Calling all snowbirds! We have short and long term vacation rentals for long term winter visitors available for stays as short as one night, and as long as a few months. Retirees, couples, families, and many other types of travelers enjoy a snowbird stay in the Sunshine State every year. There are endless lifestyle benefits to spending your winters away from the cold, and in the warm embrace of Florida! 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 thousands of affordable winter rentals in all the top destinations for snowbirds. Below please find our 16 favorite destinations for snowbird rentals in Florida, as well as a featured property you can actually book on!

Top Florida Winter Snowbird Rentals & Destinations

Clearwater, FL

About the city: When someone tells you “Florida beach” you should immediately think of Clearwater. 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. There’s no need to worry about warm weather – Clearwater averages 361 days of sunshine every year (yes, you read that right) and has the record of consecutive sunny days at 768.

Featured winter rental: Welcome to Paradise!

The Villages, FL

About the city: Simply put, The Villages is the largest gated community for seniors in the world. If you’re over 55, this is the place to be. A central location (right near Orlando), all the amenities of a town, and the population of a small city — the perks of this unique area are endless. 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. There are hundreds of restaurants to try, dozens of family pools, and even areas that are off limits for kids because we all want peace and quiet sometimes. 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

Hollywood, FL

About the city: Hollywood Beach, Florida is family-friendly, fun, and fabulous. 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, FL

About the city: Relaxing, laid-back Key West calls to beach bums who prefer their landscape pristine and untouched. Key West is famous for watersports, nightlife, beaches and historic sites. Don’t miss Duval Street, one of the most energetic strips of shops, bars and cafes in Florida. Whether you prefer culture or the outdoors, Key West has plenty to offer in a relaxed, welcoming atmosphere. Surrounded by the Gulf of Mexico, Key West offers visitors ample natural beauty and great swimming beaches.

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. Running four miles long and about two miles wide at its widest, this is a small island. The popular Old Town makes up about half of this area.

Featured winter rental: Casa de Cuba

Madeira Beach, FL

About the city: Madeira Beach, a Gulf of Mexico beach city just west of St. Petersburg, is best known for the sea-themed John’s Pass Village and Boardwalk, which serves up shops and eateries and a 1,100-foot boardwalk perfect for families. Madeira Beach’s 2.5-mile beach is ideal for lovers of fishing and endless sun. Looking to be in the action? Each October, Madeira Beach hosts the Seafood Festival at John’s Pass, which attracts as many as 130,000 visitors to its celebration of food, music, and arts and crafts.

Featured winter rental: Collwood Condos

Treasure Island, FL

About the city: In the middle of it all, but offering a world of its own. Treasure Island has the sandy beaches, family-friendly attractions, and unique restaurants that are usually reserved for the big name Florida locales. Here, you’ll have the privacy and relaxation you crave, plus the endless sunshine promised by a stay on the Gulf Coast.

The main draw for Treasure Island tourists is the three mile stretch of untouched sand along the coast. Go swimming, shelling, sunning, snorkeling, parasailing and more, or simply walk the beach and take in a memorable sunset. 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

Naples, FL

About the city: 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. Snowbirds flock here during the winter as it’s popular among retirees and those looking to escape the harsh northern winters. World class dining and shopping draw wealthy travelers to the area. The turquoise waters of the Gulf of Mexico provide endless entertainment and relaxation, too. Hunt for seashells while you pack together sand for the perfect castle. 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, FL

About the city: Sunny, friendly Cape Coral is a smart choice for those who want a quiet escape away from the hustle and bustle of the major Florida hot spots. Cape Coral is situated nearby Fort Myers and right on the Gulf of Mexico, so you won’t have to drive too far for those warm waters.

Next time you’re looking for fun & sun, skip the traditional beachside hotel and opt for one of our Cape Coral vacation rentals instead. Renowned Gulf Coast beaches, verdant golf courses and family attractions like the popular Sun Splash Family Waterpark make Cape Coral an appealing destination for visitors. With more than 400 miles of canals (more than Venice, Italy), boating, fishing and watersports are favorites among those spending time here. Walk through a nature preserve, treat yourself to find dining, or shop away the afternoon when the sun gets too hot.

