Leeward Settlement vacation rentals
Book unique vacation rentals, houses, and more on Airbnb
Top-rated vacation rentals in Leeward Settlement
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Leeward Settlement vacation rentals
Other great vacation rentals in Leeward Settlement
Guesthouse in Long bay
4.96 out of 5 average rating, 68 reviewsVilla Kendara~BK 7/27 On~Gated~SeaFront GH~View
Oct 19 – 26
Villa in Long Bay Hills
4.98 out of 5 average rating, 84 reviewsVILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY
Oct 8 – 15
Condo in Leeward Settlement
5.0 out of 5 average rating, 21 reviewsGrace’s Condo In Leeward Settlement
Jun 10 – 17
Cottage in Leeward Settlement
4.96 out of 5 average rating, 68 reviewsSandpiper Cottage, minutes from the beach
Jan 25 – Feb 1
Villa in Leeward Settlement
4.93 out of 5 average rating, 15 reviewsOcean Pearl-Brand new villa/pool in governors road
Oct 6 – 13
Home in Leeward Settlement
5.0 out of 5 average rating, 25 reviewsPiccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
Dec 3 – 10
Villa in Leeward Settlement
5.0 out of 5 average rating, 30 reviewsPerroquet | Family Villa near Leeward Beach
Sep 27 – Oct 4
Home in Leeward Settlement
4.98 out of 5 average rating, 50 reviewsCocodemer, a short walk to secluded Pelican Beach.
Nov 9 – 16
Other great vacation rentals in Leeward Settlement
Home in Leeward Settlement
4.95 out of 5 average rating, 61 reviewsPERIWINKLE | Charming Island Home|Near to Beach
Jan 13 – 20
Villa in Caicos Islands
4.94 out of 5 average rating, 87 reviewsCheers 🥂 Villa 🌴
Jan 28 – Feb 4
Villa in The Bight Settlement
4.97 out of 5 average rating, 77 reviewsIdyllic getaway villa | 250 yds to the beach
Jul 14 – 21
Condo in Caicos Islands
5.0 out of 5 average rating, 20 reviewsLil Chill -A cozy 1-Bedroom Unit near the beach
May 15 – 22
Condo in Providenciales
5.0 out of 5 average rating, 42 reviewsBeachy Chic / Grace Bay / Grandview on Grace Bay
Aug 24 – 31
Villa in Long Bay Hills
5.0 out of 5 average rating, 24 reviewsHang Five Surf Villa in Long Bay
Jul 1 – 8
Home in Grace Bay
5.0 out of 5 average rating, 14 reviewsVilla in Providenciales
Jul 27 – Aug 3
Home in Providenciales
4.96 out of 5 average rating, 82 reviewsSunny Paradise Long Bay
Nov 21 – 28
Quick stats about vacation rentals in Leeward Settlement
Total rentals
290 properties
Rentals with a pool
240 properties have a pool
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
5.2K reviews
Nightly prices starting at
€ 103 before taxes and fees
Frequently Asked Questions
Are there Leeward Settlement apartment rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 apartment rentals with pools in Leeward Settlement, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in apartment rentals in Leeward Settlement?
Experience the best of Leeward Settlement with our apartment rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there house rentals with a dedicated workspace in Leeward Settlement?
Yes! Work meets play with ease at over 40 house rentals in Leeward Settlement featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do villa rentals in Leeward Settlement have a bbq area?
Absolutely! We offer over 70 villa rentals with a bbq area in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Leeward Settlement?
Leeward Settlement has more than 70 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do villa rentals in Leeward Settlement have wifi?
Absolutely! We offer over 120 villa rentals with wifi in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do villa rentals in Leeward Settlement have a gym?
Absolutely! We offer over 20 villa rentals with a gym in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Leeward Settlement have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Leeward Settlement. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly house rentals in Leeward Settlement?
Four-legged friends are welcome in Leeward Settlement. Choose from more than 10 house rentals for guests traveling with pets.
What are the most popular amenities for Villa Rentals in Leeward Settlement?
Enhance your stay in our Villa Rentals with the most popular amenities: over 70 homes with a bbq area, over 120 homes with air conditioning, over 120 homes with wifi, over 20 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Grace Bay Vacation rentals
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- Luxury rentals Leeward Settlement
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- Villa rentals Leeward Settlement
- Rentals with a hot tub Leeward Settlement
- Beachfront rentals Leeward Settlement
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- Rentals with a washer and dryer Leeward Settlement
- Rentals with a fire pit Leeward Settlement
- Rentals with a patio Leeward Settlement
- Rentals with pools Leeward Settlement
- Kid-friendly rentals Leeward Settlement
- Rentals with a kayak Leeward Settlement
- Waterfront rentals Leeward Settlement
- Rentals with beach access Leeward Settlement
- Rentals with outdoor seating Leeward Settlement
- Monthly Rentals Leeward Settlement
- Family-friendly rentals Leeward Settlement
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