The best Florida winter rentals for 2024

Florida winter rentals

Within Sunshine State, you will find some super destinations for making the most of the Florida winter. From December through to March, the winters here remain mild and dry. With the humidity and rainfall of summer a distant memory, snowbirds will be able to soak up pleasant average highs of 74 F (23°c) down in the Florida Keys and 73 F (22°c) in Orlando. 

The cooler temperatures make this an ideal time for sightseeing trips and outdoor adventure. If you’re seeking inspiration, here are the top 5 Florida winter rental destinations for enjoying a classic vacation.

When looking to soak up the perfect winter sun break, our luxury Florida winter rentals promise to please all seasoned snowbirds. From beachfront homes on the Emerald Coast to waterway retreats and luxurious resort villas close to the golf courses and world-class attractions of Orlando, our vacation homes promise to elevate your Sunshine State getaway in every way.

#1 Cape Coral vacation rentals

One of the most popular destinations for Florida winter rentals is in Cape Coral.

Cape Coral is one of the top choices for a Florida winter vacation. With over 400 miles of canals to explore by boat, Cape Coral offers a laid-back lifestyle perfect for leisurely breaks. There’s also plenty of things to do in Cape Coral. Savor the many local bars, restaurants and farmers market, or enjoy a spot of fishing from the pier. You can also dip into the popular public river beach at the Yacht Club Community Park or one of the nearby island beaches. What’s more, Cape Coral offers the opportunity to dive into one of the many award-winning Gulf beaches (reachable by car in 45 minutes).

Into the Great Outdoors? The milder winter climes here make it the perfect time for hiking, kayaking and venturing out to the nearby nature attractions of Lovers Key State Park, Sanibel Island and Captiva Island.

When looking to stay, our Cape Coral vacation rentals offer scenic locations along the tranquil waterways. Moor up your boat and dive right into your own private pool or spillover tub. Take in the sunsets and enjoy quality time with your family and friends. For dog-friendly groups, we also offer a great range of pet-friendly rentals in Cape Coral.

Cape Coral 138 

  • 4 bedrooms — Sleeps 6 — Private infinity pool — Jacuzzi — Private boat dock & lift

With a prime waterside location perfect for boating enthusiasts, Cape Coral 138 sets the scene for an exclusive winter vacation. Kick back with an alfresco drink on the sunny terrace or under the shade of the tiki hut, before you dip into the luxurious pool or head out on the waterways. Off the water, this beautiful villa sets the scene for all-weather get togethers with family and friends. Entertain away in the huge open concept living space and enjoy the sumptuous home comfort of the inviting bedroom suites.

Cape Coral 421 

  • 4 bedrooms — Sleeps 6 — Private pool — Private boat dock & lift — Incredible waterfront setting

For swanky winter vacations in Florida, Cape Coral 421 won’t disappoint. From the minute you moor up your boat to the moment you savor a scenic alfresco meal by the poolside, this impeccable villa will impress. The contemporary decor is complemented by huge picture windows which invite the waterside lifestyle in. Within the chic open concept living space and the boutique bedroom suites, you can’t help but enjoy the ultimate Florida vacation.

#2 Orlando vacation rentals

Orlando is one of the best places to enjoy Florida in winter!

For big kid fun without the crowds, Orlando in the winter is a super time to enjoy 10 world-class theme parks. With incredible Halloween, Thanksgiving and Christmas celebrations in full swing, Disney World and the neighbouring parks offer a truly magical experience in the cooler season — with fireworks, parades, themed events and festivals.

For something extra special, the much-anticipated New Year’s celebrations here are also not to be missed, whilst those flocking to Orlando in February will enjoy the fun Mardi Gras at Universal Studios. Theme parks aside, there are some more great reasons to visit Orlando in winter.

Explore downtown Orlando and savor the amazing entertainment and dining scene of the City Beautiful. Tee-off on one of Orlando’s 24 golf courses and make the most of the top golf resorts, with one of our exclusive golf packages.

