Vacation rentals with a pool in Anguilla

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Top-rated rentals with a pool in Anguilla

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Superhost
Home in Shoal Bay Village
Shoal Bay Coastal Sanctuary, Anguilla
Shoal Bay Coastal Sanctuary is located directly on the coast with beautiful unobstructed views of the sea. It's a gracious two story home of 3 bedrooms and 3 full bathrooms--the lower level is comprised of 2 bedrooms on either side of an open plan "kitchen / dining room / living room" with the penthouse bedroom on the upper level. All rooms face onto the Caribbean and overlook the freshwater pool--every room is fully screened and air conditioned and graciously decorated in a Caribbean motif.
Jan 2 – 9
$574 per night
4.91 out of 5 average rating, 11 reviews
Superhost
Villa in Long Bay Village
Panoramic Beachfront Villa
This property, composed of two houses with two bedrooms each, is on a quiet beach near Meads Bay, with sweeping views of the ocean and beach (West facing). The property has private access to the beach via either house, and has rooftop access which is a rare way to enjoy both day and night on Anguilla (great for sunsets and stargazing). Though the villa was recently renovated, the essential elements that make the house feel like a part of the Caribbean from a bygone era are still present.
May 3 – 10
$504 per night
5.0 out of 5 average rating, 3 reviews
Superhost
Villa in Seafeathers
Oceanview villa with private pool, 5 mins to beach
Southern Comfort Villa is the perfect place for those looking for a laid back, cottage-like retreat. Our 2 bedroom, 2 bath villa sleeps 4-5 guests. The great room boasts 20 ft vaulted ceilings, a fully equipped kitchen and comfortable furnishings. Take a dip in the pool while enjoying unobstructed views of the Caribbean Sea and neighbouring islands of St. Martin and St. Barth. Enjoy a relaxing morning coffee or afternoon drink with a view on the wrap around veranda.
Aug 6 – 13
$543 per night
4.83 out of 5 average rating, 6 reviews

Popular amenities for Anguilla rentals with a pool

House rentals with a pool

Home in North Hill Village
Cloud Cottage- Cliffside villa
Jun 23 – 30
$743 per night
4.75 out of 5 average rating, 4 reviews
Home in The Valley
Asha’s Place
Dec 9 – 16
$250 per night
4.82 out of 5 average rating, 17 reviews
Home in Seafeathers
Beach Front Villa With Swimming Pool
Jan 30 – Feb 6
$374 per night
4.64 out of 5 average rating, 11 reviews
Guest favorite
Home in Little Harbour
Swim, Sun, Fun Central Location
Oct 15 – 22
$182 per night
5.0 out of 5 average rating, 6 reviews
Home in AI
Poinsettia Villa-Experience the best of west end
Jul 6 – 13
$314 per night
4.8 out of 5 average rating, 5 reviews
Guest favorite
Home in Island Harbour
Stunning ocean views in Island Harbour
Jan 1 – 8
$775 per night
4.8 out of 5 average rating, 20 reviews
Home in AI
Lockrum Point Villa Oceanside 2bdrm/2bath w/ Pool
Aug 22 – 29
$800 per night
5.0 out of 5 average rating, 3 reviews
Home in Anguilla
Villa Alison North Ridge North Hill
Aug 20 – 27
$359 per night
4.75 out of 5 average rating, 4 reviews
Home in Blowing Point
Newly Renovated 2 Bedroom Villa
Oct 12 – 19
$618 per night
New place to stay
Home in AI
Lovely Villa in Iconic Little Bay Anguilla
Sep 11 – 18
$900 per night
New place to stay
Home in Shoal Bay
Zirok Villa Shoal Bay
Jul 21 – 28
$712 per night
New place to stay
Home in Long Bay Village
Châlet Genesis
Jul 9 – 16
$625 per night
New place to stay

Condo rentals with a pool

Condo in West End
Turtles Nest Beach Resort - Beachfront 1 bedroom condo
Dec 10 – 17
$545 per night
4.68 out of 5 average rating, 44 reviews
Condo in Shoal Bay
Ocean View 1 Bedroom Condo on Shoal Bay Beach!
Nov 15 – 22
$445 per night
5.0 out of 5 average rating, 4 reviews
Condo in The Valley
Sapphire Sea Penthouse Condo
May 19 – 26
$300 per night
5.0 out of 5 average rating, 4 reviews
Condo in Sandy Hill Bay
Shangrila Anguilla -Sandy Hill
Sep 27 – Oct 4
$305 per night
New place to stay
Condo in George Hill
Anguilla 2 bedroom condo for rent
Oct 28 – Nov 4
$275 per night
New place to stay
Condo in The Valley
Ocean Terrace Condo
Dec 13 – 20
$234 per night
New place to stay
Condo in West End
Turtles Nest Beach Resort - direct Beach access 2 bedroom condo
Aug 11 – 18
$495 per night
4.89 out of 5 average rating, 9 reviews
Condo in Shoal Bay
Fountain Anguilla 2 Bedroom Garden View Condo
Jun 2 – 9
$434 per night
4.8 out of 5 average rating, 5 reviews
Condo in Shoal Bay
Fountain Anguilla Partial Ocean View 2 Bed 2 Bath
Sep 19 – 26
$425 per night
4.67 out of 5 average rating, 3 reviews
Condo in Shoal Bay
4 Bedroom/ 4 Bath- Sleeps 12 Pool View Condo Combo
Jun 6 – 13
$820 per night
5.0 out of 5 average rating, 3 reviews
Condo in West End
Turtles Nest Beach Resort - Beachfront 2 bedroom condo
Oct 16 – 23
$480 per night
4.56 out of 5 average rating, 9 reviews
Condo in Shoal Bay
Fountain Anguilla 1 Bedroom Garden View Condo
Feb 18 – 25
$460 per night
5.0 out of 5 average rating, 3 reviews

Destinations to explore