Pet-friendly holiday rentals in Leeward Settlement

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Top-rated pet-friendly home rentals in Leeward Settlement

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Superhost

Villa in Long Bay Hills

4.92 out of 5 average rating, 12 reviews

Steady Winds Hideaway - Turtle Villa 1 King Bed

Discover your private oasis in our delightful 1-bedroom villa nestled amidst lush greenery. This is a very safe and high end residential neighborhood with patrol cars nearby. Conveniently located just a short stroll away from Long Bay beach, where breathtaking sunrises and unforgettable beach memories await. Our welcome packet is available after booking. It's great for first time visitors to the island! Need more room? Adjacent villas are available to accommodate your larger groups as well.

Guest favourite

Home in Providenciales

4.86 out of 5 average rating, 7 reviews

Sunset Paradise Waterfront Dock SUP + Pontoon Opt

Relax with the whole family at this peaceful oasis. This one level home otherwise known as a ranch bungalow is located on a 2 acre, fully fenced, gated, waterfront property. There is 75 feet of waterfront on the discovery bay canal system which runs north south thru south side marina, Cooper Jack bay beach the new home to The Strand Resort and next to the Wymara Villa's. Southside Marina is home to Bob's Bar, Flamingo Divers & Caicos Adventures. Enjoy snorkeling at Smiths Reef or Coral Gardens.

Superhost

Home in Providenciales

4.86 out of 5 average rating, 73 reviews

Villa View - Sapodilla Beach & Chalk Sound

This HGTV Caribbean Life (Season 8 Episode 1) featured home has water views on 3 sides including a spectacular view of Chalk Sound. This two-level villa is located in the private Harbor Gates neighborhood and is perfect for enjoying all the wonders of Turks and Caicos. Offers direct kayak access to Chalk Sound nature preserve and a short walk to the clear shallow waters of Sapodilla Bay. The newly installed pool was added after HGTV to make this the perfect rental for families and friends.

Guest favourite

Home in Grace Bay

4.96 out of 5 average rating, 52 reviews

Hopewell Villa East/Pool & walk to Gracebay Beach

Located 5 minutes from GraceBay Beach, is Hopewell Villa East. This spacious 2 bedrooms 2 bath house is located just 2 streets from Grace Bay Beach and Coco Bistro Restaurant in a quiet, peaceful and safe residential neighborhood. If you are looking for a new, modern, clean, affordable, kids and family-friendly rental and minutes away from some of the most beautiful beaches in the world, look no further! **We have rental a car and van available. Please let me know of your interested.**

Superhost

Condo in Grace Bay

4.88 out of 5 average rating, 69 reviews

2 Bdrm Condo Grace Bay a quick walk too the Beach

Enjoy your vacation in our spacious newly renovated modern 2 bedroom condo nestled in the heart of Grace Bay. Just a few minutes stroll to Grace bay Beach were sun bathing, swimming and snorkelling awaits you. In the pristine waters of the No. 1 Best Beach in the Caribbean and No. 2 Best Beach in the World in 2020 according to Trip advisor 2020 Travellers’ Choice® Awards. Or take a 5 minute walk and enjoy some retail therapy on Grace Bay strip with our world class cuisine and shopping .

Superhost

Villa in Long Bay Hills

4.92 out of 5 average rating, 116 reviews

VILLA INFINI..PLUNGE POOL.🌴TROPICAL GETAWAY

Take it easy at this dreamy, unique and tranquil getaway. Villa Infini brings privacy and relaxation all in one. Tropical oasis landscaping that will bring you connected with nature and amplify the commencement of your personal getaway. Bali like plunge pool that can create amazing insta-worthy moments. Located in Long Bay! A 5 minute walk to Long Bay Beach, a 5 minute drive to the nearest grocery store and a 5 minute drive to Grace Bay Beach. Everything is 5 minutes away!!

Top Guest favourite

Home in Grace Bay

4.95 out of 5 average rating, 22 reviews

Welcome to Hope's Cottage!

A Cozy Cottage Style Bungalow located in Grace Bay behind Coco Bistro. 3 minute drive and 15 minute walk to the beach and shops, grocery stores and restaurants in the Grace Bay area. 2 bedrooms, 2 full bathrooms, private pool and backyard. Full Kitchen with all utensils and appliances, washer and dryer. Clean, quaint, bright with a beach cottage feel. Safe and quiet residential neighborhood and close to all amenities. We look forward to having you at Hope's Cottage!

Guest favourite

Apartment in Cooper Jack Bay Settlement

4.93 out of 5 average rating, 137 reviews

Poco Villa

Situated in the Discovery Bay Canal "Poco Villa" is a separated complete studio with a view of the canal and access to a freshwater pool and sun decK with bar and barbeque. The accommodation is a one a/c unit with a full kitchen living room and tv. Its a peacefull place surrounded by water. There are two units for rent on this property the other "Coco Villa" both being double occupancy. We do suggest our guests have a vehicle rental to explore the island.

Top Guest favourite

Guesthouse in Leeward Settlement

4.97 out of 5 average rating, 114 reviews

"The Nest Cozy Cottage"

“The Nest” Spacious and modern 1 bedroom cottage sits amongst a well-manicured garden with majestic swaying palms. Less than 150 steps away from the famous Grace Bay Beach. This cozy sanctuary is quiet and bears the true beauty of itself, it’s perfect for honeymooners or if you’re just seeking for some quiet and down time. Complete with high-speed internet, cable TV and all amenities one need for the perfect vacation, The Nest is where you want to be.

Guest favourite

Loft in Long Bay Hills

4.88 out of 5 average rating, 169 reviews

Best deal on island! On the water w/pool!

♥♥ The studio is a secluded get-away place apart from the tourist areas. It overlooks the lake of Juba Sound National Park. The studio is only a 10-minute drive to the world-famous Grace Bay Beach and Longbay Beach (kiteboarding beach)! Restaurants and nightlife are also close by. The studio is in a secure, quiet location where you can relax and enjoy your vacation. This studio is ideal for singles, couples, and kiteboarders.

Superhost

Villa in Turtle Cove

4.81 out of 5 average rating, 70 reviews

Nirvana's Nest

Nirvana's Nest is a spacious and bright villa which offers a wrap around deck and full ocean views from all rooms. Let the beaming sun and magic of the moonlight dance on your dining room table. Toast Marshmallows in the back yard on your outdoor fireplace. The Nest is conveniently located in Turtle Cove, which is a 5 minute drive to Babalua Beach and Grace Bay Beach.

Superhost

Condo in Grace Bay

4.91 out of 5 average rating, 186 reviews

22 Middle of Gracebay, Heated Pool, Gated Condo.

Granvia is center of Gracebay, very close to Gracebay Gourmet, restaurant, there is beach access close by, 6min walking to World no.1 Gracebay Beach. Security gate, privacy, Full Kitchen with Air flyer, Washer and Dryer Wi-Fi (fastest speed on island 50MBPS) 70" Samsung 4K TV with Samsung sound bar, Live TV, Movie, TV show