Snowbird rentals in Naples, Florida

Call (888) 257-7970 for additional information about long-term bookings.
Donna Fiala Eagle Lakes Community Park.

A long-term vacation to look forward to

Receive a discounted rate on many of our monthly rentals (displayed at check-out) and reductions in our usual fees. We also allow for partial payment if you book at least 45 days ahead of time.

Plus, enjoy peace of mind with our simple cancellation policy and optional travel insurance.

Beach in Naples with the pier in the background.

Start planning your Southwest Florida snowbird stay

Golf courses, glamorous outdoor pools, and the Gulf of Mexico—what more could you need for the perfect winter getaway? Indulge in some retail therapy in Naples, reel in an impressive catch on Marco Island, or relax on a stroll through nature preserves in Fort Myers. With art galleries, boat tours, fresh seafood, and the Naples Botanical Gardens, there’s something everyone can appreciate. Find a monthly vacation rental that feels like home and enjoy a warm winter.

The exterior of a vacation rental in Naples, FL with palm trees and Spanish style architecture.


The Vanderbilt

Stay within walking distance of North Vanderbilt Beach from this top-rated snowbird vacation rental. Relax in elegance, with plenty of room, a chef’s kitchen, an indoor-outdoor living space, a soaking tub, an indoor pool, paddleboards, bikes, and beautiful modern furnishings. From this Naples, FL, hideaway, the world is your oyster.

Naples snowbird-friendly rentals with pools

With Florida’s year-round mild temperatures, there’s no need to put away your bathing suit. Grab a vacation rental with a pool and make the most of the sunshine with a refreshing dip in the water.

The pool area of a vacation rental in Naples, FL.


Beachside Blessings

Split your time between the ocean and a private pool. This charming oasis has everything you need for an unforgettable getaway. Unwind with a soak in the hot tub, practice a few laps in the pool, savor warm rays and a cup of coffee in the sunroom, and enjoy plenty of space for family and friends.

Statue of a golfer in Naples.

Golfing in Naples

Southwest Florida is a golfer’s paradise, with 92 golf courses to explore in Naples alone. Putt away all winter long at scenic and historic courses, like The Fort Myers Country Club, opened in 1917. Don’t let your clubs get dusty—stay close to the action with a monthly rental.

A drone shot of a vacation rental in Naples on a golf course.


Golf-Course Oasis

Keep your golfing game strong through the winter months with a golf course just beyond your backyard. This vacation rental is located on the edge of the Lely Country Club and features pond views, a gas grill, and a heated private pool, as well as community amenities like an on-site restaurant and two public golf courses.

Pet-friendly snowbird rentals in Naples

What would a vacation be without man’s best friend? Bring Fido along for the fun with a snowbird pet-friendly vacation rental you’ll both love.

The back patio overlooking the lake with a hot tub at a vacation rental in Naples, FL.


Tranquil Lakeside Haven

Feel your stress slip away from the comfort of this pet-friendly vacation rental in Naples. Situated near Sugden Regional Park, close to Lake Avalon, and a quick walk to restaurants, you and your four-legged friend can head out for an adventure or relax on the deck overlooking the lake.

Plan a weekend trip to the Everglades

A one-of-a-kind adventure awaits on your getaway to southwest Florida. Everglades National Park is the largest stretch of tropical wilderness in the United States, boasting boardwalk trails, hiking paths, boat tours, and wildlife viewing areas. Check off your list of must-sees, like the Gumbo Limbo Tree, manatees at the Flamingo Marina, and a few alligator sightings. Whizz across the Everglades with an airboat tour, rent kayaks and enjoy exploring solo, or birdwatch from the trails.

Drone shot of a vacation rental with a dock on the water in Naples, Florida.


Fisherman's Paradise

Drop a line from the comfort of your snowbird rental. This waterfront retreat is an ideal tropical getaway, where you can ease back and savor sunsets on the canal. Take advantage of your winter away with an indoor heated saltwater pool, a lanai, a gas grill, and a private dock with room for a boat.

Explore our winter condo rentals in Naples

With resort-style amenities like ocean views, pools, and beach access, winter has never looked so good. Revel in a worry-free winter with the ideal blend of comfort and convenience.

