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Featured Cottages in Siesta Key and around

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, (166)
"Great place to stay! "
The price is €497
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key
NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259
Pool

NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259

9.8 out of 10, Exceptional, (15)
"The house had just been completely renovated due to the recent hurricane damage. Jim did an excellent job with everything to make sure our stay was top-notch. All the furnishings and appliances were brand new. We took the bikes out every day to Siesta Key Beach, which was just down the street. Absolutely amazing, and it took under 5 minutes! The rental location is very close (less than 1 mile) to fun restaurants in Siesta Key Village, with lot's of great bars and shopping. This place has it...
NEW REMODEL 5 Min walk to Bch & Village, Private Pool, On the Canal 502-639-4259
NEW: Free standing Cottage within steps to the BEACH!
Exterior

NEW: Free standing Cottage within steps to the BEACH!

9.8 out of 10, Exceptional, (6)
"Me and wife came down for the weekend. It was perfect place for us. It was very clean. It was close to beach and the town with night life and restaurants."
NEW: Free standing Cottage within steps to the BEACH!
Across The Street From #1 Beach
Beach nearby, sun-loungers, beach towels

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (314)
"Beautiful cottage with the perfect amount of space and amenities in a great location. Conveniently located down the street from the strip and right across the street from the beaches. Highly recommend to any couple whose looking to relax for the week"
Across The Street From #1 Beach
Siesta Key Old Florida Cottage, Great Location at a Great Price
Property grounds

Siesta Key Old Florida Cottage, Great Location at a Great Price

9.0 out of 10, Wonderful, (164)
"We love this cottage ! Even in a hurricane 😉"
Siesta Key Old Florida Cottage, Great Location at a Great Price
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, (66)
"Everything was wonderful and as described in the listing. The master BR sheets were loose and made it hard for me to sleep but maybe it is just different from what I am used to. I would stay here again! Everything was new and fresh!"
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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, (170)
"It was a quiet place we ended up not going very many places."
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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)
"The property is a great location with a short walk to the beach. It was clean and attractive and the beds were very comfortable and 2 full baths made it very nice for 4 friends traveling together. We had one issue with the dishwasher not working but the management company had someone there the same day to fix it. They were also very prompt is responding to any of our questions. It was on the cold side so we did not make use of the pool but keep in mind the pool that is included with this...
A Perfect Get-Away! Relaxing 3 Bedroom Home On Siesta Key!
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Beach

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

10.0 out of 10, Exceptional, (1)
"Great Vacation! Very clean and everything you needed. Name “solitude” is appropriate. Nice quiet getaway from hustle and bustle of spring break crowd. Lisa the property manager was very nice and accommodating."
The price is €305
includes taxes & fees
2 Jan - 3 Jan 2025
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Beachside Vacation Cottage at Beach Palms
Outdoor pool

Beachside Vacation Cottage at Beach Palms

6.8 out of 10, (3)
"We enjoyed our stay at the yellow cottage. So close to the beach (access 4), as well as Siesta Key Village. No need for a car, you can walk to everything. We wish the bathroom was a little larger. The configuration of the shower is close to the toilet and it’s hard to keep the floor from getting wet, when you take a shower. Other than that, we communicated with management, before and during our stay and they were very responsive. They also let us leave our luggage in their office, since we had...
Beachside Vacation Cottage at Beach Palms
Cozy, Clean & Crazily Convenient
Beach nearby

Cozy, Clean & Crazily Convenient

9.6 out of 10, Exceptional, (69)
"Great location to get anywhere you want in Siesta Key without a car. We had a market very close and anything we could possibly need for a relaxing day at the beach. It was a short four minute walk. The place was quiet and safe. We would definitely come again."
Cozy, Clean & Crazily Convenient
Siesta Key Couple's Escape - Walk to Beaches!
Fridge, microwave, stovetop, coffee/tea maker

Siesta Key Couple's Escape - Walk to Beaches!

10.0 out of 10, Exceptional, (4)
"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."
Siesta Key Couple's Escape - Walk to Beaches!
Retreat Half-mile to Beach/siesta Key Village
TV, books

Retreat Half-mile to Beach/siesta Key Village

3.0 star property
Retreat Half-mile to Beach/siesta Key Village
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
Siesta Key Village Home < Half Mi to Beach!
House (2 Bedrooms) | Private kitchen

Siesta Key Village Home < Half Mi to Beach!

3.0 star property
Siesta Key Village Home < Half Mi to Beach!
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!
Siesta Key Couple's Escape - Walk to Beaches!
Cottage (1 Bedroom) | Interior

Siesta Key Couple's Escape - Walk to Beaches!

3.0 star property
Siesta Key Couple's Escape - Walk to Beaches!
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)
"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!"
Cabana Cottage Across street from Beach and Heated Pool
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."
Nest Cottage Across street from beach and Heated Pool
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
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, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
The price is €216
includes taxes & fees
19 Jan - 20 Jan 2025
Tropical Beach Resorts
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sports facility

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (217)
"Awesome "
The price is €571
includes taxes & fees
7 Jan - 8 Jan 2025
The Residences at Siesta Key Beach by Hyatt Vacation Club
Captiva Beach Resort
Florida Family Single | Private kitchen

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1057)
"Nice and quiet place, close to the beach and dining places."
The price is €258
includes taxes & fees
2 Jan - 3 Jan 2025
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.

Frequently asked questions

Are there any family-friendly cottages in Siesta Key?
Many visitors needing a family-friendly cottage in Siesta Key pick The Inn On Siesta Key. With a 3.5-star rating and amenities like a nearby beach and beach umbrellas, it’ll feel like your home away from home. Another top option for families on holiday is Flip Flop Cottages. WiFi and laundry facilities help make this 3-star cottage a comfortable base for your Siesta Key getaway. After checking in and chilling in your cosy new digs, it’s time to hit the road and start exploring! Siesta Key Beach and Crescent Beach are fun family-friendly attractions in Siesta Key.
Why book your cottage in Siesta Key with Expedia?
We think that holidays should be a piece of cake, so if you’re searching for cottages in Siesta Key at a competitive rate, Expedia can help. Save cash and check in to a low-cost option far away from the downtown buzz, or splurge on an upscale cottage to pamper your loved ones.
How can I find cheap cottages in Siesta Key?
The simplest way to compare cheap cottages in Siesta Key is with Expedia’s convenient filter tool. Narrow down your search by amenities, star rating and budget to nab unbeatable deals in just a few clicks.