Luxury villas in Florida

USA and Canada

Florida Luxury Villas & Vacation Rentals

206 properties

View all 206 villas

Florida, the Sunshine State, pairs world-class theme parks, white-sand beaches and cosmopolitan cities with a warm climate all year. Renting a luxury villa here gives families and groups private pools, generous living space and concierge support, all close to Disney World, Miami and the Gulf coast.

Updated October 2026

  • Private-pool villas near Disney World and Orlando's theme parks
  • Beachfront living along the Atlantic coast and the Gulf of Mexico
  • Miami and Fort Lauderdale for dining, art deco and nightlife
  • Year-round warmth and an easy winter escape
  • Concierge service and direct booking with every Smiling House villa
Known forTheme parks, beaches, subtropical climate and vibrant cities
Best time to visitNovember to April for warm, drier weather; spring for fewer crowds
Nearest airportMiami (MIA), Orlando (MCO) and Fort Lauderdale (FLL) international airports
Ideal forMultigenerational families, groups, beach lovers and theme-park trips

Villas in Florida

Fort LauderdaleFour CornersKissimmee
206homes available
1–23bedrooms
up to 48guests
136with a pool

Where to stay in Florida

Orlando96Fort Lauderdale54Southwest Florida Coast20Miami Area8Tampa Bay Area7

What's on in Florida

  1. Late October

    Fort Lauderdale International Boat Show

    The world's largest in-water boat show fills the Yachting Capital of America with superyachts and marine glamour. A natural fixture for anyone chartering during a villa stay.

  2. Early December

    Art Basel Miami Beach

    The Americas' most important contemporary art fair transforms Miami into a week of exhibitions, satellite fairs and parties. Villas across the city book out months in advance.

  3. Late February

    South Beach Wine & Food Festival

    Celebrity chefs, tastings and beachside dinners across Miami Beach make this one of America's premier food festivals. Book villa dates and dinner tickets well ahead.

  4. Late March

    Miami Open

    A two-week ATP and WTA tennis event drawing the world's best players to Hard Rock Stadium. It anchors the tail end of the glamorous winter season.

  5. Late March

    Ultra Music Festival

    Downtown Miami's flagship electronic music festival, staged on the bayfront since 1999. The city hums for the whole of Miami Music Week around it.

Florida through the seasons

  1. Winter (December – March)

    The dry-season high life

    Warm, low-humidity days while the north freezes: this is Florida's social season of art fairs, regattas and packed beach clubs. Book villas early for these months.

  2. Spring (April – May)

    Hot beaches before the rains

    Sea temperatures climb and the winter crowds thin. A sweet spot for families with pools, boat days and Everglades excursions before summer humidity arrives.

  3. Summer (June – September)

    Green season with afternoon theatre

    Hot, lush and punctuated by short afternoon storms, with the best villa value of the year. Mornings on the water, afternoons by your private pool.

  4. Autumn (October – November)

    Boat-show buzz and returning sunshine

    Humidity drops, the boat show arrives and the beaches feel local again. An excellent shoulder season for golf, fishing and long waterfront dinners.

All 206 villas in Florida

Every home in Florida that can be booked with Smiling House, as a plain list.

Smiling House also offers a concierge for private chefs, transfers, ski instructors, yachts and cars, a VIP Club with first access to new residences and member rates, chalets for sale in the Gstaad region through its real estate division and instantly bookable homes with live availability.

Why choose luxury villas in Florida

Florida rewards travellers who want both excitement and space to unwind. A luxury villa offers the privacy a hotel cannot: a screened pool deck, multiple bedrooms for an extended family, a full kitchen and room to gather after a long day at the parks or on the sand. The state's mild, subtropical climate makes it an ideal winter escape, while summers suit beach and water lovers. Smiling House curates a collection of villas across the most desirable corners of the state, from Orlando resort communities to coastal retreats, each backed by concierge support that can arrange park tickets, private transfers, chefs and tee times before you arrive.

Where to stay

Orlando and the Disney World area form the heart of family Florida, with resort communities placing you minutes from the Magic Kingdom and Universal. On the Atlantic side, Miami brings art deco glamour, while neighbouring Fort Lauderdale and Hollywood offer calmer beaches and intracoastal waterways. The Gulf of Mexico coast trades crowds for sunset-facing sands and gentler waters. Florida's historical districts, from St Augustine to old-town quarters, add character for travellers who prefer heritage to high-rises. Our villas span these areas so you can match the setting to your trip, whether that means theme-park proximity, beachfront living or a city base near the nightlife.

Things to do

Orlando is the world capital of theme parks, home to the four Walt Disney World parks. Animal Kingdom brings wildlife close, Hollywood Studios stages interactive shows and stunts, EPCOT explores science and global culture, and the Magic Kingdom delights every age. Beyond Orlando, Tampa's Busch Gardens pairs roller coasters with an African safari theme. The coasts invite swimming, snorkelling, boating and long beach days, while the Gulf side is prized for fishing and serene sunsets. Cultural travellers will find art, aviation, history and science museums across Jacksonville, Sarasota, Tampa and Miami, plus subtropical wilderness and nature reserves to explore at a slower pace.

Dining and nightlife

Florida's table reflects its history and many cultures: citrus, Gulf and Atlantic seafood, southern classics and the bold flavours of Latin and Spanish kitchens, especially Cuban cooking in Miami. The state is equally known for after-dark energy. Miami Beach draws an international crowd to landmark clubs such as LIV, Story, Space and E11EVEN, several running into daylight. In Orlando, nightlife wakes once the parks close, with bars, lounges and dance floors around Universal's CityWalk and downtown's Orange Avenue. Add dinner theatre, Broadway-style productions and live concerts in the major cities for evenings that suit every group.

When to visit and getting there

The most comfortable months run from November to April, when warm, drier weather makes a welcome winter escape; spring brings fewer crowds, while summer suits beach and pool days despite afternoon storms. Florida is exceptionally easy to reach, served by major international airports at Miami, Orlando and Fort Lauderdale, with Tampa and Jacksonville adding further options. A hire car is the simplest way to move between coasts, theme parks and beach towns. Your Smiling House concierge can arrange private airport transfers, in-villa provisioning and park tickets so the practical details are handled before you land.

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