Book the Best Places to Stay in Windward Side

Find Curated Vacation Rentals, Boutique Cabins, and Stylish Eco-Friendly Acommodation in Windward Side

Property Image From $401
         

4.9 (59 Reviews)
Villa
  • Air Conditioner
  • Balcony/Terrace
  • Bedding/Linens
Property Image From $124
         

8.1 (224 Reviews)
Hotel
  • Pool
  • View
  • Ocean View
Property Image From $78
         

New
House
  • Pool
  • Balcony/Terrace
  • Sports/Activities
Property Image From $95
         

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8.4 (39 Reviews)
House
  • Pool
  • Balcony/Terrace
  • Bedding/Linens
Property Image From $258
         

7.6 (173 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Property Image From $380
         

4.9 (9 Reviews)
Villa
  • Air Conditioner
  • Pool
  • TV
Property Image From $934
         

Luxury Places to Stay in Windward Side

Over 13+ Luxury Places to Stay in or Near Windward Side
Property Image From $443
         

Property Image From $375
         

4.7 (3 Reviews)
House
  • Pool
  • Private Pool
  • Bedding/Linens
Property Image From $360
         

Property Image From $255
         

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5.8 (11 Reviews)
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Windward Side

Over 1+ Top-Rated Vacation Rentals with a Pool in or Near Windward Side
Property Image From $129
         

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8.4 (18 Reviews)
Hotel
  • Air Conditioner
  • Pool
  • Bedding/Linens

Pet-Friendly Vacation Rentals in Windward Side

Over 1+ Pet-Friendly Vacation Rentals in or Near Windward Side
Property Image From $146
         

New
Cottage
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Windward Side Varoom and Airbnb Places to Stay Under $200

Over 2+ Windward Side Varoom and Airbnb Places to Stay Under $200
Property Image From $165
         

New
Cottage
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly
Property Image From $105
         

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4.7 (72 Reviews)
Bed & Breakfast
  • Balcony/Terrace
  • Child Friendly
  • Laundry

About Windward Side Vacation Rentals

With more than 22 Windward Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Bettertrips 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 Side.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Bettertrips Windward Side, 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 Side. Places to stay near Windward Side are 363.27 ft² on average, with prices averaging $300 a night.

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

Type Count
Villas 7
Vacation Homes 6
Cottages 4
Hotels with Suites 3
B&B 1
Resorts 1

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

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

Weather in Windward Side

View the weather forecast for Windward Side before booking your Windward Side 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