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

Venice, FL

About the city: 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 winter headquarters for the Ringling Bros. and Barnum & Bailey Circus. Warm weather characterizes this gulf utopia. It offers over 300 sunny days per year, so don’t pack your umbrella. The temperature averages 90 degrees from June – September, so a summer vacation is ideal for the beach bums out there. Visiting in “shoulder season”, March-April or October-November, will still have you feeling the heat while saving on vacation rentals and other expenses. 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, FL

About the city: 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, FL

About the city: St. Petersburg, which glimmers between the Gulf of Mexico and Tampa Bay, is known for its warm weather and for holding the title of “most consecutive days with sunshine” at 768 days. Along with beautiful, award-winning beaches, St. Petersburg is a waterfront escape and perfect family getaway with so much to explore! Downtown St. Petersburg is the city’s heart, home to great shopping, restaurants, bars and attractions.

The star of the show here is St. Pete Beach. Like many Florida beaches it comes complete with sugar white sand, abundant sunshine, crashing waves, and turquoise blue Gulf waters. 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. And if that isn’t enough, next-door Clearwater Beach is a showcase of two and a half miles of more gorgeous white sand and clear waters, with a new, gently curving BeachWalk, making strolling (and rolling) a pleasure for all.

Featured winter rental: Waterfront Island Home

Port Charlotte, FL

About the city: 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 natural shoreline. It’s no surprise Port Charlotte was named to Forbes’ list of “25 Best Places to Retire in 2015”, listed among the ten best places in the United States to retire for the year 2012 by U.S. News & World Report, and was ranked at #1 in’s 2009 list of 25 Best Places to Retire.

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, FL

About the city: The majority of tourists staying in Davenport head to the Orlando area theme parks (only a 30 minute drive away) during the day. Famous attractions like Walt Disney World, Universal Studios, and SeaWorld draw millions of visitors every year. 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. To the south east, Lake Tohopekaliga offers freshwater fishing and airboat cruises along the marshes. To the north of Davenport, Lake Apopka has over 20,000 acres where visitors can hike, bird watch, and even go horseback riding.

Featured winter rental: Champions Gate Resort

Bonita Springs, FL

About the city: Sunny, friendly Bonita Springs is a smart choice for those who want a quiet escape away from the hustle and bustle of the major Florida hot spots. Bonita Springs is situated between Fort Myers and Naples, so you won’t have to drive too far for baseball and beaches.

The activities and attractions are endless in Bonita Springs, both in and out of the water. Dip your toes in the Gulf of Mexico from the soft sands of Bonita Beach Park. Don’t forget to bring your rod and reel and enjoy the top fishing.

If you’re looking for something a little off the beaten bath, head to Barefoot Beach Preserve County Park, which includes over 300 acres of undeveloped land on a barrier island. Here you can enjoy strolls on the soft sand dunes, educational walks along the preserve, and sea turtle spotting.

Featured winter rental: Modern One Bedroom

Kissimmee, FL

About the city: A short drive south of Orlando finds you in sunny, friendly Kissimmee. Here you’ll be near all the theme parks, but you’ll be away from the bustling crowds. Rentals will cost less than a stay in Orlando, so you’ll have extra cash to spend on park tickets and meals. 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, FL

About the city: Like many other Gulf Coast destinations, Fort Myers Beach features gorgeous beaches with soft sugary 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 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. The Mound House on Fort Myers Beach offers another peek into history with connections to the Calusa Indians who once lived there. 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

We are the #1 Florida vacation rental website. Our mission is to help travelers find and book the perfect rental for their next visit to Florida. Whether it is a week’s trip with your children, a romantic long weekend with your spouse, or a reunion on the beach with a large group of friends - we have Florida vacation rentals to suit every need.

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