12 Best Winter Vacation Destinations in Florida for Sun-Soaked Coastal Escapes

Winter changes the way Florida feels. The humidity drops, skies turn clearer, and the state settles into its most comfortable rhythm, warm days, cooler evenings, and the kind of weather that makes outdoor time effortless. It’s also the season when Florida becomes the easiest place in the country to escape to, especially for travelers looking to trade cold mornings for beach walks, pool days, and long dinners outside.

While summer is built for slow coastal routines, winter is when Florida feels most versatile. You can explore cities without overheating, spend full days on the water without storms cutting plans short, and enjoy the shoreline without the heavy heat that defines the warmer months.

This guide highlights the best winter vacation destinations and luxury vacation rentals  in Florida, focusing on places that shine between December and February. These are destinations where winter feels like the main event, where coastal living becomes effortless, island escapes feel calmer, and luxury vacation rentals give you a grounded place to settle in.

1. Miami

Miami in winter is Florida at its most iconic. The weather is warm without being oppressive, the city feels alive, and outdoor living becomes part of daily life again. From beach mornings to late-night dining, winter is when Miami’s energy feels easiest to enjoy.

It’s also one of the best winter vacation destinations in Florida for travelers who want a mix of coastal relaxation and culture. You can spend the day in the sun and still have a full city itinerary by night.

Things to do in Miami in winter

• Walk South Pointe Park and spend the afternoon on the beach

• Explore Wynwood murals and stop at galleries and cafés

• Book a boat day on Biscayne Bay for skyline views and ocean air

Travel tips for visiting Miami in winter

• January and February bring the most consistent weather

• Plan reservations early for popular restaurants and events

• Pack light layers, evenings can feel cooler near the water

Where to stay near Miami in winter

Wander Miami Waterfront – 10 guests, 5 bedrooms

Wander Miami Waterfront is a serene winter retreat that offers a calmer side of the city. With sweeping lake views, an expansive garden, and outdoor spaces designed for lingering, it’s ideal for travelers who want privacy without losing access to Miami’s energy. 

The pool and hot tub create an easy day-to-night rhythm, while the fire pit makes evenings feel relaxed and grounded. It’s a beautiful home base for a winter escape that blends nature, comfort, and modern luxury.

2. Fort Lauderdale

Fort Lauderdale is built around the water, and winter is when that lifestyle feels most effortless. The canals and Intracoastal Waterway become the center of the experience, with comfortable weather for boating, walking, and outdoor dining without summer humidity.

It’s one of the best Florida vacation spots in winter for travelers who want coastal calm but still enjoy city convenience, with beaches, marinas, and nightlife all close by.

Things to do in Fort Lauderdale in winter

• Take a water taxi ride through the canals and waterfront neighborhoods

• Spend the afternoon at Hugh Taylor Birch State Park

• Walk Las Olas Boulevard and enjoy outdoor dining in cooler evenings

Travel tips for visiting Fort Lauderdale in winter

• Winter weekends are popular, book activities in advance

• Mornings are ideal for boating before afternoon breezes pick up

• Plan for sunshine but bring layers for cooler evenings

Where to stay near Fort Lauderdale in winter

Wander Fort Lauderdale Intracoastal – 8 guests, 4 bedrooms 

Wander Fort Lauderdale Intracoastal offers a polished canal-front escape that feels perfectly suited to winter travel. With a private boat dock, outdoor pool, hot tub, and an elegant patio built for al fresco meals, the home encourages slow days that revolve around the water. Inside, the chef’s kitchen and wine cooler support relaxed evenings at home, while the modern fireplace adds warmth to cooler nights. It’s a refined base for travelers who want luxury living with front-row access to Fort Lauderdale’s waterfront lifestyle.

3. West Palm Beach

West Palm Beach feels refined in winter, bright, warm, and effortlessly livable. It’s a destination where mornings can start with beach time, afternoons can shift into shopping or cultural stops, and evenings naturally turn into outdoor dining without needing to plan around heat.

Winter brings West Palm Beach to life in a way that feels elegant rather than overwhelming, making it ideal for travelers who want calm luxury with a city edge.

