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The holiday season does not have to be a stereotypical “White Christmas”. You can still feel the same holiday cheer when you’re stretched out on the pool deck, soaking up the sun in Orlando. Can you think of anything better than spending the holidays with all of your favorite Walt Disney World characters? Staying at the Westgate Town Center Resort in Kissimmee puts you just a short drive from all of your Disney favorites. You can also enjoy the fine resort amenities including 14 swimming pools and hot tubs. If you are still looking for the home-like setting for your holiday celebration, Tropical Escape Vacation Homes offers three- and four-bedroom accommodations with everything you need for a happy holiday getaway. Start planning your own Orlando holiday trip today!

Showing 1-25 of 30 Holiday Resorts

Holiday Inn Resort Orlando Suites - Waterpark

Orlando, Florida, United States
$175
1-407-387-5437

Holiday Inn Resort Orlando Suites-Waterpark is a year-round destination that's perfect for celebrating the holiday of your choice. From Christmas to... more

Resort features:
  • Family
  • Meetings
  • Reunions
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos
  • Waterpark

Holiday Inn Club Vacations at Orange Lake Resort

Kissimmee, Florida, United States
$114
1-866-843-6314

Whether you're celebrating Christmas, New Year's, Valentine's or simply the summer holidays, Holiday Inn Club Vacations at Orange Lake Resort makes it... more

Resort features:
  • Beach
  • Family
  • Golf
  • Meetings
  • Reunions
  • Nature
  • Romantic
  • Luxury
  • Lake
  • Honeymoon
  • Holiday
  • Villas and Condos
  • Waterpark

Florida Vacation Homes & Villas

Davenport, Florida, United States
$85
1-866-343-1472

Florida is the perfect destination for your next holiday vacation, no matter what time of year! Florida Vacation Homes offer Kissimmee and Davenport... more

Resort features:
  • Family
  • Golf
  • Reunions
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos
  • Waterpark

Vista Vacation Rentals

Orlando, Florida, United States
$89
1-866-638-5498

Make it a holiday retreat for your family or friends with a stay at the Vista Vacation Rentals. The inn offers an unbeatable combination onsite... more

Resort features:
  • Beach
  • Family
  • Golf
  • Meetings
  • Romantic
  • Pet Friendly
  • Luxury
  • Lake
  • Honeymoon
  • Holiday
  • Villas and Condos

Sunkiss Villas

Davenport, Florida, United States
$99
1-407-479-8580

Whether you're getting away from the winter cold to celebrate Christmas and New Year's in sunny Florida or you're planning a vacation over the summer... more

Resort features:
  • Family
  • Reunions
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos

Florida Palms Vacation Villas

Davenport, Florida, United States
$159
1-863-420-6961

Whether you're planning a vacation over Christmas or the Fourth of July, Florida Palms Vacation Villas offers excellent accommodations and plenty of... more

Resort features:
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos

Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida, United States
$239
800-610-9558

Is there anything in the world that sounds better than a holiday trip to Disney World? Give the greatest Christmas present ever and stay at Wyndham... more

Resort features:
  • Family
  • Holiday

Vacation Pool Homes

Kissimmee, Florida, United States
$70
1-407-982-7224

Florida is the perfect destination for your next holiday vacation, no matter what time of year! Florida Vacation Homes, offer Kissimmee and Davenport... more

Resort features:
  • Beach
  • Family
  • Golf
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Lake
  • Honeymoon
  • Holiday
  • Villas and Condos
  • Waterpark

Florint Vacations

Orlando, Florida, United States
$110
1-877-486-8226

Treat yourself to a holiday vacation in the sun! Florint Vacations offers families, couples, and friends to getaway from the cold winters and discover... more

Resort features:
  • Family
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos
  • Waterpark

Orlando Premier Vacation Villas

Davenport, Florida, United States
$115
1-407-267-9099

When the months turn bitter cold, heading south is a fantastic idea. Celebrate Christmas in a Escape Vacation Homes villa! Bring the whole family,... more

Resort features:
  • Family
  • Golf
  • Reunions
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos

Advantage Vacation Homes

Kissimmee, Florida, United States
$99
1-407-396-2262

Whether you're celebrating the New Year or looking for a place to spend Spring Break, Advantage Vacation Rentals offers you everything you need for a... more

Resort features:
  • Family
  • Golf
  • Romantic
  • Luxury
  • Holiday

Balmoral Resort

Haines City, United States
$124
1 (866) 584-5527

Balmoral Resort is the perfect place to escape the cold at Christmastime! Besides the immaculate winter weather Orlando enjoys, the surrounding theme... more

Resort features:
  • Family
  • Golf
  • Reunions
  • Wedding
  • Nature
  • Romantic
  • Pet Friendly
  • Luxury
  • Lake
  • Honeymoon
  • Health
  • Holiday
  • Villas and Condos
  • Waterpark