Naples snowbird rental FAQ

In many cases, yes. If your reservation is eligible for a discount, you’ll see that reflected in the price when you book. Our long-term reservation sales specialists can also help answer any questions about discounts. Call (888) 257-7970 or email

You don't have to pay all at once. In fact, you’ve got a couple of different options to pay in installments. First, you can make monthly payments (over 3, 6, or 12 months) on most reservations through our partnership with Affirm. It’s easy, too—just select “Pay later with Affirm” when completing your vacation purchase.

If you book at least 45 days before your trip, your other option is to split your trip into just two payments. If the cost of your reservation is between $2,000 and $9,999, 50% is due at the time of booking. If the cost of your reservation is over $10,000, 25% is due at the time of booking. If you choose to make two payments, you must make your second payment 30 days before the start of your trip.

From October to April snowbirds visiting Naples can expect warm, sunny days that are consistent for the winter months.

Naples is known for its year-round mild temperatures, gorgeous beaches along the Gulf of Mexico, and excellent shopping on 5th Avenue South, but the area’s fun doesn’t end there. Relax on a stroll through the Naples Botanical Garden, sightsee local art galleries, cast a line at a local fishing pier, or cross a visit to Everglades National Park off your adventure list.

Book your snowbird getaway in Naples, Florida

You deserve a worry-free vacation. Search for the best home base for your getaway from Vacasa’s thousands of professionally-managed homes, condos, and resort stays. With our Premium Cleaning Program, local management teams, 24/7 customer support, and easy-to-use app, you can sit back and savor the sunshine.

Snowbird vacation inspiration

California licenses
Vacasa Seasonals Inc.
California DRE #02160171

Vacation Palm Springs Real Estate, Inc.
California DRE #01523013

Vacasa offers property management and other real estate services directly through Vacasa LLC and through Vacasa LLC's licensed subsidiaries. Click here for more information about Vacasa's licensed real estate brokerage/property manager in your state. Vacasa’s licensed real estate brokerages/property managers include: Vacasa Alabama LLC; Vacasa Arizona LLC; Vacasa of Arkansas LLC; Vacasa Colorado LLC (Micah Victory); Vacasa Delaware LLC, 302-541-8999; Vacasa Florida LLC; Vacasa Illinois LLC 481.014072, Micah Victory Managing Broker Lic# 471.021837; Vacasa Louisiana LLC, Dana MacCord, Principal Broker, ph 504.252.0155 (Licensed in LA); Vacasa Michigan LLC, 602-330-9934; Vacasa Missouri LLC, Vicki Lyn Brown, Designated Broker; Vacasa Nevada LLC; Vacasa New Hampshire LLC,45 NH-25, Meredith, NH 03253, Susan Scanlon, Broker of Record; Vacasa Minnesota, Broker: Micah Victory, license #40877637; Vacasa New Mexico LLC, 503-345-9399; Vacasa New York LLC, 888-433-0068, Susan Scanlon, Real Estate Broker; Vacasa North Carolina LLC; Vacasa Oregon LLC; Vacasa Pennsylvania LLC; Vacation Palm Springs Real Estate, Inc., California DRE #01523013, Mark Graham, California DRE #00700720; Vacasa Real Estate LLC (licensed in Texas, Debra Brock, Designated Broker); Vacasa Real Estate LLC (licensed in Washington, Robert Brush, Designated Broker); Vacasa Seasonals Inc., California DRE #02160171, Lisa Renee Stevens, California DRE #01485234; Vacasa South Carolina LLC; Vacasa South Dakota LLC; Vacasa Tennessee LLC; Vacasa Vacation Rentals of Hawaii LLC, 69-201 Waikoloa Beach Dr. Ste. #2F17, Waikoloa, HI 96738; Vacasa Vacation Rentals of Montana LLC, Terah M. Young, Licensed Property Manager; Vacasa Virginia LLC; Vacasa Wisconsin LLC; Vacasa Wyoming LLC. In Canada, this advertisement is provided by Vacasa Canada ULC, CPBC lic. number 75826, 172 Asher Rd. V1X 3H6 Kelowna, BC.