Compare vacation rentals in Anguilla from 100+ sites!

769 available vacation rental offers

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

Best Vacation rentals and Airbnb offers in Anguilla

Best family friendly Anguilla vacation rentals

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

Native Vybz 3- Cab & Car Rentals - Anguilla
9.5 42 reviews

Native Vybz 3- Cab & Car Rentals

apartment
This apartment is located near the Four Seasons Grounds, tucked behind a local souvenir shop, offering a quieter and more authentic experience than staying on the main street. It consistently receives excellent ratings for location, cleanliness, and user experience.
The accommodation features one bathroom and comfortably sleeps four guests. Amenities include air conditioning, a garden, parking, internet, and a kitchen with a fridge, allowing you to enjoy a comfortable and convenient stay.
Santosha Estate, Private Resort All To Yourselves - Anguilla
No reviews

Santosha Estate, Private Resort All To Yourselves

house
Santosha Estate, a Long Bay, Anguilla oceanfront villa near West End Village, offers secluded beach access.
This 9,000-square-foot luxury property boasts nine bedrooms sleeping up to sixteen guests, a private pool, jacuzzi, fitness center, and various water sports equipment, plus butler service and concierge.
Relaxation Right On Meads Bay Beach - Anguilla
No reviews

Relaxation Right On Meads Bay Beach

apartment, Long Bay Village
This Anguilla villa offers direct beachfront access on Meads Bay, located less than 0.6 miles from Meads Bay Beach and 5 miles from Anguilla Airport.
This spacious 3,660 sq ft residence features 5 bedrooms, 6 bathrooms, a private infinity pool, jacuzzi, and outdoor play area, accommodating up to 23 guests with complimentary WiFi.
J's Place - Anguilla
9.0 3 reviews

J's Place

apartment, East End Village
This East End Village rental is located 4.5 miles from Shoal Bay and 5 miles from Anguilla Airport, offering a peaceful escape with complimentary private parking and a private balcony.
This 7-guest capacity apartment features air conditioning, a full kitchen, two bathrooms, and a swimming pool, with check-out between 8:00 AM and 11:00 AM.

Best Anguilla vacation rentals with a pool

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

Turtle Dove Villa - Anguilla
10 1 review

Turtle Dove Villa

house
This North Hill Village villa boasts stunning Sandy Ground views from its multi-level design.
The 4-bedroom, 5-bathroom home comfortably sleeps 8 guests and features a private pool, full kitchen with dishwasher, included housekeeping, and proximity to Sandy Ground.
Sandcastle Pointe Villa - Anguilla
No reviews

Sandcastle Pointe Villa

house
SandCastle Pointe Villa is located on Anguilla's north coast, a short distance from Shoal Bay Beach and the charming Shoal Bay Village. The villa offers direct access to a private beach and is close to world-class snorkeling.
This 4-bedroom, 6-bathroom villa can comfortably accommodate up to 8 guests. It features a private gym, home theater, and a swimming pool, ensuring a luxurious and relaxing stay.
A4 Sea Side View - Anguilla
10 4 reviews

A4 Sea Side View

apartment
This one-bedroom apartment is located in Sandy Hill, just a short walk from a beautiful beach perfect for snorkeling and sunbathing. The apartment has received excellent ratings for location, cleanliness, and overall experience.
The apartment is part of an eight-unit condo, offering a cozy and intimate feel. Guests can enjoy a private sundeck patio with stunning views, a shared pool, and easy access to The Valley's shops, restaurants, and cultural attractions.
Villa Grande Downstairs Oceanview W/ Pool | 2br - Anguilla
9.4 13 reviews

Villa Grande Downstairs Oceanview W/ Pool | 2br

house
This 2-bedroom, 2-bathroom villa in Island Harbour, Anguilla, offers stunning ocean views and direct access to a shared swimming pool, with proximity to Anguilla's prime beaches, dining, and entertainment within a short walk or drive. This villa features a full kitchen, living area, a patio for sea-gazing, stairs-free entry, and on-site parking, accommodating up to 4 guests.

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 Old Taverna, a former sugar mill. Don't miss the dramatic cliffs and secluded coves along the island's northern coast, particularly at Little Bay.
  • What are the best Airbnb and vacation rentals in Anguilla?

    Tradewinds Apartments Simpson Bay, Maho Beach House - Luxe 1 Bedroom - Ocean Hideaway 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 top activity. Watersports like swimming, snorkeling, and diving are popular, especially around Sandy Island and Prickly Pear Cays. Exploring the island by car or scooter offers scenic views. Many visitors enjoy sunset cruises and fine dining experiences.
  • What are the most popular Airbnbs in Anguilla?

  • Which part of Anguilla offers the most pleasant climate?

    Anguilla enjoys a tropical climate year-round. However, the southern and western parts of the island tend to be slightly warmer and sunnier, particularly around Rendezvous Bay and Meads Bay. The northern coast can be a bit windier.
  • What are the best vacation rentals with a pool in Anguilla?

  • What airport options are there for reaching Anguilla?

    The main airport serving Anguilla is Clayton J. Lloyd International Airport (AXA). It's a relatively small airport, but it's well-connected to major hubs in the Caribbean and the US.
  • 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 some roads, particularly in the interior, can be narrow and winding. Be prepared for some bumpy roads and drive cautiously, especially at night. Rental cars are readily available.
  • What are the best rentals or Airbnbs with a jacuzzi in Anguilla?

  • What currency is used in Anguilla?

