Southwest Florida Vacation Rentals

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Make Southwest Florida your next getaway—choose from 659 great vacation rentals

Between the lush Everglades and the colorful Tampa area, Southwest Florida’s vacation rentals and destinations offer endless sunshine and relaxation. This part of the state faces the placid Gulf of Mexico, known for its mild waters and pristine beaches. Whether you’re staying in Naples for the winter or taking the family to Cape Coral for spring break, a Southwest Florida beach condo or home are going to feel just right.

Explore Southwest Florida house rentals, condo rentals, duplexes, and more

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House rentals

View 435 House rentals
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Condo rentals

View 170 Condo rentals
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Duplexes

View 14 Duplexes

Southwest Florida vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Hip Harbour
3 Bedroom | 2.5 Bath | Sleeps 7

Hip Harbour - North Fort Myers, FL

$235 avg / night
Bay Oaks 75
1 Bedroom | 1 Bath | Sleeps 4

Bay Oaks 75 - Siesta Key, FL

$262 avg / night
Bonita Sunsets
0 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Bonita Sunsets - Bonita Springs, FL

$238 avg / night
Parrot Beach Cottages Suite #1
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

$226 avg / night
Parrot Beach Cottages Suite #3
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #3 - Siesta Key, FL

$263 avg / night

View 654 more homes

Recent Southwest Florida vacation rental reviews

Nice pool, clean and near restaurants.
Sharon M. | Dec 2022
Great location…great condo. Loved stay.
William D. | Dec 2022
This beautiful home has it all. Loved the openess. All the games for game nights out on the beautiful lanai. The water pool chairs are so comfy. Kudos to the owners for thinking of every last detail. Will definitely come back.
Deb H. | Nov 2022
Southwest Florida Frequently Asked Questions

Yes, 184 of our Southwest Florida homes allow dogs—so feel free to bring Fido along. (Just make sure to check individual home listings for any limits on the number and size of dogs they allow).

Browse dog-friendly homes >

Yes. 657 of our Southwest Florida vacation rentals have internet access, so you can stay connected throughout your trip.

Browse homes with internet access >


Some of the most popular amenities in our Southwest Florida vacation rentals include:

Our standard check-in time is 4:00 p.m., and the check-out time is 10:00 a.m. Some exceptions apply—after you book, you’ll find check-in and check-out details in the Vacasa guest app or your Trip Manager.

Absolutely. Our local Southwest Florida team includes professional housekeepers who care for all our homes here. They’ll clean thoroughly and restock amenities, so everything is ready for your arrival—and all you have to do is settle in and relax.

Learn more about Vacasa Premium Clean >

No worries, plans change. Read over our cancellation policy for more information. And if you currently have a Vacasa reservation for Southwest Florida, log in to Trip Manager to see options available for your specific trip.

Book confidently. Stay comfortably.

Book confidently. Stay comfortably.
24/7 support
Easy check-in
Easy check-in
Professional cleaning
Professional cleaning


Southwest Florida vacation rentals near Fort Myers

The town of Fort Myers sits on the Caloosahatchee River where it diverges into the Pine Island Sound and San Carlos Bay, creating a variety of shorelines, communities, and destinations perfect for your next Southwest Florida vacation. Book a home in town, or stay out by the sand at a Fort Myers Beach vacation rental. Just a little south you’ll find Bonita Springs, a vacation community full of beautiful houses, sparkling pools, and endless sunshine.

Stay in a Naples vacation rental

Naples visitors know that this is one of Southwest Florida’s best spots. The town is full of lovely vacation rentals, many of which boast private pools—a popular choice for snowbirds. Head out to the Naples Pier for an afternoon of coastal fun, or bring your towels and hit the beach. No matter how you spend your time in Naples, you’re guaranteed to have a blissful Florida getaway.

Sarasota: a Southwest Florida gem

Sitting south of Bradenton, the Sarasota area offers beaches, cultural attractions, and beautiful neighborhoods. Whether you’re staying in a Siesta Key vacation rental or making the easy day trip out, you’ll love the sugary-soft sand and upscale dining and shopping there. Rent a boat or jet ski and cruise across Sarasota Bay’s calm waters, or explore the local aquarium with the kids.

With so many great vacation options in Southwest Florida, it’s no surprise we offer a wide variety of vacation rentals in the area. Come experience Gulf Coast bliss in sunny Southwest Florida—book today.