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Five Cays Settlement Rentals

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280 Houses

TC Villas // Beach Villa Shambhala // Luxurious Fully-Equipped Estate

Five Cays Settlement villa

5 bedrooms / 6 bathrooms / sleeps 16

Price per night from

$2,914

The Babbington Villa

Five Cays Settlement villa

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$916

Partial Oceanview Studio Plus Free Breakfast now 'til end June

Five Cays Settlement studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

Price per night from

$504

Partial Oceanview Studio *LongBay & Free Breakfast now 'til end June

Five Cays Settlement studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

Price per night from

$567

Oceanfront PH, Free Breakfast Now 'Til End of June, 2022

Five Cays Settlement condo

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 26 minutes

Price per night from

$2,519

Watersports, Ocean View & Free Breakfast now 'til end June!

Five Cays Settlement condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 26 minutes

Price per night from

$1,031

Finest Oceanfront Resort Luxury w/Free Breakfast now 'til end June

Five Cays Settlement condo

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 26 minutes

Price per night from

$1,489

Oceanfront & Infinity Pool View! Free Breakfast now 'til end June!

Five Cays Settlement condo

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 26 minutes

Price per night from

$1,489

Luxurious Stay at Oceanfront Resort + Free Breakfast now 'til end June

Five Cays Settlement condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$882

Lap of Luxury, Astonishing Ocean Views & Free Breakfast now 'til end June

Five Cays Settlement apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 26 minutes

Price per night from

$882

Stay in #1 LifeStyle Resort in TCI w/Free Breakfast now 'til end June

Five Cays Settlement condo

1 bedroom / 2 bathrooms / sleeps 3

Responds fast! avg. 26 minutes

Price per night from

$630

Oceanfront Resort w/2 Pools & Free Breakfast now 'til end June

Five Cays Settlement condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 26 minutes

Price per night from

$1,008

BISHOP HOUSE

Five Cays Settlement house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$201

Luxe Condo with Watersports Onsite & Free Breakfast now 'til end June

Five Cays Settlement condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 26 minutes

Price per night from

$1,008

Impressive Oceanfront Condo w/Breakfast Daily now 'til end June

Five Cays Settlement condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 26 minutes

Price per night from

$1,031

Long Bay Stay w/Pools, Kitesurfing & Free Breakfast now 'til end June

Five Cays Settlement apartment

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 26 minutes

Price per night from

$882

Kiteboarding Paradise *LongBayBch w/Free Breakfast now 'til end June

Five Cays Settlement condo

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 26 minutes

Price per night from

$1,260

Partial Oceanview Studio + Free Breakfast now 'til end June

Five Cays Settlement studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

Price per night from

$504

Partial Oceanview Plus Watersports & Free Breakfast now 'til end June

Five Cays Settlement studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

Price per night from

$504

Studio w/ Partial Sea View *LongBay & Free Breakfast now 'til end June

Five Cays Settlement studio

Studio / 1 bathroom / sleeps 2

Responds fast! avg. 26 minutes

Price per night from

$504

Exquisite Oceanfront Resort & Free Breakfast now 'til end June

Five Cays Settlement condo

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 26 minutes

Price per night from

$882

Great rentals within 20 miles that match your search

Stirling House

Grace Bay house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$2,290

Villa Oasis - an incredible hexagon shaped villa on the beach in Grace Bay

Providenciales house

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$2,209

Olde Beach House 2 double ensuites close to beach

Providenciales apartment

2 bedrooms / 2 bathrooms / sleeps 4

“Just the best vacation ever” We originally rented the 1 bedroom apt but were upgraded by our lovely host to the 2 bedroom. The apt was spacious with 2 baths, all the kitchen equipment you would need, a washer/ dryer and wifi. We were able to walk to the beach within 3 minutes or with our rental car explore all the other glorious beaches on the island. Our first night we walked to the famous "conch shack" for traditional cracked conch-yum. Other nights we cooked in after gathering supplies at the well stocked local IGa or tried a few of the marvelous local restaurants for the rum punches and sunsets. I really appreciated the quiet simplicity of the old beach house which really is a misnomer. Emma,our host, was so helpful with island information and willingly answered so many questions. She treated us to papayas off the trees just outside our room and made us feel welcome and comfortable in so many ways. I can't wait to come back.

