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Check prices for these dates

In two weeks
17 Oct - 19 Oct
In one month
31 Oct - 2 Nov
In two months
28 Nov - 30 Nov
In three months
26 Dec - 28 Dec

Featured Cottages in Southwest Florida and around

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, (68)
"Lovely and clean little place. They have bikes you can use to get around. The island has a great bike/walking trail. "
The price is €282
includes taxes & fees
5 Oct - 6 Oct
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Family Retreat w/ Heated Pool in Port Charlotte!
House (3 Bedrooms) | Interior

Family Retreat w/ Heated Pool in Port Charlotte!

3.0 star property
The price is €332
includes taxes & fees
18 Oct - 19 Oct
Family Retreat w/ Heated Pool in Port Charlotte!
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
Exterior

Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.

9.8 out of 10, Exceptional, (75)
"3rd time there and will be back! If you want to get away from it all, this is the place to go."
The price is €225
includes taxes & fees
5 Oct - 6 Oct
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
Property grounds

Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes

9.0 out of 10, Wonderful, (23)
"Loved our stay at the cottage. It was a perfect getaway for 2. Short walk to a quiet beach. Convenient to restaurants and Ding Darling.We will be back!"
The price is €346
includes taxes & fees
10 Oct - 11 Oct
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
Studio#1-Back Bay Sunsets in Matlacha
Exterior

Studio#1-Back Bay Sunsets in Matlacha

9.6 out of 10, Exceptional, (10)
"We were very impressed with the cleanliness, comforts and the central location!!"
The price is €190
includes taxes & fees
5 Oct - 6 Oct
Studio#1-Back Bay Sunsets in Matlacha
5 Mi to Dtwn: Family Getaway in Punta Gorda
House (2 Bedrooms) | Interior

5 Mi to Dtwn: Family Getaway in Punta Gorda

3.0 star property
The price is €108
includes taxes & fees
20 Oct - 21 Oct
5 Mi to Dtwn: Family Getaway in Punta Gorda
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
Terrace/patio

Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River

9.6 out of 10, Exceptional, (4)
"We would stay at the cabin again. The location is secluded enough to be quiet but close to all the local places you would want to go, including a public beach. The neighborhood is a wonderful mixture.of homes from affluent to not so affluent. The river adds a nice ambience for the location. Streaming on the TV worked well. Overal a great experience for our getaway..Comfortable and clean, Cute as the pictures!!! "
The price is €172
includes taxes & fees
5 Oct - 6 Oct
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
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, (57)
"Location was excellent! Close to beaches and some really good restaurants. I recommend the Mudbug the food was awesome and large pirtions. "
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
The "Grouper"
Exterior

The "Grouper"

9.2 out of 10, Wonderful, (38)
"Great location."
The price is €185
includes taxes & fees
5 Oct - 6 Oct
The "Grouper"
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Outdoor dining

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

9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Old Florida Fishing Cottage See The Water From Living Room on Imperial River
Property grounds

Old Florida Fishing Cottage See The Water From Living Room on Imperial River

9.8 out of 10, Exceptional, (8)
"Hosts were responsive and addressed all questions in a timely manner. Would stay there again."
The price is €190
includes taxes & fees
5 Oct - 6 Oct
Old Florida Fishing Cottage See The Water From Living Room on Imperial River
Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4
Terrace/patio

Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4

10.0 out of 10, Exceptional, (7)
"Loved the cabin feel. Spent most evenings by the river on the amazing deck. "
The price is €163
includes taxes & fees
8 Oct - 9 Oct
Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4
Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach
Exterior

Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach

10.0 out of 10, Exceptional, (3)
"We stayed over kids spring break. Great location- not far from beaches and great restaurants. "
The price is €186
includes taxes & fees
12 Oct - 13 Oct
Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

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

9.6 out of 10, Exceptional, (78)
"Its right next to everything we needed"
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4
Exterior

Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4

10.0 out of 10, Exceptional, (1)
"Close enough to the beach to enjoy the area. The place was clean and had the necessities."
The price is €163
includes taxes & fees
12 Oct - 13 Oct
Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Property grounds

The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse

9.2 out of 10, Wonderful, (50)
"Great condo, plenty of room for 3 of us, very quiet and peaceful, love the ice cream shop right next door, would definitely stay here again!"
The price is €325
includes taxes & fees
13 Oct - 14 Oct
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Cute Cottage 1.5Mi 2 Beach Duplex Has Dock on Gulf Access Imperial River
Exterior

Cute Cottage 1.5Mi 2 Beach Duplex Has Dock on Gulf Access Imperial River

9.6 out of 10, Exceptional, (5)
"Great little beach cottage in a peaceful neighborhood near the beaches!"
The price is €160
includes taxes & fees
5 Oct - 6 Oct
Cute Cottage 1.5Mi 2 Beach Duplex Has Dock on Gulf Access Imperial River
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.
Terrace/patio

Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.

9.4 out of 10, Exceptional, (6)
"Very private and clean with everything you need for the weekend."
The price is €300
includes taxes & fees
5 Oct - 6 Oct
Charming 1-bedroom cottage with AC and WiFi on a creek with private deck & dock.
Quiet Quaint Cottage Right on Gulf Access Imperial River Close To Everything
Property grounds

Quiet Quaint Cottage Right on Gulf Access Imperial River Close To Everything

10.0 out of 10, Exceptional, (9)
"We enjoyed sitting right by the Imperial River. Our cabin had a nice private patio or we could join other guest on the dock. "
The price is €220
includes taxes & fees
6 Oct - 7 Oct
Quiet Quaint Cottage Right on Gulf Access Imperial River Close To Everything
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Property grounds

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
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

Carlisle Inn

Carlisle Inn

10/10 Excellent
"The Carlisle Inn is a gem! Truely a 5-star hotel. Elligent furnishing, large rooms, Wide halls. The hot tub and pool area are superb. If you stay the restaurant in the front parking lot is a must."
Celeste 1-night trip
Posted 3 days ago
Carlisle Inn

Find out more about Southwest Florida

Find out more about Southwest Florida

Southwest Florida Cottages information

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Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between and 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 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.

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