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Watersports Holidays in Anguilla - Holiday Lettings

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26 properties with watersports onsite or nearby

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Holiday villa letting

The Valley villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £297 / night

£2,076 / week

1 / 4

Holiday villa with golf nearby in Anguilla

Meads Bay Pond villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £736 / night

£5,153 / week

1 / 20

Holiday villa with swimming pool in Anguilla

Anguilla villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £686 / night

£9,280 - £18,880 / week

1 / 42

Villa rental in Anguilla

Shoal Bay Village villa

  • 4 bedrooms
  • 7 bathrooms
  • sleeps 10

from £1,280 / night

£8,960 / week

1 / 55

Anguilla holiday villa rental

West End Village villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £573 / night

£4,008 / week

1 / 22

Anguilla holiday villa rental

Blowing Point villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £915 / night

£6,400 / week

1 / 24

Shoal Bay Village holiday villa rental

Shoal Bay Village villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £755 / night

£5,280 / week

1 / 65

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 £270 / night

£1,888 - £2,528 / week

1 / 19

Home rental in Anguilla

East End Village house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £458 / night

£3,200 / week

1 / 12

Anguilla holiday villa rental

Shoal Bay West villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 5

from £229 / night

£1,418 - £1,738 / week

1 / 15

Holiday villa with swimming pool in Little Harbour

Little Harbour villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,829 / night

£11,886 / week

1 / 29

Anguilla holiday villa rental

Blowing Point villa

  • 6 bedrooms
  • 9 bathrooms
  • sleeps 12

from £2,377 / night

£16,640 / week

1 / 22

Holiday home with swimming pool in Anguilla

East End Village house

  • 3 bedrooms
  • 5 bathrooms
  • sleeps 11

from £1,006 / night

£7,040 - £9,760 / week

1 / 57

Condo rental in Anguilla

Island Harbour condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £179 / night

£1,248 / week

1 / 17

Holiday villa in Anguilla

Long Bay Village villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

from £4,115 / night

£28,800 / week

1 / 56

Holiday villa with shared pool, golf nearby in Blowing Point

Blowing Point villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £165 / night

£1,143 - £1,527 / week

1 / 22

Anguilla holiday villa rental

Long Bay Village villa

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 20

from £5,519 / night

£38,631 / week

1 / 37

Holiday villa in Anguilla

Long Bay Village villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 11

from £4,480 / night

£31,360 / week

1 / 65

Holiday villa with swimming pool in Anguilla

Long Bay Village villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £1,323 / night

£9,259 / week

1 / 45

Holiday villa with shared pool in Anguilla

Shoal Bay Village villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,258 / night

£8,804 / week

1 / 60

Anguilla holiday home rental

West End Village house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £636 / night

£4,448 / week

1 / 15

Holiday villa with swimming pool in Anguilla

Long Bay Village villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

from £1,323 / night

£8,620 / week

1 / 49

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!

from £1,308 / night

£9,143 - £9,687 / week

1 / 61

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 £412 / night

£4,608 - £5,568 / week

1 / 65

Holiday villa rental

The Valley villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

from £91,427 / night

£639,986 / week

1 / 18

Holiday villa letting

Long Bay Village villa

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £817 / night

£5,715 / week

1 / 32

Great rentals within 20 miles that match your search

Holiday apartment rental

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £420 / night

£2,939 / week

1 / 8

Orient Bay holiday studio rental

Orient Bay studio

  • Studio
  • 1 bathroom
  • sleeps 2

from £108 / night

£755 / week

1 / 22

Holiday studio with shared pool in Marigot

Marigot studio

  • Studio
  • 1 bathroom
  • sleeps 4

from £89 / night

£494 - £974 / week

1 / 20

Holiday apartment in Baie Nettle

Baie Nettle apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £118 / night

£823 / week

1 / 11

Holiday b&b in Marigot

Marigot b&b

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

from £54 / night

£343 / week

1 / 22

Simpson Bay holiday condo rental

Simpson Bay condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £252 / night

£1,760 / week

1 / 17

Holiday home with swimming pool in Terres Basses

Terres Basses house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £1,198 / night

£8,384 - £16,769 / week

1 / 45

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 14

from £1,256 / night

£8,784 - £25,951 / week

1 / 64

Holiday villa with swimming pool in Terres Basses

Terres Basses villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 10

from £1,712 / night

£11,978 - £35,932 / week

1 / 42

Holiday home rental

Anse Marcel house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £432 / night

£3,019 - £7,187 / week

1 / 27

Terres Basses holiday home let

Terres Basses house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,010 / night

£7,065 - £19,166 / week

1 / 69

Holiday villa in Terres Basses

Terres Basses villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,141 / night

£7,988 - £21,961 / week

1 / 34

Terres Basses holiday home rental

Terres Basses house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £559 / night

£3,913 - £9,582 / week

1 / 40

Home rental in Terres Basses with swimming pool

Terres Basses house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £446 / night

£3,114 - £7,586 / week

1 / 31

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