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Check prices for these dates

Next weekend
1 Aug - 3 Aug
In two weeks
8 Aug - 10 Aug
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22 Aug - 24 Aug
In two months
19 Sept - 21 Sept

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)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The Inn On Siesta Key
Tropical Paradise On The Beach Permit VRC17-000168
Effortlessly prepare meals in this well-equipped kitchen featuring a coffee maker, oven, and microwave.

Tropical Paradise On The Beach Permit VRC17-000168

9.4 out of 10, Exceptional, (133)
"Quaint beach cottage tucked away from the hustle an bustle of the island. The upper unit had a spectacular view of the beach and sunsets.Communication with the property managers was great!We have already booked again for next year!Thank you for a wonderful stay!"
Tropical Paradise On The Beach Permit VRC17-000168
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Outdoor dining

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

10.0 out of 10, Exceptional, (133)
"Our stay was great. Everything was as advertised and expected. "
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
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, (271)
"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!
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, (278)
"This house was perfect! Close to the beach and restaurants. It had everything we needed. The fenced in backyard was great for our dog. We would definitely stay here again. "
Charming cottage in quiet area, close to beach & bay.
The "Grouper"
Enjoy scenic views of the ocean from the pier, where you can sit and relax on the benches or explore the surrounding waters by kayak.

The "Grouper"

9.6 out of 10, Exceptional, (30)
"My stay was absolutely wonderful! The location is great, very convenient. The place itself is extremely comfortable, cozy, and it had everything we needed. The hosts were kind and attentive. It was truly worth every minute."
The price is NZ$361
includes taxes & fees
31 July - 1 Aug
The "Grouper"
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$460
includes taxes & fees
4 Aug - 5 Aug
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
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$868
includes taxes & fees
20 Aug - 21 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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, (43)
"Great place "
The price is NZ$449
includes taxes & fees
3 Aug - 4 Aug
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
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
Country Cottage Home
Relax in a serene outdoor space surrounded by a tropical mural and lush greenery.

Country Cottage Home

9.4 out of 10, Exceptional, (139)
"Loved our stay at the property. Would book it again!"
Country Cottage Home
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.

9.8 out of 10, Exceptional, (10)
"nice place great location, we will stay there again"
The price is NZ$856
includes taxes & fees
27 July - 28 July
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
Moninanu - Modern Wooded Cottage in North Naples
Relax in a shaded outdoor space surrounded by lush greenery and trees, featuring wicker furniture and comfortable cushions.

Moninanu - Modern Wooded Cottage in North Naples

10.0 out of 10, Exceptional, (11)
"A great place for us to stay so we can be close to family"
Moninanu - Modern Wooded Cottage in North Naples
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$454
includes taxes & fees
9 Aug - 10 Aug
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
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
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, (89)
"Great place. Easy access to beach and surrounding amenities. Would recommend. "
Rustic & Cozy Island Original Cottage on the Beach- Bamboo Apts. C2
Across The Street From #1 Beach
Enjoy the serene coastal scenery from the shore.

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Enjoy a serene coastal setting with ocean views and lush greenery surrounding single-family homes.

Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!

9.6 out of 10, Exceptional, (21)
"Great location nicely decorated and clean"
Cozy Holmes Beach Cottage - 3/2 - 1 block from beach!
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Enjoy sunbathing and relaxation on the sandy shore, where beach umbrellas and towels are available.

Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6

8.8 out of 10, Excellent, (8)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lots of beach time"
Historical AMI 2 Bedroom, pet friendly beach cottage, sleeps 6
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
Relax by the serene pool surrounded by lush greenery and a shaded pergola.

Beautiful, well-maintained home w/ heated private pool - walk to beach & dining

9.6 out of 10, Exceptional, (79)
"We were in town for a lacrosse tournament and this house was so perfect, clean and relaxing."
Beautiful, well-maintained home w/ heated private pool - walk to beach & dining
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

Margaritaville Beach Resort Fort Myers

Margaritaville Beach Resort Fort Myers

10/10 Excellent
"Fun and beautiful resort!"
Derin 2-night trip
Posted 12 hours ago
Margaritaville Beach Resort Fort Myers

Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between NZ$361 and NZ$868 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 45 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.