Winter Timeshare Rentals in Florida

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 9–12, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$639 ($213/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 9–12, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 9–12, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$499 ($166/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–15, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$586 ($117/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–15, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$852 ($170/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–13, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$826 ($275/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,268 ($467/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–13, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$586 ($195/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–15, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,128 ($226/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–14, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$977 ($244/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,794 ($685/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–14, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–13, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$439 ($146/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 10–14, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$719 ($180/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,622 ($517/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–15, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$595 ($119/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$719 ($180/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$971 ($139/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,119 ($160/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$862 ($172/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 11–17, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$2,423 ($404/night)

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Boulder Ridge Villas at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 11–17, 2026 (6 nights)
Studio/1 bath, sleeps 5
$5,473 ($912/night)

DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,768 ($253/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,144 ($229/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

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Eagle's Nest Beach Resort

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,068 ($438/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,949 ($564/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/night)

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DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,123 ($303/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,295 ($471/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–14, 2026 (3 nights)
3 bed/3 bath, sleeps 10
$1,330 ($443/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$977 ($244/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–14, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$424 ($141/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,427 ($204/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,053 ($579/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2.5 bath, sleeps 8
$5,475 ($782/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,257 ($751/night)

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Marriott Vacation Club Pulse, South Beach

Miami Beach, Florida

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 3
$3,069 ($438/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 12–16, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$555 ($139/night)

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Westgate Town Center

Kissimmee, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,185 ($455/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)