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Family Friendly Holidays in Anguilla - Holiday Lettings

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710 family friendly properties

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Anguilla holiday villa rental

Blowing Point villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 12

from £1,876 / night

£13,131 / week

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Anguilla holiday villa rental

Blowing Point villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £563 / night

£3,940 / week

1 / 24

Villa rental in Long Bay Village

Long Bay Village villa

  • 9 bedrooms
  • 11 bathrooms
  • sleeps 21

from £5,440 / night

£38,078 / week

1 / 74

Home rental in Anguilla

East End Village house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £469 / night

£3,283 / week

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Anguilla holiday villa rental

Long Bay Village villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £3,940 / night

£27,574 / week

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Holiday villa with swimming pool in Anguilla

Long Bay Village villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £845 / night

£5,911 / week

1 / 45

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.

from £1,126 / night

£10,505 / week

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Holiday villa accommodation

Blowing Point villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £188 / night

£1,313 / week

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Holiday villa in Anguilla

The Valley villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Charming Villa near Rendezvous Bay!!!” Wow! This spacious, private, full equipped villa was just magical. Lyn the property manager was so sweet, welcoming and gave us wonderful recommendations as well as purchased food prior to our arrival so we could be comfortable while we waited for our COVID test results. Gayle was so easy to communicate with and updated us on what we needed to do for safe entry and exit into the island. Let’s get back to the villa though… we enjoyed mornings on the porch, drinking coffee and making yum breakfasts in the cute little kitchen. We also loved the evenings with all the great standup lights that could be turned on and created amazing ambiance. The beds were so comfortable and the villa set us all back in time a bit with its wooden features, beautiful cottage furniture and thoughtful decoration. The villa was set up so that Chinaberry villa was totally secluded from Bayberry villa so if you’re coming as couples and want privacy- it’s great to rent the whole property! We totally understand why people keep returning!!! If you’ve never booked with Gayle and Lyn and are considering it- you won’t have regrets! You have to see it to know. Some helpful tips: • Taxi rides from blowing point can be pricey- make sure to ask the driver the cost. It’s about 3min from the villa. We rented a vehicle and we loved that aspect- having mobility is the best. • Go check out little bay- wow! It’s stunning! • sip some coffee on the porch! • best shop is Best Buy for variety. Also- amazing fresh fish on the island… there’s a tent by the airport- we grilled an amazing mahi mahi! • we found food to be quite pricey at restaurants… so we went in search of good local spots… but also cooked at the villa tons! Here are our top picks that we got to see- Roti Hut- conch and goat rotis D&B bbq Blanchards- reasonable with epic sunset views Sunshine shack for drinks and hangout The dune for live music by Bankie Banx- sooo good! Thanks so much for the stay. Happy vacationing.

from £277 / night

£1,937 - £2,594 / week

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Holiday villa in Anguilla

The Valley villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £361 / night

£2,528 / week

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Apartment rental in George Hill

George Hill apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £282 / night

£1,876 / week

1 / 29

Holiday villa with indoor pool in Anguilla

West End Village villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £376 / night

£2,626 / week

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Holiday villa rental

Sandy Hill Bay villa

  • 7 bedrooms
  • 7 bathrooms
  • sleeps 14

from £1,407 / night

£9,848 / week

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Holiday villa letting

The Valley villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £305 / night

£2,134 / week

1 / 4

Holiday apartment in Anguilla

Sandy Hill Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £160 / night

£1,116 / week

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Holiday villa in Anguilla

East End Village villa

  • 1 bedroom
  • 3 bathrooms
  • sleeps 11

from £469 / night

£3,283 - £9,028 / week

1 / 44

Holiday villa in Sandy Hill Bay

Sandy Hill Bay villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 11

from £563 / night

£3,940 - £8,981 / week

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Shoal Bay Village holiday villa rental

Shoal Bay Village villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £774 / night

£5,417 / week

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Villa rental in Anguilla

Shoal Bay Village villa

  • 4 bedrooms
  • 7 bathrooms
  • sleeps 10

from £1,313 / night

£9,192 / week

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Rendezvous Bay holiday villa rental

Rendezvous Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £108 / night

£755 / week

1 / 18

Holiday villa with swimming pool in Anguilla

Anguilla villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £657 / night

£9,520 - £23,307 / week

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Holiday villa with golf nearby in Anguilla

Meads Bay Pond villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £736 / night

£5,153 / week

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Holiday villa in Anguilla

Long Bay Village villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

from £4,596 / night

£32,170 / week

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Anguilla holiday villa rental

Shoal Bay West villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 5

from £235 / night

£1,454 - £2,486 / week

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Holiday villa in Anguilla

Long Bay Village villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £4,221 / night

£29,544 / week

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Holiday villa with swimming pool in Little Harbour

Little Harbour villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,735 / night

£11,255 / week

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Holiday home with swimming pool in Anguilla

East End Village house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 11

from £657 / night

£4,596 - £9,028 / week

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Holiday villa letting

Sandy Hill Bay villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £857 / night

£5,999 / week

1 / 38

Holiday villa accommodation

Sandy Hill Bay villa

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £1,047 / night

£7,326 / week

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Holiday villa rental

Sandy Hill Bay villa

  • 1 bedroom
  • 3 bathrooms
  • sleeps 6

from £861 / night

£6,028 / week

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Holiday villa in Anguilla

Sandy Hill Bay villa

  • 1 bedroom
  • 4 bathrooms
  • sleeps 8

from £952 / night

£6,662 / week

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Holiday villa rental

Sandy Hill Bay villa

  • 1 bedroom
  • 5 bathrooms
  • sleeps 10

from £1,169 / night

£8,179 / week

1 / 42

Holiday villa rental

The Valley villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,032 / night

£7,222 / week

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Holiday villa with swimming pool in Anguilla

Anguilla villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £563 / night

£3,940 / week

1 / 29

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.

from £396 / night

£4,748 - £5,738 / week

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Holiday villa letting

Long Bay Village villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £656 / night

£4,590 / week

1 / 32

Little Harbour holiday villa rental

Little Harbour villa

  • 1 bedroom
  • 8 bathrooms
  • sleeps 16

from £6,384 / night

£44,684 / week

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Anguilla holiday villa rental

Anguilla villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £329 / night

£2,298 / week

1 / 14

Anguilla holiday villa rental

Long Bay Village villa

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 22

from £6,605 / night

£46,230 / week

1 / 37

Anguilla holiday villa rental

Little Harbour villa

  • 1 bedroom
  • 8 bathrooms
  • sleeps 16

from £6,820 / night

£47,741 / week

1 / 28

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