Updating

Updating

Family Friendly Holidays in Anguilla - Holiday Lettings

All filters (1)

Filters (1)

Clear filters

735 family friendly properties

Shoal Bay Village holiday villa rental

Shoal Bay Village villa

4 bedrooms • 3 bathrooms • sleeps 8

from £777 / night

£5,436 / week

1 / 65

Anguilla holiday villa rental

Shoal Bay West villa

2 bedrooms • 4 bathrooms • sleeps 5

7 reviews

from £187 / night

£1,287 - £1,578 / week

1 / 15

Holiday villa with golf nearby in Anguilla

Meads Bay Pond villa

3 bedrooms • 4 bathrooms • sleeps 6

4 reviews

from £736 / night

£5,153 / week

1 / 20

Holiday villa rental

Sandy Hill Bay villa

7 bedrooms • 7 bathrooms • sleeps 14

from £1,412 / night

£9,882 / week

1 / 9

Holiday villa rental

The Valley villa

4 bedrooms • 5 bathrooms • sleeps 10

1 review

from £1,036 / night

£7,247 / week

1 / 6

Holiday castle with swimming pool in Anguilla

Sandy Ground castle

4 bedrooms • 5 bathrooms • sleeps 10

“Back just one day and already planning the next trip to the Cast” Favorite island? Anguilla! Favorite place to stay? Grand Outlook Castle! Paul and Elise provide everything you need to have a wonderful vacation. The Castle is luxurious but comfy, outdoor showers, hammocks, good lighting in the bathroom for make up (unusual perk),sparkling pool, well appointed kitchen, high end bedding and the best housekeeper on the island! Great location, just a short drive to anywhere. Every email is returned, every need is met - the "customer service" the owners provide is top notch. Guess that is why there are so many return guests. It is very hard to leave the stunning rainbows, sunsets and visiting turtles that we were lucky enough to view each day. Can not wait to book next years stay!

97 reviews

from £894 / night

£8,471 - £10,941 / week

1 / 122

Holiday villa in Anguilla

The Valley villa

2 bedrooms • 2 bathrooms • sleeps 5

from £362 / night

£2,532 / week

1 / 4

Home rental in Anguilla

East End Village house

4 bedrooms • 4 bathrooms • sleeps 10

8 reviews

from £471 / night

£3,294 / week

1 / 12

Holiday villa with swimming pool in Anguilla

Anguilla villa

3 bedrooms • 3 bathrooms • sleeps 7

13 reviews

from £565 / night

£3,953 / week

1 / 29

Little Harbour holiday villa rental

Little Harbour villa

3 bedrooms • 3 bathrooms • sleeps 6

from £424 / night

£2,965 / week

1 / 42

Anguilla holiday apartment rental

Anguilla apartment

2 bedrooms • 2 bathrooms • sleeps 5

“Great rental on a remarkable island” We spent 3 weeks there this January and it was delightful. The 2 bedroom condo was clean and had everything we needed and the 1or 2 small items we requested were immediately procured. Ocean Terrace has easy access to food stores, beaches and good restaurants. There is a wonderful French Bakery in Island Harbour a fairly short drive away. You do need a rental car to get around. People at the condo and indeed all of the anguillans were universally nice and helpful. This is a relaxing island that is fairly sparsely populated. There are no negatives to repot.

14 reviews

from £377 / night

£2,353 / week

1 / 10

Holiday villa in Anguilla

The Valley villa

2 bedrooms • 3 bathrooms • sleeps 5

“Amazing, Relaxing Vacation in Paradise” We spent a week in anguilla at beautiful Oceana, it was nothing short of perfection. The villa is gorgeous and the views, coupled with the amazing pool, cooking facilities made our time there, just amazing! Thank you to Rick and Michelle - we truly enjoyed ourselves.

18 reviews

from £396 / night

£3,130 - £5,601 / week

1 / 92

Holiday villa in Sandy Hill Bay

Sandy Hill Bay villa

3 bedrooms • 4 bathrooms • sleeps 6

7 reviews

from £815 / night

£5,706 / week

1 / 17

Anguilla holiday villa rental

Anguilla villa

3 bedrooms • 3 bathrooms • sleeps 6

21 reviews

from £290 / night

£2,031 / week

1 / 14

Holiday apartment in Anguilla

Island Harbour apartment

1 bedroom • 1 bathroom • sleeps 2

13 reviews

from £95 / night

£800 / week

1 / 24

Holiday villa with swimming pool in Anguilla

Anguilla villa

4 bedrooms • 5 bathrooms • sleeps 8

14 reviews

from £1,195 / night

£8,360 / week

1 / 42

Anguilla holiday villa rental

Anguilla villa

5 bedrooms • 5 bathrooms • sleeps 16

“Vacation of a Lifetime” This was hands down the most beautiful, luxurious vacation I have ever had. The location is breath taking, and with porches and sliding glass doors being staple features in the villa, there is not a bad view to be seen. We felt like royalty every day we woke up at B on the Sea. We spent some time at the beaches on at the Cuisanart and Viceroy, and B on the Sea just blows them both right out of the water. For a personal, lavish vacation in paradise, B on the Sea is the only way to go.