Our Orlando vacation rentals offer exclusive locations in luxury resorts. Access the world-class resort activities and amenities, including on-site water parks and signature golf courses. From condos and townhomes to villas and mega mansions, our vast collection offers something for everyone — be it couples and families to pet-friendly groups and multigenerational stays. Choose from themed kids bedrooms and private pools to bowling alleys and game rooms!

Encore Resort 934 

  • 8 bedrooms — Sleeps 16 — Private home theater — Game room — Themed kids rooms — Private pool

Multigenerational families will fall for Encore Resort 934. Located just 10 minutes’ drive from Disney, this 8-bedroom villa offers a carefree base for all seasons. Unwind within the inviting living space or let off steam in the game room and family pool. Kids will love their themed bedrooms, whilst adults enjoy their boutique bedroom suites. If the weather turns then relax with a favorite movie in your private home theater. Don’t forget the popcorn!

Reunion Resort 10000 

  • 9 bedrooms — Sleeps 22 — Private home theater — Game room with bowling alley — Pool — Home spa

When nothing but the best will do, Reunion Resort 10000 promises the ultimate, year-round Orlando vacation. Decked out with all the dream family amenities, this 15,500 sq ft mansion invites you to kick back and enjoy every corner of this palatial home. From its grand entrance hall and home theater to its indoor basketball courts and amazing game room complete with bowling alley, this villa promises the wow factor. Those looking to unwind can soak away their cares in the private outdoor pool with spillover tub or in the villa’s very own home spa. With so many more great features, this villa promises a truly lavish Florida stay.

#3 Resorts in Florida Keys

Islamorada on the Florida Keys makes for a great winter vacation spot.

For the very best Florida sunshine, head south to the Florida Keys. Famed for its pearly white beaches, seafood, boating, scuba diving and sport fishing, this tropical destination can’t fail to impress in winter. Soak up the scenic drive from Miami and explore the chain of 42 islands which end with Key West in the south. When it comes to Florida Key resorts, Islamorada is a winter vacationer’s dream.

With crystal clear waters and spellbinding beaches, this chain of 5 islands will feel a million miles away from the deep freeze. In fact it’s so pleasant that the peak season here is from December through May! There’s plenty to see and do in Islamorada. Dip into the public beaches such as Anne’s Beach or the less crowded Library Beach. For those who enjoy getting out on the water, take up sailing, kayaking, parasailing, kite sailing, windsurfing or paddleboarding. Remember there’s also the tropical sport fishing to enjoy.

For those looking to switch off and enjoy some privacy, our exclusive Islamorada resort homes offer the perfect fit. Choose from romantic ocean view condos to accessible waterfront villas. All homes enjoy access to the resort’s amenities, its pools and private beach — for a welcome slice of paradise.

Islamorada Premium Villa 1 – Ocean Views 

  • 4 bedrooms — Sleeps 8 — Waterfront villa — 2 ocean view balconies — Pet-friendly — Resort amenities
Ocean views check, at this stylish 3-storey resort home in Islamorada.

Perfect for grown-up getaways, this scenic 3-storey waterfront villa invites you to unwind with a sundowner or two. The 3 king-size bedroom suites are perfect for couples traveling together. Equipped with a kitchen, open concept living area and 3 ocean view lounge areas, the scene is set for an effortless stay. The luxury resort features a marina, private beach, pools, spa services, a waterfront bar and fitness activities. You’ll also find complimentary water sports equipment.

Islamorada Waterfront Suite 2 – Wheelchair Accessible 

  • 1 bedroom — Sleeps 2 — Wheelchair Accessible — Ocean view balcony — Pet-friendly — Resort amenities
Florida in winter isn't so bad when you're soaking up the sun in Islamorada!

Couples will relish this beautiful 1-bedroom waterfront suite, complete with wheelchair accessible layout and stylish living space. Soak up the ocean views from the private balcony and head out into the luxury resort. Enjoy the resort pools and beach or take to the water kayaking or paddleboarding. The oceanfront bar isn’t a bad place to be either! The beautiful suite also includes daily housekeeping and access to VIP extras to enhance your vacation, such as luxury spa treatments.

