Caribbean Daily - Vacation Rentals in Windward

VILLA ELLE From US $4,432
         

|
New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Hotel Les Ondines Sur La Plage From US $1,053
         

Villa Wild Blue (3 bedrooms) From US $985
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Villa Wild Blue (1 bedroom) From US $725
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Villa Cote Sauvage (1 bedroom) From US $693
         

8.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pool

Luxury Places to Stay in Windward

Over 3549+ Luxury Places to Stay in or Near Windward

Top-Rated Vacation Rentals with a Pool in Windward

Over 3300+ Top-Rated Vacation Rentals with a Pool in or Near Windward
Villa Whalhalla-4 bed-4 bath-POINTE MILOU From US $1,477
         

10.0 (35 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Sea view, very private From US $1,045
         

10.0 (30 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Villa Tiwa 2 Bed-2 Bath Pointe Milou From US $1,051
         

10.0 (24 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Windward

Over 408+ Pet-Friendly Vacation Rentals in or Near Windward
New ! Villa Vagabond From US $1,302
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Traditional Caribbean Style house with breathtaking views From US $1,467
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Villa Yvantino beachfront (2 bedroom) From US $1,434
         

10.0 (5 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
The Perfect Honeymoon Getaway on St Barts From US $652
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Sweet Hill studio Bali From US $548
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Child Friendly
See More Pet-Friendly Vacation Rentals in Windward on PetFriendly.io

Large Vacation Homes & Villas in Windward

Over 3146+ Large Vacation Homes & Villas in or Near Windward
Villa La Vue - Stunning view & heated pool From US $871
         

|
8.3 (3 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pool
Villa Tichatola (1 bedroom) From US $820
         

9.4 (3 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Villa Marigot Bay (2 bedrooms) From US $836
         

Villa Caco (3 bedrooms) From US $1,248
         

Villa Paradise . From US $2,609
         

10.0 (4 Reviews)
Villa
  • Air Conditioner
  • Parking
  • View
Villa Lo d'Amour (3 bedrooms) From US $1,216
         

10.0 (2 Reviews)
Villa
  • Air Conditioner
  • TV
  • View

Wheelchair Accessible Vacation Homes in Windward

Over 71+ Wheelchair Accessible Vacation Homes in or Near Windward
Le Barthélemy Hotel & Spa From US $3,033
         

|
9.8 (82 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Windward Varoom and Airbnb Places to Stay Under $200

Over 4+ Windward Varoom and Airbnb Places to Stay Under $200
Fully-equipped house with pool From US $191
         

|
9.6 (5 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Cadence Studio From US $194
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Studio Iguane From US $168
         

|
9.0 (18 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View

Instantly Bookable Vacation Homes in Windward

Over 1089+ Instantly Bookable Vacation Homes in or Near Windward
Villa Lo d'Amour (2 bedrooms) From US $1,158
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • TV
  • View
Villa Wild Blue (2 bedrooms) From US $867
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • Pool
  • TV
Villa Yellow Tail (1 bedroom) From US $516
         

10.0 (1 Review)
Villa
  • Air Conditioner
  • TV
  • View
Villa Yellow Tail (2 bedrooms) From US $623
         

9.8 (7 Reviews)
Villa
  • Air Conditioner
  • TV
  • View

About Windward Vacation Rentals

With more than 3558 Windward vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Caribbeandaily 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.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Caribbeandaily Windward, 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. Places to stay near Windward are 1094.88 ft² on average, with prices averaging $3,969 a night.

Caribbeandaily makes it easy and safe to find and compare vacation rentals in Windward 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

Type Count
Villas 3089
Vacation Homes 376
Holiday Apartments 65
Hotels with Suites 18
B&B 3
Cabin Rentals 3
Cottages 1

Use these Quick Filters to Find a Vacation Rental in Windward

Pro Tip: Caribbeandaily makes it easy to compare the best listings on Caribbeandaily homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Caribbeandaily 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.

Weather in Windward

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

December - February
High 86°F       Low 73°F
March - May
High 87°F       Low 74°F
June - August
High 89°F       Low 77°F
September - November
High 90°F       Low 75°F