Things to do in West Palm Beach in winter

• Walk the Palm Beach Lake Trail for waterfront views and breezy mornings

• Explore Clematis Street and the downtown waterfront

• Spend the afternoon at Mounts Botanical Garden or local art spaces

Travel tips for visiting West Palm Beach in winter

• December and January are peak months, plan early

• Outdoor dining is best in the evenings when temperatures soften

• Consider exploring nearby Palm Beach neighborhoods for a quieter pace

Where to stay near West Palm Beach in winter

Wander Palm Beach Horizon – 6 guests, 3 bedrooms

Wander Palm Beach Horizon is a modern sanctuary designed for winter stays that feel elevated but relaxed. Set in Flamingo Park, it blends smart-home features, designer interiors, and a chef’s kitchen with a resort-style outdoor setup. A heated saltwater pool, outdoor kitchen, and light-up putting green make it easy to stay outside all day, while lush landscaping adds privacy and calm. It’s ideal for families or groups looking for a sophisticated West Palm base that balances comfort, style, and connection.

4. Hollywood

Hollywood in winter offers the best of South Florida without Miami’s constant intensity. It’s coastal, walkable, and vibrant, with warm weather that supports beach days and evenings that still feel social.

The waterfront setting gives Hollywood a slower pace than nearby cities, making it one of the best winter vacation destinations in Florida for travelers who want beach access and comfort with a touch of nightlife nearby.

Things to do in Hollywood in winter

• Walk the Hollywood Beach Broadwalk for ocean views and casual cafés

• Book a boat day from the marina and explore nearby waterways

• Spend an afternoon dining outdoors near the beach

Travel tips for visiting Hollywood in winter

• Winter is popular, book early for the best availability

• Morning beach walks are ideal before crowds arrive

• You’ll want light layers for evenings near the water

Where to stay near Hollywood in winter

Wander Hollywood Beach Villa – 12 guests, 5 bedrooms

Wander Hollywood Beach Villa is a waterfront escape built for effortless winter living. Located in the exclusive South Lake neighborhood, it offers direct ocean access and stunning water views framed by floor-to-ceiling windows. The interior is designed with high-end finishes and a chef’s kitchen, while private balconies invite slow mornings with coffee and quiet evenings under the stars. With a pool and seamless indoor-outdoor flow, it’s a refined base for travelers who want Hollywood’s coastal energy with true luxury comfort.

5. Wilton Manors

Wilton Manors is one of South Florida’s most vibrant and welcoming destinations, and winter is when it feels especially comfortable. The weather supports outdoor dining and neighborhood exploring, while the area’s canal-lined setting keeps the pace relaxed.

It’s a great choice for travelers who want something social but not tourist-heavy, close enough to Fort Lauderdale’s beaches, but with its own personality.

Things to do in Wilton Manors in winter

• Explore Wilton Drive for dining, bars, and local nightlife

• Take a paddleboard or kayak day through the canals

• Spend the afternoon relaxing at nearby Fort Lauderdale Beach

Travel tips for visiting Wilton Manors in winter

• Winter evenings can be cooler than expected, pack a light jacket

• Plan early if you’re visiting around holiday weeks

• Staying on the water makes the winter experience feel especially elevated

Where to stay near Wilton Manors in winter

Wander Wilton Manors – 4 guests, 2 bedrooms

Wander Wilton Manors is a luxury waterfront retreat that feels built for winter escape mode. With a private pool, hot tub, and boat dock, it offers a relaxed, outdoor-first lifestyle without sacrificing sophistication. The addition of a baby grand Steinway piano gives the home a unique sense of character, while paddleboards and pedal kayaks make it easy to spend winter days on the water. It’s an ideal stay for travelers who want privacy, comfort, and a refined South Florida atmosphere.

6. Islamorada

Islamorada in winter feels like a dream version of the Florida Keys. The weather is warm and steady, the ocean is clear, and outdoor living becomes the default. Winter is also when the Keys feel most accessible, less storm risk, calmer seas, and the kind of light that makes everything feel more vivid.

For travelers wondering where to travel to in Florida during winter, Islamorada is one of the most reliable answers.

Things to do in Islamorada in winter

• Book a snorkeling trip or boat charter to explore the Keys by water

• Visit Anne’s Beach for a calm shoreline escape

• Enjoy fresh seafood dining with sunset views over the ocean

Travel tips for visiting Islamorada in winter

• Book early, winter is peak Keys season

• Mornings are best for boating and water activities

• Bring layers for evenings, especially if you’ll be on the water

Where to stay near Islamorada in winter

Wander Islamorada Beach – 12 guests, 6 bedrooms

Wander Islamorada Beach is a rare oceanfront retreat set in a private cove with a natural beach, an ideal winter escape for travelers who want both luxury and authenticity. With multiple living spaces, a beachfront terrace, and a third-story oceanfront deck, the home is designed around views and outdoor time. A private pool, fire pit, kayaks, paddleboards, and shuffleboard court create an effortless mix of relaxation and activity. It’s a standout winter stay for groups who want the Keys at their most serene.

