50 Best Anguilla Villas on Holiday Lettings - Vacation rentals

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Apartments The Valley
29 properties
West End Village
25 properties
Island Harbour
21 properties
Blowing Point
18 properties
Sandy Hill Bay
15 properties
Little Harbour
11 properties
Long Bay Village
11 properties
Shoal Bay Village
8 properties
Rendezvous Bay
7 properties

Anguilla

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279 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

(3) Very Good 

19

Shoal Bay West Vacation villa rental

West End Village / Shoal Bay West

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
LOCATED DIRECT WATERFRONT STUNNING VIEWS OF SHOAL BA.Y EAST AND REEFS BEYOND! SHOAL REEF Villa has four (4) one bedroom suites with 4.5 beautiful Bathrooms, Waterfront, Washer, TV, Preferred Lifestyle, Pool, Microwave, Maid Service, Internet, Hair Dryer, Dryer, Dish W …see more

from $599 / night

$3951 / week

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from $599 / 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 $836 / night

$5850 / week

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from $836 / night

15

Merrywing Bay Vacation villa rental

West End Village / Merrywing Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
SONGBIRD VILLA - Rendezvous Bay, Anguilla, British West Indies Location: Anguilla 2 - 4 Bedrooms, 4.5 Baths , Air Conditioning Bedrooms Only, Answering Machine, BBQ, Beach Chairs, Blender, Cable, Ceiling Fans, Coffee Maker, Dish Washer, Dryer, DVD, Golf, Gym, …see more

from $917 / night

$6413 / week

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from $917 / 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 $169 / night

$897 / week

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from $169 / night

18

Vacation villa rental

Anguilla / West End Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Shoal Reef West is new to the rental market and its unique design is welcoming, relaxing; yet elegant with unique 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. A rooftop deck comp …see more

from $299 / night

$2093 / week

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from $299 / 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 $101 / night

$707 / week

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from $101 / night

11

Vacation villa with shared pool in Island Harbour

Anguilla / Island Harbour

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
CATALINA VILLA- Shoal Bay Village, Anguilla; PERFECT FOR ONE OR TWO COUPLES OR A FAMILY WITH 1-3 CHILDREN!! This cute Caribbean Style newly built (2012-14) home has two beautiful Bedrooms and each has its own En Suite Bathroom with Shower and double vanities. Perfe …see more

from $119 / night

$1743 / week

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from $119 / night

(1) Excellent 

19

Vacation villa rental

West End Village / Merrywing Bay

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
ARUSHI means " Ray Of Sunshine" This exquisite beach front property situated in the West of Anguilla at the CUISINART GOLF RESORT & SPA, this exclusive villa is one of only 12 homes on this beautiful estate.Located on a 4,400 foot long stunning white sandy beach. A Gre …see more

from $3101 / night

$21701 / week

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from $3101 / night

66

Shoal Bay Village Vacation villa rental

Anguilla / Shoal Bay Village

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $826 / night

$5776 / week

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from $826 / night

37

Vacation villa in Little Harbour

Anguilla / Little Harbour

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Suitable for children age 5+
  • Air conditioning
AVALON VILLA - Lockrum Estates, Anguilla, BEACHFRONT WITH VIEWS OF ST MARTIN Location: Anguilla - British West Indies , RARE ON ANGUILLA- has its own beautiful sandy beach with interior reef! 1 - 4 Bedrooms, 5 Baths , Air Conditioning Bedrooms Only, Bath Tub, BBQ, B …see more

from $950 / night

$8400 / week

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from $950 / night

25

Anguilla Vacation villa rental

Anguilla / Blowing Point

3 9 1 night min

  • 3 bedrooms
  • Sleeps 9
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
BRAMASOLE - Pelican Bay, Anguilla Location: Anguilla 1 - 3 Bedrooms, 3.5 Baths , Air Conditioning Whole House, BBQ, Blender, Cable, Ceiling Fans, Coffee Maker, Dish Washer, Dryer, DVD, Hair Dryer, Ice Maker, Internet, Maid Service, Microwave, Pool, Preferred Lifestyle …see more

