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Make this holiday season even more special and spend it in an Inspirato home with your favorite people. For the best availability, book your trip early for holiday weeks or New Year’s celebrations.

 

  • All Months
  • December, 2024
  • All Vacations
  • Beach
  • Mountain
  • Lifestyle
  • Metropolitan
  • All Destinations
  • St. Croix, U.S. Virgin Islands
  • Los Cabos, Mexico
  • Turks and Caicos, British West Indies
  • Breckenridge, Colorado
  • Real del Mar, Mexico
  • Kohala Coast, Big Island, Hawaii
  • Big Sky, Montana
  • Punta Cana, Dominican Republic
  • Wailea, Maui, Hawaii
  • Vail, Colorado
  • Park City, Utah
  • Deer Valley, Utah
  • Punta de Mita, Mexico
  • Aspen, Colorado
  • Grand Cayman, Cayman Islands
  • Cacique Peninsula, Costa Rica
  • Scrub Island, British Virgin Islands
  • Jackson Hole, Wyoming
  • Snowmass Village, Colorado
  • Marco Island, Florida
  • Sonoma County, California
  • Palm Springs/Coachella Valley, California
  • Newport Beach, California
  • Steamboat Springs, Colorado
  • Malibu, California
  • Florida Keys, Florida
  • Whitefish, Montana
  • San Diego, California
  • Hilton Head Island, South Carolina
  • La Paz, Mexico
  • Harbour Island, Bahamas
  • Rosemary Beach/WaterColor, Florida
  • Savannah, Georgia
  • Florence, Italy
  • Tuscany, Italy
  • Scottsdale, Arizona
  • St. Michaels, Maryland
  • Kiawah Island, South Carolina
  • Charleston, South Carolina
  • Newport Coast, California
  • Fort Lauderdale, Florida
Showing 75 results
Destination
BR
BA
OCC
FT 2
Check In
Check Out
Grand Total
St. Croix, U.S. Virgin Islands
5 BR
5.5 BA
10 OCC
5200 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$75,177
St. Croix, U.S. Virgin Islands
5 BR
4.5 BA
10 OCC
5500 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$59,302
Los Cabos, Mexico
5 BR
7.5 BA
12 OCC
8027 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$51,075
Turks and Caicos, British West Indies
5 BR
5.5 BA
10 OCC
3500 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$50,568
Turks and Caicos, British West Indies
5 BR
5.5 BA
10 OCC
3500 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$50,568
Turks and Caicos, British West Indies
5 BR
5.5 BA
10 OCC
3500 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$50,568
Breckenridge, Colorado
5 BR
5.5 BA
10 OCC
3457 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$41,927
Real del Mar, Mexico
6 BR
7.0 BA
14 OCC
11000 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$40,519
Kohala Coast, Big Island, Hawaii
4 BR
4.5 BA
8 OCC
2770 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$38,727
Big Sky, Montana
6 BR
6.0 BA
14 OCC
3962 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$37,476
Punta Cana, Dominican Republic
4 BR
4.5 BA
10 OCC
5000 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$37,087
Andaz Maui at Wailea Resort
Wailea, Maui, Hawaii
3 BR
4.0 BA
6 OCC
3234 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$36,663
Los Cabos, Mexico
6 BR
6.0 BA
12 OCC
5402 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$36,540
Vail, Colorado
3 BR
3.5 BA
6 OCC
2386 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$35,135
Andaz Maui at Wailea Resort
Wailea, Maui, Hawaii
3 BR
3.0 BA
6 OCC
2120 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$33,525
Park City, Utah
5 BR
5.5 BA
12 OCC
4553 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$33,411
Deer Valley, Utah
4 BR
4.5 BA
8 OCC
2235 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$31,678
Andaz Maui at Wailea Resort
Wailea, Maui, Hawaii
3 BR
3.0 BA
6 OCC
2120 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$31,461
Punta de Mita, Mexico
4 BR
4.0 BA
10 OCC
2324 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$29,151
Deer Valley, Utah
2 BR
2.5 BA
4 OCC
1351 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,967
Aspen, Colorado
3 BR
2.0 BA
8 OCC
1120 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,955
Grand Cayman, Cayman Islands
3 BR
2.5 BA
7 OCC
4611 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,872
Cacique Peninsula, Costa Rica
5 BR
5.5 BA
10 OCC
5470 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,476
Park City, Utah
4 BR
4.0 BA
8 OCC
2684 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,411
Breckenridge, Colorado
4 BR
4.5 BA
9 OCC
2520 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,294
Los Cabos, Mexico
4 BR
5.5 BA
8 OCC
4500 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,258
Los Cabos, Mexico
4 BR
4.5 BA
8 OCC
3059 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,258
Los Cabos, Mexico
4 BR
4.5 BA
8 OCC
3059 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$28,258
Pendry Park City
Park City, Utah
3 BR
3.0 BA
8 OCC
1751 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$27,527
Scrub Island, British Virgin Islands
6 BR
6.5 BA
12 OCC
4669 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$26,950
Crystal Springs Lodge
Jackson Hole, Wyoming
3 BR
3.5 BA
6 OCC
1616 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$26,420
Cacique Peninsula, Costa Rica
6 BR
5.0 BA
10 OCC
5300 FT 2
Check In
Sun Dec 22, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$26,239
