Compare Vacation Rentals & Airbnb in Anguilla

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Anguilla vacation rentals
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561 Rentals and Airbnb in Anguilla

Best family friendly Anguilla vacation rentals

Among the 561 accommodations in Anguilla, here are the 4 best family friendly rentals

Syl Apartment – Modern Cozy Getaway W/ Car Rental - Anguilla
9.8 23 reviews
Anguilla
21/06 – 30/06
$185/nighttotal: $1665 (9 )

Syl Apartment – Modern Cozy Getaway W/ Car Rental

1 2
apartment , The Valley
This one-bedroom flat is perfectly located in AI, just a short walk from the bustling city centre and its many attractions. The apartment has received excellent ratings for its cleanliness, location, and overall comfort, ensuring a pleasant stay.
The flat comfortably accommodates two guests and features a well-equipped kitchen with a fridge and microwave oven. You can enjoy the air conditioning, garden, and parking, as well as the added convenience of a washing machine and dryer, two smart TVs, and a secure environment with exterior cameras.
We Offer Something New  And Crisp - Anguilla
9.5 71 reviews
Anguilla
29/06 – 29/07
$90/nighttotal: $2700 (30 )

We Offer Something New And Crisp

1 2
apartment , South Hill
This charming house is located in South Hill Village, just 5km from the nearest grocery store and bakery and 9km from the beach. It has excellent user, location and cleanliness ratings.
The house has one bedroom and one bathroom. Enjoy amenities such as a swimming pool, garden, parking, air conditioning, internet and a kitchen equipped with a fridge and microwave oven.
Coralito Bay Suites & Villas - Anguilla
9.8 88 reviews
Anguilla
05/12 – 12/12
$419/nighttotal: $2933 (7 )

Coralito Bay Suites & Villas

1 2
studio , The Valley
Coralito Bay Suites & Villas is located in The Valley, just a short distance from Anguilla Airport and Shoal Bay, making it an ideal base for exploring the island. The property has received excellent ratings for its location, cleanliness, and overall guest experience.
This studio apartment offers a private patio for enjoying the Caribbean Sea views. Guests can benefit from modern amenities, such as air conditioning, a flat-screen TV, and free Wi-Fi, as well as the opportunity to snorkel in the surrounding waters.
Sandcastle Beach House - Anguilla
10 26 reviews
Anguilla
20/06 – 27/06
$4271/nighttotal: $29897 (7 )

Sandcastle Beach House

4 2
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.

Best Anguilla vacation rentals with a pool

Among the 561 accommodations in Anguilla, here are the 4 best rentals with a pool

Santosha Estate, Private Resort All To Yourselves - Anguilla
Anguilla
20/06 – 27/06
$13509/nighttotal: $94563 (7 )

Santosha Estate, Private Resort All To Yourselves

9 9
house , Long Bay Village
Santosha Estate, a luxurious beachfront property in Long Bay, Anguilla, is situated near West End Village.
This nine-bedroom villa, boasting 836 square metres of floor space, offers multiple kitchens, a private pool and jacuzzi, a fitness centre, and sleeps up to 21 guests, with additional amenities including tennis and pickleball courts, kayaks and paddleboards.
Bow Green Villa - Rendezvous Bay - Anguilla
10 2 reviews
Anguilla
01/09 – 04/09
$1166/nighttotal: $3498 (3 )

Bow Green Villa - Rendezvous Bay

1 4
apartment , Rendezvous Bay
This three-bedroom, three-bathroom apartment is located in Rendezvous Bay, just 300 metres from the beach and situated between the Aurora Resort and the Great House, offering exceptional panoramic views of St. Martin, the beach, and the ocean.
This apartment provides air conditioning, Wi-Fi, a private swimming pool, and complimentary beach amenities, accommodating up to six guests with direct beach access.
Villa Nirvana - Anguilla
9.8 27 reviews
Anguilla
09/12 – 17/12
$2178/nighttotal: $17424 (8 )

Villa Nirvana

1 6
house , North Hill
This luxurious villa is located on Seafarer's Ridge in Anguilla, offering stunning views and a private setting just a short distance from the island's best beaches. The property has consistently received excellent ratings for its cleanliness, location, and user experience.
The spacious villa has four bedrooms and four bathrooms, comfortably accommodating up to eight guests. A fully equipped gym, a private swimming pool and Jacuzzi, and a large garden with an outdoor dining area provide plenty of opportunities for relaxation and entertainment.
Sleeps 11, Kids Lounge, 5,000 Sqft - Anguilla
10 13 reviews
Anguilla
20/06 – 27/06
$2454/nighttotal: $17178 (7 )

Sleeps 11, Kids Lounge, 5,000 Sqft

1 9
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.

Frequently Asked Questions about vacation rentals in Anguilla

  • What are the must-see places in Anguilla?

