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Check prices for these dates

In two weeks
22 May - 24 May
In two months
3 Jul - 5 Jul
In three months
31 Jul - 2 Aug
In four months
28 Aug - 30 Aug

Our top choices for Siesta Key cottages

Outdoor dining

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.
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is NZ$913
includes taxes & fees
17 May - 18 May
Unwind Poolside + Walk to Beach! Sarasota Retreat
Balcony view

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is NZ$614
includes taxes & fees
10 May - 11 May
The Inn On Siesta Key
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is NZ$838
includes taxes & fees
10 May - 11 May
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior

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 NZ$509
includes taxes & fees
20 May - 21 May
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
The price is NZ$1,233
includes taxes & fees
5 May - 6 May
Yellow Palm Cottage steps from the beach
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
The price is NZ$1,236
includes taxes & fees
6 May - 7 May
Pink Mango Cottage steps from the beach
Exterior

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
Blue Dolphin Cottage steps from the beach
Outdoor dining

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
Siesta Heron 7
Terrace/patio

Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"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!"
United States
Derek N.
Nook Cottage Across street from beach and Heated Pool
Pool

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
Cabana Cottage Across street from Beach and Heated Pool
Dining

Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
United States
Keeley L.
Lookout Cottage Across street from Beach and Heated Pool
Property grounds

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"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."
United States
Marti C.
Nest Cottage Across street from beach and Heated Pool
Interior

Beach Road

Beach Road
2.0 star property
Siesta Key
Beach Road
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
Siesta Heron 6 / Sunset
Property grounds

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (7 reviews)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is NZ$455
includes taxes & fees
5 May - 6 May
Coastal Luxury 7mi to Anna Maria Private Cottage
Property grounds

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
The price is NZ$889
includes taxes & fees
27 May - 28 May
Romantic Island Getaway! Just Steps from the Beach
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is NZ$1,017
includes taxes & fees
7 May - 8 May
Direct Beachfront 2BR Cottage on Casey Key!
Exterior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (23 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is NZ$254
includes taxes & fees
15 May - 16 May
Charming cottage for 2 across warm mineral springs park
Exterior

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay

Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
cortez
10.0 out of 10, Exceptional, (104 reviews)
"Very peaceful place. Would love to come back!"
United States
Amanda G.
The price is NZ$480
includes taxes & fees
18 May - 19 May
Private historical completely renovated cottage with 60 ft dock on Sarasota Bay
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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Top Siesta Key Hotel Reviews

Cottage Across The Street From #1 Beach

Cottage Across The Street From #1 Beach

10/10 Excellent
"Super clean and cute! Two steps away from the beach made it super convenient."
Lauren R. 4-night trip
Posted 2 hours ago
Cottage Across The Street From #1 Beach

Find out more about Siesta Key

Siesta Key Cottages information

Number of reviews
675
Accommodation
54 Cottages
Lowest Price
NZ$254
Highest Price
NZ$1,236

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