50 Best Anguilla Villas on Holiday Lettings - Vacation rentals

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West End Village
19 properties
Island Harbour
18 properties
Apartments The Valley
16 properties
Blowing Point
12 properties
Long Bay Village
10 properties
Sandy Hill Bay
9 properties
Little Harbour
9 properties
Shoal Bay Village
6 properties
East End Village
6 properties

Anguilla

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1,565 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

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 $105 / night

$732 / week

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avg. 3 hours 40 minutes

from $105 / 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 $175 / night

$929 / week

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avg. 3 hours 40 minutes

from $175 / 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

(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 $855 / night

$5,979 / week

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from $855 / night

(12) Excellent 

29

Vacation villa with swimming pool in Anguilla

Anguilla

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • 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

53

Vacation home with swimming pool in Anguilla

Anguilla / East End Village

3 11 Min stay varies

  • 3 bedrooms
  • Sleeps 11
  • Min stay varies
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
Private, luxurious, oceanfront, private villa in Sea Feather’s Bay with stunning views of the Caribbean and St Martin. The modern design is ideal for relaxing vacation. Large rooms with private balconies have incredible views, ample outdoors and in-door living spaces, …see more

from $718 / night

$5,026 - $31,500 / week

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avg. 3 hours 57 minutes

from $718 / night

(13) 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 $80 / night

$590 / week

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from $80 / 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 p …see more

from $8,229 / night

$55,181 - $142,002 / week

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from $8,229 / night

(1) Excellent 

10

Vacation home with swimming pool in Anguilla

Anguilla / East End Village

8 14 1 night min

  • 8 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
Zenaida East End Village Anguilla A luxury Private Estate with Beach and Tennis courts and wonderful service on the East End of Anguilla. Everything is Cool about the location - guests have the advantage of the most elevated point on Anguilla …see more

from $2,500 / night

$17,500 / week

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from $2,500 / night

10

West End Village Vacation home rental

Anguilla / West End Village

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Nestled in the golf course of the St Regis Resort, Westgreen villa with its beautiful attention to detail & fabulous open airy feel, is the perfect getaway. Built on two levels, the villa offers tiled floors and tasteful interiors that feature a mix of wood, rattan a …see more

from $500 / night

$3,500 / week

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from $500 / night

0

Vacation villa in Anguilla

Anguilla

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Additional amenities: Board Games, Movie/Video Library, Music Library …see more

from $7,620 / night

$53,340 - $125,000 / week

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from $7,620 / night

23

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 $2,000 / night

$8,400 - $47,005 / week

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from $2,000 / night

(2) Excellent 

8

Vacation home rental

Anguilla / Blowing Point

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Nirvana Villa Shannon Hill aka Seafarer's Ridge Nr Sandy Ground Anguilla 4 Bedrooms 4 Bathrooms Private, Elevated Location above Sandy Ground This beautiful villa has been designed to fit perfectly upon its elevated position and present the best possi …see more

from $1,600 / night

$11,200 / week

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from $1,600 / night

10

Blowing Point Vacation home rental

Anguilla / Blowing Point

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Villa Modena Cove Bay Anguilla Comfortably Sleeps 10 Guests Villa Modena is private and palatial and  set upon one acre of land near the Cap Juluca Hotel on Cove Bay. A combination of a two storey main house and a one storey clubhou …see more

from $6,754 / night

$47,278 / week

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from $6,754 / night

(7) Excellent 

10

Vacation home in Anguilla

Anguilla / East End Village

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Ask about children
  • Ask about pets
James Place Apartments Mount Fortune Anguilla Perfect for 2 & 4 These newly built apartments are a perfect base from which guests can enjoy the Anguillan sun and beaches. The rooms are large and modern with private balconys …see more

from $155 / night

$1,080 / week

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from $155 / night

10

Vacation home with swimming pool in South Hill

Anguilla / South Hill

5 1 1 night min

  • 5 bedrooms
  • Sleeps 1
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Ocassa Villa Anguilla 5 Bedrooms overlooking Sandy Bay This is a stunning villa overlooking lovely Sandy Bay on the west coast of Anguilla. The villa has 5 double bedrooms with sumptuous furnishings and cool, cotton bedlinens. Living Room opens onto Infinity Pool & Balc …see more

from $1,500 / night

$10,500 / week

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from $1,500 / 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
Villa Nevaeh, Anguilla. 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. T …see more

from $5,980 / night

$41,860 - $172,501 / week

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from $5,980 / night

10

Anguilla Vacation home rental

Anguilla / George Hill

2 16 1 night min

  • 2 bedrooms
  • Sleeps 16
  • 1 night min
  • Ask about children
  • Ask about pets
Bellaconstantina Villa Little Harbour Anguilla Villa Suites Each Suite has 2 double bedrooms & 2 bathrooms Close to Anguillas Southern Coastline 4 Villa Suites overlooking the Ocean This property is a collection of 4 villa suites. Each suite has …see more

from $639 / night

$4,470 / week

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from $639 / 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 / week

