikini Tini Time offers accommodations in Siesta Key, a 14-minute walk from Siesta Key Beach and 10 miles from John and Mable Ringling Museum of Art.

Traveling by car? These cottages in Siesta Key and nearby offer free parking

Sea Escape - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

From $752.68 per night

Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

From $752.68 per night

Sea Breeze - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

From $752.68 per night

Sea Angel - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

From $752.68 per night
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Enchanted & peaceful Oasis 10 min away from one of the most beautiful beaches in the World Siesta key offers accommodations in Sarasota, 7.9 miles from John and Mable Ringling Museum of Art and 7.9...

From $412.20 per night
Scored out of 10, guest rating 9.2
Wonderful - What previous guests thought, 8 reviews

House 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 $326.33 per night
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 6 reviews

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.

From $3,640 per night

Palmetto House is located in Sarasota, just 5.7 miles from John and Mable Ringling Museum of Art and 5.7 miles from The John and Mable Ringling Museum of Art.

FAQ about cottages in Siesta Key

Cottages That Guests Love in Siesta Key

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Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 55 reviews
Beautiful location and close to the beach. Pretty and comfortable bungalow.
Guest review by
Holly
Family with young children
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 4 reviews
Amazing location of a beautifuly and well equiped cozy house. Will definitely come back
Guest review by
Agustin
Travelers with friends
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 5 reviews
Everything! 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 by
Jennifer
Family with young children
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 55 reviews
Spacious 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 by
Elias Hummel
Young couple