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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Cottages in Southwest Florida

The Inn On Siesta Key
Relax by the serene pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas for a comfortable stay.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
The Inn On Siesta Key
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Guests can enjoy a wide, sandy beach with ocean views and a scenic backdrop of trees and shrubs.

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (274)
"So many great features at this house in Bean Point including great access to the beach, Pine Street and a pool area that has it all. Thank you Dan and Lori for a wonderful stay!"
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Relax in the shaded outdoor seating area, complete with barbecue grills and a scenic view.

Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2

9.8 out of 10, Exceptional, (94)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Anna Maria Cottage with Golf Cart
Relax in a serene patio area with a light-colored sofa, small table, and lush greenery.

Anna Maria Cottage with Golf Cart

10.0 out of 10, Exceptional, (11)
"This cottage was the perfect anniversary getaway. Centrally located and easy to visit the beaches and explore the island on the provided golfcart"
Anna Maria Cottage with Golf Cart
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
Relax in this serene bedroom with a large bed, ceiling fan, and stunning outdoor views.

Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!

9.6 out of 10, Exceptional, (43)
"Proximity to things to do on the island was great!"
The price is NZ$459
includes taxes & fees
17 Aug - 18 Aug
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
The Cottage by Anna Maria Island
Enjoy a leisurely stroll along the beach, with easy access to the ocean and surrounding community.

The Cottage by Anna Maria Island

9.8 out of 10, Exceptional, (12)
"Great host ,nice property. We had a problem with the shower, but the host had it fixed almost immediately. Would definitely stay here again."
The Cottage by Anna Maria Island
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Enjoy the serene ocean views from this expansive deck.

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"We were extremely happy with our stay and Evan as our host. He went out of his way to make sure everything went smoothly including helping us find all the beach amenities. The house was excellent and just what we needed, just a short walk across the road to the beach. We would definitely stay here again!"
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
West End Paradise Unit 4E Coral 4 - One bedroom efficiency suite
Property grounds

West End Paradise Unit 4E Coral 4 - One bedroom efficiency suite

9.4 out of 10, Exceptional, (23)
"My husband and I thoroughly enjoyed our 4 night stay here! The property and neighborhood was perfect! Everything you need is provided, from kitchen to beach accessories! It was clean, and comfortable. Loved having the parking pass for the private beach area. I preferred something quiet away from the crowds, and this was perfect! I found so many beautiful shells! Can’t wait for our next trip! Would definitely book this place again!"
West End Paradise Unit 4E Coral 4 - One bedroom efficiency suite
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Stroll through lush gardens surrounded by tropical plants and palm trees.

Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!

9.6 out of 10, Exceptional, (45)
"Great place "
The price is NZ$442
includes taxes & fees
11 Aug - 12 Aug
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
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, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is NZ$850
includes taxes & fees
12 Aug - 13 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
1-bedroom cottage just a short walk to Naples Beach and Fifth Avenue South
Enjoy serene sunsets over the calm sea from this peaceful beach.

1-bedroom cottage just a short walk to Naples Beach and Fifth Avenue South

10.0 out of 10, Exceptional, (13)
"It was the perfect place for my holiday getaway visiting family!"
The price is NZ$713
includes taxes & fees
12 Aug - 13 Aug
1-bedroom cottage just a short walk to Naples Beach and Fifth Avenue South
Charming cottage in quiet area, close to beach & bay.
Guests can enjoy access to the beach via a staircase, surrounded by lush trees.

Charming cottage in quiet area, close to beach & bay.

9.8 out of 10, Exceptional, (280)
"Beautiful home and great location. Close to the beach, food and ice cream. Will definitely stay here again. Host was really responsive. "
Charming cottage in quiet area, close to beach & bay.
3 Pools, lazy river, walk to 5th ave restaurants!
Relax by interconnected pools surrounded by lush greenery and palm trees, with seating areas and sun loungers.

3 Pools, lazy river, walk to 5th ave restaurants!

9.8 out of 10, Exceptional, (116)
"Great 2 bedroom cottage. Short walk to pool and clubhouse. Home was beautiful and well maintained. Would highly recommend!!"
3 Pools, lazy river, walk to 5th ave restaurants!
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Enjoy cooking in this well-equipped kitchen with an oven, coffee maker, and ample counter space.

Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!

9.2 out of 10, Wonderful, (63)
"Had a lovely stay.. close to beach and Food. "
The price is NZ$447
includes taxes & fees
11 Aug - 12 Aug
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Enjoy a leisurely beach walk with breathtaking ocean views.

Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!

9.4 out of 10, Exceptional, (54)
"Location was excellent! Close to beaches and some really good restaurants. I recommend the Mudbug the food was awesome and large pirtions. "
The price is NZ$444
includes taxes & fees
13 Aug - 14 Aug
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views
Outdoor dining

West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views

9.8 out of 10, Exceptional, (16)
"Great property, very clean and comfortable! The pond in the backyard and wildlife was beautiful. Hosts were very responsive and accommodating!"
West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
Enjoy bird watching and relaxation on this serene beach with calm seas and a nearby coastal town.

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

9.8 out of 10, Exceptional, (23)
"Perfect place to stay. 1 mile to the village and beach access. We loved making our own meals in the grill and swimming in the pool. "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
Cottage B - 2 Blocks to the Beach, 5th Street and 3rd Ave. South
Stroll through a vibrant garden filled with a variety of flowering plants and decorative flamingo statues.

Cottage B - 2 Blocks to the Beach, 5th Street and 3rd Ave. South

9.2 out of 10, Wonderful, (5)
"Loved the cottage and the location. "
The price is NZ$1,110
includes taxes & fees
11 Aug - 12 Aug
Cottage B - 2 Blocks to the Beach, 5th Street and 3rd Ave. South
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
Enjoy a serene beach experience with expansive sand and lush greenery.

Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

9.8 out of 10, Exceptional, (39)
"Great location,nice neighborhood,well equipped. We enjoyed our stay very much!"
The price is NZ$710
includes taxes & fees
11 Aug - 12 Aug
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
Relax in the serene outdoor seating area surrounded by lush greenery and a charming brick patio.

The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.

10.0 out of 10, Exceptional, (11)
"nice place great location, we will stay there again"
The price is NZ$803
includes taxes & fees
11 Aug - 12 Aug
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
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 Southwest Florida Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"The hotel is nice, beautiful and super clean."
Yoan 2-night trip
Posted 9 hours ago
Kompose Boutique Hotel

Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between NZ$442 and NZ$1,110 per night. No matter your budget, you're sure to find an ideal place to soak up nature's beauty. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Southwest Florida?
Southwest Florida has 58 cottages to choose from. Enter your dates and destination and start planning your perfect stay today.
What is there to do in Southwest Florida near my cottage?
Whether you're into shopping, dining, history or culture, Southwest Florida is one place where it's difficult to be bored! The leading city of Tampa has loads of attractions, including Henry B. Plant Museum, Orpheum Theatre and David A. Straz Jr. Centre for the Performing Arts. If you're taking off to Sarasota, Sarasota BayWalk, Ed Smith Stadium and Robert L. Taylor Community Complex shouldn't be missed.