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from $795 / night

10

Vacation home rental

Anguilla / Blowing Point

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
Beaches Edge Villa Pelican Bay, Anguilla Sleek Crisp Lines & Comfort for 10 Guests Located close to the sandy beach of Pelican Bay, Beaches Edge Villa has been designed with striking attention to detail and clean contemporary lines throughout both the i …see more

from $1,900 / night

$13,300 / week

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from $1,900 / night

17

Anguilla Vacation villa rental

Anguilla / Sandy Hill Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
With its location along Long Pond Bay in Anguilla, the large and contemporary Villa White Cedars is a unique find. Though meant to house six visitors in three bedrooms, the spaciousness of this villa is often a surprise. The proportions are perfectly balanced, however, …see more

from $781 / night

$4,123 - $12,250 / week

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from $781 / night

10

Home rental in Anguilla with swimming pool

Anguilla / The Valley

4 12 1 night min

  • 4 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
Ani North Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 Guests This is a showcase villa perched upon a headland overlooking Little Bay on Anguilla. There are 5 bedrooms, each quite distinctive all with luxurious bed linens, en suite spa qua …see more

from $6,429 / night

$45,000 / week

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from $6,429 / 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. 2 minutes

from $5,000 / night

37

Villa rental in Anguilla

Anguilla / Long Bay Village

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Ask about pets
Find your own Caribbean paradise at Nevaeh. Set on a private, gated lot that stretches down to a half-mile of golden sand on Anguilla’s Long Bay, this luxury oceanfront vacation rental boasts stunning views and pampering service. The brand-new villa takes its design cue …see more

from $7,590 / night

$53,130 / week

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avg. 2 minutes

from $7,590 / night

(8) Very Good 

31

Vacation apartment in Anguilla

Anguilla / Island Harbour

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights 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 $120 / night

$840 / week

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from $120 / night

18

Anguilla Vacation villa rental

Anguilla / Sandy Hill Bay

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Brand new and designed in an amazingly contemporary and clean style, the Villa Colibri in the Long Pond Bay area of Anguilla will truly take your breath away. Spread out over two levels, the villa features a spacious interior suitable for up to 12 visitors at once. Just …see more

from $1,400 / night

$6,615 - $21,000 / week

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from $1,400 / 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 2018. 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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avg. 2 hours 45 minutes

from $250 / 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

(12) Excellent 

51

Vacation villa with swimming pool in Little Harbour

Anguilla / Little Harbour

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Three Dolphins, Anguilla is an Elegantly furnished Small Estate on the British West Indies Isle of Anguilla and provides a most private escape for the discriminating traveler. Overlooking its own secluded strand of white sand beach directly in front of the house it als …see more

from $1,250 / night

$8,500 - $25,000 / week

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from $1,250 / night

22

Vacation villa in Anguilla

Anguilla

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Ask about pets
Located on a secluded beach on Anguilla’s southern shore, Tequila Sunrise is a spacious and contemporary beach house on Lover’s Cove in Dropsey Bay. The villa overlooks the Caribbean Sea and offers stunning views of the mountains of St Martin. Known for its pristine whi …see more

from $900 / night

$6,300 / week

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avg. 2 minutes

from $900 / night

10

Vacation home with swimming pool in Anguilla

Anguilla / The Valley

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
Ani South Little Bay Anguilla Sleek Crisp Lines & Comfort for 10 Guests This is a showcase villa perched upon a headland overlooking Little Bay on Anguilla. There are 5 bedrooms, each quite distinctive all with luxurious bed linens, en suite spa quality b …see more

from $8,143 / night

$57,000 / week

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from $8,143 / night

10

Long Bay Village Vacation home rental

Anguilla / Long Bay Village

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
  • Air conditioning
  • Ask about pets
Beach Villa Ella Barnes Bay Beach Anguilla Sugary White Sandy Beachfront Barnes Bay Beach situated outside the villa is a crescent bay of impossibly fine sand offering beautiful views over to the nearby islands and the azure blue waters that …see more

from $363 / night

$2,541 / week

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from $363 / night

(1) Excellent 

49

Vacation villa with swimming pool in Anguilla

Anguilla / Long Bay Village

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • 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 / week

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from $1,050 / night

10

Vacation home with swimming pool in Anguilla

Anguilla / Sandy Ground

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Perfect Villa Layout This 4 bedroom villa offers the perfect layout for a relaxed, entertained, worked out and pampered experience in Anguilla. At the heart of the villa is a cool and impressive atrium area. The top floor houses the 2 master suites each with k …see more

from $1,408 / night

$9,856 / week

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from $1,408 / 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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from $325 / night

(16) Excellent 

63

Anguilla Vacation villa rental

Anguilla

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Villa "B on the Sea" is a luxurious villa overlooking the Caribbean Sea with expansive views of surrounding island! The villa is specificaly designed to be the ultimate entertainment Mecca for an exceptional paradise experience. This exclusive villa features simple lu …see more

from $1,200 / night

$11,200 / week

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from $1,200 / night

33

Vacation villa in Anguilla

Anguilla

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • 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 $2,100 / night

$14,700 / week

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avg. 2 minutes

from $2,100 / night

10

Vacation home rental

Anguilla / The Valley

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Ask about children
  • Ask about pets
Little Butterfly Apartment Little Harbour, Anguilla This lovely one bedroom luxury apartment is located on the mezzanine level of Papillion Villa in Anguilla. Perfect for the solo traveler or a couple, Little Butterfly provides a contemporary and affordable …see more

from $246 / night

$1,722 / week

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from $246 / night

17

Anguilla Vacation villa rental

Anguilla

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Ask about pets
Overlooking Cove Lagoon and just two minutes away from the pristine two half mile white sand beaches of Maundays and Cove Bay, Mystique at Sheriva is one of Anguilla’s top luxury boutique villas. Located in the chic West End, the villa is situated on a lush 10-acre alco …see more

from $450 / night

$3,150 / week

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avg. 2 minutes

from $450 / night