Responds fast! avg. 1 hour 28 minutes

Price per night from

$287

BAREFOOT PALMS, Kick Back and Relax Tiki Style!

Providenciales villa

3 bedrooms / 2 bathrooms / sleeps 6

“Fabulous Villa” I recently spent 4 days in this lovely home and highly recommend it. I have stayed at many villas in the Caribbean and none have been as well maintained or had as much attention to detail shown as Barefoot Palms. The landscaping is gorgeous with lots of palms and flowering trees. The back yard is to die for...nice pool, lounge chairs, sitting area and the best part of all - a great Tiki bar. The outdoor space is great for kids and adults, and is very private. Inside, the first thing you notice is how fresh and clean the house smells. Not musty like some villas. The layout is great and the decorating is perfect..casual and beachy, yet upscale. You can tell the owners take a lot of pride in their home. The kitchen is well stocked, there are TVs and DVD players in every room, there is an alarm system in the house, and beach chairs, coolers and umbrellas are provided. The villa is located in a quiet, gated neighborhood and is a short walk to a great beach or a short drive to the main section of Grace Bay Beach. The owners are great to work with - very responsive and can answer any and all questions about the island. I can't wait to go back!

Price per night from

$630

BEACH FRONT PROPERTY! 6 Bedroom on Grace Bay Beach ,Sleeps 14

Grace Bay villa

5 bedrooms / 7 bathrooms / sleeps 14

“What an awesome Place!” Top notch place to stay, every imaginable amenity, incredible white sand beach out your back doorstep. Incredible landscaping throughout the entire property. Long back patio overlooking the pool and beach. What a great place for the entire family to hang out and relax and the best beds I have ever slept in. I highly recommend!

Responds fast! avg. 1 hour 14 minutes

Price per night from

$4,580

Casa de Isle right off Taylor Bay

Providenciales villa

3 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$442

Sunset Point Oceanfront Villa - Taylor Bay Beach - Every room has an ocean view!

Providenciales villa

4 bedrooms / 5 bathrooms / sleeps 10

“Vacation home in Paradise!” Wonderful home, everything you need; private, gated community. Spectacular view; Ocean front-loved it

Responds fast! avg. 1 hour 16 minutes

Price per night from

$1,019

BEST OF ROYAL WEST .... OCEAN FRONT Premium Suite on Grace Bay

Grace Bay hotel apartment

1 bedroom / 1 bathroom / sleeps 4

“Paradise Found” Just returned from 6 nights at the Calabash Suite and would like to add my enthusiastic and positive comments to those of previous renters. The suite is wonderful, as nice and reasonably priced an accommodation as I think you could find on Provo. The furnishings are comfortable and tasteful, the kitchen well-equipped, the sheets and towels all of high quality and in great condition. The fact that the cleaning crew came in and performed a mid-stay cleaning helped to maintain its neat and clean condition so it always seemed fresh. The media center set-up includes a large flat screen to use in the event you wish to watch TV or a video. There's even an extra phone for free calls to the states. Andrew has gone to great lengths to make his guests feel comfortable and his gestures of providing detailed written information/instructions as well as a card and other amenities are welcome touches. We loved the location, virtually across the street from Coco Bistro and a short drive from other restaurants, the Bakery, food store and other shopping. As the resort is located near the eastern end of the beach, there isn't ever a lot of beach traffic so you never feel as though you're competing for space with others or part of a bustling resort. The resort's pool, bar and restaurant, beach facilities, towels and chairs are all available for use so you get to enjoy those resort amenities as well. As others have pointed out, the best feature of the Suite might be the veranda, which directly overlooks the beach and affords spectacular sunset photo ops. I must have taken the same photos every day our entire stay - they were just too beautiful to pass up. Andrew was a pleasure to work with, well-organized in his rental process and quick to follow-up whenever I had questions. I will - or have - made arrangements to return. Thanks, Andrew, for sharing this little part of Paradise.

