Search Southwest Florida Cottage Accommodations

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Feb - 23 Feb
In two weeks
28 Feb - 2 Mar
In one month
14 Mar - 16 Mar
In two months
11 Apr - 13 Apr

Featured Cottages in Southwest Florida

The "Grouper"
Beach

The "Grouper"

9.6 out of 10, Exceptional, (9)
"Great spot , close to beach and great dining places , very clean.One small improvement would be a 120volt outlet in the bath."
The price is AU$345
includes taxes & fees
17 Feb - 18 Feb
The "Grouper"
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Aerial view

Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!

9.6 out of 10, Exceptional, (46)
"Great location! Loved access to beach chairs, towels and bikes. Cute rental that has everything you need. Beach is walking distance. Wickies restaurant across the street is amazing!"
The price is AU$792
includes taxes & fees
17 Feb - 18 Feb
Macaw cottage, newly remodeled, walking distance to beach, shops, restaurants!
Charming cottage in quiet area, close to beach & bay.
Sun-loungers, beach towels

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

9.8 out of 10, Exceptional, (253)
"Lovely clean little cottage. Walkable to a lot. We really enjoyed the place and a very accommodating host! "
Charming cottage in quiet area, close to beach & bay.
Shell Cottage - sleeps 2
Beach nearby

Shell Cottage - sleeps 2

9.8 out of 10, Exceptional, (33)
"We could not ask for any better of a vacation"
Shell Cottage - sleeps 2
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!

9.0 out of 10, Wonderful, (51)
"The place was great. Only negatives were an uncomfortable mattress,it wanted to curl up on the edges as we moved around, and you had to stand strategically in the shower to keep water off the floor from the gap in the door."
The price is AU$750
includes taxes & fees
2 Mar - 3 Mar
Newly remodeled Parakeet cottage! Walking distance to beach, restaurants, shops!
3 Pools, lazy river, walk to 5th ave restaurants!
Outdoor pool, a heated pool

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

9.8 out of 10, Exceptional, (107)
"We have been coming to Naples Bay Resort for 15 years now & this villa was the best equipped for all of our family’s needs! We will definitely book it again, overlooking the tennis courts & pool with luxury immenitie!"
3 Pools, lazy river, walk to 5th ave restaurants!
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, (112)
"We enjoyed our stay. It is perfect for families and the location is perfect!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
Aerial view

Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!

9.6 out of 10, Exceptional, (39)
"Enjoyed the cottages. Very clean and convenient. All you need for a beach trip. Bed was better than most. "
The price is AU$791
includes taxes & fees
2 Mar - 3 Mar
Sanibel-Style on the East End! Walk to restaurants and the lighthouse. NEW!
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Aerial view

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

9.2 out of 10, Wonderful, (42)
"Only thing I didn't like was that the water in the shower started getting cold pretty quickly. Otherwise, everything was great! Specifically the customer service! I talked on the phone with Paige with Breakaway Vacations multiple times and she was incredibly friendly and helpful!"
The price is AU$932
includes taxes & fees
16 Feb - 17 Feb
The Lovebird-sleeps 3! Great value on Sanibel-walk to dining, shops and Historic East End Lighthouse
Very Cute Cottage , in Bonita- Queen Bed + 2 Rollaway Beds. Near the Beach!
Miscellaneous

Very Cute Cottage , in Bonita- Queen Bed + 2 Rollaway Beds. Near the Beach!

9.6 out of 10, Exceptional, (4)
"Clean simple location. Central to all our activities. Quaint village."
Very Cute Cottage , in Bonita- Queen Bed + 2 Rollaway Beds. Near the Beach!
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, (21)
"WAS NICE BUT NOT AS BIG AS THOUGHT IT WOULD BE"
The price is AU$949
includes taxes & fees
4 Mar - 5 Mar
Coastal Chic Cottage "Sandpiper" minutes to the beach! Free bikes
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
Aerial view

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

9.6 out of 10, Exceptional, (35)
"please was very nice and comfortable close to several places"
The price is AU$788
includes taxes & fees
14 Feb - 15 Feb
Newly remodeled Parrot Nest Toucan Cottage! Walk to beach, shops, restaurants!
West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views
Beach nearby

West End Paradise Unit 2 Seahorse 3 - two bedroom suite w/water views

9.6 out of 10, Exceptional, (17)
"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
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Beach towels

Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...

