Winter Timeshare Rentals in Greater Orlando

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
Studio/1 bath, sleeps 4
$3,295 ($824/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,362 ($295/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,054 ($264/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,734 ($217/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–29, 2026 (7 nights)
3 bed/4 bath, sleeps 12
$13,105 ($1,872/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,268 ($159/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$2,641 ($377/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,107 ($158/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23, 2026 – Jan 4, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,632 ($219/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 23, 2026 – Jan 1, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$1,764 ($196/night)

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Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 23, 2026 – Jan 2, 2027 (10 nights)
1 bed/1 bath, sleeps 4
$2,750 ($275/night)

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Hilton Grand Vacations at Tuscany Village

Orlando, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
Studio/1 bath, sleeps 5
$3,077 ($769/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23, 2026 – Jan 4, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,561 ($297/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–27, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,383 ($346/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–27, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$737 ($184/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–27, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$995 ($249/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$870 ($174/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,180 ($236/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 23–27, 2026 (4 nights)
Studio/1 bath, sleeps 5
$999 ($250/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 23–29, 2026 (6 nights)
Studio/1 bath, sleeps 5
$4,930 ($822/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
Studio/1 bath, sleeps 4
$3,534 ($883/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,886 ($412/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,118 ($303/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 23–26, 2026 (3 nights)
Studio/1 bath, sleeps 4
$1,830 ($610/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23, 2026 – Jan 4, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$1,900 ($158/night)

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Disney's Riviera Resort

Lake Buena Vista, Florida

Dec 23–31, 2026 (8 nights)
Studio/1 bath, sleeps 5
$8,118 ($1,015/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,365 ($228/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,001 ($429/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 24–26, 2026 (2 nights)
Studio/1 bath, sleeps 4
$1,123 ($562/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,886 ($412/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,118 ($303/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–27, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,660 ($553/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,003 ($167/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–29, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$2,478 ($496/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,268 ($159/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,734 ($217/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,362 ($295/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,874 ($312/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,180 ($236/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$870 ($174/night)