This luxurious North Hill Village villa boasts breathtaking Sandy Ground views from its elevated position on North Hill. The multi-level property offers four bedrooms, five bathrooms, sleeping eight guests, and features a private pool, expansive garden, and included housekeeping service; all within easy reach of Sandy Ground's amenities.
10 2 reviews
Anguilla
01/08 – 08/08
SG$2463/nighttotal: SG$17241 (7 )
New Luxury Mediterranean Coastline Villa
1 3
house , Sandy Hill
This six-bedroom Sandy Hill seaside house, sleeping twelve, offers easy access to local attractions; precise distances require further information. The property includes a kitchen with fridge and dishwasher, air conditioning, parking, and one bathroom; enjoy stunning seaside views and ample space for relaxation and family fun.
9.4 16 reviews
Anguilla
29/10 – 03/11
SG$747/nighttotal: SG$3735 (5 )
Greengard Villa - Cul De Sac, Anguilla
1 7
house , Anguilla
This four-bedroom villa is situated in a peaceful, breezy part of Anguilla, just a short walk from Rendezvous Bay and the Ferry Boat Inn restaurant. The property has received excellent ratings for user experience, location, and cleanliness. The spacious villa can accommodate up to nine guests and features a fully equipped kitchen with a fridge, microwave, dishwasher, and a garden. The property also benefits from air conditioning, parking, WiFi, and twice-weekly maid service, as well as stunning views over Rendezvous Bay.
Anguilla
20/07 – 26/07
SG$919/nighttotal: SG$5514 (6 )
Peace & Happiness, Cul De Sac, Anguilla
1 4
house , Blowing Point
This apartment in Blowing Point is located in the Cul de Sac area of Anguilla, a 10-minute drive from Rendezvous Bay, dining, golf, the marina, and the airport. This recently renovated villa offers panoramic sea views, a private infinity pool, two en-suite bedrooms accommodating up to four guests, a gourmet kitchen, and outdoor dining, with housekeeping and concierge services available.
10 8 reviews
Anguilla
04/01 – 04/02
SG$811/nighttotal: SG$25141 (31 )
Bayview Resort, Beachfront Villa W/ Stunning Views
1 2
house , Blowing Point
This beachfront apartment in Blowing Point, Anguilla, is within walking distance of the Ferry Boat Inn restaurant and the ferry terminal, offering easy access to Blowing Point beach. The two-bedroom, two-bathroom dwelling sleeps six guests and boasts a well-equipped kitchen (fridge, freezer, microwave), air conditioning, on-site laundry, parking, and a garden, plus exceptional ocean and St Maarten views.
9.8 18 reviews
Anguilla
01/09 – 04/09
SG$1290/nighttotal: SG$3870 (3 )
5br Modern Caribbean Luxury With Pool & Bay Views
1 4
house , Rendezvous Bay
Songbird Villa is located in Rendezvous Bay, a short stroll from the beach and within easy reach of amenities like high-end hotels, a golf course, supermarkets, and beach bars. The villa has received excellent ratings for user experience, location, and cleanliness. The property offers four bedrooms and four bathrooms, accommodating up to eight guests. This spacious villa includes a private infinity pool overlooking the salt pond and hills of St. Maarten, a fully equipped kitchen, air conditioning, a garden, private parking, daily housekeeping service, and 24/7 concierge service.
Anguilla
29/10 – 03/11
SG$3154/nighttotal: SG$15770 (5 )
Cliffside 4-bedroom Villa W/ Pool Near Beach
1 7
house , Anguilla
Villa Le Rêve Bleu, a modern villa, is located in the secluded Black Garden district of Anguilla, offering a tranquil escape with panoramic sea views. This luxurious villa accommodates up to 8 guests with 4 bedrooms and 5 bathrooms, featuring an infinity pool, air conditioning, a Jacuzzi, a garden, a bar, and parking, all complemented by 5-star service from Rêve Noir, including complimentary airport transfers.
10 1 review
Anguilla
20/07 – 26/07
SG$9566/nighttotal: SG$57396 (6 )
Odyssey - Kamique
1 4
house , Little Harbour
Odyssey-Kamique, a luxurious four-bedroom villa in Anguilla's Little Harbour, boasts stunning views and is situated on the South Shore, close to a private beach and within easy reach of Sandy Ground, the CuisinArt Golf Course and Spa. This wheelchair-accessible property offers a private beach with sun loungers, an infinity pool, daily concierge services, and sleeps eight guests, featuring modern interiors with a fully equipped kitchen including a microwave and dishwasher.