    Shoal Bay East, consistently ranked among the world's best beaches, is a must. Then there's Meads Bay, known for its calm waters and upscale resorts. For a historical perspective, visit the Wallblake House, a beautifully preserved Georgian-era mansion. And don't forget the breathtaking views from Crocus Bay.
  • What are the best Airbnb and vacation rentals in Anguilla?

    Tradewinds Apartments Simpson Bay, Maho Beach House - Grand Ocean Suite - 2 Bedroom and Blue Dream Apartments are the most popular Airbnb and vacation rentals in Anguilla among travelers.

  • What are the typical activities to do in Anguilla?

    Relaxing on Anguilla's stunning beaches is a given. Water sports like snorkeling, diving, and kitesurfing are popular. Exploring the island by car or scooter offers amazing coastal views. You can also enjoy fine dining at some of the Caribbean's top restaurants.
  • What are the most popular Airbnbs in Anguilla?

  • Which part of Anguilla offers the most pleasant climate?

    Anguilla enjoys a consistently warm and sunny climate year-round. However, the trade winds tend to make the northern areas, like Shoal Bay, feel slightly cooler and less humid than the southern parts of the island.
  • What are the best vacation rentals with a pool in Anguilla?

  • What airport options are there for reaching Anguilla?

    The Clayton J. Lloyd International Airport (AXA) is Anguilla's only airport, receiving flights primarily from regional hubs in the Caribbean and the US. You'll likely need a connecting flight.
  • What are the best rentals for families and kids in Anguilla?

  • Are there specific challenges to driving in Anguilla that visitors should know?

    Driving in Anguilla is generally straightforward, but the roads can be narrow in some areas, especially in the older sections of the island. Be mindful of driving on the left side of the road and pay attention to the smaller, less-traveled roads.
  • What are the best rentals or Airbnbs with a jacuzzi in Anguilla?

    The best vacation rentals or Airbnb with a jacuzzi in Anguilla are Maho Beach House - Grand Ocean Suite - 2 Bedroom, Blue Dream Apartments and The Villas On Great Bay - Villa Lavinia #9.

  • What currency is used in Anguilla?

    The East Caribbean dollar (EC$) is the official currency. However, US dollars are widely accepted throughout the island.
  • What are the top festivals to experience in Anguilla?

    Anguilla's Summer Festival, usually held in late July and early August, is a major event featuring music, dance, and competitions. The Anguilla National Trust also hosts various events throughout the year focusing on conservation and island culture.
  • What is the best time of year to visit Anguilla?

    Anguilla enjoys pleasant weather year-round. The best time to visit is typically during the shoulder seasons (April-May and September-October) for pleasant weather and fewer crowds. Hurricane season runs from June to November.
  • What are some local dishes to try in Anguilla?

    Try the fresh lobster, a local specialty. You should also sample the conch prepared in various ways, and don't miss the local fish dishes, often prepared with fresh herbs and spices. Many restaurants offer traditional Anguillian cuisine.
  • What emergency numbers should you know in case of a medical or security issue in Anguilla?

    For medical emergencies, dial 911. For police assistance, the number is 264-497-2333.
  • What etiquette tips are important when visiting Anguilla?

    Anguillians are known for their warmth and friendliness. A simple 'hello' and a smile go a long way. Respect local customs and traditions, and be mindful of the environment.
  • What are the best areas to spend a week in Anguilla?

    For a week-long stay, consider basing yourself in the areas around Shoal Bay East or Meads Bay. These locations offer a range of accommodation options, beautiful beaches, and easy access to restaurants and activities.
  • What are the best areas to spend a weekend in Anguilla?

    For a weekend trip, focus on one or two key areas. Shoal Bay East or Meads Bay are excellent choices for their stunning beaches and proximity to restaurants. Alternatively, explore the more secluded areas of the island for a quieter getaway.
  • What are the top shopping destinations in Anguilla?

    The Blowing Point Ferry Terminal area has several shops offering souvenirs, clothing, and local crafts. Many resorts also have boutiques offering a range of goods.
  • What are some off-the-beaten-path places to explore in Anguilla?

    Explore the island's interior by car or scooter, discovering hidden coves and beaches. Visit Little Bay, a secluded beach only accessible by boat or a somewhat challenging hike. Also consider exploring the island's various historical sites and nature trails.

