https://www.redweek.com/featured/winter-rentals/Caribbean en Sat, 07 Nov 2026 00:31:17 -0800 3600 New Availability! Voted #1 Resort 2026

Marriott's Aruba Surf Club

Palm Beach, Aruba

Starting at $210/night

]]> https://www.redweek.com/resort/4872/timeshare-rentals Fri, 06 Nov 2026 23:30:19 -0800 New Availability!

Divi Village Golf and Beach Resort

Oranjestad, Aruba

Starting at $100/night

]]> https://www.redweek.com/resort/5400/timeshare-rentals Fri, 06 Nov 2026 16:10:00 -0800 New Availability! Voted Top Pick 2026

Marriott's Frenchman's Cove

Southside, St. Thomas (USVI)

Starting at $299/night

]]> https://www.redweek.com/resort/5504/timeshare-rentals Fri, 06 Nov 2026 23:05:35 -0800 New Availability! Voted Top Pick 2026

Harborside Resort at Atlantis

Paradise Island, Bahamas

Starting at $160/night

]]> https://www.redweek.com/resort/4748/timeshare-rentals Fri, 06 Nov 2026 17:55:38 -0800 New Availability!

Lifestyle Holidays Vacation Resort - Puerto Plata

Puerto Plata, Dominican Republic

Starting at $70/night

]]> https://www.redweek.com/resort/5190/timeshare-rentals Fri, 06 Nov 2026 07:59:31 -0800 New Availability!

Marriott's St. Kitts Beach Club

Frigate Bay, St. Kitts

Starting at $198/night

]]> https://www.redweek.com/resort/5571/timeshare-rentals Fri, 06 Nov 2026 11:35:11 -0800 New Availability!

The Westin St. John - Sunset Bay Villas

Cruz Bay, St. John (USVI)

Starting at $250/night

]]> https://www.redweek.com/resort/6450/timeshare-rentals Fri, 06 Nov 2026 22:03:25 -0800 New Availability!

Renaissance Wind Creek Aruba - Ocean Suites

Oranjestad, Aruba

Starting at $300/night

]]> https://www.redweek.com/resort/6494/timeshare-rentals Fri, 06 Nov 2026 22:03:25 -0800 New Availability!

The Village at St. James' Club

St. John's, Antigua

Starting at $250/night

]]> https://www.redweek.com/resort/45/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability!

Coral Sands Resort

George Town, Grand Cayman, Cayman Islands

Starting at $199/night

]]> https://www.redweek.com/resort/50/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability! Voted Top Pick 2026

Divi Aruba Phoenix Beach Resort

Palm Beach, Aruba

Starting at $110/night

]]> https://www.redweek.com/resort/137/timeshare-rentals Fri, 06 Nov 2026 18:42:35 -0800 New Availability! Voted Top Pick 2026

Marriott's Aruba Ocean Club

Palm Beach, Aruba

Starting at $215/night

]]> https://www.redweek.com/resort/148/timeshare-rentals Sat, 07 Nov 2026 00:05:21 -0800 New Availability!

Limetree Beach Resort by Club Wyndham

Southside, St. Thomas (USVI)

Starting at $125/night

]]> https://www.redweek.com/resort/201/timeshare-rentals Fri, 06 Nov 2026 23:30:25 -0800 New Availability!

The Westin St. John - Virgin Grand Villas

Cruz Bay, St. John (USVI)

Starting at $150/night

]]> https://www.redweek.com/resort/4649/timeshare-rentals Fri, 06 Nov 2026 22:03:25 -0800 New Availability!

The Ritz-Carlton Club, St. Thomas

East End, St. Thomas (USVI)

Starting at $695/night

]]> https://www.redweek.com/resort/5099/timeshare-rentals Sat, 07 Nov 2026 00:05:20 -0800 New Availability!

Westgate Bimini Bay

Bailey Town, Bahamas

Starting at $175/night

]]> https://www.redweek.com/resort/7829/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability!

Morritt's Tortuga Club

East End, Grand Cayman, Cayman Islands

Starting at $113/night

]]> https://www.redweek.com/resort/53/timeshare-rentals Fri, 06 Nov 2026 13:08:59 -0800 New Availability!

Costa Linda Beach Resort

Oranjestad, Aruba

Starting at $425/night

]]> https://www.redweek.com/resort/141/timeshare-rentals Thu, 05 Nov 2026 18:21:23 -0800 New Availability!

La Cabana Beach Resort

Oranjestad, Aruba

Starting at $210/night

]]> https://www.redweek.com/resort/145/timeshare-rentals Fri, 06 Nov 2026 13:59:52 -0800 New Availability!

Hilton Vacation Club Royal Palm St. Maarten

Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $380/night

]]> https://www.redweek.com/resort/174/timeshare-rentals Fri, 06 Nov 2026 08:12:18 -0800 New Availability!

Divi Dutch Village Beach Resort

Oranjestad, Aruba

Starting at $150/night

]]> https://www.redweek.com/resort/144/timeshare-rentals Fri, 06 Nov 2026 09:35:19 -0800 New Availability!

La Quinta Beach Resort

Oranjestad, Aruba

Starting at $200/night

]]> https://www.redweek.com/resort/147/timeshare-rentals Fri, 06 Nov 2026 14:49:41 -0800 New Availability!

Divi Little Bay Beach & Racquet Club

Little Bay Beach, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $200/night

]]> https://www.redweek.com/resort/161/timeshare-rentals Fri, 06 Nov 2026 08:01:26 -0800 New Availability!

