Holiday 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.
5–12 JulIndividual Host,
£497 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.
3–10 MayProfessional Host,
£535 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.
21–28 JulIndividual Host,
£376 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
17–24 MayIndividual Host,
£823 per night
4.75 out of 5 average rating, 4 reviews
Home in The Valley
Asha’s Place
23–30 JanIndividual Host,
£233 per night
4.82 out of 5 average rating, 17 reviews
Home in Seafeathers
Beach Front Villa With Swimming Pool
20–27 SeptIndividual Host,
£369 per night
4.64 out of 5 average rating, 11 reviews
Home in AI
Poinsettia Villa-Experience the best of west end
30 Jul – 6 AugIndividual Host,
£280 per night
4.8 out of 5 average rating, 5 reviews
Guest favourite
Home in Little Harbour
Swim, Sun, Fun Central Location
15–22 OctProfessional Host,
£176 per night
5.0 out of 5 average rating, 6 reviews
Home in AI
Lockrum Point Villa Oceanside 2bdrm/2bath w/ Pool
5–12 SeptIndividual Host,
£721 per night
5.0 out of 5 average rating, 3 reviews
Guest favourite
Home in Island Harbour
Stunning ocean views in Island Harbour
1–8 JanIndividual Host,
£797 per night
4.8 out of 5 average rating, 20 reviews
Home in Anguilla
Villa Alison North Ridge North Hill
17–24 AprIndividual Host,
£333 per night
4.75 out of 5 average rating, 4 reviews
Home in Long Bay Village
Châlet Genesis
6–13 SeptIndividual Host,
£563 per night
New place to stay
Home in Shoal Bay
Zirok Villa Shoal Bay
16–23 JunIndividual Host,
£649 per night
New place to stay
Home in AI
Lovely Villa in Iconic Little Bay Anguilla
7–14 SeptIndividual Host,
£1,000 per night
New place to stay
Home in Little Harbour
Charming 4 Bedroom Estate w/ Beach Access
5–12 AugProfessional Host,
£977 per night
New place to stay

Apartment rentals with a pool

Apartment in West End
Turtles Nest Beach Resort - Beachfront 1 bedroom condo
22 Feb – 1 MarProfessional Host,
£497 per night
4.67 out of 5 average rating, 42 reviews
Apartment in Shoal Bay
Ocean View 1 Bedroom Condo on Shoal Bay Beach!
9–16 JunProfessional Host,
£366 per night
5.0 out of 5 average rating, 4 reviews
Apartment in The Valley
Sapphire Sea Penthouse Condo
21–28 JulIndividual Host,
£288 per night
5.0 out of 5 average rating, 4 reviews
Apartment in Sandy Hill Bay
Shangrila Anguilla -Sandy Hill
19–26 Aug
£281 per night
New place to stay
Apartment in George Hill
Anguilla 2 bedroom condo for rent
5–12 Jun
£248 per night
New place to stay
Apartment in The Valley
Ocean Terrace Condo
13–20 Dec
£211 per night
New place to stay
Apartment in West End
Turtles Nest Beach Resort - direct Beach access 2 bedroom condo
19–26 OctProfessional Host,
£461 per night
4.89 out of 5 average rating, 9 reviews
Guest favourite
Apartment in West End
Turtles Nest Beach Resort - Oceanfront 3 Bedroom condo
25 Oct – 1 NovProfessional Host,
£675 per night
5.0 out of 5 average rating, 6 reviews
Apartment in Shoal Bay
Fountain Anguilla 2 Bedroom Garden View Condo
14–21 MayProfessional Host,
£402 per night
4.8 out of 5 average rating, 5 reviews
Apartment in Shoal Bay
Fountain Anguilla Partial Ocean View 2 Bed 2 Bath
20–27 OctProfessional Host,
£362 per night
4.67 out of 5 average rating, 3 reviews
Apartment in Shoal Bay
4 Bedroom/ 4 Bath- Sleeps 12 Pool View Condo Combo
11–18 JunProfessional Host,
£759 per night
5.0 out of 5 average rating, 3 reviews
Apartment in Shoal Bay
Fountain Anguilla 1 Bedroom Garden View Condo
24–31 OctProfessional Host,
£289 per night
5.0 out of 5 average rating, 3 reviews

Destinations to explore