Winter Timeshare Rentals in Greater Orlando

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Disney's Riviera Resort

Lake Buena Vista, Florida

Dec 1–2, 2026 (1 night)
Studio/1 bath, sleeps 5
$622 ($622/night)

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Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

Dec 1–5, 2026 (4 nights)
1 bed/1 bath, sleeps 5
$7,010 ($1,752/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 1–3, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,277 ($639/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 2–6, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$648 ($162/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 4–7, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$535 ($178/night)

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Westgate Town Center

Kissimmee, Florida

Dec 4–11, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,022 ($432/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Grand Beach Resort

Orlando, Florida

Dec 5–12, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$1,660 ($237/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,600 ($514/night)

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Blue Tree Resort at Lake Buena Vista

Orlando, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$760 ($109/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 5–9, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,330 ($332/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

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Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 6–13, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$2,478 ($354/night)

Westgate Lakes Resort & Spa

Orlando, Florida

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$777 ($111/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–12, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$786 ($131/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–10, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$559 ($186/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–10, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$367 ($122/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–13, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$535 ($178/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 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$977 ($244/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)

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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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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 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,427 ($204/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 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,144 ($229/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/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)
1 bed/1 bath, sleeps 4
$595 ($119/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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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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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 12–18, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,379 ($397/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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Westgate Town Center

Kissimmee, Florida

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,932 ($276/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–19, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$972 ($162/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 13–20, 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 13–19, 2026 (6 nights)
3 bed/2 bath, sleeps 10
$1,497 ($250/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–19, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$972 ($162/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–19, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$693 ($115/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 13–19, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,903 ($484/night)