Winter Rentals in Florida

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The Charter Club of Marco Beach

Marco Island, Florida

Dec 6–13, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 12–19, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,186 ($455/night)

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The Charter Club of Marco Beach

Marco Island, Florida

Dec 13–20, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,750 ($393/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 14, 2025 – Jan 5, 2026 (22 nights)
1 bed/1 bath, sleeps 6
$1,660 ($75/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$480 ($96/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–19, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$367 ($73/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 14–21, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

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Westgate Town Center

Kissimmee, Florida

Dec 14–21, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$2,641 ($377/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$971 ($139/night)

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Grand Beach Resort

Orlando, Florida

Dec 14–20, 2025 (6 nights)
3 bed/3 bath, sleeps 8
$1,407 ($234/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$888 ($178/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 14–18, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$1,110 ($278/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$1,550 ($221/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,987 ($284/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–17, 2025 (3 nights)
1 bed/1 bath, sleeps 4
$243 ($81/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$746 ($124/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 6
$555 ($111/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

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Westgate Town Center

Kissimmee, Florida

Dec 14–21, 2025 (7 nights)
4 bed/4 bath, sleeps 16
$666 ($95/night)

Westgate Lakes Resort & Spa

Orlando, Florida

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$2,205 ($315/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–20, 2025 (6 nights)
1 bed/1 bath, sleeps 4
$484 ($81/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 10
$3,622 ($517/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 6
$405 ($81/night)

Verified & Protected Voted Top Pick 2025

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$2,313 ($463/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–16, 2025 (2 nights)
3 bed/3 bath, sleeps 10
$977 ($488/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,088 ($155/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$552 ($79/night)

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The Townhouses at St. Augustine Beach and Tennis Resort

St. Augustine Beach, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2.5 bath, sleeps 6
$998 ($143/night)

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Club Wyndham Panama City Beach

Panama City Beach, Florida

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 6
$777 ($130/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$999 ($166/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–21, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$606 ($87/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,258 ($323/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 14–18, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$1,725 ($431/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–18, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$430 ($108/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–18, 2025 (4 nights)
1 bed/1 bath, sleeps 4
$305 ($76/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$1,534 ($256/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,968 ($424/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–17, 2025 (3 nights)
2 bed/2 bath, sleeps 8
$336 ($112/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,488 ($355/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 14–19, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$555 ($111/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,110 ($222/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$832 ($139/night)