Search Cottages in Southwest Florida

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In two weeks
3 Oct - 5 Oct
In two months
14 Nov - 16 Nov
In three months
12 Dec - 14 Dec
In four months
9 Jan - 11 Jan

Cottages in Southwest Florida

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, (279)
"Everything was amazing; no detail was missed. Castaway Cottage is the perfect spot. Our group could not stop talking about all the things we loved, especially the pool and outdoor shower! "
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!
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, (287)
"Clean and quiet and the best location for a weekend getaway! "
Charming cottage in quiet area, close to beach & bay.
The "Grouper"
Exterior

The "Grouper"

9.4 out of 10, Exceptional, (36)
"Great location."
The price is SAR 371
SAR 795 total
includes taxes & fees
21 Sep - 22 Sep
The "Grouper"
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, (67)
"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 SAR 559
SAR 1,209 total
includes taxes & fees
29 Sep - 30 Sep
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
Country Cottage Home
Property grounds

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Perfect place for short stay. Great little cottage in a private quiet setting. Nothing super fancy but everything you need and exceptionally clean. "
Country Cottage Home
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, (17)
"It was the perfect place for my holiday getaway visiting family!"
The price is SAR 365
SAR 1,634 total
includes taxes & fees
25 Sep - 26 Sep
1-bedroom cottage just a short walk to Naples Beach and Fifth Avenue South
Cozy Getaway with pool and minutes to the beach!!!
Outdoor dining

Cozy Getaway with pool and minutes to the beach!!!

9.6 out of 10, Exceptional, (25)
"Nice place, clean, loved that it was close to the beach and the pool was great after the beach. Owners very nice and helpful "
Cozy Getaway with pool and minutes to the beach!!!
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)
"We enjoyed our stay so much! Just right for us with short walks to the Beach and Bay, peaceful back porch and comfy beds. It is a beautiful and clean house in the trees. Evan is a helpful host with great communication. We hope to go back again. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Romantic Getaway, #302, 2 min walk to the beach.
Exterior

Romantic Getaway, #302, 2 min walk to the beach.

9.4 out of 10, Exceptional, (62)
"Cute place - really nice location and super vibe "
Romantic Getaway, #302, 2 min walk to the beach.
Shell Cottage - sleeps 2
Exterior

Shell Cottage - sleeps 2

9.6 out of 10, Exceptional, (38)
"There were a few quirky things. Could not put the AC higher than 75 or it would freeze up the AC.We were only allowed 1 roll of TP we had to buy our own. And it said cookware is provided…1 small 6-8 inch skillet was supplied. And 1 small sauce pan. Everything else was fine."
Shell Cottage - sleeps 2
Keys stilt cottage lower unit
Property grounds

Keys stilt cottage lower unit

9.6 out of 10, Exceptional, (34)
"We visited for the Naples US pickleball open for try week. This home gave us everything we needed. It was clean and nicely put together. Would definitely stay again."
Keys stilt cottage lower unit
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

9.4 out of 10, Exceptional, (6)
"Loved the cottage and the location. "
Cottage B - 2 Blocks to the Beach, 5th Street and 3rd Ave. South
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
On the beach, sun loungers, beach towels

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (127)
"We enjoyed our stay and will definitely come back. Very clean! Comfy beds . Well stocked "
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
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, (15)
"nice place great location, we will stay there again"
The price is SAR 413
SAR 2,163 total
includes taxes & fees
22 Sep - 23 Sep
The Historic Coquina Cottages C is 2 Blocks to the Beach, 5th Avenue and 3rd St.
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
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!
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

9.6 out of 10, Exceptional, (120)
"Beautiful quiet stay on the water. I would definitely stay here again!"
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
The Cottage by Anna Maria Island
Outdoor dining

The Cottage by Anna Maria Island

9.0 out of 10, Wonderful, (14)
"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
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)
"Completely new inside, clean and just the right size for the 2 of us. Location is walkable to the beach (as long as your not carrying too many things). Or you can drive a couple minutes to Bowman's. Overall good accomodations. "
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 SAR 559
SAR 1,195 total
includes taxes & fees
21 Sep - 22 Sep
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
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

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Had a wonderful stay I will definitely recommend to others "
Lori 2-night trip
Posted 2 days ago
The Westin Sarasota

Frequently asked questions

How much do cottages in Southwest Florida cost?
Prices for cottages in Southwest Florida range between SAR 795 and SAR 2,163 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 62 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 vacations 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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