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  2. Windward Coast
  3. Vacation Rentals with Pools

Windward Coast Vacation Rentals with Pools

House
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like-icon10.0
Exceptional
(29 Reviews)
2 Bedrooms 1 Bath 4 Guests 1000 ft²
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
US $273/Night 7 Nights - US $1,911
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Resort
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like-icon8.0
Excellent
(458 Reviews)
9 Baths 23 Guests 377.93 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
US $423/Night 7 Nights - US $2,963
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Condo
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1 Bedroom 1 Bath
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
US $2,892/Night 7 Nights - US $20,244
Apartment
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like-icon10.0
Exceptional
(17 Reviews)
1 Bedroom 1 Bath 3 Guests 400 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
US $143/Night 7 Nights - US $1,002
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House
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5 Bedrooms 2 Baths 10 Guests 1797.57 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $2,342/Night 7 Nights - US $16,394
Apartment
Map-icon
like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 5 Guests 1095 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
US $383/Night 7 Nights - US $2,683
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House
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1 Bedroom 1 Bath 4 Guests 419.79 ft²
  • Oceanfront
    Oceanfront
  • Spa
    Spa
More amenities
US $976/Night 7 Nights - US $6,832
House
Map-icon
like-icon10.0
Exceptional
(2 Reviews)
2 Bedrooms 2 Baths 4 Guests 900 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $404/Night 7 Nights - US $2,826
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House
Map-icon
3 Bedrooms 3 Baths 6 Guests 2055.91 ft²
  • Pool
    Pool
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $936/Night 7 Nights - US $6,552
House
Map-icon
like-icon9.6
Exceptional
(142 Reviews)
2 Bedrooms 2 Baths 4 Guests
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
US $906/Night 7 Nights - US $6,343
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Apartment
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1 Bedroom 1 Bath 4 Guests 796.53 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
US $173/Night 7 Nights - US $1,211
House
Map-icon
like-icon9.6
Exceptional
(45 Reviews)
1 Bedroom 1 Bath 4 Guests 416 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $686/Night 7 Nights - US $4,805

Why Choose Rent By Owner for your Windward Coast Vacation Rentals with Pools?

What makes our Vacation Rentals with Pools special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Weekly Weather Forecast for Windward Coast

Booking Steps

01

Search Properties

Use our filters to find the right property that fits your needs.
02

Select a Rental

Click on your preferred listing to view details, amenities, and pricing.
03

Book Online

Follow the link to finalize your reservation directly on the partner’s website.

Indoor Features

  • Fully-equipped kitchens with modern appliances
  • Comfortable living areas with flat-screen TVs
  • Free Wi-Fi for staying connected
  • Air conditioning and heating for year-round comfort
  • In-unit washers and dryers for convenience
  • Luxurious bedrooms with premium bedding
  • Spa-like bathrooms with soaking tubs or walk-in showers

Frequently Asked Questions About Windward Coast Rentals with Pools

2. How many Rentals With Pools are available in Windward Coast?

Currently, the total number of properties listed by RBO in 2026 is over 180 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Rentals With Pools in Windward Coast. 

More Rentals You May Like Near Windward Coast

Cottage
Map-icon
like-icon9.6
Exceptional
(13 Reviews)
2 Bedrooms 2 Baths 4 Guests 828 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $621/Night 7 Nights - US $4,345
House
Map-icon
like-icon9.6
Exceptional
(8 Reviews)
2 Bedrooms 2 Baths 4 Guests 2900 ft²
  • Private Pool
    Private Pool
  • Pool
    Pool
More amenities
US $461/Night 7 Nights - US $3,227
House
Map-icon
like-icon9.4
Exceptional
(168 Reviews)
1 Bedroom 1 Bath 2 Guests 500 ft²
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
US $716/Night 7 Nights - US $5,010
Apartment
Map-icon
like-icon9.4
Exceptional
(164 Reviews)
1 Bedroom 1 Bath 2 Guests 500 ft²
  • Pool
    Pool
  • Ocean View
    Ocean View
More amenities
US $681/Night 7 Nights - US $4,770
Bed & Breakfast
Map-icon
like-icon9.2
Exceptional
(105 Reviews)
2 Bedrooms 1 Bath 3 Guests
  • Hot Tub
    Hot Tub
  • Pool
    Pool
More amenities
US $380/Night 7 Nights - US $2,659
House
Map-icon
like-icon9.0
Exceptional
(94 Reviews)
2 Bedrooms 1 Bath 9 Guests 1250 ft²
  • Oceanfront
    Oceanfront
  • Hot Tub
    Hot Tub
More amenities
US $339/Night 7 Nights - US $2,375
Cottage
Map-icon
2 Bedrooms 1 Bath 5 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $378/Night 7 Nights - US $2,649
Apartment
Map-icon
2 Bedrooms 1 Bath 3 Guests
  • Pool
    Pool
  • Kitchen
    Kitchen
More amenities
US $282/Night 7 Nights - US $1,977
Cottage
Map-icon
3 Bedrooms 2 Baths 6 Guests
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $250/Night 7 Nights - US $1,750
Apartment
Map-icon
1 Bedroom 1 Bath 2 Guests
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
US $155/Night 7 Nights - US $1,088
House
Map-icon
like-icon10.0
Exceptional
(229 Reviews)
5 Bedrooms 5 Baths 14 Guests 4400 ft²
  • Oceanfront
    Oceanfront
  • Pool
    Pool
More amenities
US $3,047/Night 7 Nights - US $21,326
House
Map-icon
like-icon10.0
Exceptional
(116 Reviews)
4 Bedrooms 4 Baths 8 Guests 3200 ft²
  • Private Pool
    Private Pool
  • Oceanfront
    Oceanfront
More amenities
US $679/Night 7 Nights - US $4,750