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

    Anguilla has several cultural events throughout the year, including the Anguilla Summer Festival, which features music, dance, and competitions. There are also smaller, local celebrations and events throughout the year, often tied to religious holidays or local traditions.
  • What is the best time of year to visit Anguilla?

    The best time to visit Anguilla is during the shoulder seasons (April-May and September-October), when the weather is still warm and sunny but crowds are smaller. The summer months (June-August) can be hot and humid, while hurricane season runs from June to November.
  • What are some local dishes to try in Anguilla?

    Try the fresh seafood, such as lobster, conch, and snapper. Anguilla also offers delicious local dishes like Johnny Cakes (fried cornbread), fungi (a cornmeal and okra dish), and various stews and curries.
  • What emergency numbers should you know in case of a medical or security issue in Anguilla?

    For medical emergencies, dial 911. For police assistance, contact the Royal Anguilla Police Force.
  • What etiquette tips are important when visiting Anguilla?

    Anguilla is a relaxed island, but it's always polite to be respectful of local customs and traditions. Dress modestly when visiting churches or other religious sites. Tipping is customary in restaurants and for service providers.
  • What are the best areas to spend a week in Anguilla?

    For a week-long stay, consider staying in the areas of Shoal Bay East, Meads Bay, or Rendezvous Bay. These areas offer a mix of beautiful beaches, restaurants, and activities.
  • What are the best areas to spend a weekend in Anguilla?

    A weekend in Anguilla could easily be spent enjoying Shoal Bay East or Meads Bay. These areas offer easy access to beaches, restaurants, and water sports.
  • What are the top shopping destinations in Anguilla?

    The main shopping areas are located in The Valley, Anguilla's capital. You'll find duty-free shops, boutiques, and local craft markets offering a variety of goods. Many resorts also have shops within their premises.
  • What are some off-the-beaten-path places to explore in Anguilla?

    Explore the island's rugged northern coast, including areas like Little Bay and the secluded coves. Rent a car or scooter to discover hidden beaches and scenic viewpoints. Consider a boat trip to Prickly Pear Cays for a more secluded beach experience.

Best Anguilla vacation rentals with parking

Signature Properties Bluestone I - Anguilla
10 43 reviews

Signature Properties Bluestone I

apartment
This 2-bedroom, 2-bathroom condo in Upper South Hill offers stunning island views and is located just a 5-minute drive from West End beaches and a 2-minute drive to Sandy Ground, with the Blowing Point ferry terminal and a grocery store within a 1-mile radius.
This fully furnished and air-conditioned residence accommodates up to 4 guests, featuring a full kitchen with a fridge, freezer, and microwave, a garden, furnished terrace, bar, BBQ grill, and on-site parking within a gated perimeter.
Jamie's Apartments
Island Living At Its Finest - Anguilla
10 1 review

Jamie's Apartments Island Living At Its Finest

apartment
This Island Harbour condo offers direct access to Anguilla's waters from its unique position on the Eastern Sea Rocks.
This pet-friendly, 2-bathroom apartment accommodates up to 6 guests and features a kitchen with a fridge, air conditioning, and internet, all with panoramic ocean views from private terraces.
James Hughes Cozy In West End - Anguilla
9.8 123 reviews

James Hughes Cozy In West End

apartment
The James Hughes apartment is located in West End, Anguilla, close to popular beaches like Maundays Bay, Meads Bay, and Shoal Bay West. The apartment consistently receives excellent ratings for location, cleanliness, and overall user experience.
The unit features a bedroom, bathroom, and a patio with seating, comfortably accommodating two guests. Amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, and a car rental option for exploring the island at your own pace.
The Big Squeeze - Anguilla
9.5 8 reviews

The Big Squeeze

apartment
This studio apartment is located in The Valley, steps from the city centre's cafes and restaurants, offering convenient access to downtown amenities.
This modern unit features a private entrance and parking, air conditioning, and internet, with a guest capacity of one and a luxury spa-feel bathroom.

Best Anguilla vacation rentals with a balcony

Châlet Genesis - Anguilla
10 6 reviews

Châlet Genesis

house, Meads Bay
Châlet Genesis is a 3-bedroom villa located in Meads Bay, just 1.9 kilometers from Meads Bay Beach and 9 kilometers from Anguilla Airport.
The 3-bathroom villa features a private pool, a balcony, and a fully equipped kitchen, comfortably accommodating up to 15 guests.
Spectacular Views - Anguilla
No reviews

Spectacular Views

apartment, Long Path
This spacious 3520 sq ft apartment is located in Long Path, 3.9 miles from Shoal Bay and 2.5 miles from Anguilla Airport.
This family-friendly accommodation offers 5 bedrooms, 6 bathrooms, a fully equipped kitchen, air conditioning, a swimming pool, a Jacuzzi, and a terrace with sea views, accommodating up to 23 guests.
Qt's Escape - Anguilla
No reviews

Qt's Escape

apartment, South Hill Village
This one-bedroom condo is located in South Hill Village, Anguilla, 2.5 miles from Anguilla Airport.
This apartment offers 2 bathrooms, a balcony, free WiFi, air conditioning, and a modern kitchen with a fridge and microwave, accommodating up to 7 guests.
Island Paradise Apartments - Anguilla
9.8 5 reviews

Island Paradise Apartments

apartment, The Valley
Island Paradise Apartments is located in The Valley, just a short distance from Crocus Bay Beach and about 4 miles from Shoal Bay.
This 2-bedroom, 1-bathroom apartment sleeps up to 7 guests and features a fully equipped kitchen, a private terrace, a garden, and free parking.
©2026 cozycozy.com