Leeward holiday rentals

We found 1,638 holiday rentals — enter your dates for availability

Discover a selection of 63 homes, 54 apartments and other holiday rentals in Leeward that are perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include cable TV and a washer and dryer. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.

Popular Leeward destinations on Stayz

Gustavia

Gustavia

Find spaces that suit your style

  • Peace of mind
    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time
    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home
    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less
    More space, more privacy, more amenities — more value

Choose a holiday rental for your Leeward getaway

Learn about the unique charm of Leeward with a stay in a holiday home rental. This city has something for everyone. Orient Bay Beach and Maho Beach are just a couple of the must-see attractions in the area. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Exploring the natural landscape of Leeward

Whether you're an adventurous traveller or just want to take in the scenery, Leeward is a great place to get out in nature. Here are some of the area’s most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Orient Bay Beach (16.5 mi / 26.6 km)
  • Maho Beach (19.5 mi / 31.3 km)
  • Flamands Beach (0.5 mi / 0.8 km)
  • St. Jean Beach (1.1 mi / 1.8 km)
  • Lorient Beach (2.1 mi / 3.4 km)
  • Gouverneur Beach (2.5 mi / 4 km)

Transport options to and around Leeward

The nearest airport is in Gustavia (SBH-Gustaf III), located 1 mi (1.6 km) from the city centre.

Frequently asked questions

What is the most popular type of holiday home accommodation in Leeward?
Villas are the most popular style of holiday home in Leeward, according to our data. Even if you’ve got a different idea about what you want, Stayz has holiday homes in loads of shapes and sizes. Filter our options to find your perfect Leeward pad.
How much does it cost to rent a holiday home in Leeward?
Length of stay, property type and time of year are some factors that can affect the price of a holiday home. Simply enter your travel dates to find your ideal escape. From cosy chalets to expansive villas, all Stayz holiday homes offer amazing value.
How much does it cost to rent a beach house in Leeward?
When you travel and the style and size of the property will influence how much you’ll pay for your beachside holiday home. Enter your Leeward travel dates to view your options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the amenities and features you want in your holiday home.
What are popular home amenities in Leeward?
A fridge, a private pool and a microwave oven are rated the most popular home amenities in Leeward. Whether you’re travelling alone, with your significant other or a group of family members, Stayz will help you find a holiday home that fits your style with all the conveniences you’re looking for.
Are there large group holiday homes in Leeward?
Take your pick of 104 holiday homes in Leeward that can accommodate a group of 10 or more people. Whether you’re organising a trip with the family or a special event like a birthday party, there’s plenty of space to get your loved ones together under the same roof.
Can I find two-bedroom holiday homes in Leeward?
You can select from 341 two-bedroom holiday homes in Leeward. Settle the kids into the second room or fill it with a couple of your best friends. There’s plenty of space for whoever’s fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Leeward?
There are 182 holiday homes with WiFi in Leeward. If you want to disconnect from the world during your escape, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Stayz.
How old do you have to be to rent a holiday home in Leeward?
Age restrictions can differ between properties on Stayz, so double-check the rules of the holiday home in Leeward you’re considering. But typically, it’s 16, 18 or 21.
How long can I rent a holiday home in Leeward for?
The length of time you can book a holiday home in Leeward is up to the property. Just enter your selected dates to display a list of options offering extended stays. With tons of features such as air conditioning and laundries, as well as some offering weekly or monthly discounts, you’re sure to find the perfect place to call your home away from home in Leeward.

Explore destinations around Leeward

More Holiday Rentals ideas

Hat Head Holiday Rentals
Standard Link for Hat Head
Hobart Holiday Rentals
Standard Link for Hobart
Thredbo Holiday Rentals
Standard Link for Thredbo
Yamba Holiday Rentals
Standard Link for Yamba
Tuncurry Holiday Rentals
Standard Link for Tuncurry
Port Macquarie Holiday Rentals
Standard Link for Port Macquarie
Castlemaine Holiday Rentals
Standard Link for Castlemaine
Sawtell Holiday Rentals
Standard Link for Sawtell
South Perth Holiday Rentals
Standard Link for South Perth
Caloundra Holiday Rentals
Standard Link for Caloundra
Bonaire Holiday Rentals
Standard Link for Bonaire
Sorrento Holiday Rentals
Standard Link for Sorrento
Port Fairy Holiday Rentals
Standard Link for Port Fairy
Metung Holiday Rentals
Standard Link for Metung
Camp Holiday Rentals
Standard Link for Camp
Fremantle Holiday Rentals
Standard Link for Fremantle
Exuma Holiday Rentals
Standard Link for Exuma
Noosa Holiday Rentals
Standard Link for Noosa
Safety Beach Holiday Rentals
Standard Link for Safety Beach
St. George Holiday Rentals
Standard Link for St. George
Killcare Holiday Rentals
Standard Link for Killcare
Patonga Holiday Rentals
Standard Link for Patonga
Bunbury Holiday Rentals
Standard Link for Bunbury
Jimmys Beach Holiday Rentals
Standard Link for Jimmys Beach
Harbor Island Holiday Rentals
Standard Link for Harbor Island
Sunshine Coast Holiday Rentals
Standard Link for Sunshine Coast

People also search for

Tortola Villas
Standard Link for Tortola
Western Australia Farmstay
Standard Link for Western Australia
Pet-friendly holiday rentals in Merimbula
Standard Link for Merimbula
Exuma Cottages
Standard Link for Exuma