Fall Rentals
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($200/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,110 ($250/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($300/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,619 ($340/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–22, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($350/night)
Hyatt Beach House Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,306 ($299/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($300/night)
Marriott's Oceana Palms
Riviera Beach, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,268 ($425/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($250/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Oct 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,704 ($220/night)
Hyatt Beach House Resort
Key West, Florida- Oct 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,765 ($399/night)
Hyatt Windward Pointe Resort
Key West, Florida- Oct 22–25, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,594 ($480/night)
Hyatt Beach House Resort
Key West, Florida- Oct 22–25, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,495 ($450/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Oct 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,856 ($240/night)
Eagle's Nest Beach Resort
Marco Island, Florida- Oct 23 – Nov 6, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($350/night)
Marriott's Villas at Doral
Miami, Florida- Oct 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,153 ($410/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Oct 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,165 ($150/night)
Summer Bay Orlando Resort
Clermont, Florida- Oct 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,242 ($160/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Oct 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,165 ($150/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Oct 23–30, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,306 ($299/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 24–30, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($140/night)
Summer Bay Orlando Resort
Clermont, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,001 ($259/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($160/night)
Umbrella Beach Resort
Holmes Beach, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,742 ($225/night)
Parc Soleil by Hilton Grand Vacations
Orlando, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $932 ($120/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,428 ($315/night)
Club Wyndham Panama City Beach
Panama City Beach, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,396 ($180/night)
Hyatt Beach House Resort
Key West, Florida- Oct 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $999 ($300/night)
Hyatt Beach House Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,196 ($154/night)
Westgate Lakes Resort & Spa
Orlando, Florida- Oct 24–31, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,866 ($241/night)
Hilton Grand Vacations at SeaWorld
Orlando, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,358 ($175/night)
Hilton Grand Vacations at Tuscany Village
Orlando, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,165 ($150/night)
Hyatt Beach House Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,204 ($155/night)
Club Wyndham Royal Vista
Pompano Beach, Florida- Oct 24–28, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $599 ($135/night)
The Galleon Resort
Key West, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($375/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 24–29, 2026 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,082 ($195/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Oct 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $971 ($125/night)
Sheraton PGA Vacation Resort
Port St. Lucie, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,200 ($285/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,165 ($150/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 25–31, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $999 ($150/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Oct 25–30, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $610 ($110/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Oct 25 – Nov 13, 2026 (19 nights)
- 1 bed/1 bath, sleeps 4
- $3,132 ($150/night)
Sheraton Vistana Resort
Orlando, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($200/night)
Westgate Town Center
Kissimmee, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,165 ($150/night)
Westgate Town Center
Kissimmee, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,542 ($199/night)
Marriott's Legends Edge at Bay Point
Panama City Beach, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $777 ($100/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Oct 25–30, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $610 ($110/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Oct 25 – Nov 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($457/night)