Southwest Florida Vacation Rentals

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Make Southwest Florida your next getaway—choose from 270 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, studios, and more


House rentals

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Condo rentals

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View 8 Studios

Southwest Florida vacation rentals for every getaway

Dog-friendly Hot tub Internet
Parrot Beach Cottages Suite #1
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

From $117
Lemon Bay Retreat 3D Tour
2 Bedroom | 2 Bath | Sleeps 6 (4 Adults Max)

Lemon Bay Retreat - Englewood, FL

From $111
Mangrove View on Oyster Creek 3D Tour
2 Bedroom | 2 Bath | Sleeps 6

Mangrove View on Oyster Creek - Englewood, FL

From $155
Pineapples and Palm Trees 3D Tour
4 Bedroom | 2 Bath | Sleeps 8

Pineapples and Palm Trees - Sarasota, FL

From $170
Lover's Key Resort 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Lover's Key Resort - Fort Myers Beach, FL

From $97

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Recent Southwest Florida vacation rental reviews

This house has everything you need! Safe neighborhood. Close to a lot of good restaurants and things to do.
Thomas S. | Nov 2021
This home was a nice place to spend Thanksgiving. We loved the weather and all the local shopping, restaurants and beach not far away at all, Thank you for a fun time
tom p. | Nov 2021
Nice condo and great location!
Kathleen M. | Nov 2021

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.