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.

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Guest favorite

Guesthouse in Long bay

4.96 out of 5 average rating, 68 reviews

Villa Kendara~BK 8/10 On~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

Jan 25 – Feb 1

$325 per night

Guest favorite

Condo in The Bight Settlement

4.97 out of 5 average rating, 76 reviews

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 21 – 28

$400 per night

Guest favorite

Guest suite in Long Bay Hills

4.98 out of 5 average rating, 44 reviews

SunSeaSand Poolside Studio Unit A - Long Bay Hills

SunSeaSand, your premier boutique resort, offers a prime location just a brief 3-minute stroll away from the stunning Long Bay Beach and 5-minute joyride to Grace Bay's restaurants and resorts, positioning it as the destination in Turks and Caicos for your upcoming retreat. Whether you're seeking a romantic getaway, a memorable family vacation, or a trip with friends, SunSeaSand guarantees delight with our convenient location and thoughtful amenities—ensuring an effortless, pleasurable stay.

Mar 28 – Apr 4

$234 per night

Guest favorite

Condo in Providenciales

5.0 out of 5 average rating, 42 reviews

Beachy Chic / Grace Bay / Grandview on Grace Bay

Voted #1 Beach Destination in the World! We are located directly in the Heart of Grace Bay Beach...Location, Location, Location! With only 18 Beach Front units , you have privacy, location, and convenience. The "Grandview on Grace Bay" is an all Beach Front resort located directly on Grace Bay Beach, and included as one of the most beautifully placed properties on the island. Beach chairs are located at the pool and beach for your convenience, and placed out for you each day! Enjoy!

Aug 21 – 28

$650 per night

Guest favorite

Apartment in Providenciales

5.0 out of 5 average rating, 9 reviews

Tropical Paradise Beach Frnt Penthouse Pool SUV K4

Esencia sits directly on Long Bay. This quiet and rural area has three miles of open white sand beach and sparkling clear turquoise water. It is ideal for the person who wants to be close to nature and seeks peace, quiet and natural beauty. This is the ‘wild’ side of Provo - natural, undeveloped, and simply close to nature and the sea. Here the beach is wide and flat with pure white sand. Our many palm trees provide shade and beauty and add to the feeling of privacy and naturalness.

Jul 30 – Aug 6

$625 per night

Guest favorite

Condo in Grace Bay

4.9 out of 5 average rating, 20 reviews

Grace Bay Beach Front 2 BDR/ 2BTH Condo

Grandview is a boutique, oceanfront, private condominium building of 18 units on beautiful Grace Bay, with direct access to the expansive, sandy beach. Our 2nd floor Unit is contemporary, completely refurbished, with 2 bedrooms, 2 bathrooms and a fully equipped kitchen. The covered terrace/balcony provides dining, lounging, and BBQing, all overlooking the gardens, pool and beautiful ocean. Guests can enjoy a new, fully equipped gym, bikes, kayaks, paddle boards and beach toys.

Sep 7 – 14

$728 per night

Guest favorite

Villa in Providenciales

4.95 out of 5 average rating, 91 reviews

Villa DelEvan 4D / 1-bedrm villa

Centrally located on the Grace Bay Beach, a perfect place for luxury, rest & tasting the best island cuisine. Close to everything you need for a great vacation: Walking dist. from 4 restaurants - Mango Reef, Shark Bite, Baci & Simone’s. 10 min drive to the famous island Fish Fry, 15 min drive to the Airport, 5 min drive to the supermarket. Gated property, private parking, 24hr security. Boating/fishing/sightseeing/wind surfing & more. Water sports pick-up on property.

Aug 24 – 31

$595 per night

Guest favorite

Condo in Providenciales

5.0 out of 5 average rating, 15 reviews

Luxury Condo Somerset on Grace Bay!

Ocean Aria Residence-luxury condo at the exclusive Somerset Resort on Grace Bay. Open concept style living/dining area, spacious master bedroom with king bed, walk in closet and en suite bath.The second bedroom is located on the lower level with two twin beds and cozy sitting area. Condo's 2nd bathroom is located on the upper level. Queen size sofa bed in the living room can easily accommodate an extra guest.This is a ground floor unit and it has a view of a croquet lawn.

Nov 6 – 13

$720 per night

Guest favorite

Condo in Wheeland Settlement

4.94 out of 5 average rating, 109 reviews

Couple’s Retreat! Ocean, pool, and garden views!

Free cancellation! Oceanside oasis with pool, ocean and garden views. Escape to the pristine blue waters at Northwest Point. Pool, ocean and hot tub within steps of condominium. Free access to kayaks and SUPs, snorkel gear, owners beach chairs, loungers and miles of secluded beach for walking, exploring or beachcombing. Airport is appoximately a 15 minute drive from Northwest Point Condominiums (formerly Northwest Point Resort).

Aug 13 – 20

$233 per night

Superhost

Apartment in Caicos Islands

4.89 out of 5 average rating, 18 reviews

Spectacular view 2 bedroom condo Grandview 205

Enjoy island beachfront living at the Grandview in a beautiful 2nd floor unit with family or friends at this modern, stylish place. Steps away from Grace Bay Beach and vibrant turquoise colored ocean, within walking distance to many fine dining & casual island eateries, fully stocked supermarket and shops! 1800 sqft of luxury living space in the heart of Grace Bay

May 5 – 12

$825 per night

Guest favorite

Apartment in Providenciales

4.97 out of 5 average rating, 217 reviews

The Old Beach House 2 bedroom

We have two Garden apartments downstairs that we renovated. One two bedroom two bathroom, and one 1 bed 1 bathroom. Just a 3 minute walk from a white sandy beach. You can walk to Da Conch shack restaurant along the beach in 5-10 minutes. Off the beaten trail. We live upstairs with our 2 potcakes Buster and Boxer.

Apr 19 – 26

$392 per night

Superhost

Guest suite in Long Bay Hills

4.78 out of 5 average rating, 144 reviews

Sea La Vie - Beachside Studio Unit #3

Located in a secluded Beachside property, 500 ft from Long Bay Beach, and 5-minutes drive from Grace Bay Resorts and shops, this private Studio unit with it own private entry and patio, can accommodate up to 2 guests, with a queen size bed. It is located on the ground floor, roughly 10 yards from the pool.

Sep 18 – 25

$161 per night