Discover your perfect Leeward Settlement Vacation Rentals.
Discover Your Perfect Leeward Settlement Vacation Homes
Best Vacation Homes in Leeward Settlement
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- 249 ft² Villa
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Leeward Settlement Luxury Rentals
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Leeward Settlement Pet Friendly Vacation Rentals
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Leeward Settlement Large Vacation Homes
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- 4799 ft² House
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Why Choose Rent By Owner for your Leeward Settlement Vacation Rental Homes?
What makes our Vacation Rentals special?
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How to Book Your Leeward Settlement Vacation Rental Home
What's our booking process?
Booking Steps
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Explore and book the perfect rental in Leeward Settlement
Common Vacation Rentals Amenities
What amenities can you expect?
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
Other Places to Stay in Leeward Settlement
Leeward Settlement Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Leeward Settlement?
There are a lot of options in Leeward Settlement. If you plan on staying in the Leeward Settlement area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Leeward Settlement:
- VillaKendara~DEALS 9/13-10/21~BeachFront~Private~Gated GuestHouse~Panoramic View
- Byculla 4 BR Villa - Canal Front
- Popular ocean front villa now offering 20% off a night for the next five months.
- Villa Vivace - New Luxurious Seaside Home
- SunsetOne Beach Villa - Golf Cart 6 seats, Kayaks, SUPs; Free Beach Set Up
- Kick Back and Relax Tiki Style!
- Private Resort Style Villa and Pool close to beaches
- Leeward Canal, Grace Bay - Kayaks, SUPs & Beautiful Pool - Villa Cariad
- Beauty and the Beach!
- Barefoot Bliss - Leeward villa with private pool & short walk to the beach
2. How many vacation rentals have private pools in Leeward Settlement?
There are 164 vacation rentals with private pools near Leeward Settlement. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Leeward Settlement are best for families?
If you are looking for a family-friendly vacation home in Leeward Settlement, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Leeward Settlement:
4. How many Rentbyowner vacation rentals are available in Leeward Settlement?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 365 in the Leeward Settlement area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Leeward Settlement.
Leeward Settlement Top Rated Vacation Rentals
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