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Vacation rentals with a pool in Leeward Settlement

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Leeward Settlement

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Superhost
Villa in Providenciales
Gardenia Villa
Gardenia Villa. This contemporary Oasis is perfect for a small family or couples, located steps away from the world’s #1 Grace Bay Beach. The villa entrance opens to a bright entryway leading to the living room area with a spectacular view through a wall of sliding doors to the covered deck and pool. The open plan is perfect for entertaining with the dining and kitchen area all part of the living space. The upstairs is flanked by 2 queen sized bedrooms and ensuite bathrooms.
Dec 25 – Jan 1
$700 per night
4.9 out of 5 average rating, 110 reviews
Guest favorite
Condo in Providenciales
★★★★★ Modern Condo | Amazing Pool | On Site Spa
• Located in the exclusive Northern section of Grace Bay • Ground level with direct pool access • Hot tub • Highest Rated Spa on Island • Fully equipped kitchen • Private front patio + grill • Garage parking for 1 car • Onsite washer + dryer • Fitness center access • Queen sofa bed with extra linens in living room • Onsite full service spa • Porta-Crib • WiFi • Beach toys, coolers, DVD collection, & games • Take-one/leave-one liquor cabinet • Buy Travel Insurance
Jan 6 – 13
$564 per night
4.9 out of 5 average rating, 189 reviews
Guest favorite
Home in Grace Bay
Follow Your Dreams Villa!
This a New Super Cool Upper Floor Loft Bedroom for one couple. Private Pool! Downstairs full Kitchen and 65" Giant TV entertainment area! Full Kitchen, Dishwasher, Laundry, all you need & more. Just behind Coco Bistro/Coco Van and 2 minutes by car to Beach! Grace Bay Beach that is! This is a Totally Private Villa for 2 Guests Only! Just landscaped with Palms around the Private pool! Great Location & New! Thanks for checking out "Follow Your Dreams!
Feb 3 – 10
$399 per night
4.98 out of 5 average rating, 104 reviews

Popular amenities for Leeward Settlement rentals with a pool

House rentals with a pool

Guest favorite
Home in Providenciales
Villa Cocuyo Micro Villa with pool
Feb 25 – Mar 4
$375 per night
4.96 out of 5 average rating, 284 reviews
Guest favorite
Home in TC
The LightHouse Cottage- 2 bed private villa *pool*
Feb 7 – 14
$519 per night
4.97 out of 5 average rating, 152 reviews
Guest favorite
Home in Providenciales
Modern Caribbean 1 - Breathtaking Views & Pool
May 17 – 24
$573 per night
4.96 out of 5 average rating, 140 reviews
Guest favorite
Home in Leeward Settlement
Cocodemer, a short walk to secluded Pelican Beach.
Sep 5 – 12
$330 per night
5.0 out of 5 average rating, 46 reviews
Guest favorite
Home in Leeward Settlement
Piccolo Ponte -Waterfront 3BR Caribbean Villa-Pool
May 15 – 22
$736 per night
5.0 out of 5 average rating, 23 reviews
Guest favorite
Home in Leeward Settlement
Ocean Pearl-Getaway 2 bed home/pool nearby beach
Jul 14 – 21
$473 per night
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Providenciales
Sunny Paradise Long Bay
Aug 8 – 15
$428 per night
4.97 out of 5 average rating, 78 reviews
Guest favorite
Home in Providenciales
Sea Villa @ The Sun and Sea Villas
Jul 4 – 11
$249 per night
5.0 out of 5 average rating, 16 reviews
Guest favorite
Home in Leeward Settlement
Pelican Paradise Villa - Leeward Beach
Jun 5 – 12
$893 per night
4.95 out of 5 average rating, 21 reviews
Guest favorite
Home in Grace Bay
Welcome to Hope's Cottage!
Oct 5 – 12
$405 per night
4.91 out of 5 average rating, 11 reviews
Guest favorite
Home in Grace Bay
Private Family Villa in Grace Bay w/pool + yard
Feb 14 – 21
$818 per night
4.95 out of 5 average rating, 85 reviews
Guest favorite
Home in Grace Bay
THE GECKO HOUSE awesome pool 🌞 - Grace Bay
May 26 – Jun 2
$275 per night
4.93 out of 5 average rating, 99 reviews

Condo rentals with a pool

Guest favorite
Condo in Grace Bay
22 Middle of Gracebay, Heated Pool, Gated Condo.
Jun 30 – Jul 7
$281 per night
4.96 out of 5 average rating, 137 reviews
Guest favorite
Condo in Grace Bay
Luxury 1 Bedroom - Central Grace Bay
Jul 29 – Aug 5
$325 per night
5.0 out of 5 average rating, 138 reviews
Superhost
Condo in Providenciales and West Caicos
🌴 YOUR FABULOUS APARTMENT IN PARADISE 🌞
Oct 24 – 31
$225 per night
4.85 out of 5 average rating, 380 reviews
Guest favorite
Condo in Grace Bay, Providenciales
1 Bedroom Luxury Grace Bay Condo
Dec 25 – Jan 1
$625 per night
4.99 out of 5 average rating, 107 reviews
Guest favorite
Condo in Turtle Cove
🏖🏝Modern Luxury Ocean View One Bedroom Condo🏖🏝
Dec 4 – 11
$270 per night
4.95 out of 5 average rating, 133 reviews
Guest favorite
Condo in Providenciales
Paradise Nest Penthouse-Million Dollar Ocean Views
Aug 6 – 13
$591 per night
4.93 out of 5 average rating, 113 reviews
Superhost
Condo in The Bight Settlement
Modern Boutique Style Condo and La Vista Azul
Jun 7 – 14
$256 per night
4.86 out of 5 average rating, 117 reviews
Guest favorite
Condo in Leeward Settlement
Grace’s Condo In Leeward Settlement
Oct 31 – Nov 7
$269 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Condo in Grace Bay
BEACH FRONT on Grace Bay Gorgeous 1 bedroom 2 bath
Aug 11 – 18
$478 per night
4.92 out of 5 average rating, 39 reviews
Guest favorite
Condo in The Bight Settlement
Coral Condo on Grace Bay Beach
Dec 3 – 10
$499 per night
4.97 out of 5 average rating, 72 reviews
Guest favorite
Condo in Caicos Islands
Lil Chill -A cozy 1-Bedroom Unit near the beach
Sep 7 – 14
$195 per night
5.0 out of 5 average rating, 14 reviews
Guest favorite
Condo in Providenciales
NEW! Romantic Getaway, 3 Mins to the Beach !
Sep 3 – 10
$299 per night
5.0 out of 5 average rating, 5 reviews

Quick stats about vacation rentals with a pool in Leeward Settlement

Total rentals

260 properties

Rentals with dedicated workspaces

110 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

210 properties are a good fit for families

Total number of reviews

3.4K reviews

Nightly prices starting at

$20 before taxes and fees

Destinations to explore