All you snowbirds out there, we have the perfect rental for you! We have a wide variety of both short and long term rental options. There are so many people that can benefit from a break to the sun. This is a popular option in the winter for retirees, but they are not the only ones that take advantage of the warmer weather for holidays or even seasons. This has become even more popular with younger generations as remote work has become more prevalent. Whether you are planning Thanksgiving in Florida, Christmas in Florida, or a multi-month getaway, we can guarantee that you’ll find yourself wanting to stay longer.

We have lots of affordable winter rentals in all the top destinations for snowbirds. Below you will find our 16 favorite destinations for snowbird rentals in Florida, as well as a featured property you can actually book on!

Top Winter Snowbird Rentals & Destinations in Florida:


Named by TripAdvisor as the best beach in America for 2018, which is high praise and deserved. Almost a million visitors come here every year to enjoy the award-winning sun, sand, and surf along Clearwater Beach. You’ll never run out of things to do seaside or on land, you simply have to know where to look. But your search, as always, should begin at the ocean. Clearwater currently has the record of 768 consecutive sunny days.

Featured winter rental: Welcome to Paradise!

The Villages

 This is one of the most popular places for retirees. This community is conveniently located near Orlando and is the type of community where you know all your neighbors, and the main mode of transport is a golf cart. Yes, there’s private garbage collection, a bank, TV and radio stations, and so much more — isolated only in this one-of-a-kind neighborhood. They have lots of restaurants, family friendly pools and ones that are adult only for the couples looking to unwind. Parks are everywhere too. Plus fishing, shopping, and so much more. It’s so popular that almost 20 people are moving to the area, daily!

Featured winter rental: Snowbird Haven


With pristine beaches and one of America’s best boardwalks to explore, you’ll find plenty to do and see here. Nestled between Fort Lauderdale and Miami in Broward County, Hollywood is the best of both worlds: sunny days in the sand mixed with adventure attractions. Hollywood’s famous Boardwalk was named one of “America’s Best by Travel + Leisure magazine” and it’s among the first beaches in Florida to be designated as a Blue Wave Beach That means it’s among the nation’s cleanest, safest, and most user-friendly beaches. What are you waiting for? Book now!

Featured winter rental: Oceanside Luxury Home

Key West

Relaxing, laid-back Key West calls to beach bums who prefer their landscape pristine and untouched. Key West has a great nightlife, beautiful beaches, tons of history and great snorkeling. They also have a lot of cool shops and restaurants to check out for some of the freshest seafood around! 

History buffs love the island’s maritime history and legends of its famous residents, while partygoers can’t get enough of Duval Street. Located closer to Cuba than to Miami, Key West offers endless Latin and Cuban cultural influences from the cuisine to the music and art. 

Featured winter rental: Casa de Cuba

Madeira Beach

Madeira Beach is best known for their beach and boardwalk. This is a great place for families. They have lots of shops and places to eat and check out. Fishing is also popular here. In October they host a well-known Seafood Festival that is a lot of fun with food, activities and live entertainment.

Featured winter rental: Collwood Condos

Treasure Island

In the middle of it all, but offering a world of its own. The main draw for Treasure Island tourists is the three mile stretch of untouched sand along the coast. They offer all sorts of water activities like snorkeling, seashell collecting, parasailing and a lot more. To get away from the crowds, try spreading out at Sunset Vista Trailhead Park which has soft sand and amazing beach walking opportunities. Start your shell collection here! Many of the area’s top attractions can be found right on the warm Gulf waters. Parasailing, deep sea fishing, snorkeling, SCUBA, and more are all available for reputable tour companies. Try one, or try them all on your next vacation.

Featured winter rental: Sunsets & Surf Sounds


Upscale, charming Naples serves as a perfect backdrop for a glitzy Florida vacation. This sophisticated beach destination is located right along the Gulf of Mexico, on southern Florida’s “Paradise Coast”. Miles of fine sand beaches, gentle turquoise waters, and friendly locals are synonymous with this area. Shoppers delight in searching for antiques, home furnishings, clothes and jewelry.

With its beautiful neighborhoods and grand architecture, the atmosphere is elegant, yet relaxing. We have hundreds of Naples vacation rentals on our website, so you’ll be able to choose the perfect property for your group. Take a fan boat through the Everglades to experience southern Florida’s amazing ecosystem. Don’t forget to pack your clubs – this city is famous for its incredible golfing.

Featured winter rental: Vanderbilt Bay

Cape Coral

Cape Coral is situated near Fort Myers and right on the Gulf of Mexico, so you won’t have to drive too far for those warm waters. Walk through a nature preserve, treat yourself to find dining, or shop away in the afternoon when the sun gets too hot. They also have great golf courses, water parks, fishing and other watersports.

There’s no bad to visit with average temperatures in the 80s, but this town is dubbed the “Winter Wonderland” since so many northerners come down to visit when the weather turns cool. There’s an average 70 degree daytime in the winter, with little to no precipitation. Contrast that to the summer months where it is hot, humid, and there’s a short thunderstorm almost every day. Outdoorsy travelers love it here as it boasts over 350 sunny days per year!

