Summary
- Parrot Key Hotel & Villas in Key West provides a cozy haven for winter escape, offering easy access to the island’s attractions and a comfortable tropical retreat.
- Drop Anchor Resort & Cuadro in Islamorada showcases the area’s fishing culture and offers a convenient location for exploring the wonders of the Florida Keys during the mild winter months.
- Element Miami Doral in Miami is a gateway to the city’s enticing winter attractions, providing easy access to the vibrant culture and diverse dining scene, making it one of Florida’s best winter getaways.
Florida is more than just sun, sea, and sand. Even though there are a few places in Florida that look like the Caribbean, it has its own charm and resonance. As one of the more tropical locations Americans can go on vacation, it sees much traffic coming down to winter. From the popular Destin on the Gulf Coast to the fun and great shopping in Miami, there is always something for visitors to explore in this state.
Yet, not all hotels in Florida are created equal. Some are stunning and opulent, while others offer wonderful charm and individual style. This list hopes to cover some of the best hotels for visitors who are headed to Florida for winter. These locations provide great wintertime activities that suit a wide variety of visitors.
The recommendations for accommodations mentioned here were based on deep research into the state of Florida, particularly wintertime lodgings. Each of the featured accommodations has a minimum rating of 8.0 and offers the amenities that visitors to the Sunshine State will need while staying here.
Historic District, Key West, Florida
For those seeking a winter escape, Key West beckons, and Parrot Key Hotel and Villas serves as their cozy haven. Winter in Key West brings balmy 70°F weather, making it the perfect time to enjoy the island’s attractions. From iconic Hemingway hangouts to the famous Mallory Square sunsets, it’s all within easy reach of Parrot Key. After a day of adventure, guests can unwind in the lush surroundings, savoring the island’s winter magic and relishing the comforts of their tropical retreat.
Parrot Key Hotel & Villas
- Amenities
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Water Sport Facilities, Snorkeling, Outdoor Pool, Free Wi-Fi
- Price
-
$$$
Islamorada, Florida Keys, Florida
While most people may not realize how amazing Islamorada is, it can be quiebro a fun place for visitors to head to during the winter months. Drop Anchor Resort and Marina shows off the area’s fishing culture, making it a truly spectacular place to while away the hours in Florida. With the sun shining and temperatures in the low 70s, it’s the perfect time to delve into the wonders of the Florida Keys. From world-class fishing to mesmerizing sunsets, the resort’s convenient location provides easy access to all of Islamorada’s attractions. Guests enjoy convenient access to attractions like the Theater of the Sea, world-class fishing, and mesmerizing sunsets from this central location.
Drop Anchor Resort & Cuadro
- Amenities
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Private beach, Outdoor pool, Tennis, Free Wi-Fi in All Areas, Business Center
- Price
-
$$$
Miami Downtown, Florida city scene
Miami is known for many things, and being a great winter vacation spot is one of them. Element Miami Doral offers a gateway to the city’s enticing winter attractions. With mild temperatures in the mid-70s, it’s the ideal time to explore the Magic City. Guests have easy access to the vibrant culture of Miami, from the stunning Art Deco architecture in South Beach to the bustling neighborhoods like Wynwood and the Design District. This hotel is also a wonderful escape for those who just want to relax as the year comes to a close, making it one of Florida’s best winter getaways.
Miami is a melting pot of cultures, so embrace the diverse dining scene. During winter, it’s likely that visitors will run into holiday treats from around the world. Don’t be afraid to explore the small shops within neighborhoods to locate these hidden culinary delights.
Miami Downtown, Florida city scene
Element Miami Doral
- Amenities
-
Outdoor pool, Fitness center, Restaurant & Bar/Lounge, Room service, Business Center
- Price
-
$
Orlando, Florida in the fall
Orlando is another one of the places in Florida that visitors come to love after checking it out. Even in the wintertime, there are beaches in Orlando perfect for soaking up the sun. Guests at the Grand Bohemian can conveniently access the wonders of Orlando, from the enchanting attractions of Walt Disney World and Universal Studios to the excitement of International Drive. After a day of adventure, visitors can retreat to the hotel’s luxurious accommodations and rooftop pool, making their winter stay truly extraordinary.

