Surfbreakrentals - Vacation Rentals in Windward Islands

Property Image From $103
         

8.7 (1273 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From $186
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $180
         

9.8 (8 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $318
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $272
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Property Image From $1,112
         

Luxury Places to Stay in Windward Islands

Over 1349+ Luxury Places to Stay in or Near Windward Islands
Property Image From $4,004
         

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10.0 (2 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • TV
Property Image From $1,692
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $1,580
         

Property Image From $1,447
         

8.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From $1,315
         

New
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
Property Image From $1,152
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $1,125
         

New
Boat Rental
  • Bedding/Linens
  • Child Friendly
  • Laundry
Property Image From $1,119
         

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9.3 (16 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Windward Islands

Over 570+ Top-Rated Vacation Rentals with a Pool in or Near Windward Islands
Property Image From $192
         

Property Image From $141
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $343
         

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10.0 (12 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Windward Islands

Over 80+ Pet-Friendly Vacation Rentals in or Near Windward Islands
Property Image From $390
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $189
         

10.0 (9 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $141
         

8.6 (143 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Property Image From $944
         

9.2 (7 Reviews)
Villa
  • Air Conditioner
  • Pet Friendly
  • TV
Property Image From $258
         

Large Vacation Homes & Villas in Windward Islands

Over 195+ Large Vacation Homes & Villas in or Near Windward Islands
Property Image From $453
         

10.0 (8 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Property Image From $112
         

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8.1 (40 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace
Property Image From $138
         

10.0 (7 Reviews)
Villa
  • Parking
  • View
  • Ocean View
Property Image From $882
         

10.0 (5 Reviews)
Villa
  • Pool
  • Bedding/Linens
  • Wellness Facilities
Property Image From $252
         

10.0 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • TV
Property Image From $249
         

10.0 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool

Wheelchair Accessible Vacation Homes in Windward Islands

Over 149+ Wheelchair Accessible Vacation Homes in or Near Windward Islands
Property Image From $83
         

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8.6 (33 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pool
Property Image From $179
         

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9.0 (1074 Reviews)
Hotel
  • Air Conditioner
  • TV
  • Wheelchair Accessible
Property Image From $237
         

10.0 (2 Reviews)
Condo
  • Air Conditioner
  • Parking
  • TV
Property Image From $206
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV

Windward Islands Varoom and Airbnb Places to Stay Under $200

Over 850+ Windward Islands Varoom and Airbnb Places to Stay Under $200
Property Image From $179
         

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8.6 (103 Reviews)
Apartment
  • Air Conditioner
  • Balcony/Terrace
  • Child Friendly
Property Image From $177
         

10.0 (1 Review)
House
  • Parking
  • Pool
  • Balcony/Terrace
Property Image From $184
         

10.0 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From $189
         

10.0 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Property Image From $123
         

10.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Property Image From $122
         

Property Image From $88
         

10.0 (4 Reviews)
Ski Chalet
  • Air Conditioner
  • TV
  • Balcony/Terrace

Instantly Bookable Vacation Homes in Windward Islands

Over 431+ Instantly Bookable Vacation Homes in or Near Windward Islands
Property Image From $115
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pool
  • TV
Property Image From $357
         

Property Image From $257
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Security/Safety
  • Wellness Facilities
Property Image From $200
         

10.0 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

About Windward Islands Vacation Rentals

With more than 1358 Windward Islands vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Surfbreakrentals and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Windward Islands.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Surfbreakrentals Windward Islands, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Windward Islands. Places to stay near Windward Islands are 675.9 ft² on average, with prices averaging $228 a night.

Surfbreakrentals makes it easy and safe to find and compare vacation rentals in Windward Islands with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Windward Islands

Type Count
Holiday Apartments 567
Vacation Homes 467
Villas 144
Ski Chalet Rentals 62
B&B 29
Hotels with Suites 20
Hostels 9
Cabin Rentals 8
Resorts 8
Cottages 3
Others 3

Use these Quick Filters to Find a Vacation Rental in Windward Islands

Pro Tip: Surfbreakrentals makes it easy to compare the best listings on Surfbreakrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Surfbreakrentals homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Windward Islands.

Weather in Windward Islands

View the weather forecast for Windward Islands before booking your Windward Islands Vacation Rentals to confirm your best time to go.

December - February
High       Low
March - May
High       Low
June - August
High       Low
September - November
High       Low