9.1 9 reviews
Anguilla
25/12 – 02/01
SG$1511/nighttotal: SG$12088 (8 )
Amazing Views In A Beautiful Villa
1 4
house , Seafeathers
This stunning four-bedroom villa in Seafeathers offers breathtaking Caribbean Sea views and is located just a short distance from the town centre and popular beaches. The property has consistently received excellent ratings for its cleanliness, location and overall user experience. The villa is spacious and tranquil, perfect for a relaxing getaway. Guests can enjoy a private swimming pool, a garden, a gazebo with a bar, and a fully equipped kitchen with a fridge, freezer, microwave oven, and dishwasher.
9.4 16 reviews
Anguilla
09/10 – 12/10
SG$206/nighttotal: SG$618 (3 )
1 Bd Apt At Da'vida's Crocus Bay #4
1 1
house , Crocus Bay Beach
This Crocus Bay cottage, a 20-second stroll from Crocus Bay Beach, enjoys a central location between West End resorts and Shoal Bay East, approximately 5 km from Anguilla Airport and close to The Valley. The one-bedroom, one-bathroom property, sleeping two guests, offers a kitchen with fridge and microwave, air conditioning, garden, parking, and is situated on the grounds of Da'Vida Beach Club restaurant, potentially providing access to further amenities.
10 5 reviews
Anguilla
04/01 – 04/02
SG$1913/nighttotal: SG$59303 (31 )
Waterfront Pickleball/tennis/pool Secluded Villa
1 2
house , Island Harbour
This contemporary villa is located at the end of Island Harbour, offering complete privacy and solitude just 100 metres from the waterline. The property has received excellent user, location and cleanliness ratings. This modern house has four bathrooms and can accommodate up to eight guests. Enjoy the benefits of a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, a garden, parking and high-speed internet access, plus hiking trails right outside your door.
9.2 5 reviews
Anguilla
29/10 – 03/11
SG$3039/nighttotal: SG$15195 (5 )
6 Br Villa With Concierge, Amenities, & Pool
6 7
house , Baie des Crocus
This six-bedroom, six-and-a-half-bathroom Anguilla villa is situated in a secluded hillside community, a short 8-24 km drive from Crocus Bay's restaurants and beaches. The property boasts a private infinity pool, a 24-hour fitness centre (hours may vary seasonally), and caters to groups of up to twelve guests, offering complimentary beach access to Crocus Bay and Rendezvous Bay on selected days.
Best Anguilla villas and holiday homes with a pool
Among the 310 accommodations in Anguilla, here are the 4 best villas and holiday homes with a pool
10 26 reviews
Anguilla
25/12 – 02/01
SG$25652/nighttotal: SG$205216 (8 )
Sandcastle Beach House
10 4
house , The Valley
Sandcastle Beach House is situated in The Valley, just a short distance from Crocus Bay Beach and Shoal Bay, offering a tranquil escape in a prime location. The property boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. This spacious villa features four bedrooms, making it ideal for families or groups of friends. The property offers a range of amenities, including a private pool and hot tub, a well-equipped kitchen, daily room service, and a host of activities like cycling, fishing, and snorkeling.
10 3 reviews
Anguilla
29/10 – 03/11
SG$1775/nighttotal: SG$8875 (5 )
4-bed Villa, Pool, Parking
4 7
house , Anguilla
Villa Farina, a luxurious beachfront property on Anguilla's southern coast, offers stunning ocean views and is conveniently located near various attractions. This four-bedroom, four-bathroom villa boasts 2,750 square metres of living space, sleeps eight guests, includes a private pool, complimentary vehicle, butler and babysitting services, and high-speed internet access.
9.8 53 reviews
Anguilla
09/10 – 12/10
SG$390/nighttotal: SG$1170 (3 )
White Sands Anguilla - Sea
3 1
house , Blowing Point Village
This beautiful villa is located in Blowing Point Village, just 6.9 miles from Shoal Bay and 3.7 miles from Anguilla Airport, making it a convenient base for exploring the island. The property consistently receives excellent ratings for its location, cleanliness, and overall experience. The spacious villa offers 232 square metres of living space and can comfortably accommodate up to 6 guests. It features a fully equipped kitchen, a private patio with outdoor dining, a hot tub, and a swimming pool, as well as laundry services, air conditioning, and free Wi-Fi.
9.9 18 reviews
Anguilla
01/09 – 04/09
SG$868/nighttotal: SG$2604 (3 )
Oceanview Villa With Private Pool, 5 Mins To Beach
1 4
house , Seafeathers
Southern Comfort Villa sits in Seafeathers, offering stunning, uninterrupted views of the Caribbean Sea and the neighbouring islands of St. Martin and St. Barth. This property has received excellent ratings for its location, cleanliness, and overall user experience. The villa has two bedrooms and two bathrooms, comfortably accommodating up to five guests. Enjoy a fully equipped kitchen, a private pool, a wrap-around veranda, air conditioning, and free Wi-Fi, all while soaking in the breathtaking Caribbean scenery.