Best Anguilla vacation rentals with parking

Anguilla Oceanfront Retreat-water Access & Views - Anguilla
Anguilla
09/12 – 17/12
$2154/nighttotal: $17232 (8 )

Anguilla Oceanfront Retreat-water Access & Views

1 6
house , Little Harbour
Villa Bénie, a beachfront villa in Little Harbour, offers direct oceanfront access on the south side of Anguilla, just a few kilometres from Clayton J. Lloyd International Airport and Blowing Point ferry terminal.
This spacious villa accommodates up to 10 guests with five bedrooms, three bathrooms, and an outdoor shower, boasting a Great Room with integrated kitchen, dining, and living areas, and features like air conditioning, Wi-Fi, and extensive outdoor spaces for enjoying the sea.
Villa Anguillitta - Anguilla
10 7 reviews
Anguilla
28/11 – 05/12
$2960/nighttotal: $20720 (7 )

Villa Anguillitta

3 3
B&B , Blowing Point Village
This beachfront property in Sandy Point is located just two kilometres from the Blowing Point Ferry Terminal and Pelican Bay, offering easy access to the island's attractions. It boasts excellent user ratings, ensuring a comfortable and enjoyable stay.
The villa features four bathrooms and a patio, perfect for relaxing in the island's warm weather. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, sauna, and fitness centre, making it ideal for a luxurious and active getaway.
3 Pools/3 Hot Tubs/2 Golf Carts - 2 Min. To Beach - Anguilla
Anguilla
20/06 – 27/06
$9263/nighttotal: $64841 (7 )

3 Pools/3 Hot Tubs/2 Golf Carts - 2 Min. To Beach

1 9
house , West End
Villa Mystique is situated in West End, overlooking Cove Lagoon, a short distance from the white sandy beaches of Maundays and Cove Bay. This luxurious property offers stunning views of the Caribbean Sea and neighbouring St. Martin, providing complete privacy and tranquility.
The villa has five grand suites, nine bathrooms, three pools and a state-of-the-art gym, accommodating up to 12 guests. Enjoy a fully-equipped fitness centre, private chef, twice-daily housekeeping, laundry service, evening security, and a private concierge who can cater to any needs.
Peaceful Garden-view Studio – Suite #2 - Anguilla
9.8 59 reviews
Anguilla
20/06 – 27/06
$162/nighttotal: $1134 (7 )

Peaceful Garden-view Studio – Suite #2

1 2
apartment , Island Harbour
This oceanfront studio is situated at Arawak Beach Club, just 5km from Shoal Bay, a 5-minute walk from a supermarket and 10km from Captain's Bay, offering a peaceful and convenient location. It has consistently received excellent ratings for its cleanliness, location and user experience.
The studio comfortably accommodates two guests and offers a private deck with stunning Caribbean views. Guests can enjoy a fully equipped kitchen, complimentary kayaks and paddleboards, access to the Arawak Beach Club's pool and amenities, and high-speed internet.

Best Anguilla vacation rentals with a balcony

Syl Apartment - Modern, Car Rental Available - Anguilla
9.8 5 reviews
Anguilla
05/12 – 12/12
$227/nighttotal: $1589 (7 )

Syl Apartment - Modern, Car Rental Available

1 2
apartment , North Side
SYL Apartment, a self-catering flat in Anguilla's North Side, is conveniently located 3.9km from Shoal Bay Beach and 3.1km from Anguilla Airport.
This 45-square-metre one-bedroom apartment sleeps three, boasting a fully equipped kitchen, air conditioning, a private terrace, garden, parking, and free Wi-Fi.
Gumbsie Villas - Anguilla
Anguilla
05/12 – 12/12
$847/nighttotal: $5929 (7 )

Gumbsie Villas

1 2
apartment , The Valley
This Gumbsie Villas apartment is situated in The Valley, 4.19 kilometres from Shoal Bay and 5.95 kilometres from Anguilla Airport.
This one-bedroom flat offers air conditioning, a fully equipped kitchen, complimentary private parking, and free high-speed Wi-Fi, with direct access to a terrace boasting garden views.
Island Paradise Apartments - Anguilla
9.7 4 reviews
Anguilla
01/09 – 04/09
$330/nighttotal: $990 (3 )

Island Paradise Apartments

2 4
apartment , The Valley
Island Paradise Apartments is located in The Valley, a short 6.4 kilometre drive from Shoal Bay.
This two-bedroom apartment, ideal for families, offers a private terrace, a fully equipped kitchen and a garden, perfect for relaxing after a day exploring the island.
Aurora Anguilla Resort & Golf Club - Anguilla
9.5 407 reviews
Anguilla
29/06 – 29/07
$1585/nighttotal: $47550 (30 )

Aurora Anguilla Resort & Golf Club

1 2
resort , Rendezvous Beach
The Aurora Anguilla Resort & Golf Club is situated on the beach in Anguilla, just a short drive from Blowing Point and Ferry Terminal and Anguilla Clayton J. Lloyd Airport. It has consistently received excellent ratings for its cleanliness and location, ensuring a comfortable and enjoyable stay.
The resort offers a range of accommodation options, including spacious suites with cable TV and Bose music systems. There are also a variety of amenities and activities available, such as a spa, gym, tennis courts, and multiple dining options, making it an ideal choice for families and couples seeking a relaxing and luxurious getaway.
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