Leeward Islands Short Term Stay

10.0
Exceptional
(1 Review)
1 Bedroom 1 Bathroom
Ocean View House
  • Ocean View
  • Balcony/Terrace
  • View
ZA R3,333/Night For 7 Nights ZA R23,321
10.0
Exceptional
(20 Reviews)
377 ft² 4 Guests 1 Bedroom 1 Bathroom
Ocean View House
  • Ocean View
  • Balcony/Terrace
  • View
ZA R4,519/Night For 7 Nights ZA R31,630
10.0
Exceptional
(36 Reviews)
538.2 ft² 4 Guests 1 Bedroom 1 Bathroom
Family Friendly Bed & Breakfast
  • Balcony/Terrace
  • Parking
  • Internet
ZA R2,060/Night For 7 Nights ZA R14,416
10.0
Exceptional
(1 Review)
1 Bedroom 1 Bathroom
Family Friendly Resort
  • Balcony/Terrace
  • View
  • Kitchen
ZA R4,866/Night For 7 Nights ZA R34,063
10.0
Exceptional
(7 Reviews)
1076 ft² 6 Guests 2 Bedrooms 3 Bathrooms
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
ZA R5,711/Night For 7 Nights ZA R39,972
10.0
Exceptional
(5 Reviews)
2152.78 ft² 8 Guests 4 Bedrooms 2 Bathrooms
Free Cancellation House
  • Balcony/Terrace
  • View
  • Parking
ZA R5,409/Night For 7 Nights ZA R37,853
10.0
Exceptional
(5 Reviews)
560 ft² 3 Guests 1 Bedroom 1 Bathroom
Ocean View House
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
ZA R1,821/Night For 7 Nights ZA R12,745
10.0
Exceptional
(3 Reviews)
538.2 ft² 8 Guests 2 Bedrooms 2 Bathrooms
Free Cancellation Apartment
  • Balcony/Terrace
  • View
  • Parking
ZA R1,837/Night For 7 Nights ZA R12,860
10.0
Exceptional
(4 Reviews)
2153 ft² 6 Guests 2 Bedrooms 3 Bathrooms
Ocean View Villa
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
ZA R8,933/Night For 7 Nights ZA R62,531
10.0
Exceptional
(2 Reviews)
2690.98 ft² 6 Guests 1 Bedroom 1 Bathroom
Family Friendly Villa
  • Balcony/Terrace
  • View
  • Parking
ZA R4,072/Night For 7 Nights ZA R28,502
10.0
Exceptional
(4 Reviews)
2691 ft² 6 Guests 2 Bedrooms 3 Bathrooms
Ocean View Villa
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
ZA R8,674/Night For 7 Nights ZA R60,711
10.0
Exceptional
(2 Reviews)
538.2 ft² 2 Guests 1 Bedroom 1 Bathroom
Free Cancellation Apartment
  • Pool
  • Balcony/Terrace
  • View
ZA R1,892/Night For 7 Nights ZA R13,241

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Why Choose Rent By Owner for your Leeward Islands Short Term Stay?

What makes our Short Term Stay 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 Leeward Islands

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 Leeward Islands Short-term Rentals

1. What are the top Short Term Stays in Leeward Islands?

There are a lot of options in Leeward Islands. If you plan on staying in the Leeward Islands area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Short Term Stays in Leeward Islands:

2. How many Short Term Stays are available in Leeward Islands?

Currently, the total number of properties listed by RBO in 2026 is over 1 in the Leeward Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Short Term Stays in Leeward Islands. 

More Rentals You May Like Near Leeward Islands

10.0
Exceptional
(4 Reviews)
646 ft² 3 Guests 1 Bedroom 1 Bathroom
Family Friendly Ski Chalet
  • Balcony/Terrace
  • Kitchen
  • Air Conditioner
ZA R4,404/Night For 7 Nights ZA R30,835
10.0
Exceptional
(1 Review)
1937.5 ft² 8 Guests 3 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
ZA R6,601/Night For 7 Nights ZA R46,212
10.0
Exceptional
(4 Reviews)
3 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Private Pool
  • Pool
  • Kitchen
ZA R2,201/Night For 7 Nights ZA R15,409
10.0
Exceptional
(3 Reviews)
8 Guests 3 Bedrooms 2 Bathrooms
Group Friendly Villa
  • Air Conditioner
  • Internet
  • Child Friendly
ZA R7,407/Night For 7 Nights ZA R51,856
10.0
Exceptional
(2 Reviews)
5382 ft² 12 Guests 6 Bedrooms 5 Bathrooms
Ocean View Villa
  • Private Pool
  • Pool
  • Ocean View
ZA R56,952/Night For 7 Nights ZA R398,657
10.0
Exceptional
(2 Reviews)
807 ft² 6 Guests 1 Bedroom 2 Bathrooms
Family Friendly Apartment
  • Pool
  • Balcony/Terrace
  • Kitchen
ZA R7,107/Night For 7 Nights ZA R49,754
10.0
Exceptional
(1 Review)
1722 ft² 6 Guests 3 Bedrooms 2 Bathrooms
Apartment
  • Internet
  • Child Friendly
  • Laundry
ZA R4,245/Night For 7 Nights ZA R29,710
10.0
Exceptional
(1 Review)
5 Guests 2 Bedrooms 1 Bathroom
House
  • Air Conditioner
  • Internet
  • Child Friendly
ZA R3,459/Night For 7 Nights ZA R24,215
10.0
Exceptional
(1 Review)
258 ft² 2 Guests 1 Bedroom 1 Bathroom
Family Friendly House
  • Fireplace/Heating
  • Balcony/Terrace
  • Kitchen
ZA R2,783/Night For 7 Nights ZA R19,481
10.0
Exceptional
(1 Review)
4 Guests 2 Bedrooms 1 Bathroom
Couples Retreat House
  • Internet
  • Child Friendly
  • Laundry
ZA R2,328/Night For 7 Nights ZA R16,303
10.0
Exceptional
(1 Review)
291 ft² 2 Guests 1 Bedroom 1 Bathroom
Ocean View House
  • Pool
  • Ocean View
  • Balcony/Terrace
ZA R2,306/Night For 7 Nights ZA R16,138
9.2
Exceptional
(13 Reviews)
6 Guests 2 Bedrooms 2 Bathrooms
Ocean View House
  • Oceanfront
  • Ocean View
  • Balcony/Terrace
ZA R5,526/Night For 7 Nights ZA R38,681

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