Best family friendly Anguilla villas and holiday home
Among the 310 accommodations in Anguilla, here are the 4 best family friendly villas and holiday homes
10 3 reviews
Anguilla
01/08 – 10/08
SG$363/nighttotal: SG$3267 (9 )
Chocolate Moose
1 3
house , Anguilla
This apartment is situated just under 10 kilometres from Sandy Ground Beach, offering beautiful views of the ocean and neighbouring St. Maarten. Guests have consistently rated the accommodation, location, and cleanliness as excellent. The apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. Amenities include air conditioning, parking, internet access, and a kitchen equipped with a fridge.
10 3 reviews
Anguilla
29/10 – 03/11
SG$3039/nighttotal: SG$15195 (5 )
6 Br Villa On Crocus Bay With Pool & Concierge
6 7
house , Baie des Crocus
This CéBlue Villa is located on a hillside overlooking Crocus Bay, just a short walk from the beach and its renowned snorkeling spots. The surrounding area is peaceful and offers stunning sunset views. This six-bedroom villa can accommodate up to 12 guests and includes five bathrooms, a private pool, and a spacious outdoor living area. The villa also offers a fully equipped kitchen, daily housekeeping, and access to the Da'Vida Beach Club, which provides a range of amenities and activities.
8.9 14 reviews
Anguilla
01/08 – 10/08
SG$636/nighttotal: SG$5724 (9 )
Villa Catalina, Two Bedroom Cottage With Seaview
2 3
bungalow , Village de Shoal Bay
Catalina Villa is situated in Shoal Bay East, Anguilla, just 50 metres from the famous Shoal Bay Beach and a 3-minute drive from the main beach access point. This bungalow has received excellent ratings for location, cleanliness and overall experience. The villa offers 2 bedrooms and 2 bathrooms, accommodating up to 4 guests. The property features a fully equipped kitchen with Bosch appliances, a spacious living area, and a large covered porch with stunning ocean views.
10 55 reviews
Anguilla
09/10 – 12/10
SG$1382/nighttotal: SG$4146 (3 )
Lockrum Point Villa: Seaside Villa 3 Bed/3 Bath/pool
4 1
house , Lockrum Bay
This property is located in Blowing Point, Anguilla, just a short distance from Pelican Bay and Rendezvous Bay Beach, and close to the Blowing Point Ferry Terminal. It has consistently received excellent ratings for its location, cleanliness, and overall user experience. This spacious 325 square metre house offers a comfortable and well-equipped living space, perfect for families or groups. Enjoy the private pool, Jacuzzi, and terrace, along with access to a fully equipped kitchen, laundry facilities, and a range of amenities for a relaxing and enjoyable stay.
Frequently asked questions about villa rentals in Anguilla
What are the must-see attractions in Anguilla?
Anguilla boasts stunning beaches, of course! Shoal Bay East is consistently ranked among the world's best. Then there's Rendezvous Bay, known for its calm waters, perfect for families. For a historical perspective, visit the Old Wallblake House, a beautifully preserved Georgian mansion. And don't miss the picturesque Little Bay, with its dramatic cliffs and secluded cove.
The main airport serving Anguilla is Clayton J. Lloyd International Airport (AXA). It's a relatively small airport, but it's conveniently located and well-connected to other Caribbean islands and the US. Many travellers fly into San Juan, Puerto Rico (SJU) and then take a connecting flight to Anguilla.
What are the best villa rentals with a pool in Anguilla?
The official currency of Anguilla is the East Caribbean dollar (EC$), but US dollars are widely accepted throughout the island. Most businesses will readily accept either currency.
What are the best villa rentals with a jacuzzi in Anguilla?
Driving in Anguilla is generally safe, but it's important to be aware that the roads can be narrow and winding in some areas, particularly outside of the main towns. Driving on the left is standard, as it is in the UK. Remember to drive cautiously, especially at night.
What are the best villa rentals for families and kids in Anguilla?
How can you avoid cultural misunderstandings while in Anguilla?
Anguillians are known for their warm hospitality, but it's always a good idea to be respectful of local customs. Dress modestly when visiting churches or other religious sites. A simple 'Good morning' or 'Good evening' goes a long way, and taking the time to learn a few basic phrases in English will be appreciated. Remember to be patient and observant, and you'll have a wonderful time.
What are the best pet friendly villa rentals in Anguilla?
What are the headline festivals hosted in Anguilla?
Anguilla hosts several festivals throughout the year. The Anguilla Summer Festival is a major event, typically held in July and August, featuring music, dance, and cultural performances. There's also the Anguilla Literary Festival, attracting writers and book lovers.
What are the best villa rentals with parking in Anguilla?
Where are the best spots for a weekend stay in Anguilla?
