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Watersports Holidays in Anguilla - Holiday Lettings

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379 properties with watersports onsite or nearby

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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

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Home rental in Anguilla

East End Village house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £469 / night

£3,283 / week

1 / 12

Holiday villa with swimming pool in Anguilla

Long Bay Village villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £845 / night

£5,911 / 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 letting

The Valley villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £305 / night

£2,134 / week

1 / 4

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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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

1 / 56

Holiday villa with swimming pool in Little Harbour

Little Harbour villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £1,735 / night

£11,255 / week

1 / 29

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

1 / 53

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 £655 / night

£4,584 / week

1 / 32

Anguilla holiday villa rental

Long Bay Village villa

  • 9 bedrooms
  • 12 bathrooms
  • sleeps 22

from £6,605 / night

£46,230 / week

1 / 37

Holiday villa rental

The Valley villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 7

from £93,789 / night

£656,518 / week

1 / 18

Holiday villa in Sandy Hill Bay

Sandy Hill Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £933 / night

£6,529 / week

1 / 17

Holiday villa with shared pool, golf nearby in Blowing Point

Blowing Point villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £169 / night

£1,126 - £1,520 / week

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Holiday villa with swimming pool in Anguilla

Long Bay Village villa

  • 5 bedrooms
  • 7 bathrooms
  • sleeps 10

from £1,085 / night

£8,916 / 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 £844 / night

£5,909 - £9,028 / week

1 / 52

Anguilla holiday villa rental

West End Village villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £573 / night

£4,008 / week

1 / 22

Great rentals within 20 miles that match your search

Terres Basses holiday villa rental

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,273 / night

£8,910 / week

1 / 42

Holiday apartment with tennis court in Orient Bay

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £71 / night

£460 - £920 / week

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Holiday condo with shared pool in Oyster Pond

Oyster Pond condo

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £457 / night

£3,195 - £4,506 / week

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Holiday apartment with shared pool in Simpson Bay

Simpson Bay apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £223 / night

£1,557 - £2,867 / week

1 / 29

Holiday apartment with shared pool, golf nearby in Philipsburg

Philipsburg apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

from £563 / night

£3,752 / week

1 / 13

Holiday villa with swimming pool in Orient Bay

Orient Bay villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 16

from £436 / night

£2,613 - £4,887 / week

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Holiday villa with swimming pool in Marigot, Saint Martin

Marigot, Saint Martin villa

  • 6 bedrooms
  • 18 bathrooms
  • sleeps 12

from £1,501 / night

£10,505 / week

1 / 4

Holiday apartment rental

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £71 / night

£460 - £920 / week

1 / 38

Terres Basses holiday home rental

Terres Basses house

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £3,863 / night

£27,031 - £69,625 / week

1 / 37

Simpson Bay holiday villa rental

Simpson Bay villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £773 / night

£5,407 - £14,744 / week

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Holiday apartment in Cupecoy Bay

Cupecoy Bay apartment

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £335 / night

£2,335 - £4,014 / week

1 / 27

Simpson Bay holiday villa rental

Simpson Bay villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 12

from £1,698 / night

£11,878 - £22,936 / week

1 / 61

Holiday villa in Marigot, Saint Martin

Marigot, Saint Martin villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £296 / night

£1,345 - £5,410 / week

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Holiday apartment in Oyster Pond

Oyster Pond apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £400 / night

£2,795 / week

1 / 15

Holiday home rental

Grand Case house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £516 / night

£3,604 - £7,372 / week

1 / 60

Holiday villa with swimming pool, golf nearby in Philipsburg

Philipsburg villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £329 / night

£2,298 / week

1 / 39

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