Find your Leeward Islands vacation rental. Select a location/area links above.
Wimco is THE source for private villa rentals in the Caribbean, with over 23 years of experience. Our selection of Anguilla villas range from beachside cottages to luxury homes....
Elegant Villa and Cottage - private sandy beach
- 3 Bedroom
- 3 Bath
- Pool
- Private Sandy Beach
This elegant and secluded three-bedroom luxury villa and cottage are set into one acre of lush tropical gardens with its own little sandy beach. The bay has shallow water with sea grass and is great for snorkeling or enjoying the kayaks....
Desert Rose - 11,000 square foot cliff top estate
- 4 Bedroom
- 4 Bath
- Pool
- Air Conditioning
Desert Rose is a luxurious 11,000 square foot, 4 acre estate perched on top of a cliff offering breathtaking vistas of the sea. The villa is located in Island Harbour....
Villa Nirvana 0 Panoramic view overlooking the beach
- 4 Bedroom
- 4 Bath
- Pool
- Air Conditioning
Beautiful new villa centrally located in North Hill village overlooking the harbour at Sandy Ground. 180 degree view of St. Maarten, the harbour and the spectacular sunsets....
Villa Jasmine
- 2 Bedroom
- 2 Bath
- Pool
- Panoramic View
Villa Jasmine is located in the northwestern part of Anguilla and offers luxury, relaxation and spectacular ocean view. Beautiful Meads Bay beach, Malliouhana Hotel and Spa....
Tequila Sunrise - Private Retreat
- 3 Bedroom
- 3 Bath
- Pool
- Ocean View
At Tequila Sunrise, refined sophistication marries the natural exuberance of island living. Tequila is a contemporary three-bedroom villa situated on the secluded southern coast of Dropsey Bay....
Nevis Villa HC SEA
- 3 Bedroom
- Pool
- Outdoor Dining
- Maid Service
SEASTONE VILLA is a unique property overlooking the straits of St. Kitts. Nestled in a grotto of rocks and landscaped hillside, Seastone is Hurricane Cove's largest and most private villa....
3 Bedroom 3 Bath - Historic Vervain Mill
- 3 Bedroom
- 3 Bath
- Historic Property
- Pool
The Historic Vervain Mill is located on two acres of land on the southeast side of the island, partway up the hill towards Mt. Nevis, where ocean breezes cool and refresh....
Wimco is THE source for private villa rentals in the Caribbean, with over 23 years of experience. Our selection of Nevis villas range from beachside cottages to luxury homes....
Villa SAB HKU
- 3 Bedroom Villa
- Pool
- Spa
- Maid Service
Haiku is a form of Japanese poetry where the predominant theme is peace, tranquility and harmony between nature and man. Based on a 16th Century Japanese home....
WMB CAR
- 2 Bedroom Villa
- Pool
- Outdoor Dining
- WiFi
Recently renovated by the enthusiastic new owners, Carolina Cottage is one of the premiere rental accommodations on the beautiful island of Saba. Perched comfortably....
Villa GEY FAV
- Troy Hill
- 3 bedrooms 2 baths
- Pool
- Jacuzzi
Our beautiful, Sabanian house Villa Fairview has a very unique location on the island Saba. At 1000 feet, Fairview overlooks the charming village of Windwardside in the middle of the island....
Wimco is THE source for private villa rentals in the Caribbean, with over 23 years of experience. Our selection of Saba villas range from beachside cottages to luxury homes....
MAS CAR
- Automatic Generator
- Security Gate
- Maid Service
- Beach Accessories
From the Great Room, a curved staircase leads to the oversized second-level master suite and home office. This master suite features a cathedral ceiling with Raffles East India fans....
C GUI
- 4 Bedroom
- 5 Bath
- Pool
- Beachfront
A combination of an antique and contemporary décor makes this gorgeous and spacious, fully air-conditioned 4+1-bedroom beach front villa a unique place for a wonderful vacation....
- Gated community
- Air conditioned
- Large screen TV
- 200 references
Private infinity pool for your exclusive use. Breathtaking panoramic view overlooking Great Bay, Philipsburg and the Caribbean Sea, spectacular by day and by night....
Villa Pointe des Fleurs
- 4 Bedroom
- 4 Bath
- Pool
- 100 ft to beach
Villa Pointe des Fleurs is situated on a dramatic cliff side setting overlooking Baie Rouge Beach. Guests can descend a private stairway to a secluded sandy beach....
- Beachfront
- Private hillside
- Daily maid srvc.
- Moderate to Luxe
Wimco is THE source for private villa rentals in the Caribbean, with over 23 years of experience. Our selection of St Maarten villas range from beachside cottages to luxury homes....
Villa Silver Rainbow
- 5 Bedroom
- 6 Bath
- Pool
- Ocean View
Villa Silver Rainbow is located in the private complex of Domaine du Levant in Petit Cul de Sac, St Barts. This villa has 5 bedrooms, 6 bathrooms and a heated pool....
Villa Pralin
- 2 Bedroom
- 2 Bath
- Pool
- Maid Service
Villa Pralin (WV PRA) is an elegant villa located in Anse des Cayes, St Barts. Every care has been given to make this villa charming and comfortable. The two bedrooms are situated on either side of the large living room....
Villa Beverly
- 4 Bedroom
- 4 Bath
- Pool
- Ocean Views
Villa BEV is an elegant and very private villa located on Mt. Jean, St Barts. This 4 bedroom villa offers privacy and an amazing view of the ocean, and the surrounding islands....
- Beachside villas
- Daily Maid
- Book online
- Local office
Wimco is THE source for private villa rentals in St Barts. With over 23 years of experience on St Barts we give you exclusive access to the most desirable villas on the island....
Wimco is THE source for private villa rentals in the Caribbean, with over 23 years of experience. Our selection of St Maarten villas range from beachside cottages to luxury homes....
Fabulous Villas and Condos throughout the Caribbean
- From 1-5 Bedroom
- Ocean Views
- Private Pools
- Great Locations
CONDOS, VILLAS, HOMES, APT'S, DAILY, WEEKLY AND MONTHLY - We have a tremendous selection of premier properties throughout the Caribbean. Contact us and we will find your perfect vacation hideaway....
Home, 4 bedrooms, 4 baths.
- Waterfront
- 4 Bedrooms/baths
- Tri-level deck
- 40-foot pool
Waterfront on St.Maarten LAGOON. 4 master bedrooms each with bath in 2,300 square foot air conditioned villa with 2000 foot tri-level deck and 40-foot pool....
We hope that you find the exact Leeward Islands vacation rental you are looking for, right here! Our large selections of private and professionally managed lodgings aresecond to none. Please feel free to contact us if you need any help or have any questions. We have been dealing with Leeward Islands lodgings for almost 10 years and are very confident that you will find the perfect accommodations here at 10,000 Vacation Rentals.
