50 Best Anguilla Villas on Holiday Lettings - Vacation rentals

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West End Village
17 properties
Island Harbour
14 properties
Apartments The Valley
11 properties
Blowing Point
10 properties
Long Bay Village
8 properties
Sandy Hill Bay
8 properties
Little Harbour
7 properties

Anguilla

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2,204 Vacation rentals

(6) Very Good 

15

Anguilla Vacation villa rental

West End Village / Shoal Bay West

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Child friendly
The CATALINA Shoal Bay Villa is a new ocean view, Caribbean style, high quality, affordable development on ¼ acre of land. The villa is rented for holidays or longer term.The unique private residence villa is elegant, inviting, exceptional with conveniences designed for …see more

from $150 / night

$995 / week

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from $150 / night

66

Shoal Bay Village Vacation villa rental

Anguilla / Shoal Bay Village

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 0.25 mi
  • Child friendly
“Dreamcatcher” – the clue is in the name…! ​On a low ridge overlooking the splendour that is Shoal Bay East, one of the top ten beaches in the world. Sit back and gaze over the unobstructed and breathtaking views of the turquoise Caribbean waters. Let your mind wan …see more

from $825 / night

$5,775 / week

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avg. 2 hours 44 minutes

from $825 / night

26

Anguilla Vacation home rental

Anguilla / West End Village

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
2 bedroom house in typical creole amid a large garden features. large spacious kitchen and very airy 5mn walk from beautiful beaches paradisiacal diving equipment (masks snorkels and fins) ballad possibility horse painted gallery; ure and crafts breakfast and meals on r …see more

from $113 / night

$787 / week

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from $113 / night

40

Vacation home in West End Village

Anguilla / West End Village

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
old house creole with art gallery located 5 min has oied of paradisiacal beaches 2 bedrooms with 2 double beds and an additional ciuchage 1 spot on the couch 1 bathroom as well as an outdoor shower spacious kitchen and very airy great relaxing hammock corner terrace the …see more

from $188 / night

$999 / week

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from $188 / night

(2) Excellent 

20

Vacation villa with golf nearby in Anguilla

West End Village / Meads Bay Pond

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Golden sun, aquamarine sea, azure sky, soft white sand, beautiful unspoilt and uncrowded beach at Rendezvous Bay Beach, Bow Green Villa with swimming pool , fantastic haute cuisine of Anguilla near by,and indulgent luxury Spa near by are waiting for you. Bow Gre …see more

from $907 / night

$6,345 / week

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from $907 / night

(12) Excellent 

29

Vacation villa with swimming pool in Anguilla

Anguilla

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Take in the beautiful panaromic views of St. Martin, the beautiful ocean and parts of the island while sitting on the deck drinking your morning coffee or cocktail! Large open air living space with dining room, sitting area as well as chaises to enjoy your day. Two la …see more

from $500 / night

$3,500 / week

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from $500 / night

(2) Excellent 

20

Vacation villa in Anguilla

Anguilla / Blowing Point

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Are you an eco-friendly person? Most of know we have to start thinking about the environmental impact of many parts of our lives, including travel. This is why the Villa Solaire Standard is the environmentally friendly traveler's ideal find. Set on an astonishingly beau …see more

from $500 / night

$3,500 - $14,000 / week

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from $500 / night

30

Condo rental in Anguilla

Anguilla / The Valley

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Imagine waking up in the morning and gazing across the deep blue Caribbean Sea to the distant island of St. Martin, shuffling onto one of two roomy balconies, cup of java in hand, feeling the sea breeze caress & smelling the fresh salt air - sun shining down on you as y …see more

from $321 / night

$1,282 / week

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from $321 / night

26

Anguilla Vacation villa rental

Anguilla / Long Bay Village

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Zebra is perched atop magnificent Meads' Bay Hill and just a short stroll away from one of the finest beaches in the Caribbean. The home offers the discerning vacationer a blend of cool, eclectic design in a peaceful and tranquil setting. The villa is built on two …see more