Auberge Private Residences at Esperanza
Los Cabos, Mexico
4 BR
4.0 BA
10 OCC
3300 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$26,146
Snowmass Village, Colorado
2 BR
2.0 BA
5 OCC
932 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$25,834
Marco Island, Florida
5 BR
4.5 BA
10 OCC
3550 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$25,495
Sonoma County, California
4 BR
4.5 BA
8 OCC
6600 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$25,411
Auberge Private Residences at Esperanza
Los Cabos, Mexico
4 BR
4.5 BA
10 OCC
3300 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$24,847
Auberge Private Residences at Esperanza
Los Cabos, Mexico
4 BR
4.5 BA
10 OCC
3300 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$24,847
Palm Springs/Coachella Valley, California
3 BR
3.5 BA
6 OCC
3075 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$24,255
Real del Mar, Mexico
4 BR
4.5 BA
8 OCC
5597 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$24,116
Breckenridge, Colorado
4 BR
4.5 BA
10 OCC
2956 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$24,049
Newport Beach, California
4 BR
3.5 BA
8 OCC
2449 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$23,870
Steamboat Springs, Colorado
4 BR
3.5 BA
8 OCC
2258 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$23,430
Malibu, California
2 BR
3.5 BA
5 OCC
1800 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$22,885
Punta de Mita, Mexico
3 BR
3.0 BA
8 OCC
2324 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$21,924
Florida Keys, Florida
4 BR
4.5 BA
10 OCC
4067 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$21,853
Whitefish, Montana
4 BR
4.5 BA
8 OCC
3548 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$20,942
Steamboat Springs, Colorado
4 BR
4.0 BA
10 OCC
1937 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$20,649
Marco Island, Florida
3 BR
2.0 BA
6 OCC
2190 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$20,582
Scrub Island, British Virgin Islands
4 BR
4.5 BA
8 OCC
3753 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$19,250
Scrub Island, British Virgin Islands
4 BR
4.0 BA
8 OCC
3673 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$19,250
San Diego, California
5 BR
4.5 BA
12 OCC
4027 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$19,106
Hilton Head Island, South Carolina
6 BR
6.0 BA
12 OCC
5779 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$17,702
La Paz, Mexico
3 BR
3.0 BA
8 OCC
2800 FT 2
Check In
Fri Dec 20, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$17,539
Harbour Island, Bahamas
2 BR
2.0 BA
4 OCC
1760 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$16,555
Rosemary Beach/WaterColor, Florida
5 BR
6.0 BA
12 OCC
3900 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$16,386
Savannah, Georgia
6 BR
6.0 BA
11 OCC
4872 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$13,976
Florence, Italy
3 BR
3.0 BA
6 OCC
3000 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$13,891
Rosemary Beach/WaterColor, Florida
6 BR
5.0 BA
12 OCC
3332 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$13,806
Tuscany, Italy
4 BR
4.0 BA
8 OCC
4700 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$13,721
The Rocks Luxury Residence Club Scottsdale
Scottsdale, Arizona
3 BR
3.0 BA
6 OCC
3000 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$13,409
St. Michaels, Maryland
6 BR
6.5 BA
12 OCC
5072 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$13,383
Kiawah Island, South Carolina
4 BR
4.5 BA
9 OCC
2837 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$12,972
Charleston, South Carolina
2 BR
2.5 BA
4 OCC
1308 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$12,677
Rosemary Beach/WaterColor, Florida
6 BR
5.5 BA
14 OCC
4257 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$11,943
The Resort at Pelican Hill
Newport Coast, California
2 BR
2.5 BA
6 OCC
2193 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$9,625
The Resort at Pelican Hill
Newport Coast, California
2 BR
2.5 BA
6 OCC
2193 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$9,625
Conrad Fort Lauderdale Beach
Fort Lauderdale, Florida
2 BR
2.0 BA
4 OCC
1200 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$9,583
Conrad Fort Lauderdale Beach
Fort Lauderdale, Florida
2 BR
2.0 BA
4 OCC
1200 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$9,583
Conrad Fort Lauderdale Beach
Fort Lauderdale, Florida
2 BR
2.0 BA
4 OCC
1200 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$8,458
Conrad Fort Lauderdale Beach
Fort Lauderdale, Florida
1 BR
1.5 BA
2 OCC
920 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$7,417
Tuscany, Italy
2 BR
2.5 BA
4 OCC
3200 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$6,930
Rosemary Beach/WaterColor, Florida
2 BR
2.0 BA
4 OCC
1520 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$6,607
Wheelman House Healdsburg
Sonoma County, California
1 BR
1.0 BA
2 OCC
600 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$4,223
Wheelman House Healdsburg
Sonoma County, California
1 BR
1.0 BA
2 OCC
450 FT 2
Check In
Sat Dec 21, 2024
Check Out
Sat Dec 28, 2024
Est. Value
$4,223

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