50 Best Anguilla Villas on Holiday Lettings - Vacation rentals

Close

View larger map

Also consider

West End Village
20 properties
Island Harbour
13 properties
Blowing Point
10 properties
Little Harbour
9 properties
Apartments The Valley
9 properties
Sandy Hill Bay
7 properties
Long Bay Village
7 properties

Anguilla

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

181 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

Book View

from $150 / 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

Book View

from $119 / night

(3) Very Good 

19

Shoal Bay West Vacation villa rental

West End Village / Shoal Bay West

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights 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

Book View

from $599 / 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 $104 / night

$724 / week

Book View

from $104 / 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 $843 / night

$5895 / week

Book View

Responds fast!
avg. 2 hours 29 minutes

from $843 / 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

Book View

from $950 / 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

Book View

from $3101 / 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

Book View

from $917 / 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

Book View

from $299 / 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 $174 / night

$928 / week

Book View

from $174 / 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

Book View

from $777 / 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

Book View

from $826 / 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 on Captains Ridge, Island Harbour with a panoramic view of the Atlantic Ocean. Enjoy the ocean view from the master bedroom, master bathroom, living/dining area, kitchen and laundry area. S …see more

from $106 / night

$742 / week

Book View

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 - $7000 / week

Inquire View

from $575 / 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 $316 / night

$1263 / week

Book View

from $316 / night

11

Condo rental in The Valley with shared pool

Anguilla / The Valley

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • 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

$1750 / week

Book View

from $250 / 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 - $3500 / week

Inquire View

from $385 / night

4

Vacation villa in Anguilla

Anguilla / The Valley

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 0.9 mi
  • Child friendly
  • Pet friendly
Lovely decor adorns this delightful two bedroom villa which includes an open kitchen, bar and dining room with vaulted ceilings; two equal air conditioned master bedroom suites, private hot tub, lush gardens and roof top sun lounge. Each master suite has memory foam bed …see more

from $285 / night

$1995 / week

Book View

from $285 / night

(1) Very Good 

10

Vacation home with swimming pool in Anguilla

Anguilla

5 10 1 night min

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

from $1250 / night

$8750 - $13300 / week

Inquire View

from $1250 / night

(1) Excellent 

8

Vacation home rental

Anguilla

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Nirvana Villa Shannons 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 possible panoramic views from every room an …see more

from $1400 / night

$9800 - $11200 / week

Inquire View

from $1400 / 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 - $10500 / week

Inquire View

from $1000 / 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 exter …see more

from $1250 / night

$8750 - $13300 / week

Inquire View

from $1250 / night

(7) Very Good 

12

Home rental in Anguilla

Anguilla / East End Village

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

$3500 / week

Book View

from $325 / night

32

Vacation villa in Anguilla

Anguilla / Little Harbour

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Ask about children
  • Ask about pets
Descend upon a lush landscape that envelope a stately stature of the 6679 square foot Ocassa Villa. This captivating villa faces west and reveals breathtaking views, a distinctive design and a peaceful sunset. Ocassa Villa offers you a refined island experience, blissf …see more

from $1200 / night

$8000 / week

Book View

from $1200 / 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

Book View

from $110 / night

26

Vacation villa in The Valley

Anguilla / The Valley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets
Like a towering ivory sculpture perched on the majestic cliffs overlooking Anguilla’s Little Bay, the four bedroom Ani North has been designed and fitted to offer an unforgettable Caribbean vacation. Unique to Ani North is the home’s dramatic stair atrium with massive s …see more

from $5100 / night

$35700 / week

Book View

Responds fast!
avg. 2 minutes

from $5100 / night

10

Vacation home with swimming pool in Anguilla

Anguilla

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 bathrooms, AC, W …see more

from $6286 / night

$44000 - $57000 / week

Inquire View

from $6286 / night

10

Vacation home with swimming pool in Anguilla

Anguilla

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 kingsize be …see more

from $1208 / night

$8456 - $9856 / week

Inquire View

from $1208 / 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 $2900 / night

$20300 - $77000 / week

Inquire View

from $2900 / night

(4) Excellent 

24

Anguilla Vacation villa rental

Anguilla

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 $6400 / night

$44800 / week

Book View

Responds fast!
avg. 2 minutes

from $6400 / night

46

Vacation villa in Anguilla

Anguilla

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
Indigo Villa, a luxurious Anguillian estate with 9 air-conditioned bedrooms fronted by beautiful white sands and coral reefed blue sea, awaits you. Each room has a view of the Caribbean Sea and the terrace opens to a marvelous patio vista of pool, palms, sea, sand and t …see more

from $6861 / night

$48020 - $125000 / week

Inquire View

from $6861 / night

24

Vacation villa with swimming pool in Anguilla

Anguilla / Island Harbour

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 $1250 / night

$8750 - $18550 / week

Book View

from $1250 / 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 - $4470 / week

Inquire View

from $502 / 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

Inquire View

from $1500 / 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

Book View

from $450 / night

(9) Excellent 

12

Vacation villa in Anguilla

Anguilla / The Valley

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.4 mi
  • Child friendly
Come and enjoy wonderful accommodations on the island of Anguilla. Our wonderful property on Rendezvous Bay is a perfect getaway with friends or family. Up to three bedrooms, with wonderful living areas provide special back drops for your special days on Anguilla. …see more

from $295 / night

$2065 - $4375 / week

Book View

Responds fast!
avg. 1 hour 32 minutes

from $295 / 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 - $7000 / week

Inquire View

from $800 / 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 - $1470 / week

Inquire View

from $156 / night

10

Anguilla Vacation home rental

Anguilla / The Valley

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
Oceana Villa Anguilla Close to Sandy Beaches Anguilla famously has 33 beaches and Oceana is close to several: one of the nearest is Crocus Bay.  Viewed from Oceana and just a five minute drive this is a long, relatively untouched, quiet beach, except for the Da Vida res …see more

from $520 / night

$3640 - $4550 / week

Inquire View

from $520 / 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 $5200 / night

$36400 - $143750 / week

Inquire View

from $5200 / night