7. Marathon

Marathon offers a more laid-back Keys experience, with the same winter sunshine but a calmer, less polished vibe than some of the Upper Keys. It’s ideal for travelers who want beach access, ocean views, and a slower pace without losing that unmistakable Keys atmosphere.

Winter is the perfect time to visit Marathon, warm days, low humidity, and easy outdoor living.

Things to do in Marathon in winter

• Spend the day on the beach and enjoy the Keys’ calmer winter waters

• Visit local marinas and book a fishing charter

• Take a drive across the Overseas Highway for scenic stops

Travel tips for visiting Marathon in winter

• Winter sunsets arrive early, plan evening beach time accordingly

• Book boat activities ahead, especially in January and February

• Consider renting a car for exploring nearby Keys islands

Where to stay near Marathon in winter

Wander Marathon Haven – 8 guests, 4 bedrooms

Wander Marathon Haven is a beachfront retreat that captures everything winter in the Keys should feel like. With direct access to a private stretch of sand, a pool and hot tub, and a spacious balcony with panoramic ocean views, the home is designed for days that start slowly and end outside. It’s ideal for travelers who want to wake up to the water, spend full afternoons in the sun, and settle into an easy coastal rhythm without ever needing to leave the property.

8. Sanibel

Sanibel in winter feels timeless. The beaches are calm, the air is comfortable, and the island’s nature-forward atmosphere becomes easier to enjoy without summer heat. It’s one of the best winter vacation destinations in Florida for travelers who want an escape that feels restorative rather than busy.

Winter is also prime season for long walks, shelling, and outdoor dining with fewer compromises.

Things to do in Sanibel in winter

• Go shelling early in the morning when tides are lower

• Explore J.N. “Ding” Darling National Wildlife Refuge

• Rent bikes and ride the island’s quiet, scenic paths

Travel tips for visiting Sanibel in winter

• Winter demand is high, book early

• Pack layers for cooler evenings near the Gulf

• Plan a few slow days; Sanibel is best enjoyed unhurried

Where to stay near Sanibel in winter

Wander Sanibel Views – 6 guests, 3 bedrooms

Wander Sanibel Views is a newly renovated beachfront condo designed for executive-level comfort and luxury. With one of the largest floor plans in Gulfside Place, the home blends designer furnishings and high-end appliances with direct access to the sand from a walk-out patio. The community itself elevates the stay, offering two Olympic-sized pools, tennis courts, saunas, and a robust fitness center. It’s an ideal winter base for travelers who want refined island living with resort-style amenities.

9. Captiva

Captiva in winter feels like a private island dream, warm days, quieter beaches, and sunsets that become the highlight of every evening. The pace is slow, the atmosphere is exclusive, and the natural setting makes it easy to disconnect from everything else.

If you’re looking for a luxury winter escape that feels peaceful and immersive, Captiva is one of Florida’s best.

Things to do in Captiva in winter

• Watch sunset from the beach, Captiva’s western views are unforgettable

• Spend the day shelling along the shoreline

• Take a boat trip around nearby islands for wildlife and water views

Travel tips for visiting Captiva in winter

• Plan ahead for dining and supplies, island life is slower and more limited

• Pack light layers for evenings

• Winter is peak season here, so booking early matters

Where to stay near Captiva in winter

Wander Casa Captiva – 12 guests, 5 bedrooms

Wander Casa Captiva is a sophisticated coastal sanctuary built for winter relaxation. With a sparkling pool, hot tub, and direct beach access, the home makes it easy to spend days in the sun and evenings unwinding in total comfort. The setting feels private and refined, ideal for travelers who want Captiva’s calm atmosphere with the elevated experience of a luxury retreat. It’s a perfect winter stay for groups or families who want island living at its most effortless.

10. Marco Island

Marco Island is polished, peaceful, and designed for winter travel. The beaches are wide, the Gulf water stays inviting, and the island’s calm luxury vibe makes it ideal for travelers who want comfort without constant activity.

Winter is also a great season for boating and wildlife excursions here, warm enough to stay outside all day, without summer humidity.

