Southwest Florida Vacation Rentals

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Make Southwest Florida your next getaway—choose from 233 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

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House rentals

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Condo rentals

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Studios

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Southwest Florida vacation rentals for every getaway

Popular
Dog-friendly Hot tub Internet
Bonita Sands 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Bonita Sands - Bonita Springs, FL

From $80
Parrot Beach Cottages Suite #3
1 Bedroom | 1 Bath | Sleeps 4 (2 Adults Max)

Parrot Beach Cottages Suite #3 - Siesta Key, FL

From $112
Lover's Key Resort 3D Tour
1 Bedroom | 1 Bath | Sleeps 4

Lover's Key Resort - Fort Myers Beach, FL

From $74
Parrot Beach Cottages Suite #2
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #2 - Siesta Key, FL

From $104
Parrot Beach Cottages Suite #1
0 Bedroom | 1 Bath | Sleeps 2

Parrot Beach Cottages Suite #1 - Siesta Key, FL

From $90

View 228 more homes

Recent Southwest Florida vacation rental reviews

Convenient neighbourhood, cute and beach style interior. This review was submitted while the home was managed by a different property management company.
. | Oct 2021
Beautiful and clean home loved the private pool and area. The manager of the property was friendly, timely and helpful when needed.
Debra L. | Sep 2021
Great place in a great location! Less than a minute walk to the beach and about 3 minute walk to Siesta Key Village. Parrot Beach Cottages is our “go to” for Florida getaways!
Gene F. | Sep 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.