For a short break, consider staying in the areas around Shoal Bay East or Rendezvous Bay. These locations offer easy access to stunning beaches and a variety of restaurants and bars. Many hotels and villas in these areas cater to weekend getaways.
Where are the best places to stay for a week in Anguilla?
For a longer stay, you might explore the wider range of accommodation options across the island. Areas like Meads Bay, with its luxurious resorts, or the more secluded areas of the island offer different experiences. Consider your priorities – relaxation, watersports, nightlife – when choosing your location.
Best Anguilla villas and holiday homes with a kitchen
9.0 2 reviews
Anguilla
09/10 – 12/10
SG$376/nighttotal: SG$1128 (3 )
White Sands Anguilla Sand Unit
1 1
house , The Valley
This Valley holiday home, situated 6km from Anguilla Airport and 13km from Shoal Bay, offers convenient access to key attractions. The 232 square metre property boasts one bedroom, two bathrooms, and sleeps eleven guests, featuring a private pool, Jacuzzi, garden, and fully equipped kitchen with appliances including a dishwasher and washing machine.
9.4 13 reviews
Anguilla
04/01 – 04/02
SG$458/nighttotal: SG$14198 (31 )
Villa Grande Downstairs Oceanview W/ Pool | 2br
2 2
house , Island Harbour
This villa in Island Harbour offers direct access to a swimming pool and stunning ocean views, located just minutes from Anguilla's premier beaches, dining, and entertainment. This accessible 2-bedroom, 2-bathroom property sleeps 4 guests and features a fully equipped kitchen, on-site parking, and a patio overlooking the sea, ideal for those seeking a relaxing Caribbean getaway.
Anguilla
01/08 – 08/08
SG$522/nighttotal: SG$3654 (7 )
"By The Sea" Oceanfront Villa
1 3
house , Blowing Point
This Anguillan-style villa is located directly on the oceanfront in Blowing Point, offering immediate sea access and proximity to local amenities. This two-bedroom villa accommodates up to four guests with direct oceanfront access, featuring a kitchen with fridge, freezer, and microwave, air conditioning in the bedrooms, and a garden, with pets welcome and internet provided.
Anguilla
04/01 – 04/02
SG$333/nighttotal: SG$10323 (31 )
Jared's Place
2 2
house , The Quarter
This holiday home is situated in The Quarter, 1.9 kilometres from Anguilla Airport and 6.4 kilometres from Shoal Bay. This property accommodates up to eight guests across two bedrooms and two bathrooms, offering air conditioning, WiFi, and a fully equipped kitchen, with a private terrace for enjoying the surroundings.
Best Anguilla villas and holiday homes with parking
9.9 69 reviews
Anguilla
01/09 – 04/09
SG$647/nighttotal: SG$1941 (3 )
Villa En Bord De Mer Piscine, Jacuzzi Et Kayaks
1 4
house , Island Harbour
This oceanfront villa is located in Island Harbour, just 5km from Shoal Bay and within walking distance of bars and restaurants. It has excellent user, location, and cleanliness ratings. The villa is a 2-bedroom, 2-bathroom property that can accommodate up to 6 guests. It includes a private pool, Jacuzzi, and outdoor shower, along with two kayaks and two paddle boards for exploring the surrounding waters.
9.8 5 reviews
Anguilla
01/09 – 04/09
SG$797/nighttotal: SG$2391 (3 )
Châlet Genesis
3 4
house , Meads Bay
Châlet Genesis is located in Meads Bay, a short 2 km from Meads Bay Beach and 9 km from Anguilla Airport. This 3-bedroom villa offers a private garden and balcony, perfect for enjoying the beautiful Anguilla weather, as well as a swimming pool, a terrace, and parking for up to 15 guests.
10 13 reviews
Anguilla
29/10 – 03/11
SG$2228/nighttotal: SG$11140 (5 )
Sleeps 11, Kids Lounge, 5,000 Sqft
4 7
house , Village de Shoal Bay
Villa Okeanos is located just 150 metres above the sea rocks in Shoal Bay East, Anguilla, a short distance from the world-renowned beach. The property has excellent user, location and cleanliness ratings. This four-bedroom, three-bathroom villa can accommodate up to 10 guests. The property features an infinity pool, BBQ grill, outdoor dining area, a bar under a covered patio, and a dedicated Kids Lounge.
Anguilla
01/09 – 04/09
SG$6367/nighttotal: SG$19101 (3 )
Luxury Villa
1 4
house , George Hill
This luxurious villa is located in George Hill, Anguilla, approximately 5 kilometres from Anguilla Airport. The 610 square metre property boasts ten bathrooms, sleeps 39 guests, and includes a private pool, terrace, fully equipped kitchen, free Wi-Fi, and free private parking.