from $777 / night

$5439 / week

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from $777 / night

10

Anguilla Vacation home rental

Anguilla / Shoal Bay Village

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Black Pearl Villa Shoal Bay East Anguilla Mediterranean Pergolas, Domes & Verandas Black Pearl Villa has been designed in a cool Mediterranean style and features an exotic dome roof, a curved barrel roof, romantic pergolas and breezy verandas. 4 Bedroom Suites with Outd …see more

from $1800 / night

$12600 / week

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from $1800 / night

(11) 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

(3) Very Good 

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 overlooking Island Harbour village, miles of ocean, and Scilly Cay. Enjoy the ocean view from the master bedroom, master bathroom, living/dining area, kitchen and laundry area. Second bedr …see more

from $106 / night

$742 / week

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from $106 / night

10

Home rental in Anguilla with swimming pool

Anguilla / Island Harbour

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Quixotic Villas, Harbour Ridge, Island Harbour, Anguilla Quixotic Villas are a collection of private retreats that nestle amongst Harbour Ridge offering stunning ocean views and relaxing, comfortable Caribbean accommodations. There are four definitive villas, Villa Amor …see more

from $575 / night

$4025 / week

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from $575 / night

(6) Excellent 

10

Vacation home in Anguilla

Anguilla / West End Village

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Ask about children
  • Ask about pets
West End Bay Holiday Suites Self Catering Suites WEST END BAY ANGUILLA WI The perfect choice for a great quality stay on Anguilla - low rates Overlooking Stunning Shoal Bay West Just a 4 minute stroll away from a stunning white sandy beach, Shoal Bay West. Perfect for s …see more

from $156 / night

$1092 / week

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from $156 / night

21

Vacation home with shared pool in Sandy Hill Bay

Anguilla / Sandy Hill Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
Located on the breezy and cool hilltop of Sandy Hill bay at Seafeathers, you'll find Emerald on the Sea. The villa is located within a five minute drive from the Sandy Hill beach main entrance where you can truly enjoy nature from the sound of the waves crashing complim …see more

from $660 / night

$4620 / week

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from $660 / night

(3) Excellent 

20

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 $748 / night

$5233 / week

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from $748 / night

10

Anguilla Vacation home rental

Anguilla

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 surround Anguilla. Beach cha …see more

from $333 / night

$2329 / week

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from $333 / 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 and …see more

from $385 / night

$2695 / week

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from $385 / night

16

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 $1400 / night

$9800 - $21000 / week

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from $1400 / 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 $450 / night

$3150 / week

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from $450 / 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 $296 / night

$1182 / week

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from $296 / night

(9) Very Good 

10

Anguilla Vacation villa rental

Anguilla

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Mainstay is a privately owned villa situated on a ½ acre right on the Caribbean Sea. It offers 3 bedrooms, 2 full baths and a 1/2 bath. Our lovely pool and large deck offers spectacular southern views of St. Martin & other neighboring islands. Mainstay is a very sp …see more

from $297 / night

$2000 - $4800 / week

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from $297 / night

10

Vacation home with swimming pool in Anguilla

Anguilla / The Valley

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
Lotus Blossum Villa The Valley Anguilla 2 Double Bedrooms & 1 Double Studio Lotus Blossum is a peaceful, relaxing property, prisitne, light and beautifully finished with 2 double bedrooms and a self contained studio on the lower level. The bedrooms have contemporary art …see more

from $1500 / night

$10500 / week

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from $1500 / night

10

Vacation home rental

Anguilla

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 interior and exteri …see more

from $1250 / night

$8750 / week

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from $1250 / night

36

Vacation villa with swimming pool in Anguilla

Anguilla / Shoal Bay Village

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Tamarind villa overlooks the Atlantic on the north eastern end of the island. This villa is just a five minute drive from Shoal Bay East, one of the most beautiful beaches in the Caribbean. With its large principle rooms and comfortable settings, its the perfect place f …see more

from $792 / night

$5544 - $9800 / week

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from $792 / night

10

Vacation home rental

Anguilla

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Ask about pets
Sand Castle Villa Limestone Bay Anguilla Beachfront 4 Bedroom Villa Sand Castle Villa boasts 4 bedrooms, 2 kingsize, 1 Queensized and a twin room, perfect for a group of friends or large family to enjoy. Close to the stunning Anguillan coast and blessed with its own bea …see more