Sea Palace Resort

Philipsburg, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $150/night

]]> https://www.redweek.com/resort/177/timeshare-rentals Fri, 06 Nov 2026 14:42:54 -0800 New Availability!

The Westin St. John - Bay Vista Villas

Cruz Bay, St. John (USVI)

Starting at $155/night

]]> https://www.redweek.com/resort/200/timeshare-rentals Fri, 06 Nov 2026 22:03:25 -0800 New Availability!

La Vista Beach Resort

Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $225/night

]]> https://www.redweek.com/resort/4762/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability!

Dawn Beach Club

St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $143/night

]]> https://www.redweek.com/resort/5980/timeshare-rentals Fri, 06 Nov 2026 06:10:23 -0800 New Availability!

Hilton Vacation Club Flamingo Beach St. Maarten

Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $225/night

]]> https://www.redweek.com/resort/179/timeshare-rentals Fri, 06 Nov 2026 20:14:49 -0800 New Availability!

Windjammer Landing Villa Beach Resort

Castries, St. Lucia

Starting at $225/night

]]> https://www.redweek.com/resort/221/timeshare-rentals Fri, 06 Nov 2026 22:02:13 -0800 New Availability!

Morritt's Grand Resort

East End, Grand Cayman, Cayman Islands

Starting at $215/night

]]> https://www.redweek.com/resort/52/timeshare-rentals Sat, 07 Nov 2026 00:05:21 -0800 New Availability!

Morritt's Tortuga Seaside

East End, Grand Cayman, Cayman Islands

Starting at $150/night

]]> https://www.redweek.com/resort/5629/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability!

The Westin St. John - Coral Vista Villas

Cruz Bay, St. John (USVI)

Starting at $220/night

]]> https://www.redweek.com/resort/6381/timeshare-rentals Fri, 06 Nov 2026 22:03:25 -0800 New Availability!

Paradise Island Beach Club

Paradise Island, Bahamas

Starting at $285/night

]]> https://www.redweek.com/resort/20/timeshare-rentals Fri, 06 Nov 2026 06:58:28 -0800 New Availability!

Barcelo Aruba

Palm Beach, Aruba

Starting at $400/night

]]> https://www.redweek.com/resort/134/timeshare-rentals Fri, 06 Nov 2026 22:03:25 -0800 New Availability!

Casa del Mar Beach Resort

Oranjestad, Aruba

Starting at $200/night

]]> https://www.redweek.com/resort/140/timeshare-rentals Fri, 06 Nov 2026 09:52:19 -0800 New Availability!

Royal Islander Club la Plage

St. Maarten, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $235/night

]]> https://www.redweek.com/resort/171/timeshare-rentals Fri, 06 Nov 2026 14:01:28 -0800 New Availability!

Hyatt Hacienda Del Mar

Dorado, Puerto Rico

Starting at $300/night

]]> https://www.redweek.com/resort/4750/timeshare-rentals Thu, 05 Nov 2026 10:54:41 -0800 New Availability!

Wyndham St. Thomas, a Margaritaville Vacation Club Resort

East End, St. Thomas (USVI)

Starting at $300/night

]]> https://www.redweek.com/resort/6410/timeshare-rentals Fri, 06 Nov 2026 06:53:33 -0800 New Availability!

Reef Beach Resort

East End, Grand Cayman, Cayman Islands

Starting at $235/night

]]> https://www.redweek.com/resort/6553/timeshare-rentals Fri, 06 Nov 2026 02:10:28 -0800 New Availability!

Eagle Aruba Resort

Oranjestad, Aruba

Starting at $200/night

]]> https://www.redweek.com/resort/146/timeshare-rentals Fri, 06 Nov 2026 23:30:16 -0800 New Availability!

Oyster Bay Beach Resort

Philipsburg, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $150/night

]]> https://www.redweek.com/resort/159/timeshare-rentals Fri, 06 Nov 2026 02:10:28 -0800 New Availability!

Morritt's The Londoner

East End, Grand Cayman, Cayman Islands

Starting at $295/night

]]> https://www.redweek.com/resort/6326/timeshare-rentals Thu, 05 Nov 2026 22:30:08 -0800 New Availability!

Wyndham Grand Rio Mar, a Margaritaville Vacation Club Resort

Rio Grande, Puerto Rico

Starting at $275/night

]]> https://www.redweek.com/resort/6411/timeshare-rentals Fri, 06 Nov 2026 23:30:26 -0800 New Availability!

Alexandra Resort and Spa

Grace Bay, Turks and Caicos Islands

Starting at $750/night

]]> https://www.redweek.com/resort/191/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability!

Flamingo Beach Villas

Simpson Bay, Dutch side (Sint Maarten), Sint Maarten & Saint Martin

Starting at $500/night

]]> https://www.redweek.com/resort/4879/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability!

The Crane, a Hilton Grand Vacations Club

St. Philip, Barbados

Starting at $600/night

]]> https://www.redweek.com/resort/6719/timeshare-rentals Thu, 05 Nov 2026 14:30:09 -0800 New Availability!

Moon Palace The Grand - Punta Cana

Punta Cana, Dominican Republic

Starting at $2,000/night

]]> https://www.redweek.com/resort/7833/timeshare-rentals Thu, 05 Nov 2026 02:10:28 -0800 New Availability!

Paradise Beach Villas

Oranjestad, Aruba

Starting at $325/night

]]> https://www.redweek.com/resort/149/timeshare-rentals Fri, 06 Nov 2026 10:04:47 -0800