50 Best Anguilla Villas on Holiday Lettings - Vacation rentals

Close

View larger map

Also consider

West End Village
27 properties
Island Harbour
24 properties
Little Harbour
17 properties
Blowing Point
16 properties
Sandy Hill Bay
14 properties
Rendezvous Bay
12 properties
Apartments The Valley
6 properties
Long Bay Village
6 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

459 Vacation rentals

Travelers going to Anguilla are booking December dates now. Secure your vacation rental today and have the perfect trip.

(5) Very Good 

15

Anguilla Vacation villa rental

West End Village / Shoal Bay West

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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 fo  …see more

from $150 / night

$995 - $2500 / 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 $249 / night

$1743 - $7450 / week

Book View

from $249 / night

(2) Excellent 

19

Shoal Bay West Vacation villa rental

West End Village / Shoal Bay West

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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

$3950 / week

Book View

from $599 / night

10

Anguilla / West End Village

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $385 / night

$2695 - $3500 / week

Inquire View

from $385 / night

18

Vacation villa rental

Anguilla / West End Village

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • 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 completes  …see more

from $495 / night

$3465 / week

Book View

from $495 / night

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

Book View

from $97 / 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 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

Book View

from $1000 / night

(1) Excellent 

19

Vacation villa rental

West End Village / Merrywing Bay

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • 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 $3100 / night

$21700 / week

Book View

from $3100 / 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 $1150 / night

$8050 - $8400 / week

Book View

from $1150 / 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 $450 / night

$3150 / week

Book View

from $450 / night

(6) Excellent 

10

Anguilla / West End Village

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Ask about children
  • Ask about pets

 …see more

from $156 / night

$1092 - $1470 / week

Inquire View

from $156 / 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 $298 / night

$1191 / week

Book View

from $298 / 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 $804 / night

$5625 / week

Book View

from $804 / night

7

Anguilla / South Hill

1 2 Min stay varies

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

 …see more

from $95 / night

$665 / week

Book View

from $95 / 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 you  …see more

from $825 / night

$5775 / week

Book View

from $825 / night

10

Anguilla / The Valley

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $570 / night

$3990 - $4550 / week

Inquire View

from $570 / 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

$855 - $1283 / week

Book View

from $161 / night

5

Anguilla

3 1 Min stay varies

  • 3 bedrooms
  • Sleeps 1
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $1540 / night

$10780 / week

Inquire View

from $1540 / night

10

Anguilla

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
  • Air conditioning
  • Ask about pets

 …see more

from $333 / night

$2329 - $2541 / week

Inquire View

from $333 / night

8

Anguilla

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $3600 / night

$25200 / week

Inquire View

from $3600 / night

26

Anguilla / The Valley

4 8 6 nights min

  • 4 bedrooms
  • Sleeps 8
  • 6 nights min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning

 …see more

from $486 / night

$2915 - $5280 / week

Book View

from $486 / night

(6) Very Good 

12

Anguilla / Island Harbour

4 10 3 nights min

  • 4 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Child friendly

 …see more

from $325 / night

$2275 / week

Book View

from $325 / night

24

Anguilla

6 10 Min stay varies

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

 …see more

from $6400 / night

$44800 - $57400 / week

Inquire View

from $6400 / night

10

Anguilla

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $2500 / night

$17500 - $35000 / week

Inquire View

from $2500 / night

19

Anguilla

4 6 7 nights min

  • 4 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $1000 / night

$7000 / week

Inquire View

from $1000 / night

(7) Very Good 

13

Anguilla

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $1250 / night

$8750 - $12250 / week

Inquire View

from $1250 / night

(3) Excellent 

15

Anguilla

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $475 / night

$3325 - $7000 / week

Inquire View

from $475 / night

(2) Very Good 

17

Anguilla / Blowing Point

7 12 Min stay varies

  • 7 bedrooms
  • Sleeps 12
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $1800 / night

$12600 - $46998 / week

Inquire View

from $1800 / night

(3) Excellent 

14

Anguilla

8 16 Min stay varies

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

 …see more

from $3571 / night

$24997 - $94997 / week

Inquire View

from $3571 / night

10

Anguilla / Shoal Bay Village

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets

 …see more

from $1800 / night

$12600 - $17500 / week

Inquire View

from $1800 / night

15

Anguilla

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

 …see more

from $2822 / night

$19750 / week

Inquire View

from $2822 / night

(2) Excellent 

12

Anguilla / Rendezvous Bay

2 4 Min stay varies

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

 …see more

from $246 / night

$1722 - $2940 / week

Inquire View

from $246 / night

7

Anguilla

3 1 Min stay varies

  • 3 bedrooms
  • Sleeps 1
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from $487 / night

$3409 / week

Inquire View

from $487 / 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 $98 / night

$686 / week

Book View

from $98 / 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 $800 / night

$5600 / week

Inquire View

from $800 / night

43

Anguilla / Little Harbour

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Ask about children
  • Ask about pets

 …see more

from $7620 / night

$53340 - $109942 / week

Book View

from $7620 / night

(1) Excellent 

16

Anguilla

7 12 Min stay varies

  • 7 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly

 …see more

from $2000 / night

$14000 - $47000 / week

Inquire View

from $2000 / night

6

Anguilla

1 2 Min stay varies

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

 …see more

from $995 / night

$6965 - $10500 / week

Inquire View

from $995 / 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

$1925 - $2765 / week

Inquire View

from $275 / night

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page