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Featured Cottages in Siesta Key and around

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (175)
"The team at the INN take such care and pride. Everything is prestige condition, fully equipped kitchen and outdoor amenities for pool and beach. Our cabana was a little smaller so I would get the 3br next time for the space. 5STAR!"
The price is €254
includes taxes & fees
4 May - 5 May
The Inn On Siesta Key

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (172)
"The location and cleanliness was top notch. I would recomend to stay there.The description needs to be updated. It says the place has a murphy Bed. It doesn't. It has a blow up.matress.for the 3rd bed. That was a problem since i need 3 actual beds. I had 1 couple and two friends that didnt share a bed. The description made that not be a problem but it was a problem.. Other then the bed situation in the description it was very good. The description of any place is super important. That needs to...
The price is €527
includes taxes & fees
15 May - 16 May
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

9.6 out of 10, Exceptional, (73)
"Perfectly located! This is across from markets, food and directly in front of the free trolley. If you fly in you have everything you need! The bed set up makes this a perfect girls weekend or a family of 4 getaway. Heated pool was wonderful. Easy beach access. Wagons with beach chairs. Simple check in and out. Great communication directly with the owner. This is the one you want!"
The price is €277
includes taxes & fees
10 May - 11 May
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (17)
"We spent February at Sophie's Cottage and found it incredible. Newly remodeled (after the hurricanes), the vintage Siesta Key cottage is just perfect for our needs and wants. New mattresses (upscale and very comfortable), new appliances, HVAC works great, with plentiful TV's and connections, what more could we ask for? Not very much, as the location against the canal, with a heated pool, and chairs, was the perfect place to find warmth from the cold winter weather elsewhere. The landscaping...
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Everything was described accurately. Walking distance to beach and restaurants. Dave communicated everything we needed to know. The only thing you could possibly dislike would be the road noise because the bedroom window faces toward Beach Road but Spring Break brings out activity into and out of the village until the bars close. "
Across The Street From #1 Beach

Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

10.0 out of 10, Exceptional, (2)
"The property was very nice and clean. It's also in a great location - very close to the beach and the Village. I will definitely stay here again."
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

10.0 out of 10, Exceptional, (4)
"For our girls getaway we like to have a pool, the ocean, a comfortable place to stay and a deck with a view to read and relax. The place was very comfortable, the pool was great, the ocean a 1/2 mile walk and the lanai was nice as well. There wasn't much of a view as it overlooked the main road - which you can't tell from the pictures. Overall a great place to stay and experience Siesta Key."
The price is €286
includes taxes & fees
5 May - 6 May
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Prem 2Bed/2Bath Gate House Cottage with private beach access!

9.6 out of 10, Exceptional, (63)
"Loved this place!! The location was perfect!! The house could use a little updating but overall was great. Will be staying there again!!"
Prem 2Bed/2Bath Gate House Cottage with private beach access!

Remodeled Siesta Key Escape – Walk to the Beach!

10.0 out of 10, Exceptional, (6)
"Clean house in great location to beaches and restaurants!"
Remodeled Siesta Key Escape – Walk to the Beach!

Remodeled Siesta Key Escape Walk to the Beach!

3.0 star property
Remodeled Siesta Key Escape Walk to the Beach!

Nest Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (2)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
Nest Cottage Across street from beach and Heated Pool

Siesta Key Village Home < Half Mi to Beach!

3.0 star property
Siesta Key Village Home < Half Mi to Beach!

Cozy Cottage with Hot Tub

10.0 out of 10, Exceptional, (2)
"This property was amazing! The home was very clean, well appointed, nicely decorated and was perfectly located near both the beach and the village. They had bicycles for us to use, and a beach wagon with sun umbrellas, beach chairs, and beach towels making our short trek to the beach a breeze. Paige was an incredibly attentive and responsive host and their entire maintenance and cleaning crew (especially Jeff) were so helpful and welcoming. We loved how convenient this property's location was...
Cozy Cottage with Hot Tub

Close to the beach! Pool acccess and Private Backyard - Crescent Cottage

10.0 out of 10, Exceptional, (1)
"This was the perfect spot for the two of us! Parking right outside our door, king size bed, just the right size kitchen, private side yard and walking distance to the beach and shopping and restaurants! We'd choose this again! Great set-up!"
Close to the beach! Pool acccess and Private Backyard - Crescent Cottage

Nook Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
The price is €390
includes taxes & fees
4 May - 5 May
Nook Cottage Across street from beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (5)
"The Inn at Siesta Key was perfect for our trip. It was super clean, had everything we needed and then some. The owner is very accommodating and was there for anything we needed. Will definitely be back!"
The price is €708
includes taxes & fees
10 May - 11 May
Cabana Cottage Across street from Beach and Heated Pool

A Perfect Get-Away! Relaxing 3 Bedroom Home On Siesta Key!

8.0 out of 10, Very good, (2)
"Love the private beach access. Needed more towels and supplies and were able to obtain them through the office."
A Perfect Get-Away! Relaxing 3 Bedroom Home On Siesta Key!

Sarasota Vacation Rental w/ Pool & Game Room!

3.0 star property
Sarasota Vacation Rental w/ Pool & Game Room!

Scenic Siesta Key Home ~ 1 Mi to Village & Beach!

2.5 star property
Scenic Siesta Key Home ~ 1 Mi to Village & Beach!

Haven cottage Across street from beach and Heated Pool

9.8 out of 10, Exceptional, (6)
"Wonderful staff, very clean and convenient to village and beach. You can't go wrong."
Haven cottage Across street from beach and Heated 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.
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Other property types in Siesta Key

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4641)
"Stayed in the new section of rooms, very clean, no issues. will stay here again. "
The price is €165
includes taxes & fees
27 May - 28 May
Tropical Beach Resorts

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

10.0 out of 10, Exceptional, (20)
"This house is perfect for large groups with its many living areas, bedrooms, and bathrooms. The HUGE jacuzzi on the porch is A. Huge TV screens everywhere, even outside.The location is very convenient with a short walk to both the beach and restaurants, shops, etc. The beach is awesome! We had a great time and highly recommend!"
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1085)
"This hotel is in the perfect spot close to beach and restaurants. But far enough from village to be lost."
The price is €219
includes taxes & fees
1 May - 2 May
Captiva Beach Resort
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.