Price per night from

$745

Leisure in Paradise

Providenciales apartment

1 bedroom / 1 bathroom / sleeps 3

“Brilliantly friendly place in an excellent location” We spent 2 weeks in La Casita, 2 adults and 2 children under 5, rented the ground floor apartment, which is at the front of the property, facing east. The room was spacious enough for the spare bed and the baby cot and there was plenty of storage for our clothes, toiletries and other things. The room was equipped with tv, Wi-Fi, fridge, high powered microwave, kettle and cutlery/plates. All beds had netting over them and the room had aC as well as a ceiling fan. The bathroom had a great shower and two basins, which was very handy with two kids around. The hot water seem to never run out, which is handy when the whole family has 2 showers a day. There was a brand new soap in the bathroom as well as kitchen towels and insect repellent. The veranda was enclosed, perfect for late night drinks without the night bugs, and sunny breakfasts in the morning. We had 2 beach chairs, a beach umbrella and kids' beach toys at our disposal. There was a bbq, mini electric stove and pots for us to use. The pool was well kept and very pleasant. The best beach on Earth was literally 5 minute walk away from the house, so if you want to pop back to the house for something you don't need a 30 minute round trip. La Casita is located in the safe Leeward area of the island, a quiet and guarded residential area, a far difference from the hustle and bustle of the busy resorts, yet close enough to town if you wanted to eat out. If you walk about 10 minutes on the beach you end up at a resort beach (which are still public), you can walk into their restaurant for a lovely meal. The hosts were very accommodating, approachable and friendly. At the time of booking they were more than happy to answer any of my questions, and I had a lot of them, and they did not disappoint. I have already recommended La Casita to a friend, who booked a week in September. I would not hesitate to recommend this friendly, quiet and lovely place to anybody.

Price per night from

$228

Romantic vacation at La Casita

Providenciales studio

Studio / 1 bathroom / sleeps 2

“Loved evey minute” We spent 11 wonderful days in the upper unit , and loved every minute of it . The owners were very friendly , but not imposing . The landscaping, pool area was lovely . Short walk to a deserted beach .Four minute drive to Cafe Market at Blue Haven for breakfast with the friendliest staff and best prices on island . This was our fourth trip to Provo , and cannot say enough accolades about the island . In general, hotels are terribly overpriced .La Casita is very reasonably priced , but at the same time is very high quality . Car is a must, as is the case most anywhere in Provo if you are to experience it at its best . There is a lower unit available that seemed very sufficient if you are traveling with friends and need additional space, or are on a lesser budget.

Price per night from

$258

SunSea houses (Sea house)

Providenciales villa

2 bedrooms / 1 bathroom / sleeps 4

“Turk and Caicos Island” The property is wonderful, it is away from the beaten path, but yet with in 5 mintnutes of most things. The kitchen is very well equipped and any issue a addressed immediately. To clarify, we broke a shower head, within an hour it was repaired. No muss non fuss. The owners and the property management team were great to deal with.

Price per night from

$287

SunSea houses (Sun house)

Long Bay Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$401

Romantic cottage 3 mins from stunning Grace Bay beach.

