Our Snowbird picks: Naples, FL vacation rentals with a pool

Enclosed vacation home pool in Naples, FL with views of nearby golf course
Aerial view of vacation home and lawn in Naples, FL

When it comes to snowbird-friendly vacation rentals, Naples, Florida, really steals the show. Here, you’ll find endless sunshine, more golf courses than you could possibly play, and a variety of fabulous vacation rentals with pools. Naples makes an ideal winter getaway, and we doubt you’ll want to spend the season here without your own personal pool—especially when rentals with pools are so abundant.

Tour a few of our favorite Naples, Florida, vacation rentals with pools for that taste of the tropics you’ve been craving.

Orange Grove Naples vacation rental

Would you like a side of citrus to go with your Naples vacation? This cheerful orange rental with a pool provides a refreshing escape for snowbirds. There’s space for as many as six guests to spread out, and you’ll love beating the Florida heat in the private pool.

Make your next Naples, FL vacation rental Orange Grove.

Blue Heron Breeze at Briarwood Naples vacation rental

Naples snowbirds know that heating your pool might not be necessary, but it’s certainly a nice option. At this vacation rental, there’s just a minimal extra fee to get the pool nice and toasty. The patio provides the perfect setting for relaxation in or out of the pool.

Make your next Naples, FL vacation rental Blue Heron Breeze at Briarwood.

Sans Souci Naples vacation rental

Linger a while in this Naples vacation rental’s pool overlooking the canal, and you just might forget what season it is. The back patio and pool here are the perfect remedy for those winter blues. This home’s upscale, European-inspired decor is the icing on your snowbird-friendly cake.

Make your next Naples, FL vacation rental Sans Souci.

Terrazo Retreat Naples vacation rental

Life’s peachy at this tropical-hued vacation rental with a pool. Take a refreshing dip surrounded by palm fronds, or hang out inside where it’s air-conditioned. When you’re ready for a little more action, take one of the rental’s bikes out for a neighborhood ride.

Make your next Naples, FL vacation rental Terrazo Retreat.

Water Vista Villa Naples vacation rental

It’s definitely worth flying south for the winter to see the waterfront view from this home’s back porch and pool. Whether you’re relaxing inside or poolside, this lovely three-bedroom home is a great home base for Naples recreation.

Make your next Naples, FL vacation rental Water Vista Villa.

Secret Splash Naples vacation rental

Welcome to Naples, Florida, vacation rental heaven! An enclosed backyard holds a private pool oasis, plus a grill and plenty of lounge furniture. If you’re here for a snowbird retreat, you’ll feel right at home in no time.

Make your next Naples, FL vacation rental Secret Splash.

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