Winter Rentals in Florida

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

Dec 21–28, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,550 ($221/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$1,330 ($190/night)

Verified & Protected

Sheraton Vistana Villages

Orlando, Florida

Dec 21–27, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$699 ($117/night)

Verified & Protected

Hilton Vacation Club Aqua Sol Orlando West

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
3 bed/3 bath, sleeps 10
$2,200 ($314/night)

Verified & Protected

Marriott's Oceana Palms

Riviera Beach, Florida

Dec 21–27, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$3,851 ($642/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$777 ($111/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–28, 2025 (7 nights)
4 bed/4 bath, sleeps 12
$4,385 ($626/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,960 ($280/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 21–26, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$3,731 ($746/night)

Verified & Protected

Club Wyndham Sea Gardens

Pompano Beach, Florida

Dec 21–28, 2025 (7 nights)
Studio/1 bath, sleeps 2
$998 ($143/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$4,712 ($673/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 21–28, 2025 (7 nights)
Studio/1 bath, sleeps 4
$1,877 ($268/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2.5 bath, sleeps 8
$1,110 ($159/night)

Verified & Protected Voted Top Pick 2025

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,804 ($401/night)

Verified & Protected

Marriott's Harbour Lake

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$999 ($143/night)

Verified & Protected

Hyatt Beach House Resort

Key West, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,696 ($385/night)

Verified & Protected

Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 21–28, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,054 ($151/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,110 ($159/night)

Verified & Protected

Daytona Beach Regency

Daytona Beach, Florida

Dec 21–27, 2025 (6 nights)
1 bed/1 bath, sleeps 4
$1,330 ($222/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 22–29, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)

Verified & Protected

Marriott's Villas at Doral

Miami, Florida

Dec 22–28, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$1,660 ($277/night)

Verified & Protected

Marriott's Legends Edge at Bay Point

Panama City Beach, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$2,204 ($441/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 22–29, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$3,077 ($440/night)

Verified & Protected Voted Top Pick 2025

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 22–27, 2025 (5 nights)
Studio/1 bath, sleeps 4
$1,330 ($266/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 22–27, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$832 ($166/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 22–27, 2025 (5 nights)
Studio/1 bath, sleeps 4
$555 ($111/night)

Verified & Protected

Marriott's Sabal Palms

Orlando, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 6
$2,094 ($419/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 22–29, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

Verified & Protected

Marriott's Lakeshore Reserve

Orlando, Florida

Dec 22–29, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 22–26, 2025 (4 nights)
Studio/1 bath, sleeps 4
$1,328 ($332/night)

Verified & Protected

Marriott's Royal Palms

Orlando, Florida

Dec 22–26, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$777 ($194/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,110 ($222/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 6
$1,927 ($385/night)

Verified & Protected

Sheraton Vistana Villages

Orlando, Florida

Dec 22–29, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,588 ($227/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–29, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$887 ($127/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,385 ($277/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 22–27, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$832 ($166/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 22–26, 2025 (4 nights)
1 bed/1 bath, sleeps 4
$1,440 ($360/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 22–27, 2025 (5 nights)
Studio/1 bath, sleeps 4
$777 ($155/night)

Verified & Protected Voted Top Pick 2025

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 22–29, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,704 ($243/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$999 ($200/night)

Verified & Protected

Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–27, 2025 (5 nights)
Studio/1 bath, sleeps 4
$2,750 ($550/night)

Verified & Protected

Marriott's Lakeshore Reserve

Orlando, Florida

Dec 22–27, 2025 (5 nights)
Studio/1 bath, sleeps 4
$1,054 ($211/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 22–29, 2025 (7 nights)
Studio/1 bath, sleeps 4
$1,660 ($237/night)

Verified & Protected

Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 23, 2025 – Jan 1, 2026 (9 nights)
Studio/1 bath, sleeps 5
$8,200 ($911/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 23–26, 2025 (3 nights)
2 bed/2 bath, sleeps 8
$610 ($204/night)