Search Chalets in Siesta Key

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months
No exact matches found, but these alternatives could be just right

Recommended hotels in Siesta Key

Azul Resort Siesta Key

Azul Resort Siesta Key
3.0 star property
South Village
8.8 out of 10, Excellent, (114 reviews)
"Amazing place friendly people the beautiful beaches are amazing 100% recommend "
United States
Antonio
The price is €209
includes taxes & fees
12 May - 13 May
Azul Resort Siesta Key

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
[escape to paradise] siesta key beach getaway

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is €291
includes taxes & fees
5 May - 6 May
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Beachside villa in Siesta Key | Canal Front | pool

Beachside villa in Siesta Key | Canal Front | pool
Siesta Key Village
9.8 out of 10, Exceptional, (19 reviews)
"Nice clean and a short walk to everything!"
United States
Ralph S.
Beachside villa in Siesta Key | Canal Front | pool

Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (71 reviews)
"Perfect little place for a long weekend away. Conveniently located by everything "
United States
Emily D.
The price is €362
includes taxes & fees
26 Apr - 27 Apr
Siesta Cooler: Only Minutes Walk to Siesta Beach!

[Sunny in Siesta] king bed + walk to beach

[Sunny in Siesta] king bed + walk to beach
South Village
9.8 out of 10, Exceptional, (13 reviews)
"Great location and accommodation. "
United States
ESTELEN
[Sunny in Siesta] king bed + walk to beach

Walk to Beach, Siesta Key Villa 2, Pool View. Daily Rentals

Walk to Beach, Siesta Key Villa 2, Pool View. Daily Rentals
Sarasota
9.6 out of 10, Exceptional, (35 reviews)
"Everything was great! "
United States
Emma D.
The price is €313
includes taxes & fees
26 Apr - 27 Apr
Walk to Beach, Siesta Key Villa 2, Pool View. Daily Rentals

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ
Siesta Key Village
9.0 out of 10, Wonderful, (14 reviews)
"We enjoyed our stay at Everglades Villa. The location was the best feature as we were able to walk to Siesta Key Village and the beach. "
United States
Lisa S.
Sleeps 8 • Steps to Siesta Key Beach • Pool • BBQ

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The price is €419
includes taxes & fees
11 May - 12 May
The Inn On Siesta Key

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

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is €262
includes taxes & fees
28 Apr - 29 Apr
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

[Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (29 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
The price is €286
includes taxes & fees
30 Apr - 1 May
[Beach Elements] pool view withprivate beach access

Lulu's Key House Kemp Ridley 1/1 Downstairs

Lulu's Key House Kemp Ridley 1/1 Downstairs
3.5 star property
Siesta Key Village
10.0 out of 10, Exceptional, (4 reviews)
"Absolutely beautiful place. Very clean, easy check-in, wonderful location"
United States
Christine
The price is €478
includes taxes & fees
12 May - 13 May
Lulu's Key House Kemp Ridley 1/1 Downstairs

Siesta Key Beachside Villas

Siesta Key Beachside Villas
2.5 star property
Siesta Key Village
9.0 out of 10, Wonderful, (970 reviews)
"Great location and nice staff!"
United States
Eduardo Guerrero
The price is €253
includes taxes & fees
25 May - 26 May
Siesta Key Beachside Villas

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
Siesta Key Village-Suite #1: A block to the Beach!

VILLA 5, Siesta Key, Pool View. King Bed. Daily rentals

VILLA 5, Siesta Key, Pool View. King Bed. Daily rentals
Sarasota
9.6 out of 10, Exceptional, (113 reviews)
"Very comfortable beds and linens, extremely clean room and beds. "
United States
Jesica Aznar
The price is €258
includes taxes & fees
5 May - 6 May
VILLA 5, Siesta Key, Pool View. King Bed. Daily rentals

LUXURY HOUSE BY THE CANAL ☀️

LUXURY HOUSE BY THE CANAL ☀️
Siesta Key
9.6 out of 10, Exceptional, (118 reviews)
"Was very clean, easy to access, quiet and had all we needed for a great beach vacation."
United States
Denelle G.
The price is €473
includes taxes & fees
27 Apr - 28 Apr
LUXURY HOUSE BY THE CANAL ☀️

Siesta Key Village-Suite #4: A block to the Beach!

Siesta Key Village-Suite #4: A block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (41 reviews)
"A great location with easy walk to the beach!"
United States
Alan M.
The price is €325
includes taxes & fees
26 Apr - 27 Apr
Siesta Key Village-Suite #4: A block to the Beach!

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,241 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is €187
includes taxes & fees
28 Apr - 29 Apr
Captiva Beach Resort

Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool

Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ Pool
Siesta Key
8.8 out of 10, Excellent, (55 reviews)
"Host was fine"
United States
Jane L.
The price is €521
includes taxes & fees
4 May - 5 May
Lakefront Siesta Key Vacation Rental Home within Small Private Resort W/ 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Siesta Key Hotel Reviews

Find out more about Siesta Key

Siesta Key Chalets information

Number of reviews
3,243
Accommodation
8 Chalets
Lowest Price
€187
Highest Price
€521