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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Southwest Florida and around

The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (182)
"Great place to stay! "
The price is €244
includes taxes & fees
20 Aug - 21 Aug
The Inn On Siesta Key
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 €238
includes taxes & fees
25 Aug - 26 Aug
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
19 Aug - 20 Aug
Family Retreat w/ Heated Pool in Port Charlotte!
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 €173
includes taxes & fees
18 Aug - 19 Aug
Spacious Cottage 1.5 Mi To Beach Kitchen W&D King Bed Dock On The Imperial River
Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach
Terrace/patio

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 €188
includes taxes & fees
18 Aug - 19 Aug
Large Deck On Imperial Gulf Access River Kayak Launch Kit W&D 1.3M To Beach
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Beach nearby

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 €227
includes taxes & fees
14 Sept - 15 Sept
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
Beach nearby

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 €348
includes taxes & fees
18 Aug - 19 Aug
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4

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 €164
includes taxes & fees
18 Aug - 19 Aug
Updated 2024 King Bed Kit W/D Dock On Imperial River 1.3 Mi to Beach Sleeps 4
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, (5)
"We stayed at the star fish little home away from home. This place was exactly as pictured. My neice and I absolutely loved this place and would highly recommend this to others. Price was well worth the stay to have privacy and all the amenities needed. We ate at local restaurants Coconut Joes was amazing and beach is close and absolutely beautiful!!"
The price is €164
includes taxes & fees
18 Aug - 19 Aug
Peaceful Cottage On Imperial River W Dock W&D Kitchen King Bed Can Sleep 4
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 €191
includes taxes & fees
18 Aug - 19 Aug
Old Florida Fishing Cottage See The Water From Living Room on Imperial River
Studio#1-Back Bay Sunsets in Matlacha
Interior

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 €177
includes taxes & fees
30 Aug - 31 Aug
Studio#1-Back Bay Sunsets in Matlacha
Port Charlotte Home w/ Pool - 8 Mi to Beaches!
House (3 Bedrooms) | Interior

Port Charlotte Home w/ Pool - 8 Mi to Beaches!

3.0 star property
9.4 out of 10, Exceptional, (3)
"Everything was clean and comfortable. We will be booking again!!!"
The price is €352
includes taxes & fees
20 Aug - 21 Aug
Port Charlotte Home w/ Pool - 8 Mi to Beaches!
The "Grouper"
Beach

The "Grouper"

9.6 out of 10, Exceptional, (31)
"Great location."
The price is €184
includes taxes & fees
15 Sept - 16 Sept
The "Grouper"
Spacious Port Charlotte Home w/ Lanai!
House (4 Bedrooms) | Interior

Spacious Port Charlotte Home w/ Lanai!

3.0 star property
The price is €404
includes taxes & fees
23 Aug - 24 Aug
Spacious Port Charlotte Home w/ Lanai!
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)
"Exactly "
The price is €256
includes taxes & fees
18 Aug - 19 Aug
Country Cottage, 40 Acres, Outdoor Kitchen w/ B-que, Campfire, & Horse Stables.
Spacious 3 Rooms 1.5 Mi 2 Beach On Gulf Access River W/ Dock Close 2 Everything
Property grounds

Spacious 3 Rooms 1.5 Mi 2 Beach On Gulf Access River W/ Dock Close 2 Everything

10.0 out of 10, Exceptional, (1)
"I highly recommend these properties. Unit was just as described. Very comfortable and with everything you need. I will definitely be back! "
The price is €176
includes taxes & fees
18 Aug - 19 Aug
Spacious 3 Rooms 1.5 Mi 2 Beach On Gulf Access River W/ Dock Close 2 Everything
1-bedroom cottage just a short walk to Naples Beach and Fifth Avenue South
Sun-loungers, beach towels

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 €421
includes taxes & fees
14 Sept - 15 Sept
1-bedroom cottage just a short walk to Naples Beach and Fifth Avenue South
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
18 Aug - 19 Aug
Cute Cottage 1.5Mi 2 Beach Duplex Has Dock on Gulf Access Imperial River
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, (49)
"3rd time staying at Parrot Nest. Like everything about this little place. "
The price is €265
includes taxes & fees
20 Aug - 21 Aug
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Beachy Port Charlotte Home w/ Hot Tub & Pool!
House (3 Bedrooms) | Interior

Beachy Port Charlotte Home w/ Hot Tub & Pool!

3.0 star property
Beachy Port Charlotte Home w/ Hot Tub & 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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Top Southwest Florida Hotel Reviews

Sunseeker Resort Charlotte Harbor

Sunseeker Resort Charlotte Harbor

10/10 Excellent
"We had a great time - everything we needed in one place so many options for dining, comfortable, clean rooms and a beautiful pool area with plenty of seating. Super fun for a long weekend. The staff was very customer focused. Would highly recommend."
Megan 3-night trip
Posted 12 hours ago
Sunseeker Resort Charlotte Harbor

Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between €227 and €585 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.