Search Siesta Key Cottage Rentals from CA $152

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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Browse Select Siesta Key Cottages

The Inn On Siesta Key
The Cabana, 2 Bedroom 2 Bath (1 King, 2 Twins) | Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (175)
"Outstanding service. Room and facility was very clean. Staff is amazing. We would strongly recommend The Inn and we plan on returning for our next vacation "
The price is CA $312
CA $404 total
includes taxes & fees
May 11 - May 12
The Inn On Siesta Key
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (172)
"It was a quiet place we ended up not going very many places."
The price is CA $310
CA $813 total
includes taxes & fees
May 15 - May 16
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Sun loungers, beach towels

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

9.6 out of 10, Exceptional, (73)
"Its right next to everything we needed"
The price is CA $152
CA $427 total
includes taxes & fees
May 10 - May 11
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
Sun loungers

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

9.8 out of 10, Exceptional, (18)
"We had an amazing time at Sophie’s Cottage. We lucked out and got a renovated home due to the Hurricanes. The proximity to the beach and town are great. Short bike ride to both. Jim, the owner, helped us immediately with any issues. Our kids caught snappers, catfish, jacks, sting rays and needle fish off of the dock of the home. Great time, great home, great location!!! "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
Across The Street From #1 Beach
Beach nearby, sun loungers, beach towels

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Great accommodations, great location."
Across The Street From #1 Beach
Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!
Beach nearby

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
Beach

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

10.0 out of 10, Exceptional, (4)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is CA $192
CA $440 total
includes taxes & fees
May 5 - May 6
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Prem 2Bed/2Bath Gate House Cottage with private beach access!
A heated pool

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

9.6 out of 10, Exceptional, (63)
"Everything was just right!"
Prem 2Bed/2Bath Gate House Cottage with private beach access!
Remodeled Siesta Key Escape – Walk to the Beach!
Fridge, microwave, stovetop, coffee/tea maker

Remodeled Siesta Key Escape – Walk to the Beach!

10.0 out of 10, Exceptional, (6)
"Overall the location and cottage was good. We had a few issues but the Property Manager was quick to respond and made sure we were accommodated. My husband and I would recommend."
Remodeled Siesta Key Escape – Walk to the Beach!
Remodeled Siesta Key Escape Walk to the Beach!
Cottage (1 Bedroom) | Interior

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
Pool

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."
The price is CA $402
CA $662 total
includes taxes & fees
May 8 - May 9
Nest Cottage Across street from beach and Heated Pool
Siesta Key Village Home < Half Mi to Beach!
House (2 Bedrooms) | Interior

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
Exterior

Cozy Cottage with Hot Tub

10.0 out of 10, Exceptional, (2)
"We loved the home and location and would definitely stay here again!"
Cozy Cottage with Hot Tub
Close to the beach! Pool acccess and Private Backyard - Crescent Cottage
Beach

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
Terrace/patio

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!"
Nook Cottage Across street from beach and Heated Pool
Cabana Cottage Across street from Beach and Heated Pool
Terrace/patio

Cabana Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (5)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
Cabana Cottage Across street from Beach and Heated Pool
A Perfect Get-Away! Relaxing 3 Bedroom Home On Siesta Key!
Beach

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!
Outdoor dining

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!
House (2 Bedrooms) | Private kitchen

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
Terrace/patio

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
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4642)
"Wonderful stay. I enjoy that the resort is so close to the beautiful beach and also local dining and shopping."
The price is CA $219
CA $279 total
includes taxes & fees
May 11 - May 12
Tropical Beach Resorts
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Pool

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

10.0 out of 10, Exceptional, (20)
"It was my 50th birthday and the place was amazing! Contacted management for a few questions and they responded immediately. I will definitely rent again and certainlt recommend this property. Thank you for a memorable trip!"
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Captiva Beach Resort
Florida Family Single | Private kitchen

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1087)
"Close to beach and pool ."
The price is CA $263
CA $345 total
includes taxes & fees
May 5 - May 6
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.