Contempo Vacation Homes

Davenport, Florida, United States
$171
1-863-424-2226

Celebrate the winter holidays in sunny Florida! When you stay with Contempo Vacation Homes, you can getaway from the chilly winter weather and bask in... more

Resort features:
  • Family
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos

Luxury Reunion Rentals

Windermere, Florida, United States
$229
1-407-705-7634

Whether you're planning a holiday retreat with your friends over Christmas or looking to getaway with the family while the kids are on Spring Break,... more

Resort features:
  • Family
  • Golf
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos

The Grove Resort Orlando

Orlando, Florida, United States
$169
1-844-901-1122

Celebrate your favorite holiday in Orlando, Florida! The Grove Resort Orlando welcomes families and couples alike to celebrate their favorite time of... more

Resort features:
  • Family
  • Meetings
  • Reunions
  • Wedding
  • Nature
  • Fishing
  • Romantic
  • Luxury
  • Lake
  • Honeymoon
  • Holiday
  • Spa
  • Villas and Condos
  • Waterpark

Orlando Luxury Escapes Vacation Rentals

Orlando, Florida, United States
$145
1-407-956-4355

Get out of the snow, and into the sun for your next holiday vacation! Orlando Luxury Escapes Vacation Rentals has room for everyone in their spacious... more

Resort features:
  • Family
  • Golf
  • Nature
  • Romantic
  • Luxury
  • Honeymoon
  • Health
  • Holiday
  • Waterpark

Vacome Luxury Rentals

Davenport, Florida, United States
$99
1-855-661-3700

Head to Orlando for the perfect vacation no matter what time of year! Escape the cold and come during the winter or celebrate your kid's summer... more

Resort features:
  • Beach
  • Family
  • Golf
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos

Orlando Sunshine Villas

Orlando, Florida, United States
$95
+1 (407) 766-9685

Sun is always in season in Orlando! Escape the icy conditions and celebrate your December holiday in Orlando. You can make the stay even more magical... more

Resort features:
  • Family
  • Golf
  • Reunions
  • Wedding
  • Romantic
  • Luxury
  • Lake
  • Honeymoon
  • Holiday
  • Waterpark

Tropical Escape Vacation Homes

Davenport, Florida, United States
$190
1-863-588-3777

Start a new holiday tradition with Tropical Escape Vacation Homes! Come on down to beautiful Orlando and settle into one of their luxury... more

Resort features:
  • Family
  • Golf
  • Reunions
  • Romantic
  • Pet Friendly
  • Luxury
  • Honeymoon
  • Holiday
  • Villas and Condos

Favorite Vacation Homes

Clearmont, United States
$116
1-407-284-4912

Take the family to sunny Florida for a holiday to remember! Enjoy the fun adrenaline filled rides and water parks of Disney World and its parks. Swim... more

Resort features:
  • Family
  • Golf
  • Reunions
  • Romantic
  • Luxury
  • Honeymoon
  • Holiday
  • Timeshare

Avanti Resort

Orlando, Florida, United States

Getaway for the holidays at this luxurious Orlando resort. Located in the heart of Orlando's International Drive, Avanti Resort is the perfect hub for... more

Resort features:
  • Family
  • Reunions
  • Holiday
  • Honeymoon
  • Luxury
  • Romantic
  • Villas and Condos

The Florida Hotel and Conference Center

Orlando, Florida, United States
$99
1-407-859-1500

The Florida Hotel and Conference Center is the perfect place for your next holiday vacation. Whether you're here for Christmas, New Year's,... more

Resort features:
  • Meetings
  • Family
  • Reunions
  • Holiday
  • Luxury

Florida Paradise Villas

Kissimmee, Florida, United States
$160
1.866.939.7376

What better way to celebrate a holiday than with a getaway to fun-filled Orlando, Florida? Stay with Florida Paradise Villas and you'll be just... more

Resort features:
  • Family
  • Golf
  • Reunions
  • Nature
  • Fishing
  • Romantic
  • Pet Friendly
  • Luxury
  • Holiday
  • Villas and Condos

Leabridge Vacations

Davenport, Florida, United States
$115
1-407-413-5123

Invite the whole family for a sunny holiday this season! Leabridge Vacations features sprawling properties that can sleep up to ten guests and feature... more

Resort features:
  • Family
  • Golf
  • Romantic
  • Honeymoon
  • Holiday

Buena Vista Palace Hotel and Spa

Lake Buena Vista, Florida, United States
$99
1.866.397.6516

For any occasion, this is the hotel for you. You'll find six restaurants and cafes for dining, tennis, volleyball, and basketball courts, a video... more

Resort features:
  • Family
  • Golf
  • Meetings
  • Romantic
  • Luxury
  • Holiday
  • Spa

Showing 1-25 of 30 Holiday Resorts

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