Waterfront vacation rentals in Leeward Settlement

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Leeward Settlement

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Guest favorite
Home in TC
The LightHouse Cottage- 2 bed private villa *pool*
"The Lighthouse" is your own private cottage, with a lighthouse tower and stellar ocean views! Built in 2019, it is nestled within the quiet neighborhood of Thompson's Cove, only 5 minutes from the airport, and 10 minutes from pretty much anywhere else on Provo. We are located right on the canal and a short 3 minute walk to the beach. Enjoy our kayaks, SUPs and snorkel gear. Take a leisurely 15 minute walk down the beach, and you will find "Da Conch Shack", known for their rum punches!
Feb 7 – 14
$519 per night
4.97 out of 5 average rating, 152 reviews
Superhost
Apartment in Providenciales
Beautiful Sunset Villa with Infiniti Pool
Beautiful Sunset Villa is nestled in the heart of Chalk Sound, Providenciales where guests are guaranteed a home away from home experience. It enjoys unique trade winds in a private and safe community close to restaurants and the beach. Beautiful Sunset Villa provides views of the famous Chalk Sound turquoise waters, featuring a private Infiniti pool, extensive pool deck, a dedicate kitchen and dining area with full air conditioning. View the video below! https://youtu.be/13YyhYECZQA
Sep 20 – 27
$227 per night
4.92 out of 5 average rating, 146 reviews
Guest favorite
Apartment in Caicos Islands
Palm Point Loft - Waterfront Canal
Palm Point Loft is the perfect spot for you to come and experience the peace and beauty of Providenciales. Located canal side, this private and spacious 2 bedroom second floor apartment is centrally located, 5 mins to Grace Bay Beach, restaurants and grocery stores. The unit is airy and bright offering a private sanctuary for guests to relax on their own balcony - the perfect place to unwind and enjoy the gentle breeze off the water while watching the sunset.
Apr 22 – 29
$275 per night
4.85 out of 5 average rating, 126 reviews

Popular amenities for Leeward Settlement waterfront rentals

Waterfront apartment rentals

Guest favorite
Apartment in Providenciales
Serene Caribbean Deluxe Beach Front Studio Pool K2
May 1 – 8
$368 per night
4.87 out of 5 average rating, 60 reviews
Superhost
Apartment in Caicos Islands
Spectacular view 2 bedroom condo Grandview 205
Jun 10 – 17
$825 per night
4.85 out of 5 average rating, 13 reviews
Guest favorite
Apartment in Providenciales
Pelican View #4 amazing beach views
Sep 23 – 30
$147 per night
5.0 out of 5 average rating, 34 reviews
Superhost
Apartment in Providenciales
Sunny Daze - Condo By the Water
Aug 13 – 20
$395 per night
4.96 out of 5 average rating, 47 reviews
Superhost
Apartment in Providenciales
2 Bdrm, Stunning Marina View | On The Water
Jul 6 – 13
$626 per night
5.0 out of 5 average rating, 4 reviews
Guest favorite
Apartment in Kew Town Settlement
Island's Eye Queen Studio Reserve II/vehicle opt
Apr 28 – May 5
$162 per night
4.85 out of 5 average rating, 20 reviews
Superhost
Apartment in The Bight Settlement
Exquisite Yacht Club Townhome
May 14 – 21
$714 per night
New place to stay
Superhost
Apartment in Venetian Road Settlement
Flamingo lake 2-bedroom suite
Sep 7 – 14
$545 per night
New place to stay
Apartment in Providenciales
Beautiful Apt near Beach, No Hidden Fees
Aug 31 – Sep 7
$325 per night
4.93 out of 5 average rating, 41 reviews
Guest favorite
Apartment in Venetian Road Settlement
OCEAN ORCHID
Apr 17 – 24
$592 per night
4.94 out of 5 average rating, 81 reviews
Apartment in Long Bay Hills
Charming waterfront cottage in wildlife preserve
Apr 29 – May 6
$468 per night
5.0 out of 5 average rating, 3 reviews
Apartment in Providenciales
Precious Lodging
Mar 19 – 26
$222 per night
4.67 out of 5 average rating, 30 reviews