from $620 / night

$4,340 - $12,600 / week

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from $620 / night

(6) Excellent 

28

Vacation apartment in Anguilla

Anguilla / Island Harbour

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 3 mi
  • Air conditioning
  • Private garden
Quiet neighborhood. Fully furnished, spacious air conditioned private apartment on Captains Ridge, Island Harbour with a panoramic view of the Atlantic Ocean. Very spacious apartment (over 2,000 square ft). Enjoy the ocean view from the master bedroom, master bathroom, …see more

from $135 / night

$945 / week

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from $135 / night

15

Blowing Point Vacation villa rental

Anguilla / Blowing Point

10 18 5 nights min

  • 10 bedrooms
  • Sleeps 18
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
To avoid cancellation please contact us before request booking to confirm the availability! Within the sea-side garden is a dining pavilion with seating for 10 and barbeque dining area on a private beach with beautiful white sand and direct access to the crystal clear s …see more

from $1,100 / night

$7,700 / week

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from $1,100 / night

(8) Very Good 

12

Home rental in Anguilla

Anguilla / East End Village

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly
Great for groups! Enjoy breathtaking ocean views, prevailing sea breezes and stargazing nightly on the wrap-around porch. Minutes away from the world's most unspoiled and secluded beaches, crystal clear water, hiking trails and snorkeling. This space is unique because …see more

from $325 / night

$2,275 / week

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avg. 1 hour 59 minutes

from $325 / night

(3) Excellent 

21

Vacation villa in Anguilla

Anguilla / South Hill

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
Exclusively situated for viewing this most iconic scenic spot in Anguilla, this modern penthouse atop a luxurious gated resort home offers the best in luxury, location and lifestyle. Awaken to a beautiful view of St. Martin or the Bay; enjoy a light breakfast made from …see more

from $549 / night

$3,843 / week

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from $549 / night

(12) Very Good 

24

Vacation apartment in Anguilla

Anguilla / Island Harbour

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Child friendly
Perfect for 2 Vacation Rental Near Island Harbor and Shoal Bay Beaches James Place Apartments are located in a quiet secure and well maintained community. It is a perfect base from which guests can enjoy the sun, beaches, and relax. The rooms are spacious, modern a …see more

from $110 / night

$750 / week

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from $110 / night

45

Anguilla Vacation villa rental

Anguilla / West End Village

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
  • Ask about pets
Going beyond luxury, the eight-bedroom Villa Nevaeh sets an entirely new bar in terms of opulence and amenities. Located along Long Bay in Anguilla, it features a full household staff, a golf simulator, a tennis and basketball court, and more. The Balinese inspired desi …see more

from $5,200 / night

$36,400 - $143,750 / week

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from $5,200 / night

(2) Excellent 

22

Anguilla Vacation villa rental

Anguilla / West End Village

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Ask about pets
Located in Maundays Bay in Anguilla, Harmony at Sheriva villa successfully harmonizes traditional Caribbean style with touches from the Far East. Known for its pristine white sand beaches and clear turquoise seas, Anguilla offers a casual island tempo so you can get the …see more

from $5,000 / night

$35,000 / week

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avg. 42 minutes

from $5,000 / night

(3) Excellent 

32

Vacation villa rental

Anguilla / Long Bay Village

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Beach Palm Villa is the BEST VALUE VILLA rental at Meads Bay in Anguilla * 2 en-suite bedrooms * private swimming pool * steps from Meads Bay Beach - one of the world's best beaches * beach chairs and umbrellas set up on Meads Bay Beach * fully equipped granite counter …see more

from $695 / night

$4,865 - $6,265 / week

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from $695 / night

(15) Excellent 

92

Vacation villa in Anguilla

Anguilla / The Valley

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Oceana, Anguilla offers tranquility, romance, and casually elegant tropical living. The villa's open design maximizes sea views and ocean breezes, inviting you to experience a private vacation retreat. Set on a breezy hillside overlooking picturesque Crocus Bay, this br …see more

from $475 / night

$3,325 - $5,215 / week

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avg. 3 hours 6 minutes

from $475 / night

20

Anguilla Vacation villa rental

Anguilla / Blowing Point

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
If you are part of the green revolution and you want to travel but also support those aligned with your cause, then the stunning Villa Solaire Premier in Anguilla is for you. Sitting over Lockrum Bay and offering truly unprecedented views of the sea and the islands in t …see more

