Winter Timeshare Rentals in Florida

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Sheraton Vistana Villages

Orlando, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,110 ($222/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–31, 2026 (12 nights)
2 bed/2 bath, sleeps 8
$3,308 ($276/night)

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Las Palmeras by Hilton Grand Vacations

Orlando, Florida

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 2
$1,550 ($221/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,935 ($215/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,260 ($323/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 4
$1,705 ($341/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,198 ($171/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,693 ($813/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,875 ($277/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,016 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,669 ($953/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,731 ($533/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,114 ($279/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 19–20, 2026 (1 night)
Studio/1 bath, sleeps 4
$415 ($415/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,114 ($279/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 9
$6,020 ($1,204/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 2, 2027 (13 nights)
1 bed/1 bath, sleeps 4
$2,567 ($197/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$959 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 2, 2027 (13 nights)
2 bed/2 bath, sleeps 8
$3,487 ($268/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,586 ($370/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,563 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$3,948 ($658/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,955 ($492/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 20–24, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$1,878 ($470/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$710 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–23, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$959 ($320/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–23, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$499 ($166/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,180 ($197/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,858 ($408/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–23, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,712 ($673/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,818 ($273/night)

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Hyatt Sunset Harbor Resort

Key West, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2.5 bath, sleeps 6
$4,711 ($673/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,397 ($171/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,384 ($626/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
Studio/1 bath, sleeps 5
$2,536 ($634/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,222 ($603/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$2,789 ($199/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,968 ($424/night)

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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)