Things to do in Marco Island in winter

• Take a wildlife cruise through the Ten Thousand Islands

• Walk Tigertail Beach for shelling and long shoreline views

• Enjoy waterfront dining and sunset views along the coast

Travel tips for visiting Marco Island in winter

• Mornings are ideal for boat trips and outdoor excursions

• Book activities ahead, winter is a popular season here

• Evenings can be cooler than expected near the water

Where to stay near Marco Island in winter

Wander Marco Lagoon – 8 guests, 4 bedrooms

Wander Marco Lagoon is a luxury waterfront retreat that feels designed for winter calm. With ocean views, a private pool and hot tub, and a dedicated outdoor dining area, the home encourages slow, outdoor-first days. The setting feels serene and elevated, perfect for travelers who want to wake up to water views and spend evenings outside under soft Gulf air. It’s a strong winter base for families or groups seeking comfort, privacy, and a true coastal escape.

11. Ponte Vedra Beach

Ponte Vedra Beach offers a quieter kind of winter escape. Located on Florida’s northeast coast, it combines wide, open beaches with a more refined, residential feel. Winter weather here is cooler than South Florida, but still comfortable, especially for travelers who prefer mild temperatures over tropical heat.

It’s a great choice for travelers who want calm coastal living with easy access to St. Augustine.

Things to do in Ponte Vedra Beach in winter

• Take long beach walks and enjoy quieter shorelines

• Visit nearby St. Augustine for history, dining, and holiday charm

• Spend the afternoon golfing or exploring coastal nature trails

Travel tips for visiting Ponte Vedra Beach in winter

• Pack layers, evenings can be chilly compared to South Florida

• Winter mornings are perfect for beach walks without crowds

• Plan day trips to nearby coastal towns for variety

Where to stay near Ponte Vedra Beach in winter

Wander Ponte Vedra Oceanfront – 12 guests, 6 bedrooms

Wander Ponte Vedra Oceanfront is a beachfront luxury home built for winter comfort and coastal elegance. With expansive ocean views, a private hot tub, and direct beach access, it’s designed for travelers who want the Atlantic at their doorstep. A pool table and fire pit add warmth and entertainment for evenings in, creating a stay that feels both relaxing and social. It’s a refined winter escape for travelers who want quieter beaches without sacrificing luxury.

12. Orlando & Kissimmee

Orlando and Kissimmee are smart winter choices for families and groups who want warm weather without relying entirely on the beach. Cooler temperatures make theme park days far more comfortable, and winter is one of the best times to explore the area without the summer heat.

It’s also a strong destination for travelers who want a home base built around entertainment, pool time, game rooms, and evenings spent together.

Things to do in Orlando in winter

• Spend a day at Walt Disney World or Universal without peak summer heat

• Explore Winter Park for dining, shopping, and scenic boat tours

• Plan a day trip to nearby natural springs for clear water and outdoor time

Travel tips for visiting Orlando in winter

• December and holiday weeks are extremely busy, plan early

• Pack layers for evenings, especially in January

• Take advantage of early mornings for theme parks and outdoor activities

Where to stay near Orlando in winter

Wander Orlando High Seas – 22 guests, 8 bedrooms

Wander Orlando High Seas is built for winter family travel, offering luxury comfort with entertainment at the center. A private outdoor pool makes warm afternoons easy, while the movie theater and game room create a full resort-style experience indoors. It’s ideal for groups who want a stay that feels exciting even between outings.

Wander Pebble Beach Retreat – 20 guests, 9 bedrooms

Wander Pebble Beach Retreat offers a similar luxury experience with a stronger focus on relaxation and group fun. With a pool, hot tub, movie theater, arcade machine, and full-size pool table, it’s designed for travelers who want the comfort of a private resort, perfect after a day exploring Orlando’s attractions.

Ready to Plan Your Florida Winter Escape?

Winter is Florida’s most effortless season, the time of year when the state feels warm, open, and built for outdoor living. Wander’s luxury vacation rentals in Florida offer a wide range of experiences, from Miami’s energy and Fort Lauderdale’s waterways to quiet Gulf islands and the sun-soaked Florida Keys.

Whether you’re planning a city-meets-beach escape, an island retreat, or a family trip built around comfort and entertainment, winter is when Florida delivers its most reliable version of luxury travel. With Wander’s vacation homes across the state’s most desirable coastal and resort destinations, it’s easy to find a place that feels like more than just somewhere to stay, a home base that makes the season feel even better.