16 reviews

from £975 / night

£9,097 / week

1 / 63

Holiday villa with swimming pool in Anguilla

Long Bay Village villa

3 bedrooms • 4 bathrooms • sleeps 6

7 reviews

from £741 / night

£6,082 / week

1 / 45

Holiday villa letting

Long Bay Village villa

2 bedrooms • 3 bathrooms • sleeps 4

3 reviews

from £563 / night

£3,936 - £5,068 / week

1 / 32

Holiday home with swimming pool in Anguilla

East End Village house

3 bedrooms • 5 bathrooms • sleeps 11

from £812 / night

£5,682 - £7,812 / week

1 / 53

Holiday apartment in Anguilla

Sandy Ground apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £283 / night

£1,977 / week

1 / 11

Holiday villa with swimming pool in Anguilla

Long Bay Village villa

5 bedrooms • 7 bathrooms • sleeps 10

1 review

from £931 / night

£5,946 - £16,987 / week

1 / 49

Holiday villa in Anguilla

East End Village villa

1 bedroom • 3 bathrooms • sleeps 11

from £471 / night

£3,294 / week

1 / 44

Holiday villa in Anguilla

The Valley villa

3 bedrooms • 3 bathrooms • sleeps 8

12 reviews

from £248 / night

£1,737 - £2,915 / week

1 / 19

Holiday villa with indoor pool in Anguilla

West End Village villa

3 bedrooms • 4 bathrooms • sleeps 6

from £377 / night

£2,636 / week

1 / 24

Little Harbour holiday villa rental

Little Harbour villa

4 bedrooms • 5 bathrooms • sleeps 8

from £416 / night

£2,906 / week

1 / 39

Holiday villa letting

The Valley villa

1 bedroom • 1 bathroom • sleeps 2

from £306 / night

£2,142 / week

1 / 4

Holiday villa rental

The Valley villa

3 bedrooms • 4 bathrooms • sleeps 7

6 reviews

from £942 / night

£6,588 / week

1 / 18

Holiday villa with swimming pool in Little Harbour

Little Harbour villa

5 bedrooms • 5 bathrooms • sleeps 10

13 reviews

from £1,606 / night

£10,413 / week

1 / 29

Holiday villa in Sandy Hill Bay

Sandy Hill Bay villa

2 bedrooms • 4 bathrooms • sleeps 11

from £565 / night

£3,953 / week

1 / 44

Villa rental in Blowing Point with swimming pool

Blowing Point villa

5 bedrooms • 6 bathrooms • sleeps 10

from £1,768 / night

£12,377 / week

1 / 22

Holiday villa with shared pool in Anguilla

Blowing Point villa

5 bedrooms • 6 bathrooms • sleeps 10

2 reviews

from £2,013 / night

£14,087 / week

1 / 13

Holiday apartment in Anguilla

Sandy Hill Bay apartment

2 bedrooms • 1 bathroom • sleeps 3

from £142 / night

£989 / week

1 / 34

Holiday villa with swimming pool in South Hill

South Hill villa

2 bedrooms • 2 bathrooms • sleeps 6

6 reviews

from £282 / night

£1,687 / week

1 / 30

Holiday villa rental

Seafeathers villa

5 bedrooms • 6 bathrooms • sleeps 11

“A luxurious getaway par excellence” The Villa Gardenia provided the ideal setting for our week in paradise. The villa accommodated three couples (one with young child) with ease. With warm colors and a bright, airy, open layout, we never wanted to leave. Whether lingering in the kitchen after a meal, lounging on the adjoining living room's sofa or (most of all) spending hours by the gorgeous pool, the Villa Gardenia was a delight. We can't wait to return!

10 reviews

from £848 / night

£5,930 - £21,743 / week

1 / 52

Anguilla holiday villa rental

Long Bay Village villa

9 bedrooms • 12 bathrooms • sleeps 22

6 reviews

from £5,767 / night

£40,367 / week

1 / 37

Anguilla holiday villa rental

Blowing Point villa

5 bedrooms • 5 bathrooms • sleeps 10

1 review

from £942 / night

£6,588 / week

1 / 24

Anguilla holiday villa rental

Blowing Point villa

6 bedrooms • 9 bathrooms • sleeps 12

5 reviews

from £1,380 / night

£9,658 / week

1 / 22

Holiday villa with shared pool, golf nearby in Blowing Point

Blowing Point villa

3 bedrooms • 3 bathrooms • sleeps 6

3 reviews

from £104 / night

£791 - £1,141 / week

1 / 22

Little Harbour holiday villa rental

Little Harbour villa

1 bedroom • 8 bathrooms • sleeps 16

from £5,836 / night

£40,849 / week

1 / 30

×

Also consider