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The best cottages in Siesta Key

Check out our selection of great cottages in Siesta Key

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Review score

Sea Dream - 171 offers accommodations in Siesta Key, a 1-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

The property was immaculate despite the devastation from the hurricane. We felt so cozy & comfortable in the condo. The hosts thought of everything! From complimentary cupcakes to beach chairs & towels, we felt so pampered during our stay.
Review score
Wonderful
9 reviews
Price from
$384
1 night, 2 adults

Siesta Heron Suites & Villas features air-conditioned accommodations in Siesta Key. With lake views, this accommodation offers a swimming pool. Outdoor seating is also available at the vacation home.

The location was convenient, and the place was clean and stocked with all the basic essentials. The deck was a great bonus—really nice for relaxing. Check-in and check-out were smooth and hassle-free, which I appreciated. The kitchen is well-stocked with both a Keurig and a drip coffee maker, so bring your favorite coffee, plus your own sugar and creamer. If you're particular about cleanliness, you might want to bring your own paper towels and liquid hand soap for the bathroom. The provided towels were large but felt more like beach towels, so consider bringing your own if you're picky about that. Dish soap and a sponge were provided, but don’t forget to bring extra trash bags as the owners recommend.
Review score
Very Good
224 reviews
Price from
$132.29
1 night, 2 adults

Sea Escape - 172 is located in Siesta Key, just a 1-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

Close to the beach and Main Street
Review score
Very Good
6 reviews
Price from
$384
1 night, 2 adults

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.

Everything but
Review score
Very Good
48 reviews
Price from
$202.58
1 night, 2 adults

Location Siesta 1 mile away Home with HOT SPA is a recently renovated vacation home in Sarasota where guests can make the most of the indoor pool and garden.

This was one of the best stays that we have had in Sarasota! The location is great. The house amenities were superior. This smart home was gorgeous. We enjoyed the spa, grill, and patio immensely. Everything in the home was clean, smelled amazing, well thought out, and easy to use. We look forward to booking again.⭐️⭐️⭐️⭐️⭐️
Review score
Wonderful
9 reviews
Price from
$209
1 night, 2 adults

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.

Great location and very clean and comfortable
Review score
Wonderful
40 reviews
Price from
$247.50
1 night, 2 adults

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.

The location was good, and the master bed was comfortable, and everything was clean. After a power outage, the internet went out and the host was able to coordinate a trip from Comcast within a day.
Review score
Wonderful
24 reviews
Price from
$247.50
1 night, 2 adults

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.

The feel of being home. Clean and beautiful yet comfy and realistic
Review score
Wonderful
8 reviews
Price from
$117.45
1 night, 2 adults

Offering a garden, Welcome to The Bray Escape 4 miles to Siesta Key provides accommodations in Sarasota. This vacation home features air-conditioned accommodations with a patio.

Perry and comfortable
Review score
Exceptional
20 reviews
Price from
$230
1 night, 2 adults

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.

Very quiet street and short walk to beach. The pool was very nice and kitchen was very well equipped
Review score
Wonderful
27 reviews
Price from
$189.53
1 night, 2 adults
All 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 this month

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Enjoy breakfast in Siesta Key!

  • Review score
    Exceptional · 6 reviews

    Villa Vista Mare - 675 is located in Siesta Key, just a few steps from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Review score
    Wonderful · 7 reviews

    6.1 miles from Sarasota Opera in Siesta Key, Canal Lower-Gorgeous 3 bed 3 bath near SK Village provides accommodations with access to a hot tub.

    Guest review
    prime location. everything is within a 5 min walk.
  • Review score
    Wonderful · 5 reviews

    Just a 4-minute walk from Siesta Key Beach and 0.8 miles from Crescent Beach, Pink Flamingo Unit, Steps to Beach, Siesta Key Village & Pet-Friendly features accommodations in Siesta Key with an...

  • Review score
    Wonderful · 7 reviews

    Jamaica Royale - 49 is located in Siesta Key, just 7.1 miles from Sarasota Opera and 7.1 miles from Marina Jack Restaurant And Marina.

