Compare Vacation Rentals & Airbnb in Anguilla

769 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • priceline
  • tripadvisor
  • tripcom
  • sonder
  • homestay
  • hostelworld
  • hotelscom
  • agoda
Anguilla vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

769 Rentals and Airbnb in Anguilla

Best family friendly Anguilla vacation rentals

Among the 769 accommodations in Anguilla, here are the 4 best family friendly rentals

Sandcastle Villa - Anguilla
10 26 reviews

Sandcastle Villa

house, Crocus Hill
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.
We Offer Something New  And Crisp - Anguilla
9.5 72 reviews

We Offer Something New And Crisp

apartment
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.
Syl Apartment - Modern, Car Rental Available - Anguilla
9.8 7 reviews

Syl Apartment - Modern, Car Rental Available

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.
White Sands Anguilla Sand Unit - Anguilla
9.0 2 reviews

White Sands Anguilla Sand Unit

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.

Best Anguilla vacation rentals with a pool

Among the 769 accommodations in Anguilla, here are the 4 best rentals with a pool

Sea Whisper - Anguilla
10 10 reviews

Sea Whisper

apartment
This apartment in Sandy Hill Beach offers a peaceful retreat within 500 meters of local attractions.
This one-bedroom, one-bathroom flat accommodates up to three guests and features air conditioning, a kitchen, internet, a swimming pool, and parking, ideal for a relaxing seaside break.
Lockrum Point Villa: Oceanside-4bdrm/4bath W/ Pool - Anguilla
10 56 reviews

Lockrum Point Villa: Oceanside-4bdrm/4bath W/ Pool

house
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.
Villa Steps From The Beach - Anguilla
10 3 reviews

Villa Steps From The Beach

house
This luxurious five-bedroom Limestone Bay villa, a two-minute stroll from a secluded white-sand beach, offers 1022 square metres of Moroccan-inspired living space.
The property boasts a private infinity pool, fitness centre, and ample parking, sleeping up to ten guests in king-size suites, each with an en-suite bathroom and included housekeeping.
Beachfront Estate W/ Pool+tennis Court - Anguilla
10 10 reviews

Beachfront Estate W/ Pool+tennis Court

apartment
Zenaida Tennis and Beach Estate, situated on the Anguilla coast, offers direct beach access and breathtaking views of St. Martin and St. Barts.
This luxurious seven-bedroom, eight-bathroom property, sleeping up to 15 guests, boasts a vanishing-edge pool, Har-Tru tennis court, hot tub, gourmet kitchen, and three acres of tropical gardens; poolside yoga and massage services are available.

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

Akayita's Escape - 3bd With 3 Private Baths - Anguilla
9.1 11 reviews

Akayita's Escape - 3bd With 3 Private Baths

apartment
This three-bedroom, three-bathroom house in Sea Feathers Bay, East End, offers a peaceful retreat close to East End's beaches and attractions, though precise distances aren't specified.
This self-catering property sleeps six, boasting a fully equipped kitchen with fridge and microwave, a garden, parking, in-house laundry, a Smart TV, and private en-suite bathrooms in each bedroom.
Sapphire Sea Penthouse Condo - Anguilla
9.8 8 reviews

Sapphire Sea Penthouse Condo

apartment
This two-bedroom apartment is situated on the top floor of Ocean Terrace, a building conveniently located near shops and restaurants in The Valley, just minutes away from the beautiful Shoal Bay East beach. The apartment has received excellent ratings for user experience, location, and cleanliness, making it a desirable choice for travellers.
The apartment can accommodate up to six guests and features a full kitchen, spacious living and dining areas, and walk-in closets. Guests can enjoy a range of amenities including air conditioning, ceiling fans, cable TV, high-speed Wi-Fi, a swimming pool, a garden, a fitness centre, and parking.
Central 6 Bedroom Home With Pool & Ocean Views - Anguilla
9.5 4 reviews

Central 6 Bedroom Home With Pool & Ocean Views

apartment
This apartment is located in The Valley, Anguilla, just a short distance from the beaches and shops of the town centre, offering stunning views of St. Martin/St. Maarten. It has received excellent ratings for location, cleanliness, and user experience.
This property offers a choice of 2, 3, 4, or 5 bedrooms, comfortably accommodating up to 6 guests. Amenities include a fully equipped kitchen, air conditioning, a swimming pool, a garden, parking, and on-demand services such as daily cleaning, car rental, and massages.
Anguilla Sunrise Penthouse - 2 Bed/2-bath - Anguilla
9.8 31 reviews

Anguilla Sunrise Penthouse - 2 Bed/2-bath

apartment
This penthouse apartment is located in Shoal Bay, a short distance from the famous "World's Best Beach" of the same name, offering a tranquil and picturesque setting. The apartment has received excellent ratings for its location, cleanliness, and overall experience, making it a highly sought-after choice for travellers.
The spacious penthouse apartment offers a large and open layout, comfortably accommodating up to six guests. A range of amenities are available for guests to enjoy, including a fully equipped kitchen, a private balcony, and a washer and dryer, ensuring a comfortable and convenient stay.

Best Anguilla vacation rentals with a balcony

Thrush Nest View Studio Apartment - Anguilla
9.5 25 reviews

Thrush Nest View Studio Apartment

studio, The Valley
Thrush Nest View Studio is situated in The Valley, Anguilla, 4km from Shoal Bay and 4km from Anguilla Airport, offering easy access to both beach and airport.
This self-contained apartment boasts a 72 square metre floor area, sleeping up to two guests, and includes a fully equipped kitchen, private parking, a terrace, garden, air conditioning and free Wi-Fi.
Aurora Anguilla Resort & Golf Club - Anguilla
9.5 266 reviews

Aurora Anguilla Resort & Golf Club

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.
Breezee - Anguilla
9.3 8 reviews

Breezee

apartment, Long Path
This two-bedroom apartment is situated just 11 miles from Shoal Bay and 2.5 miles from Anguilla Airport, making it a convenient base for exploring the island. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property can accommodate up to four guests and features a well-equipped kitchen, multiple bathrooms, and a private patio with mountain views. Enjoy the convenience of air conditioning, free Wi-Fi, and parking, as well as the opportunity to relax in the garden and on the balcony with sea views.
Châlet Genesis - Anguilla
10 6 reviews

Châlet Genesis

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.
©2026 cozycozy.com