Winter Rentals
Verified & Protected
The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 6–13, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,403 ($486/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Dec 6–13, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $1,768 ($253/night)
Verified & Protected
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
Marriott's Summit Watch
Park City, Utah- Dec 6–13, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $1,877 ($268/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2025 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Verified & Protected
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 6–13, 2025 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $9,290 ($1,327/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 6–13, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 6–13, 2025 (7 nights)
- 2 bed/3 bath, sleeps 6
- $6,946 ($992/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 7–14, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,492 ($1,070/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,548 ($650/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)
Verified & Protected
Voted Top Pick 2025
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 12–19, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $887 ($127/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,707 ($672/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 12–19, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,738 ($391/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Dec 12–24, 2025 (12 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($284/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,066 ($438/night)
Verified & Protected
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)
Verified & Protected
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($346/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 13–20, 2025 (7 nights)
- 3 bed/3 bath, sleeps 8
- $7,492 ($1,070/night)
Verified & Protected
Voted Top Pick 2025
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Dec 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,439 ($206/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,877 ($268/night)
Verified & Protected
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 13–20, 2025 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $9,290 ($1,327/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Newport Coast Villas
Newport Coast, California- Dec 13–20, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,422 ($346/night)
Verified & Protected
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 14–18, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,330 ($332/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 14–18, 2025 (4 nights)
- 2 bed/2 bath, sleeps 8
- $430 ($108/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)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 14–18, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,725 ($431/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 14–18, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($987/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 14–20, 2025 (6 nights)
- 1 bed/1 bath, sleeps 4
- $484 ($81/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)
Verified & Protected
Voted Top Pick 2025
Marriott's Barony Beach Club
Hilton Head Island, South Carolina- Dec 14–19, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $888 ($178/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 14–18, 2025 (4 nights)
- 1 bed/1 bath, sleeps 4
- $305 ($76/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 14–19, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($222/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 14–21, 2025 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,650 ($1,093/night)
Verified & Protected
Voted Top Pick 2025
Marriott's MountainSide at Park City
Park City, Utah- Dec 14–19, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($441/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $944 ($135/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($159/night)
Verified & Protected
Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Dec 14–21, 2025 (7 nights)
- 3 bed/3 bath, sleeps 10
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 14–18, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($415/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)
Verified & Protected
Voted Top Pick 2025
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 14–21, 2025 (7 nights)
- 3 bed/3 bath, sleeps 8
- $5,470 ($781/night)
Verified & Protected
Marriott's Summit Watch
Park City, Utah- Dec 14–19, 2025 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,104 ($221/night)
Verified & Protected
Eagle Trace at Massanutten
McGaheysville, Virginia- Dec 14–21, 2025 (7 nights)
- 1 bed/1 bath, sleeps 6
- $305 ($44/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
Verified & Protected
Grand Timber Lodge
Breckenridge, Colorado- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Desert Springs Villas II
Palm Desert, California- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($198/night)