  • Review score
    Exceptional · 13 reviews

    Siesta Key Beach 665 #1 offers accommodations in Siesta Key, a few steps from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

    Guest review
    Spacious enough for a family of 4. Very conveniently close to the beach. Great amenities
  • Review score
    Exceptional · 24 reviews

    Siesta Key Beach - Tropea 665 #3 offers accommodations in Siesta Key, a few steps from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

    Guest review
    plenty of room. comfortable beds. close to the beach.
  • Review score
    Exceptional · 7 reviews

    Our House At The Beach, East Tower, 5th Fl offers accommodations in Siesta Key, a 6-minute walk from Siesta Key Beach and 700 yards from Crescent Beach.

  • Review score
    Wonderful · 5 reviews

    LuLu's Key House Green 1/1 Upstairs offers accommodations in Siesta Key, 6.7 miles from Marina Jack Restaurant And Marina and 7.6 miles from Sarasota County Visitor Information Center And History...

These cottages in Siesta Key have options with FREE cancellation

  • Siesta Heron Suites & Villas

    Siesta Key
    Free cancellation options available
    Review score
    Very Good · 224 reviews

    Siesta Heron Suites & Villas features air-conditioned accommodations in Siesta Key. With lake views, this accommodation offers a swimming pool. Outdoor seating is also available at the vacation home.

    Guest review
    Close to all but not right in the middle of everything.. quite & clean
  • Offering an outdoor swimming pool, Jellyfish Unit, Walk to Beach & Siesta Key Village, Pet-Friendly offers accommodations in Siesta Key.

  • Crescent Beach Villas

    Siesta Key
    Free cancellation options available
    Review score
    Wonderful · 22 reviews

    Crescent Beach Villas enjoys a location in Siesta Key, a 3-minute walk from Crescent Beach and 11 miles from The John and Mable Ringling Museum of Art.

    Guest review
    Close to the beach , great location and privacy , the pool was great !
  • Sun and Sea

    Siesta Key
    Free cancellation options available
    Review score
    Wonderful · 26 reviews

    Sun and Sea offers accommodations in Siesta Key, a 2-minute walk from Crescent Beach and 11 miles from The John and Mable Ringling Museum of Art.

    Guest review
    Great location..close to beach, free trolley. Lovely place!
  • Crescent Arms Condominiums

    Siesta Key
    Free cancellation options available
    Review score
    Wonderful · 9 reviews

    Providing free bikes, Crescent Arms Condominiums features accommodations in Siesta Key. This vacation home provides accommodations with a patio.

    Guest review
    Great location, very clean, hosts very communicative and helpful, had everything we needed
  • Sea Escape - 172

    Siesta Key
    Free cancellation options available
    Review score
    Very Good · 6 reviews

    Sea Escape - 172 is located in Siesta Key, just a 1-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Review score
    Excellent · 12 reviews

    Heat of Siesta Village Walk to Beach w heated Pool is located in Siesta Key, just a 7-minute walk from Siesta Key Beach and 9.5 miles from The John and Mable Ringling Museum of Art.

    Guest review
    location to downtown and beach access was an easy walk
  • Canal 315 - Right in Siesta Key Village!

    Siesta Key
    Free cancellation options available
    Review score
    Excellent · 7 reviews

    Canal 315 - Right in Siesta Key Village! offers accommodations in Siesta Key, a 7-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

    Guest review
    The location is fantastic! There were six of us and we had plenty of room. The back bathroom is beautiful. When I had questions, they were answered super quick!! We would rent here again.

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

  • Review score
    Wonderful · 9 reviews

    Sea Dream - 171 offers accommodations in Siesta Key, a 1-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

    Guest review
    Very clean, well decorated, close to shops and food, and beach!
  • Review score
    Exceptional · 1 review

    Siesta Key home 5 min from beach offers accommodations in Siesta Key, 8.6 miles from The John and Mable Ringling Museum of Art and 5.1 miles from Sarasota Opera.