Featured winter rental: Villa Florida Vacation


Inspired by the city of the same name in Italy, Venice, Florida uses strategic waterways and a breezy gulf coast setting to attract thousands of travelers each year. This town takes the phrase “easy living” to a whole new level. Named one of the “Happiest seaside towns in the USA,” by Coastal Living, this Sarasota County hot spot is known for its sandy beaches, relaxed attitude, and friendly locals.

Originally a tarpon fishing village settled in the 1870s, it was revived after 1960, when it replaced Sarasota as the location for the Ringling Bros and Barnum & Bailey Circus. It offers over 300 sunny days per year, so don’t pack your umbrella. The temperature rarely dips below 70, so a light sweater is all you’ll need — saves room in your suitcase for more bathing suits.

Featured winter rental: Country Club Condo

New Smyrna Beach

Same question, different location. Ever been to Florida’s Central Atlantic Coast? Think white sandy shorelines and charming little beach towns. You’ll find all that and more in New Smyrna. This area is rooted in local culture and that shines through in the cozy downtown area with shops, art museums, and coastal architecture galore.

Your family will enjoy discovering the hidden adventures offered here, like the drivable beach, eco-tourism, and unique history. If you love the outdoors, and you love to surf, you won’t find a better Central Florida locale than New Smyrna Beach. Beyond surfing, the conditions are ideal for kayaking, parasailing, fishing, and more. This hip town attracts thousands of surfers every year. The beach itself is 13 miles long and you’ll never feel “cramped” by other visitors.

Featured winter rental: The Flip Flop Spot

St. Petersburg

The star of the show here is St. Pete Beach. This beach has white soft sand, clear blue water and lots of waves to boogie board. Spend the day laying out under the hot sun and walking for miles down this flawless beach. Keep your eyes peeled for a leaping dolphin! 35 miles of flawless beachfront await you here. They also have a great downtown with lots of shops and restaurants to check out when you need a break from the sun.

Featured winter rental: Waterfront Island Home

Port Charlotte

Found along Florida’s welcoming Gulf Coast, Port Charlotte is perfectly positioned for water activities of all kinds. Traverse more than 165 miles of waterways through Charlotte Harbor and into the Gulf of Mexico while enjoying the views of the natural shoreline. Bring your sunscreen because Port Charlotte is HOT! The good news is it’s surrounded by water, so a cool dip is a short walk or drive away. Better yet, your vacation rental may have a pool included, so you’ll enjoy the privacy of a backyard swim. 

Featured winter rental: Boater’s Paradise

Lake Davenport

The majority of tourists staying in Davenport head to the Orlando area theme parks (only a 30 minute drive away) during the day. The Davenport area also has its fair share of fun things to do, so don’t miss out! Pack your clubs. The town has two large, 18-hole golf courses, the Highlands Reserves Golf Club and Ridgewood Lakes Golf & Country Club.

You’ll find endless outdoor recreation activities in Davenport. There are marshes to fish and ride airboats. Lake Apopka also has over 20,000 acres where visitors can hike, bird watch, and even go horseback riding.

Featured winter rental: Champions Gate Resort

Bonita Springs

There is so much to do in Bonita Springs including beautiful Gulf Coast beaches, kayaking, sand dunes to explore, fishing, golfing and county parks like Little Hickory Island Beach Park and Bonita Beach Park to check out. This is a great place to visit if you are looking for outdoor adventures. The beaches are endless and the wildlife is everywhere.  

Featured winter rental: Modern One Bedroom


Kissimmee is a great alternative to staying in Orlando. You can be near the action, but not right in the middle of it. This area also boasts better rental prices than some other areas. So you get a deal without having to give up everything that a theme park vacation has to offer. This area also offers activities for those who love outdoor exploration, with exotic plants and animals in the local nature preserves.

Featured winter rental: Kissimmee Cottage

Fort Myers Beach

Fort Myers Beach has some of the most amazing beaches with the softest sand. However, that’s only the beginning of the attractions in this family-friendly city. You can sign up for a dolphin eco-tour or fishing charter. Take a tour of nearby islands like Cabbage Key and Cayo Costa. You can even catch an MLB spring training game since both the Boston Red Sox and the Minnesota Twins head here for pre-season practice.

Fort Myers Beach also boasts a small-town charm. Some visitors like to stay in one of the island’s adorable cottages during their visit. Be sure to tour the grand Fort Myers estates where Henry Ford and Thomas Edison used to spend their winters. For another educational opportunity, check out the IMAG History & Science Center where you can check out pythons, salamanders, and other creatures in the Living Lab.

Featured winter rental: Beachfront Elegance


Matt Moretti has worked in the travel and vacation rental industry for over a decade. He loves helping travelers find the best places to eat, the best things to do, and the perfect vacation rental for their trip.