9.6 out of 10, Exceptional, (40)
"The property was as described and absolutely amazing! It was beautiful inside, beds were comfortable, living area had comfortable furniture. Amenities were excellent. Not a bad thing to say about this place. Easy check in/out. Will definitely stay there again! "
Charming Cottage, FREE Wi-Fi & Trolley, Close to Gulf & Bay Beach, Stroll the...
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
Beach

Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS

9.8 out of 10, Exceptional, (36)
"Good communication, great location, private and clean. We never left the island! Enjoyed using the bikes and private beach access. Close to all restaurants but in a residential like setting. Would highly recommend this cute cottage. Would definitely return."
The price is AU$995
includes taxes & fees
2 Mar - 3 Mar
Gorgeous Coastal Cottage "Ibis" Minutes to the beach and free bikes! JULY SAVINGS
Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
Fridge, microwave, oven, stovetop

Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.

9.6 out of 10, Exceptional, (8)
"We had a wonderful stay at this lovely, clean house! As a family of five, we found the space sufficient for everyone to feel comfortable. The house is well-maintained and welcoming, with all the essentials provided. While it's a bit far to walk downtown or the pier, we rented a car, which made getting around super easy. Overall, we had a great experience and would highly recommend this property to others."
Lake front cottage less than 1mile from Fifth Ave S. The heart of old Naples.
Cozy and Private our island home on North Captiva is the perfect escape
Outdoor pool, a heated pool

Cozy and Private our island home on North Captiva is the perfect escape

8.6 out of 10, Excellent, (7)
"I booked this house because of the location and fantastic price. It was adorable and exactly as expected. I couldn't get the dryer door to open but I think that may have been operator error. The property managers, Duncan and Laurie with Tortuga, went above and beyond to make my stay not just ok, but exceptional. I would have missed the ferry due to my plane delay had Duncan not reached out to give me additional options. He even called the ferry captain to make sure he new I was coming for the...
Cozy and Private our island home on North Captiva is the perfect escape
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Miscellaneous

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

9.6 out of 10, Exceptional, (8)
"The hostess was very nice, and helpful. Place was clean, comfy and we had everything we needed for our short stay. "
The price is AU$523
includes taxes & fees
23 Feb - 24 Feb
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Property grounds

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (181)
"We were actually at a property in Venice Beach, a house with private pool. It was very nicely decorated and so comfortable. Close to everything. We had a blast."
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Classic dog-friendly cottage with kitchen, washer/dryer, & central AC
Outdoor dining

Classic dog-friendly cottage with kitchen, washer/dryer, & central AC

10.0 out of 10, Exceptional, (3)
"The houde was super cute and cozy, the trees in the yard were huge and breath taking. Super easy to get too, and to get to other places. The town is super cute and decorated for chridtmas !"
Classic dog-friendly cottage with kitchen, washer/dryer, & central AC
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.
Don't see what you're looking for?
See all available properties in Southwest Florida
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Southwest Florida

The Suites at Fishermen’s Village- 2 Bedroom Suites
Outdoor pool

The Suites at Fishermen’s Village- 2 Bedroom Suites

3.0 star property
9.8 out of 10, Exceptional, (754)
"Such funny and the accommodations were amazing"
The price is AU$585
includes taxes & fees
2 Mar - 3 Mar
The Suites at Fishermen’s Village- 2 Bedroom Suites
Bellasera Resort
Lobby

Bellasera Resort

4.0 star property
9.6 out of 10, Exceptional, (2104)
"The hotel was lovely and the staff was wonderful. We will be going back soon. Don't miss the breakfast and lunch at the hotel. It was fantastic!"
The price is AU$1,347
includes taxes & fees
18 Feb - 19 Feb
Bellasera Resort
Hyatt Vacation Club at Coconut Cove, Bonita Springs
Lobby

Hyatt Vacation Club at Coconut Cove, Bonita Springs

4.0 star property
9.2 out of 10, Wonderful, (504)
"Nice place"
The price is AU$779
includes taxes & fees
25 Feb - 26 Feb
Hyatt Vacation Club at Coconut Cove, Bonita Springs
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.

Frequently asked questions

How much do cottages in Southwest Florida cost?
You’ll pay between AU$345 and AU$995 per night for cottages in Southwest Florida. Whatever your budget, a wonderful stay is only clicks away on Expedia. This price was 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?
Browse our 28 cottages in Southwest Florida and then book your favourite. Whether you’re dreaming of a holiday with the fam or a break with buddies, your perfect stay is just a few clicks away with Expedia.
What is there to do in Southwest Florida near my cottage?
Whether you enjoy food, shopping, history or sightseeing, Southwest Florida offers it all, and more! The top city of Tampa has lots of things to see and do, including Florida Aquarium, Tampa Theatre and Tampa Museum of Art. If you’re on your way to Naples, Naples Beach, Naples Zoo at Caribbean Gardens and Collier County Museum are worth putting on your itinerary.