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Beachfront vacation rentals in Leeward Settlement

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Top-rated beachfront rentals in Leeward Settlement

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

Guest favorite
Guesthouse in Long bay
Villa Kendara~3/30-4/6 OPEN~Gated~SeaFront GH~View
Private~Gated~Seafront~Unique Loc~Beautiful by Nature~Panoramic Water & Bay Views~A+ Sunrises/Sunsets~5 min to Grace Bay, Stores, Restaurants, Marina~Exclusive ”Johnson Guide to Provo & Car Travel Guide~LOFT FOR KIDS~Fully Equipped~Loaded with Supplies~Pool, CoralStone Deck, Pergola for Shade, BBQ, AC, Fans, TV, DVD, Phone, Wi-Fi, Snorkel Gear, Portable Beach Chairs & Umbrella~Island Partner Discounts for Car Rental, Water Sports/Eco-Tours, Cruise, Massages~Swim, Snorkel, KiteBoard, PaddleBoard
Jul 13 – 20
$310 per night
Guest favorite
Condo in The Bight Settlement
Coral Condo on Grace Bay Beach
• Gorgeous 1 bedroom oceanfront condo on the top floor of Coral Gardens on Grace Bay Beach • Stunning ocean view • Relaxed, modern coastal decor • Newly renovated, fully appointed kitchen & stainless steel appliances • Centrally located with world-renowned snorkeling & water sport activities • 2 pools • Complimentary Beach chairs & towels • High Speed Internet/Cable, SmartTV • Direct Beach access, close walk to Wymara Resort, West Bay Club, Beach House, & Windsong • Somewhere Cafe Restaurant
Oct 15 – 22
$499 per night
Guest favorite
Condo in Grace Bay
BEACH FRONT on Grace Bay Gorgeous 1 bedroom 2 bath
Welcome to Coral Gardens! We have a fully renovated 1 bedroom condo overlooking the turquoise sea in Grace Bay! Relax on our spacious patio and listen to the waves roll in! We have a washer and dryer in-suite. Additional guests can use the queen sized sofa bed and full bathroom. Enjoy snorkeling right outside and enjoy lunch at "Somewhere Cafe". Relax, rejuvenate and get away from real life! *Note* Currently there is construction next door and we have discounted our rates (as shown)
Feb 19 – 26
$649 per night

Popular amenities for Leeward Settlement beachfront rentals

Pet-friendly beachfront home rentals

Superhost
Home in Providenciales
Villa View - Sapodilla Beach & Chalk Sound
Sep 7 – 14
$482 per night
Superhost
Villa in Caicos Islands
Aventine Villa
Aug 23 – 30
$700 per night
Superhost
Vacation home in Wheeland Settlement
Lovely Cozy Villa Vibes and Rental car
Feb 4 – 11
$182 per night
Apartment in Providenciales
Jade’s Hideaway-marina condo…walk to the beach
Apr 16 – 23
$333 per night
Apartment in Providenciales
Yacht Club, Easy Walk to Beach, W/Pool & Views
Oct 22 – 29
$383 per night
Home in Providenciales
Silver Palm Beach House T&C Villa
Jun 24 – Jul 1
$835 per night
Villa in North Caicos
Baldwin Camp Rental -Villa #1
Oct 9 – 16
$225 per night
Guesthouse in The Bight Settlement
Pink Heart Bungalow
May 6 – 13
$500 per night
Condo in Wheeland Settlement
lovely one bedroom apartment.
Aug 22 – 29
$580 per night
Guest favorite
Room in Providenciales
A Room with a View
Sep 27 – Oct 4
$251 per night
Resort in Long Bay Hills
Oceanview Studio @LongBay Beach!
Jan 29 – Feb 5
$826 per night
Villa in North Caicos
Baldwin Camp Rental- Villa #2
May 5 – 12
$225 per night

Beachfront home rentals with a pool

Guest favorite
Guest suite in Long Bay Hills
SunSeaSand Poolside Studio Unit A - Long Bay Hills
Jun 9 – 16
$204 per night
Guest favorite
Cottage in Providenciales
The Hideaway / Modern Zen Studio with Private Pool
Oct 25 – Nov 1
$302 per night
Guest favorite
Villa in Providenciales
‘My Little Hideaway’ at Lucayan Cays
Sep 6 – 13
$300 per night
Guest favorite
Condo in Turtle Cove
Queen Angel Condo with Pool and Ocean View
Nov 18 – 25
$266 per night
Superhost
Bungalow in Providenciales
Harbour House Sapodilla Bay - See our Difference
Jan 16 – 23
$599 per night
Guest favorite
Guesthouse in Providenciales
SLP-Gorgeous 1BR Cottage, Pool, 3min to Beach,
Jan 27 – Feb 3
$220 per night
Guest favorite
Condo in Wheeland Settlement
Newly Renovated 2 Bedroom/2 Bath Beach Front Condo
Jul 14 – 21
$400 per night
Superhost
Cottage in Whitby
Caicos Cottage, 2 bdrm/2 bath beachfront w/pool
Jan 21 – 28
$756 per night
Superhost
Vacation home in Wheeland Settlement
Beautiful 2 bed/2 bath Oceanview Beachfront Resort
Sep 13 – 20
$225 per night
Guest favorite
Condo in Wheeland
Oceanfront two bedroom condo with stunning views
Feb 19 – 26
$400 per night
Superhost
Condo in Wheeland Settlement
Palmas Del Mar Oceanview and Northwest Point Resort
Feb 9 – 16
$275 per night
Superhost
Condo in Wheeland Settlement
Stunning one bdrm ocean front views-pool, hot tub
Jul 15 – 22
$300 per night

Private beachfront home rentals

Superhost
Apartment in Providenciales
Beachfront Rental Beach Hut
Jul 15 – 22
$175 per night
Guest favorite
Apartment in Providenciales
Pelican View #4 amazing beach views
Sep 19 – 26
$138 per night
Guest favorite
Home in Whitby
Flamingo's Nest at Whitby Beach (North Caicos)
Jun 30 – Jul 7
$171 per night
Guest favorite
Guesthouse in Bottle Creek
Creek View Cottage on beautiful Bottle Creek
Oct 28 – Nov 4
$135 per night
Superhost
Condo in Whitby
Sanctuary by the Sea
Jan 20 – 27
$180 per night
Cottage in Leeward Settlement
Silver Palms Cottage
Jan 9 – 16
$735 per night
Guest favorite
Condo in Grace Bay
Beachfront Studio, Royal West Indies Resort Bldg 1
Aug 14 – 21
$316 per night
Guest favorite
Condo in Grace Bay
Prime Grace Bay 2 BR with Beach, Pool & Tennis
Aug 1 – 8
$349 per night
Guest favorite
Villa in Providenciales
Sorrento Beach front Luxury Villa
Sep 4 – 11
$845 per night
Guest favorite
Home in Long Bay Hills
Private Pool Villa Ocean View Steps Long Bay Beach
Nov 18 – 25
$971 per night
Guest favorite
Condo in Caicos Islands
Luxury Beachfront 2 bed/2 bath condo on Grace Bay
Aug 14 – 21
$775 per night
Home in Long Bay Hills
Valhead Villa
May 14 – 21
$780 per night

Quick stats about beachfront rentals in Leeward Settlement

Total rentals

30 properties

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Rentals with a pool

30 properties have a pool

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

240 reviews

Nightly prices starting at

$20 before taxes and fees

Destinations to explore