Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 4–12, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,202 ($150/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 4–18, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$3,199 ($229/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 4–18, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,406 ($172/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/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
$3,164 ($452/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 5
$4,498 ($643/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–8, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$451 ($150/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–19, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,161 ($154/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,206 ($601/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,058 ($580/night)

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Shell Island Beach Club

Sanibel Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,618 ($374/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–10, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$670 ($134/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
$831 ($119/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,641 ($377/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–13, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,202 ($150/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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Lighthouse Resort & Club

Sanibel Island, Florida

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 6
$2,750 ($393/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–9, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$555 ($139/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$786 ($131/night)

Sheraton Vistana Resort

Orlando, Florida

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

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–11, 2026 (5 nights)
3 bed/3 bath, sleeps 10
$2,205 ($441/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–19, 2026 (13 nights)
2 bed/2 bath, sleeps 8
$1,956 ($150/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$577 ($115/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–9, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$367 ($122/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–9, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$639 ($213/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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Vacation Village at Parkway

Kissimmee, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$944 ($135/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–10, 2026 (4 nights)
3 bed/3 bath, sleeps 10
$1,550 ($388/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–10, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$471 ($118/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,568 ($510/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)