Search Cottages in Southwest Florida

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sept - 14 Sept

Browse Select Southwest Florida Cottages

The Inn On Siesta Key
Relax by the serene pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas for a comfortable stay.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (180)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The Inn On Siesta Key
2 Mi to Anna Maria Island: Newly Built Home!
Interior

2 Mi to Anna Maria Island: Newly Built Home!

3.0 star property
2 Mi to Anna Maria Island: Newly Built Home!
Marco Island Home w/ Heated Pool + Screened Lanai!
House (4 Bedrooms) | Front of property

Marco Island Home w/ Heated Pool + Screened Lanai!

3.0 star property
10.0 out of 10, Exceptional, (5)
"Amazing stay!"
Marco Island Home w/ Heated Pool + Screened Lanai!
Palm View
Relax in an outdoor space with a hammock, table, and chairs, surrounded by lush potted plants.

Palm View

3.5 star property
10.0 out of 10, Exceptional, (1)
Palm View
Naples Retreat With Private Pool & Spa!
House (3 Bedrooms) | Interior

Naples Retreat With Private Pool & Spa!

3.0 star property
Naples Retreat With Private Pool & Spa!
Pet-friendly Naples Vacation Rental w/ Fire Pit!
House (3 Bedrooms) | Interior

Pet-friendly Naples Vacation Rental w/ Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
"We came to spend time with my sister for Easter and we were very pleased with this property. It was nice and clean and enough space for my family. "
Pet-friendly Naples Vacation Rental w/ Fire Pit!
Luxury Ave Maria Rental w/ Private Pool & Spa!
Relax by the pool surrounded by lounge chairs and umbrellas.

Luxury Ave Maria Rental w/ Private Pool & Spa!

3.0 star property
Luxury Ave Maria Rental w/ Private Pool & Spa!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 1 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.