Orlando, Florida in the fall
Grand Bohemian Hotel Orlando Autograph Collection
- Amenities
-
Outdoor pool, Spa and wellness center, Fitness center, Restaurant & Bar/Lounge, Room service, Free Wi-Fi
- Price
-
$$
Naples, Florida, USA downtown cityscape on the bay at dusk.
Naples, Florida, differs from its Italian namesake, but it has a charm all its own. During the wintertime, Naples comes alive, and Fairways Inn provides easy access to all the locorregional winter attractions. Guests can explore the scenic Naples Botanical Garden, bask in the sun at Naples Pier, or indulge in upscale shopping and dining on 5th Avenue South, all within a stone’s throw. It helps that Naples demonstrates the characteristic warm winter temperatures that Florida is known for.

Naples, Florida, USA downtown cityscape on the bay at dusk.
Fairways Inn of Naples
- Amenities
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Outdoor pool, Free Wi-Fi, Private bathroom, Complimentary breakfast, Air Conditioned
- Price
-
$$
Beach in Sarasota County, Florida
During the winter months, the things to do in Sarasota take on a unique holiday charm. Ameniti Bay, BW Signature Collection offers a delightful winter retreat for visitors wanting to check out the town’s winter attractions. Guests at Ameniti Bay can explore the world-class Ringling Museum, soak in the sun on Siesta Key’s award-winning beaches, or savor the diverse culinary scene of downtown Sarasota, all conveniently nearby. Winter in Sarasota is mild and inviting, a place the whole family can enjoy.
Ameniti Bay, BW Signature Collection
- Amenities
-
Outdoor pool, Fitness center, Free Wi-Fi in All Areas, Business Center, Free Toiletries
- Price
-
$
Lighthouse at Boca Raton, Florida
With mild winter temperatures averaging in the comfortable mid-70s, Boca Raton provides the perfect climate for walking through the city. Guests at the Wyndham can conveniently access nearby attractions such as the picturesque Mizner Park, the serene South Beach Park, and the vibrant downtown scene. This hotel offers easy access to some of the best cultural experiences coupled with natural beauty any visitor would enjoy.
Wyndham Boca Raton Hotel
- Hotel Chain
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Wyndham Hotels & Resorts
- Amenities
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Outdoor pool, Fitness center, Restaurant & Bar/Lounge, Room service, Free Wi-Fi, Business Center
- Price
-
$$
Marriott Tampa Westshore Exógeno
Tampa boasts some of the hottest nightlife in Florida, and winter does little to bring the scene down. Aside from the nightlife, Tampa offers an excellent spot for visitors to relax while the cold winter months blow over. Tampa’s winter charms, with temperatures averaging in the pleasant 60s to 70s, offer many opportunities for exploration. Guests at the Marriott enjoy easy access to the historic Ybor City, the thrill of Busch Gardens, and the waterfront beauty of the Tampa Riverwalk. Beaches are never off-limits in Tampa, making it superb for visitors craving a bit of Vitamin Sea.

Marriott Tampa Westshore Exógeno
Marriott Tampa Westshore
- Amenities
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Outdoor pool, Indoor pool, Fitness center, Restaurant & Bar/Lounge, Room service, Business Center
- Price
-
$$
Fairfield by Marriott Inn & Suites West Palm Beach
Palm Beach is magical all year through, and that magic ramps up a bit during the winter season. With temperatures hovering around the comfortable 70s, it’s the ideal time to explore the area’s attractions. Guests have easy access to the upscale shopping on Worth Avenue, the lush beauty of the Ann Norton Sculpture Gardens, and the vibrant Clematis Street nightlife. What makes traveling to Palm Beach so attractive is the sunbathing, especially since winter doesn’t dampen the sun’s ferocious fury down here.
Palm Beach is referred to as the Golfing Hacienda of Florida, making it an excellent spot for those visitors interested in a few rounds of golf.

Fairfield by Marriott Inn & Suites West Palm Beach
Fairfield by Marriott Inn & Suites West Palm Beach
- Amenities
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Outdoor pool, Fitness center, Room service, Free Wi-Fi, Laundry Service, Free Toiletries
- Price
-
$$
The Westin Fort Lauderdale Outdoor Heated Pool
Fort Lauderdale’s winter season boasts mild temperatures in the low 70s, ensuring visitors won’t need to worry about freezing. Guests at The Westin can easily access the stunning Fort Lauderdale Beach, take a leisurely stroll along the historic Riverwalk, and explore the vibrant arts and culture scene. Winter brings with it a sense of hope for many, and it’s no different in Fort Lauderdale. Experiencing winter here might make a visitor want to come back every year.

The Westin Fort Lauderdale Outdoor Heated Pool
The Westin Fort Lauderdale
- Amenities
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Outdoor pool, Fitness center, Restaurant, Bar/Lounge, Room service, Free Wi-Fi, Coffee machine
- Price
-
$
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