#4 Siesta Key rentals

Siesta Key offers plenty of escapism for those looking to evade the cooler winter climate.

Home to some of the best beaches in America, Siesta Key offers a winter paradise for those hoping to avoid the snow. With miles of pearly white sand for company, this popular Florida destination promises a timeless spot of escapism.

From endles beach days and afternoons of golf to shopping sprees at Siesta Key Village and taking in the night lights at the Selby Botanical Gardens, Siesta Key offers the chance to kick back and enjoy the simple pleasures in life.

Of course when looking where to stay, opt for a luxury villa and really make the most of your Winter Sun getaway. Our exclusive Siesta Key vacation homes provide the perfect sanctuary after a day by the ocean or sightseeing. With private pools and stylish boutique interiors, each home offers a beautiful and bespoke vacation experience.

Siesta Key 1 

  • 4 bedrooms — Oceanfront — Elevator — Roof top deck — Heated pool and spa — Man-made beach

Soak up a prime oceanfront setting overlooking the Gulf of Mexico! Effortlessly stylish and ready for full vacation mode, Siesta Key 1 sets the scene for a fun group getaway. Inside, the contemporary vacation home is equipped with luxury mod cons, including an elevator to all floors. Enjoy the private heated pool and spa, which is accompanied by a sunny lawn and man made beach. Located in a private gated community, guests will enjoy reaching all the must-have amenities of Siesta Key Village with ease.

Siesta Key 2

  • 8 bedrooms — Sleeps 18 — Ocean views — A/C Elevator — Balcony — Private pool — Spillover tub

This chic, coastal 8-bedroom retreat places guests a short walk from Siesta Beach and an easy stroll/bike ride away from Siesta Key Village. Inside Siesta Key 2, the stunning decor is complemented by elevator access to all floors and 2 levels of balconies. Each one affords views of the Gulf and Siesta Beach. Outside, the immaculate vacation rental enjoys extensive outdoor lounge space, perfect for alfresco dining and relaxation. A custom heated pool offers the main attraction, alongside a 6-8 person spa.

#5 Fort Myers vacation homes

Fort Myers is a great vacation spot for snowbirds seeking winter sun!

Fort Myers is perfect for enjoying a laid-back vacation where you can dip in and sightsee. Soak up the mild temperatures and mellow winter sun-drenched beaches, or check out the local cultural sites and art festivals. Visit the ancient structure of Mound House on Estero Bay and explore the fascinating history of the Calusa Indians. You can also enjoy wildlife walks and kayak tours. Nature fans will love exploring the 5 miles of hiking trails which meander through Lovers Key State Park. Pack a picnic and enjoy a classic day here, collecting pretty seashells and boating.

Dive into the local maritime life with a trip to the Ostego Bay Foundation Marine Science Center or with a spot of fishing along the pier. The Fort Myers Beach also offers a great spot for relaxing by the ocean and dolphin spotting.

Those looking to stay and soak up the winter sun with family and friends, should treat themselves to a Fort Myers vacation home. Offering more space, privacy and luxury than a hotel room, check-in to your home-away-from-home today.

Fort Myers 5 

  • 4 bedrooms — Waterfront location — Private covered pool — Spillover tub — BBQ — Private boat dock

Located in the prestigious gated community of Old Pelican Bay, Fort Myers 5 offers a scenic waterfront vacation base overlooking a mangrove nature preserve. Available for monthly rentals, this beautiful home offers every excuse snowbirds need to banish those winter blues. Inside, the comfortable family home offers plenty of space for year-round entertaining. Guests can enjoy relaxing and entertaining on the covered poolside terrace and 2nd floor balcony, before dipping into the private pool and spillover tub. The boat dock will also be a dream come true for keen boaters hoping to explore the Intracoastal Waterway.

Book with Top Villas

When staying in Florida, you’re guaranteed a first-class service with Top Villas. Our exclusive condos and luxury villas with pools all promise a luxury vacation. You’ll find our Guest Experience team also on hand to help enhance your stay, with a plethora of amazing Concierge services

Come and stay and discover why Florida in winter is heard to beat!

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