50 Best Anguilla Villas on Holiday Lettings - Vacation rentals

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Island Harbour
31 properties
West End Village
29 properties
Little Harbour
21 properties
Sandy Hill Bay
20 properties
Blowing Point
20 properties
Rendezvous Bay
15 properties
Long Bay Village
14 properties
Shoal Bay Village
5 properties

Anguilla

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493 Vacation rentals

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26

Anguilla / West End Village

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from $97 / night

$674 / week

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from $97 / night

(2) Excellent 

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 $600 / night

$3950 / week

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from $600 / night

(5) 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 desig  …see more

from $150 / night

$995 / week

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from $150 / night

(1) 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 $791 / night

$5535 / week

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from $791 / night

11

Vacation villa with shared pool in Island Harbour

Anguilla / Island Harbour

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • 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 $249 / night

$1743 / week

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from $249 / night

37

Vacation villa in Little Harbour

Anguilla / Little Harbour

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • 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 $1201 / night

$8400 / week

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from $1201 / night

15

Merrywing Bay Vacation villa rental

West End Village / Merrywing Bay

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool
SONGBIRD VILLA - Rendezvous Bay, Anguilla, British West IndiesLocation: Anguilla2 - 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 $1000 / night

$7000 / week

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from $1000 / 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

(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  …see more

from $3100 / night

$21700 / week

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from $3100 / 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  …see more

from $826 / night

$5776 / week

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from $826 / night

18

Vacation villa rental

Anguilla / West End Village

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
'Octagon' 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  …see more

from $951 / night

$6651 / week

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from $951 / night

40

Anguilla / West End Village

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly

 …see more

from $161 / night

$856 / week

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from $161 / night

28

Anguilla / Island Harbour

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 3 mi
  • Child friendly
  • Air conditioning

 …see more

from $99 / night

$687 / week

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from $99 / night

30

Anguilla / The Valley

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly

 …see more

from $304 / night

$1215 / week

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from $304 / night

51

Anguilla / Blowing Point

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly

 …see more

from $1400 / night

$9801 - $49001 / week

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from $1400 / night

(1) Excellent 

25

Anguilla / Blowing Point

6 10 Min stay varies

  • 6 bedrooms
  • Sleeps 10
  • Min stay varies
  • Child friendly

 …see more

from $2100 / night

$14701 - $32200 / week

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from $2100 / night

(12) Excellent 

29

Anguilla

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from $451 / night

$3151 / week

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from $451 / night

(2) Excellent 

18

Anguilla / Rendezvous Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly

 …see more

from $1321 / night

$9240 - $26041 / week

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from $1321 / night

27

Anguilla / Little Harbour

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $900 / night

$6300 - $10500 / week

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from $900 / night

31

Anguilla / Island Harbour

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly

 …see more

from $4001 / night

$28001 - $70001 / week

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from $4001 / night

36

Anguilla / Little Harbour

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly

 …see more

from $2784 / night

$19481 - $79000 / week

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from $2784 / night

32

Anguilla / Little Harbour

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly

 …see more

from $7621 / night

$53341 - $125000 / week

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from $7621 / night

20

Anguilla / Blowing Point

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly

 …see more

from $500 / night

$3500 - $14001 / week

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from $500 / night

(1) Excellent 

10

Anguilla / Rendezvous Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

 …see more

from $275 / night

$1926 - $2765 / week

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from $275 / night

45

Anguilla

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $7621 / night

$53341 - $125000 / week

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from $7621 / night

26

Anguilla / Rendezvous Bay

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $650 / night

$4551 - $21700 / week

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from $650 / night

37

Anguilla / Long Bay Village

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $7591 / night

$53130 - $172495 / week

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from $7591 / night

18

Anguilla / Blowing Point

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $951 / night

$6650 - $9801 / week

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from $951 / night

32

Anguilla

6 1 Min stay varies

  • 6 bedrooms
  • Sleeps 1
  • Min stay varies
  • Child friendly
  • Ask about pets

 …see more

from $400 / night

$2801 / week

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from $400 / night

31

Anguilla / Long Bay Village

7 14 14 nights min

  • 7 bedrooms
  • Sleeps 14
  • 14 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $9286 / night

$65002 - $125000 / week

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from $9286 / night

14

Anguilla

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $726 / night

$5075 - $7001 / week

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from $726 / night

(2) Excellent 

41

Anguilla / Little Harbour

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $8601 / night

$60201 - $126126 / week

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from $8601 / night

18

Anguilla / The Valley

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $5100 / night

$35700 - $112876 / week

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from $5100 / night

30

Anguilla / Sandy Hill Bay

7 16 Min stay varies

  • 7 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $2401 / night

$16801 - $50051 / week

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from $2401 / night

(3) Excellent 

23

Anguilla / Sandy Ground

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
  • Air conditioning

 …see more

from $1249 / night

$8743 - $15400 / week

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from $1249 / night

12

Anguilla

2 1 4 nights min

  • 2 bedrooms
  • Sleeps 1
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $801 / night

$5601 / week

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from $801 / night

7

Anguilla / South Hill

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Child friendly

 …see more

from $96 / night

$666 / week

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from $96 / night

27

Anguilla

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

 …see more

from $3500 / night

$24501 - $77000 / week

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from $3500 / night

18

Anguilla / Blowing Point

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $2551 / night

$17850 - $49001 / week

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from $2551 / night

30

Anguilla

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Child friendly

 …see more

from $7750 / night

$54250 - $126126 / week

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from $7750 / night