from $900 / night

$6,300 - $21,000 / week

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from $900 / night

49

Vacation villa with swimming pool in Anguilla

Anguilla / Long Bay Village

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Twin Palms VIllas at Meads Bay Feature Two Villas on One Estate: *Coconut Palm (3 bedrooms / 4 bathrooms) *Beach Palm (2 bedrooms / 3 bathrooms) *Connected to each other by a lit garden path *These are the BEST VALUE VILLA RENTALS at Meads Bay. Each villa features: * p …see more

from $1,050 / night

$7,350 - $9,450 / week

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from $1,050 / night

51

Anguilla Vacation villa rental

Anguilla / Blowing Point

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
Large, luxurious, and ideally located are just a few of the terms that can be used to describe the Villa Beaches Edge properties. A group of two upscale villas, they are set directly on the waterfront of Anguilla\'s Pelican Bay and offer amazing sea views, as well as ap …see more

from $1,400 / night

$9,800 - $49,000 / week

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from $1,400 / night

(5) Excellent 

45

Vacation villa with swimming pool in Anguilla

Anguilla / Long Bay Village

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Coconut Palm Villa is the BEST VALUE VILLA rental at Meads Bay in Anguilla. * 3 en-suite bedrooms * private swimming pool * steps from Meads Bay Beach - one of the world's best beaches * beach chairs and umbrellas set up on Meads Bay Beach * fully equipped granite count …see more

from $795 / night

$5,565 - $7,350 / week

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from $795 / night

24

Vacation villa with indoor pool in Anguilla

Anguilla / West End Village

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Octagon' is new to the rental market and its unique design is welcoming, homely, elegant and attention to detail can be seen throughout. As soon as you enter one of the entrance gates you are greeted with a sense of tranquility. With three (3) bedrooms all with ensuit …see more

from $400 / night

$2,800 / week

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from $400 / night

(3) Excellent 

22

Anguilla Vacation villa rental

Anguilla / West End Village

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Bow Green is walking distance to Rendezvous Bay Beach which is one of the best beaches in Anguilla. Great views of St Martin and close to Anguilla Great House, Sun Shine Shack and Cuisinart Golf Resort. It is three bedroom villa and sleeps six and has a very private l …see more

from $1,199 / night

$8,390 / week

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from $1,199 / night

22

Little Harbour Vacation villa rental

Anguilla / Little Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to our retreat, Lockrum Point Villa (LPV). Literally, steps from Lockrum Bay, this amazing two-level Seaside villa sets the stage for luxurious relaxing and entertaining. The villa comes with breath-taking views of the sea and St. Martin, a private pool and a ra …see more

from $500 / night

$3,500 / week

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from $500 / night

14

Vacation villa in West End Village

Anguilla / West End Village

5 4 Min stay varies

  • 5 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
Antilles Pearl at Altamer is an extravagant three-floor villa reserved only for those who appreciate the finer things in life. Located in lovely Shoal Bay West on the island of Anguilla, this massive seaside estate boasts amazing views of the crystal clear Caribbean Sea …see more

from $1,929 / night

$13,503 / week

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Responds fast!
avg. 43 minutes

from $1,929 / night

14

Vacation villa in Anguilla

Anguilla / West End Village

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Antilles Pearl at Altamer is an extravagant three-floor villa reserved only for those who appreciate the finer things in life. Located in lovely Shoal Bay West on the island of Anguilla, this massive seaside estate boasts amazing views of the crystal clear Caribbean Sea …see more

from $3,214 / night

$22,498 / week

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Responds fast!
avg. 42 minutes

from $3,214 / night

11

Villa rental in Anguilla

Anguilla

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Ask about pets
7 Palms Villa design is Caribbean Casual with Breathtaking views that juts out for an incredibly living experience. The Caribbean Island interiors and living spaces are perfect for a tropical vacation. With spacious indoor and outdoor living and dining areas, 7 Palms An …see more

from $1,995 / night

$13,965 - $36,015 / week

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from $1,995 / night

(4) Excellent 

24

The Valley Vacation villa rental

Anguilla / The Valley

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Like an ivory sculpture on the majestic cliffs overlooking Anguilla’s Little Bay, the six bedroom Ani South has been designed to offer an unforgettable Caribbean vacation. Unique to Ani South is its configuration, accessible to guests via an elevator, roll-in showers, p …see more

