Holiday rentals with a pool in Leeward Settlement

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Top-rated rentals with a pool in Leeward Settlement

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

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Top guest favourite

Villa in The Bight Settlement

4.98 out of 5 average rating, 128 reviews

Grace Bay villa | Pool | 3min walk to Beach & Reef

A modern beach villa with its own private pool. Sleeps up to 4 adults in separate rooms. Just 250 steps from the azure blue waters and soft white corals sands of Grace Bay beach. In a quiet off-street location. Perfect for a romantic getaway. With its quiet secluded garden and pool area, many of our guests come to celebrate birthdays, anniversaries, and honeymoons in full privacy. Walk to coral reef snorkeling in 3 mins plus several restaurants. Large grocery supermarket & shops are nearby.

Guest favourite

Cottage in Long Bay Hills

4.94 out of 5 average rating, 106 reviews

Flame Tree Cottage|Ocean view&pool.Walk to beach

Built in 2013. 1 bedroom 2 bathroom cottage with PRIVATE POOL. Sunrise & ocean view from the front deck and only 1/4 mile to the beach. Perfect for 2, but can sleep up to 6. Full kitchen, 2 bathrooms + outdoor shower. No bathtub. Propane Grill. AC in master bedroom. WIFI throughout & local cell provided. This quaint clutter-free 1200 square foot home is surrounded by indigenous foliage, cactus', succulents and native stonework. A rental car is recommended to explore all the island has to offer!

Guest favourite

Apartment in Providenciales

4.9 out of 5 average rating, 115 reviews

Amazing Grace Bay Views, Terraces Pools & Location

This Pristine, private poolside studio condo is beautiful, turquoise, peaceful & tranquil - as is Turks & Caicos. It is special - cool, casual, chill and comfortable - like the Provo vibe. Live the Villa Estate lifestyle like its your own estate, pool, 6,000 sq ft deck with chaise lounges and umbrellas, and Hot Tub! Enjoy cocktails & dine on your private veranda or large terrazza deck & watch the sunrise/sunset while enjoying the 180 degree panoramic views of Grace Bay. ! In a word, Paradise.

Superhost

Flat in Providenciales

4.91 out of 5 average rating, 182 reviews

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

Superhost

Apartment in Providenciales

4.83 out of 5 average rating, 134 reviews

Modern Garden Corner Suite Condo In Lush Garden🌿🌴🌊

I'm happy to share my professionally re-designed, newly renovated modern, corner unit suite. It's a relaxing oasis with lush palm trees and landscaping surrounding my balcony. My space is open, 1350 Sq Ft one bedroom condo plus the second “bedroom” is in the open studio style like a hotel. The suite has huge glass doors and many windows that allow the beautiful sunshine in all day. The resort has a beautifully landscaped terrace & two massive pools, hot tub & gym. All new furnishings.

Guest favourite

Home in Grace Bay

4.92 out of 5 average rating, 113 reviews

Tropical Carabas Villa!

Peaceful Villa Near Grace Bay Beach🌴 Relax in this serene villa with a full kitchen and outdoor grill, perfect for dining in. Just a minute’s drive or 15-minute walk to Grace Bay Beach and steps from Coco Bistro. The villa includes air-conditioned bedrooms, a new living room AC, private pool, beach towels, cooler, and lounge chairs. Surrounded by lush landscaping with great Wi-Fi, it’s your perfect peaceful retreat. Enjoy the best of comfort and convenience during your stay!🌴

Top guest favourite

Guest house in Long Bay Hills

4.99 out of 5 average rating, 171 reviews

Juba Sunset

Waterfront Private apartment that is fully furnished. Private deck. fantastic views overlooking Juba Sound. within 7mins to Grace Bay, world famous Grace Bay Beach and shops. Very quiet and safe area. Infinity edge pool included. Glorious sunsets. BBQ on the waterfront. Only a couple of mins away from popular Kite Surfing spot. There is also a Kayak available for guests use down on the waterfront. This is the only rental unit on property, you will be the only guests.

Superhost

Cottage in Providenciales

4.8 out of 5 average rating, 5 reviews

Swan Cottages

This charming pair of newly renovated waterfront cottages with a brand new 28-foot pool is a 2-minute walk from the scenic Sopadilla Bay Beach and Las Brisas Restaurant and walking distance to the exclusive Taylor Bay Beach. Located directly on the Chalk Sound National Park with views of its breathtaking blue waters, this beautiful, idyllic location is perfect for kayaking and paddle boarding. Rare sightings of dolphins have been made in this area.

Guest favourite

Villa in Long Bay Hills

4.84 out of 5 average rating, 117 reviews

Long Bay Beach Private Pool Villa with VIP Extras!

A luxurious stay in a 2-story villa w/high ceilings, huge windows & designer finishes - 3 stylish bedrooms all with ensuite bathrooms & superb ocean views from upstairs - You'll have a gorgeous private pool & sun lounge area all to yourselves - 5-min drive to world-famous Long Bay Beach & 10-min to the famous Grace Bay - Fully-fenced in and gated property - Good fiber Wi-Fi, laptop-friendly workspaces for remote worker & washer & dryer.

Guest favourite

Apartment in Wheeland Settlement

4.95 out of 5 average rating, 121 reviews

Couple’s Retreat with ocean views and hot tub!

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).

Top guest favourite

Home in TC

4.98 out of 5 average rating, 179 reviews

“The Lighthouse”, Private Pool, Ocean Views, Beach

The Lighthouse private cottage features a tower fashioned after a lighthouse affording stellar ocean views Private pool just outside living room doors! Deck & patio lounge w/ BBQ for fun & sun Nestled in the Thompson Cove Canal area and just a 3-minute walk to the beach WiFi, Smart TV with Netflix. Book now for a relaxing yet adventurous getaway! Kayaks, SUPs & snorkel gear included!

Top guest favourite

Home in Grace Bay

4.97 out of 5 average rating, 115 reviews

Charming Gecko House Island Vibes - Grace Bay

Affordable and charming house situated in a quiet residential neighborhood in Grace Bay just a short 8 minute walk (less than a 3 minute ride) to the world famous Grace Bay Beach. And yes, we have a pool!!! Ideal for solo travelers and a couple! Close to the beach and steps away from the very popular Coco Bistro Restaurant and Coco Van!