Providenciales cottage

3 bedrooms / 2 bathrooms / sleeps 5

“"Total Bliss"” My husband and I had a wonderful, relaxing vacation spent at "Columbus Cottage" The whole experience; the Island, the house/pool, amazing beach, the restaurants and the people really exceeded our expectations! We immediately felt so comfortable and relaxed in your peaceful Island paradise. The location was perfact - even without a car, the taxi works ok- we now know what to expect for next time! It's Island Time... Spent the mornings at the beach, short walk nice way to start the day. The beach is amazing and private... afternoons poolside :), and went into town for dinner usually timing with a sunset view over the water. Many wonderful restaurants to choose from! We didnt feel the need to do any tours, golf or explore as expected since we were perfactly content with the total bliss right there within easy reach! Denise was very warm and welcoming, genuinely concerned for our well being - she thoughtfully had a bouquet of flowers and an anniversary card awaiting us when we arrived! - and was nice enough to make arrangements with a taxi driver for our needs throughout the week. We loved the beautiful furnishings in the 'cottage' - But have to say, the private pool was our favorite perk! The setting is very private even though there are neighbors on both sides -can't see homes from property. Thank you also for providing the Wifi - It was helpful to be able to check in. The home also provided plenty of security if that is a concern - although it's in a quiet neighborhood - we felt fine.. This was our 1st "home" rental so we were initially a bit cautious but Jane was very personable, responsive and provided us with plenty of info in advance to satisfy our concerns...seem like lovely people. Looking forward to a return visit!

Responds fast! avg. 2 hours 55 minutes

Price per night from

$407

Windhaven 2 Bedroom Villas on Long Bay Beach

Long Bay Beach villa

2 bedrooms / 2 bathrooms / sleeps 4

“Exceptional!” Loved our time at windhaven! There are so many amazing things about this place, I hope I will not forget any in my review. The villas are extremely well equipped and decorated simply and tastefully. They have state of the art appliances (including a washer, dryer and Weber BBQ), surround sound with multiple docking stations, large storage facilities on the deck for outdoor equipment like kites and boards, great amenities, a cooler for day trips, beautiful and comfortable furniture, emergency kits, kayaks, there is a shared pool and the grounds are kept beautifully. The manager is fantastic and always makes sure that all your needs are met. The location is fantastic! The beach is extremely safe and quiet. The water is calm and even on windier days, very safe for children. Never any undertow. The clarity is unmatched. There is a grocery store located 5 min away by car. It has everything you can imagine. Great vegan selection with amazing produce and beautiful fish and meat options. The prices are reasonable (we spend Christmas in Barbados, so the pricing TCI are much cheaper!)The shopping is right around the corner from the gourmet grocery store. Windhaven is amazing for kiters but is also perfect for non-kiters. It would be an ideal place for an intimate wedding. The grounds are beautiful and the beach, in my opinion, much nicer and appropriate for a wedding than Garce Bay. We have already booked for the next few years!!! It is that amazing.

Price per night from

$1,088

Beachfront Casual Luxury....8 bedrooms

Long Bay Beach villa

4 bedrooms / 10 bathrooms / sleeps 16

“Perfect spot for family and friends” Loved my vacation at Windhaven. Beautiful grounds, stunning beachfront villas with cooling ocean breezes and a perfect soft sand beach that stretches for miles. Lots of space to lounge by the pool or in a hammock or on the beach decks. Ideal for paddling or kiting. I will be going back with friends and family.

Price per night from

$4,809

Villa Wyakha - 1 BR On Beach - Ocean view - Pool - Tiki Huts (Unit # 2)

Long Bay Beach villa

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$501

The Breeze House , 3bedroom canal front with pool

Providenciales villa

3 bedrooms / 2 bathrooms / sleeps 6

“Stimulating and relaxing; it washed all the stresses away” The house is modern with clean lines, built on top of a hill. The views from the infinity pool and deck look over the wild salina with the sea in the background whose everchanging colours we tried unsuccessfully to photograph. No-one overlooks the property, and yet it is within 5-10mins drive of the famous Grace Bay beach and all the restaurants and bars. There is an even shorter 2min drive to another long empty beach. The agent was extremely good giving us all the information and help we needed to make our stay a delight. We took the ferry to another island and explored. We had a snorkelling trip. We thought about fishing or horse riding or cycle riding or playing golf but were quite happy just exploring the local culture and relaxing in the wonderful clear blue water of the sea or our pool.

Responds fast! avg. 1 hour 28 minutes

Price per night from

$344

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