from $6,400 / night

$44,800 / week

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avg. 42 minutes

from $6,400 / night

(5) Excellent 

19

Vacation villa in Anguilla

Anguilla / South Hill

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Exclusively situated for viewing this most iconic scenic spot in Anguilla, this modern penthouse atop a luxurious gated resort home offers the best in luxury, location and lifestyle. Awaken to a beautiful view of St. Martin or the Bay; enjoy a light breakfast made from …see more

from $399 / night

$2,793 / week

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from $399 / night

25

Vacation villa with swimming pool in Anguilla

Anguilla / Island Harbour

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
Villa Soleil at Captains Bay is a fully air conditioned villa with luxury appointments throughout. . From every vantage point, the villa has the most spectacular views of any villa on the island. Breathtaking views of the ocean from the front and rear of the villa; vi …see more

from $950 / night

$6,650 / week

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from $950 / night

11

Condo rental in The Valley with shared pool

Anguilla / The Valley

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Fantastic, well-appointed 2BR 2BA condo available for December 2017. This property is centrally located on the Island of Anguilla and is convenient to some of the most sought-after beaches and restaurants in the Caribbean. Ocean Terrace Condos overlooks the Island of …see more

from $250 / night

$1,750 / week

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from $250 / night

0

Vacation villa with shared pool in Anguilla

Anguilla

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
Additional amenities: Computer Available …see more

from $3,500 / night

$24,500 - $77,000 / week

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from $3,500 / night

33

Villa rental in Anguilla

Anguilla

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
Set right along the sands of Meads Bay in Anguilla, the stunning and contemporary Villa The Beach House offers classic tropical living with an added note of luxury. From the pool terrace to the interiors, you will find this villa a remarkable experience, and ideal setti …see more

from $10,714 / night

$75,000 - $168,000 / week

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from $10,714 / night

30

Vacation villa in Anguilla

Anguilla

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
Villa Le Bleu on Anguilla is a magnificent high-end property right on the water overlooking wonderful views of neighboring St. Martin. This fabulous estate is situated in a prime location on a lushly landscaped ten-acre homesite at the edge of Little Harbour Bay. Two pr …see more

from $7,750 / night

$54,250 - $126,126 / week

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from $7,750 / night

19

Anguilla Vacation villa rental

Anguilla / Blowing Point

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
With more than three private acres of tropical gardens and grounds, and more than seven thousand square feet of upscale living space, the Villa Paradise on Blowing Point in Anguilla easily matches its name. However, the views of St. Martin in the distance, the long stre …see more

from $1,200 / night

$8,400 - $47,005 / week

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from $1,200 / night

33

Vacation villa in Anguilla

Anguilla

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets
The Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first …see more

from $2,000 / night

$14,000 / week

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avg. 42 minutes

from $2,000 / night

(3) Very Good 

17

Vacation villa rental

Anguilla / Blowing Point

7 12 Min stay varies

  • 7 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets
Treat yourself to the holiday you deserve in sunny Anguilla. Villa Paradise is a seven bedroom villa located in the coveted Blowing Point area of this idyllic tropical island. The layout and enormous deck spaces of this waterfront residence assure that you will enjoy a …see more

from $2,000 / night

$14,000 / week

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avg. 42 minutes

from $2,000 / night

48

Anguilla Vacation villa rental

Anguilla

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly
A true villa resort escape on the island of Anguilla, CeBleu is set along the scenic beauty of Crocus Bay and provides up to eight, full-size villas for guests to enjoy. Each villa has six bedrooms and six baths, and can accommodate up to 10 adults and 2 children at onc …see more

from $454 / night

$3,180 - $39,865 / week

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from $454 / night

33

Vacation villa rental

Anguilla

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets
The Bird of Paradise Villa is a true gem for the connoisseur. Named one of the “Top 20 Villas in the World” by Islands Magazine, this Anguillan oasis offers the exclusivity of a boutique hotel, the privacy of an enclave and the top tier services and amenities of a first …see more

from $1,925 / night

$13,475 / week

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Responds fast!
avg. 42 minutes

from $1,925 / night