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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Featured Cottages in Southwest Florida and around

The Inn On Siesta Key
The Lookout, 1 King Bedroom 1 Bath | Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The price is €281
includes taxes & fees
21 Aug - 22 Aug
The Inn On Siesta Key
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
Property grounds

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

10.0 out of 10, Exceptional, (275)
"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
Exterior

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
Exterior

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!
Property grounds

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 €238
includes taxes & fees
21 Aug - 22 Aug
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
The Cottage by Anna Maria Island
Outdoor dining

The Cottage by Anna Maria Island

9.6 out of 10, Exceptional, (13)
"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
Terrace/patio

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

10.0 out of 10, Exceptional, (34)
"Had a great family vacation. We spent lots of time on the beach & fishing off the dock. We were especially grateful for your turtle education thank you for letting us partake in that. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
West End Paradise Unit Coral 4 - One bedroom efficiency suite
Exterior

West End Paradise Unit 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 Coral 4 - One bedroom efficiency suite
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Exterior

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

9.6 out of 10, Exceptional, (46)
"Great place "
The price is €231
includes taxes & fees
22 Aug - 23 Aug
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
The price is €448
includes taxes & fees
24 Aug - 25 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
Outdoor dining

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

10.0 out of 10, Exceptional, (15)
"It was the perfect place for my holiday getaway visiting family!"
The price is €423
includes taxes & fees
14 Sept - 15 Sept
1-bedroom cottage just a short walk to Naples Beach and Fifth Avenue South
Charming cottage in quiet area, close to beach & bay.
Exterior

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

9.8 out of 10, Exceptional, (282)
"Excellent location. House looks exactly like pics. Very clean and decorated beautifully. Short walk to beach. Restaurants within walking distance overall great location. Quiet area, easy checkin. Everything we needed was supplied in house. Would definitely stay again for a longer trip. "
Charming cottage in quiet area, close to beach & bay.
3 Pools, lazy river, walk to 5th ave restaurants!
Exterior

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

9.8 out of 10, Exceptional, (117)
"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!
Fridge, microwave, coffee/tea maker

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 €239
includes taxes & fees
25 Aug - 26 Aug
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Property grounds

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 €232
includes taxes & fees
22 Aug - 23 Aug
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
West End Paradise Unit Seahorse 3 - two bedroom suite w/water views
Outdoor dining

West End Paradise Unit 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 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
Property grounds

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
Property grounds

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 €580
includes taxes & fees
21 Aug - 22 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
Outdoor dining

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 €365
includes taxes & fees
15 Sept - 16 Sept
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.
Terrace/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 €462
includes taxes & fees
24 Aug - 25 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

Hilton Naples

Hilton Naples

10/10 Excellent
"Good times"
Lisa 1-night trip
Posted 9 hours ago
Hilton Naples

Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between €231 and €580 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.
Why book your cottage in Southwest Florida with Expedia?
We think that holidays should be stress-free, so if you're searching for cottages in Southwest Florida at the perfect price, Expedia can help. Keep the budget in check and pick a low-cost option far away from the city rush, or book a luxury cottage to pamper your loved ones.