Winter Rentals
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 14–21, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,641 ($377/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($159/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($159/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 17–22, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $530 ($106/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($198/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 18–22, 2025 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,326 ($331/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 18–22, 2025 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,326 ($331/night)
Verified & Protected
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 18–22, 2025 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,326 ($331/night)
Verified & Protected
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 18–25, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($190/night)
Verified & Protected
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 18–25, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 18–19, 2025 (1 night)
- 2 bed/2 bath, sleeps 8
- $205 ($205/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $999 ($143/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–24, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $555 ($111/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,107 ($158/night)
Verified & Protected
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 19–24, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($332/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,192 ($170/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Dec 19–22, 2025 (3 nights)
- 2 bed/2 bath, sleeps 8
- $502 ($167/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,096 ($299/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,527 ($218/night)
Verified & Protected
Westgate Palace
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–27, 2025 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($248/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,220 ($174/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,220 ($174/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $888 ($127/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–27, 2025 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($248/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,042 ($292/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($198/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Marriott's Harbour Lake
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $722 ($103/night)
Verified & Protected
Westgate Vacation Villas
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,166 ($167/night)
Verified & Protected
Orlando International Resort Club
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $555 ($79/night)
Verified & Protected
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,358 ($194/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $955 ($136/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–28, 2025 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,385 ($173/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Hilton Vacation Club Aqua Sol Orlando West
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 3 bed/3 bath, sleeps 10
- $1,550 ($221/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,586 ($370/night)
Verified & Protected
Marriott's Royal Palms
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,273 ($182/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,286 ($184/night)
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,220 ($174/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 20–26, 2025 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,889 ($315/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,894 ($556/night)
Verified & Protected
Marriott's Harbour Lake
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($190/night)
Verified & Protected
Sheraton Vistana Villages
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,231 ($176/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,088 ($155/night)