  • Review score
    Exceptional · 3 reviews

    Sea Foam - 173 offers accommodations in Siesta Key, a 1-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Review score
    Excellent · 3 reviews

    Mimosa - 5251B offers accommodations in Siesta Key, a 7-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

    Guest review
    Location was close bars, restaurants and beach access.
  • Review score
    Very Good · 48 reviews

    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.

    Guest review
    Close to beach, to downtown and all the restaurants.
  • Review score
    Excellent · 48 reviews

    Providing an outdoor swimming pool, Beautiful property on Siesta Key features accommodations in Siesta Key. This villa provides air-conditioned accommodations with a patio.

    Guest review
    Beautiful property. It had everything needed for a wonderful stay.
  • Lookout

    Siesta Key
    Free parking
    Review score
    Very Good · 8 reviews

    Lookout is located in Siesta Key, just a 3-minute walk from Siesta Key Beach and 10 miles from The John and Mable Ringling Museum of Art.

  • Review score
    Excellent · 6 reviews

    Located in Siesta Key in the Florida region, Fanta-Sea on the Beach 49 by Beachside Management has a terrace and sea views. It features free WiFi and free bikes.

    Guest review
    The location was amazing. It was very clean and decorated nice.

FAQ about cottages in Siesta Key

Cottages That Guests Love in Siesta Key

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  • Review score
    Excellent · 222 reviews
    The cottage was perfect. The garden is beautiful, very tropical zen vibes.
    Guest review by
    Michelle
    Family with young children
  • Review score
    Excellent · 48 reviews
    Beautiful location and close to the beach. Pretty and comfortable bungalow.
    Guest review by
    Holly
    Family with young children
  • Review score
    Excellent · 222 reviews
    The place was perfect!!! Nice and clean. Close to Siesta Key Village and next to the beach. We stayed in cottage 1, and the outside shower was amazing. Have private sitting area and fish pond is right outside out front door. Definitely will be staying again.
    Guest review by
    Sandy
    Travelers with friends
  • Review score
    Exceptional · 3 reviews
    Amazing location of a beautifuly and well equiped cozy house. Will definitely come back
    Guest review by
    Agustin
    Travelers with friends
  • Review score
    Wonderful · 368 reviews
    Superb location, just a few steps away from the Point of the Rocks beach, close to the Toasted Mango breakfast café, and to the shops and restaurants (Captain Curt's and others). The accommodation is in a nice set of bungalows arranged into a U-shape, with a swimming pool in the center of the "U". There is a outside table for each room.
    Guest review by
    Roman
    Young couple
  • Review score
    Wonderful · 368 reviews
    We loved our stay at the Twin Palms. The room was spacious and very clean. The pool was warm and we had a great time lounging around. Great staff communication and I appreciated the supply cabinet for extra conditioner. Everyone that we met there was so nice! We plan to stay next year here for a few weeks!
    Guest review by
    Jessica
    Young couple
  • Review score
    Wonderful · 3 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
  • Review score
    Excellent · 222 reviews
    We loved the vibe of the outdoor space and the condo was beautiful. The porch was perfect. Cottage 2 was very clean and recently updated with a pretty esthetic. Extremely close to the beach and they had all the gear we could have needed. They had plenty of toiletries, paper goods and trash bags which is rare in our experience.
    Guest review by
    Mary Beth
    Family with young children
  • Review score
    Excellent · 48 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
  • Review score
    Good · 10 reviews
    SUPER DECEITFUL PHOTO AND MANAGEMENT!!!!! You are renting the tiny blue shack on right edge of this photo. Literally a 100 year old granny cottage. BUNGALOW!!!! Yet several photos of a large raised deck. FILTHY RUSY BROKEN LAWN FURNITURE. ALMOST A FOOT OF LEAVES THROUGH PATIO AREA Property hasnt been raked for MONTHS
    Guest review by
    Peter
    Young couple