Waterfront house rentals

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 Long Bay Hills
Vision Kite- Longbay beach house
Oct 5 – 12
$765 per night
4.82 out of 5 average rating, 17 reviews
Guest favorite
Home in Providenciales
Private beach, Pool & Master Suite
Oct 19 – 26
$600 per night
5.0 out of 5 average rating, 8 reviews
Superhost
Home in Venetian Road Settlement
Brighter Days Villa
May 21 – 28
$442 per night
4.91 out of 5 average rating, 11 reviews
Guest favorite
Home in Long Bay Hills
Private water front villa – 5 mins from Grace Bay!
Jan 16 – 23
$400 per night
5.0 out of 5 average rating, 18 reviews
Guest favorite
Home in Providenciales
TC Villas -Sea Edge Villa -Romantic & Luxurious
Oct 19 – 26
$709 per night
5.0 out of 5 average rating, 10 reviews
Guest favorite
Home in Whitby
Flamingo's Nest at Whitby Beach (North Caicos)
Nov 22 – 29
$193 per night
4.99 out of 5 average rating, 70 reviews
Superhost
Home in Providenciales
Villa View - Sapodilla Beach & Chalk Sound
Jul 21 – 28
$481 per night
4.87 out of 5 average rating, 54 reviews
Superhost
Home in Cooper Jack Bay Settlement
New 2-bedroom Sunset villa!
Jun 3 – 10
$484 per night
New place to stay
Superhost
Home in Providenciales
Villa Thalassa - High above Chalk Sound Cozy Cove
Nov 25 – Dec 2
$900 per night
New place to stay
Guest favorite
Home in TC
*NEW* Harbour House - 2 Bd 2.5 Bath Waterfront
May 4 – 11
$932 per night
5.0 out of 5 average rating, 12 reviews

Waterfront condo rentals

Guest favorite
Condo in Wheeland Settlement
Couple’s Retreat! Ocean, garden & pool views!
Aug 16 – 23
$243 per night
4.95 out of 5 average rating, 105 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 Providenciales
The Yacht Club-Relaxed Vibe-1 BR-Pool-Beach
Jan 12 – 19
$244 per night
4.98 out of 5 average rating, 47 reviews
Guest favorite
Condo in Grace Bay
Luxury Grace Bay Beachfront - Perfection!
Nov 1 – 8
$675 per night
5.0 out of 5 average rating, 12 reviews
Guest favorite
Condo in Grace Bay
Grace Bay Beach Front 2 BDR/ 2BTH Condo
Aug 27 – Sep 3
$802 per night
4.89 out of 5 average rating, 18 reviews
Guest favorite
Condo in Providenciales
Luxury 2-Bed Condo - Somerset on Grace Bay
Jun 9 – 16
$796 per night
5.0 out of 5 average rating, 15 reviews
Guest favorite
Condo in Turtle Cove
Queen Angel Condo with Pool and Ocean View
Sep 12 – 19
$266 per night
4.93 out of 5 average rating, 41 reviews
Guest favorite
Condo in Providenciales
Romantic Escape with Stunning Pools & Sunset Views
Aug 31 – Sep 7
$375 per night
4.92 out of 5 average rating, 97 reviews
Guest favorite
Condo in Grace Bay
Splendid condo walks out to Grace Bay Beach
Feb 24 – Mar 3
$978 per night
4.95 out of 5 average rating, 55 reviews
Guest favorite
Condo in providenciales
The Yacht Club ≋ 2 Bedroom (E1)
Jan 3 – 10
$807 per night
4.91 out of 5 average rating, 46 reviews
Superhost
Condo in Whitby
Sanctuary by the Sea
Jul 6 – 13
$180 per night
4.93 out of 5 average rating, 27 reviews

Quick stats about waterfront rentals in Leeward Settlement

Total rentals

40 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Rentals with a pool

40 properties have a pool

Family-friendly rentals

40 properties are a good fit for families

Total number of reviews

720 reviews

Nightly prices starting at

$230 before taxes and fees

Destinations to explore