Pricing unknown

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Pricing unknown

18

Vacation villa with swimming pool in Anguilla

Anguilla

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
This elegant and secluded three bedroom luxury villa and cottage is set on one acre of lush tropical gardens and a small sandy beach. The bay has shallow water and is great for snorkeling or enjoying the kayaks which are furnished with the villa. Once you arrive, it …see more

from $1750 / night

$12250 / week

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from $1750 / night

10

Anguilla Vacation home rental

Anguilla

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 2 double bedrooms, 2 bat …see more

from $502 / night

$3510 / week

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from $502 / night

31

Vacation home with shared pool in West End Village

Anguilla / West End Village

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
Situated directly on Long Bay; Villa Nevaeh offers the pinnacle of refined comfort and privacy for guests who choose Anguilla for the ultimate Caribbean escape. This beachfront vacation villa boasts five bedrooms; including a finely-appointed guesthouse with a second fu …see more

from $5200 / night

$36400 / week

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from $5200 / night

13

Vacation villa in Anguilla

Anguilla

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Air conditioning
This lovely villa is situated in the Sea Rocks on the northeast side of the island. Sea Rocks has long been an exclusive residential area for full time residents and the villa renters. It is quite beautiful and secluded.  This villa is short 5 minute drive or 20 m …see more

from $408 / night

$2849 - $5250 / week

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from $408 / night

10

Island Harbour Vacation home rental

Anguilla / Island Harbour

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Kiki Villa Shoal Bay Anguilla 10 minute stroll from Shoal Bay Beach This stunning property built in the mediterranean villa style has a pristine white exterior, a pool, terraces and sun deck overlooking Shoal Bay in the distance. Shoal Bay Beach is just a 10 minute stro …see more

from $800 / night

$5600 / week

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from $800 / night

21

Vacation villa with swimming pool in Anguilla

Anguilla

4 8 4 nights min

  • 4 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Palm Villa is located within the Indigo Reef Development in the West End of Anguilla. Indigo Reef is a group of one to four bedroom homes with a community pool and barbecue area and steps away from the small and quiet West End beach. Shoal Bay West is just a ten minute …see more

from $1334 / night

$9338 / week

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from $1334 / night

18

Vacation villa in Anguilla

Anguilla

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Ask about pets
Stretching across the horizon like an ivory sculpture, White Cedars villa offers all the perks required for a truly memorable island holiday. Allow the sensual features of this private three bedroom villa to overtake your senses and soul. Located on the remote isle of A …see more

from $589 / night

$4123 / week

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from $589 / night

10

Vacation home with swimming pool in Anguilla

Anguilla

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 $1000 / night

$7000 / week

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from $1000 / night

(2) Excellent 

32

Vacation villa rental

Anguilla / Island Harbour

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Ask about children
  • Ask about pets
Relax and enjoy a view of endless Caribbean blue at the edge Villa Amarilla’s infinity pool. Located in Anguilla, this five bedroom architectural gem boasts a décor as beautiful as the island’s natural surroundings, created in collaboration with award-winning interior d …see more

from $2500 / night

$17500 / week

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from $2500 / night

27

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
The Caribbean is Sea Villa's muse. Its interiors mirror the serene waters' spectrum of blue and green hues, drawing the eye and soul beyond windows and terraces to the horizon, the infinity edge pool and back in seamless transitions. There are four master suites with t …see more

from $3500 / night

$24500 - $77000 / week

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from $3500 / night

35

Vacation villa in Anguilla

Anguilla

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
Moonraker Villa awaits you; a luxury signature 15,500 sq ft villa where modern luxury meets old world Anguilla for total seclusion, peace, relaxation and tranquility, or, as they say in Anguilla, lime out!! The villa is finished with Italian travertine and ceramic tiles …see more

from $2880 / night

$20160 - $30240 / week

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from $2880 / night

1