The 10 best cottages in Siesta Key, US | Booking.com
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Cottages in Siesta Key

Find the cottages that appeal to you the most

The best cottages in Siesta Key

Check out our selection of great cottages in Siesta Key

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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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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 SAR 2,667.85 per night
  • Siesta Key Beach Resort and Suites

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 8.3
    Very Good - What previous guests thought, 688 reviews

    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.

    From SAR 1,261.88 per night
  • Siesta Key Beachside Villas

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 8.7
    Excellent - What previous guests thought, 396 reviews

    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.

    From SAR 1,177.55 per night
  • Florinda 3bdr/2bth 2car garage with New Pool

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 53 reviews

    Florinda 3bdr/2bth 2car garage with New Pool is located in Sarasota, just 7.8 miles from The John and Mable Ringling Museum of Art and 4.2 miles from Sarasota Opera.

  • Crescent Beach 1011 #1

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 9.1
    Wonderful - What previous guests thought, 24 reviews

    Crescent Beach 1011 #1 is located in Sarasota, just 11 miles from The John and Mable Ringling Museum of Art and 12 miles from Sarasota International Convention Center.

    From SAR 1,475.47 per night
  • Cozy Beach House next to Siesta Key

    Sarasota
    Free cancellation options available
    Scored out of 10, guest rating 9.2
    Wonderful - What previous guests thought, 4 reviews

    Cozy Beach House next to Siesta Key offers accommodations in Sarasota, 10 miles from The John and Mable Ringling Museum of Art and 6 miles from Sarasota Opera.

    From SAR 1,633.35 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 SAR 1,218.26 per night
  • Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 3 reviews

    Offering 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 SAR 2,040.23 per night

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

  • 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 SAR 2,112.81 per night
  • Scored out of 10, guest rating 8.9
    Excellent - 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 SAR 2,465.37 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 3 reviews

    8.3 miles from The John and Mable Ringling Museum of Art in Sarasota, Siesta Key Waterfront Estate W Pool Privacy! offers accommodations with access to a fitness center.

    From SAR 3,824.85 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 SAR 1,814.35 per night
  • Scored out of 10, guest rating 9.1
    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 SAR 1,204.56 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 SAR 13,651.82 per night
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 20 reviews

    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.

    From SAR 1,320.50 per night
  • Scored out of 10, guest rating 8.6
    Excellent - What previous guests thought, 29 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 SAR 1,827.39 per night

Enjoy breakfast in Siesta Key and nearby

  • 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 offers accommodations in Siesta Key, a 15-minute walk from Siesta Key Beach and 11 miles from John and Mable Ringling Museum of Art.

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

  • Scored out of 10, guest rating 10.0
    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.

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

    Isla 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

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  • Scored out of 10, guest rating 8.2
    Very Good - What previous guests thought, 53 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, 53 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