If you’ve been dreaming of the perfect Caribbean vacation, then pack your bags and head on over to Anguilla. This destination is filled with white sandy beaches, coconut trees, open-sided beach bars, barbecues and live reggae music. Life here is slow-paced and the perfect place to just relax and recharge and really get away from your usual busy lifestyle. And there’s so much to do at Anguilla. You can enjoy water activities like open water kayaking, diving and paddle boarding. You can also relax and lounge on the beach, or even get a massage. You can rent horses to tour the island, go snorkeling or pamper yourself at one of the spas. And if you want total privacy while you’re here, be sure to book a place among this list of the best Vrbo accommodations in Anguilla. Scroll down to learn more.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on August 28, 2025.
1. Oceanfront Caribbean retreat (from USD 321)
This is the best rental deal in Anguilla, the perfect Carribean retreat for you and your family or your best friends. This vacation rental is directly on the sea with a private deck, perfect for happy hour sunset drinks or enjoying your current read with a cup of coffee. The shallow waters of Sandy Hill Bay is a great way to get some exercise or cool down with swimming. If you prefer to lounge by or swim in the pool, there is a large pool in the area. The condo has a full kitchen, spacious living and dining area with TV and WiFi. There are two bedrooms with queen beds and a children’s room with two twin beds. Books, games, and toys are also provided for your entertainment. Rates are year-round and do not change, especially during the holidays.
Sandy Hill Bay, Sandy Hill Bay, Anguilla
Top guest reviews
Host:
The owner was a huge help to us when we had flight problems and she was very responsive with any questions we hadThey are a gentle generous people very helpful and kindThey met us at the ferryamazing weather Great for small familythe caretaker is friendly and helpful and solved many problemsLocation:
Location is perfect close to supermarkets and amazing beaches everywhereSandy Hill Club is a very quiet area with a salt water pool and a sandy beach at a 5 min walk away over rocky terrain (wear shoes)We were told many times by the locals at restaurants on the beach at bars "have a good time you are on vacationIt is convenient to grocery and other shopping as well as some of Anguilla's best restaurants If you are looking for a peaceful and relaxing getaway without paying luxury resort prices - this is ...This is one of the best bargains on the Island Walk to secluded beach just steps from your doorwayCleanliness:
It was neat and cleanThe pool is nice and clean and the chaises are very comfyThe condo itself was very clean and welcoming everything in working orderthe balcony looks over the pool and the ocean and the rest of the islandRead more reviewsAmenities & Room:
w/one or two children (bunk beds) everything you need for cooking and laundry facilitiesThe queen-size bed is soft and comfortable andThe unit could use a deep cleaningThe bed was super-comfortable and the linens were of nice qualityand it stayed comfortable enough that we'd only want AC for some nights
2. Open-plan luxury villa (from USD 1490)
Villa B on the Sea is the newest two-story luxury villa in the Caribbean with five private ensuite bedrooms. The first floor has an open plan gourmet kitchen and living area with full glass doors that open up to panoramic Caribbean views and the first pool. There are three bedrooms on the main level, the master suite with a sitting area against glass window walls overlooking the sea and marble stone bath, and the children’s room with two twin beds plus another bedroom with a queen bed. The rest of the bedrooms are on the second level, as well as a wading spa-style pool, with a home theater and entertainment deck, and an outdoor gazebo with a kitchen and eating area.
Seafeathers, Seafeathers, Anguilla
Top guest reviews
Host:
The movie theater was fun for us to watch football games and moviesWe were a family of 16 with all our children and grandchildren and the house was perfectAll the locals were super friendly and happyDefinitely a very well appointed clean and beautiful houseWe'd all head back to the house late afternoon to hang out for a couple hours around the pool before getting cleaned up and heading out to dinnerLocation:
The beaches in Anguilla are beautifulThe house is in a private area on the island and not within walking distance to any restaurantsIt is a very short drive from the best restaurants and beaches on the islandbut it is great toobut they are a lot of restaurants within an easy driveRead more reviewsAmenities & Room:
The master bedroom absolutely wonderfulThe outdoor spaces were incredible alsoI especially enjoyed relaxing by the pools and having dinner outside on the top floor dining areaThe villa is very spacious and offered plenty of room for our family and friendsThe property is very well maintained and provided excellent views without sacrificing privacy
3. Clubhouse suite by Shoal Bay (from USD 575)
This Clubhouse Suite on the Bellamare Estate has a large living area, a kitchen, a patio and two bedrooms that can sleep four people easily. The Master bedroom has a king bed and even an outdoor jetted tub. Located on the edge of Shoal Bay, Bellamare Estate sits on one of the best beaches in the world. There is also a large pool with lounge chairs and a gazebo. There is a grocery nearby where you can stock up on food and cook in the fully equipped kitchen. At the end of the day, relax on one of the lounge chairs or living area set up in the patio.
Shoal Bay Village, Anguilla, Anguilla
Top guest reviews
Host:
Jerdell was very helpful and even met us at the ferryWe had a wonderful week at the Clubhouse Suite at Bellamare Jerdell was super welcoming and met us at the ferry with our rental Jeep and gave us a tour of the house including the fridge that he s...The villa and the people were great and it was really nice being so close to Shoal Bay beachLocation:
We spent every day on that beach and went out to eat in the nearby village to Ben's Pit Stop and other restaurantsEvery morning we walked from the house down the path to a private beach and loved our ritual of walking around the point wading in the water just a little to get the the bigger beach with lots o...it was a restful vacation in an amazing placeRead more reviewsAmenities & Room:
The house is big with two spacious bedrooms each with their own bathroomAnd the view from the deck (all with brand new furnishing) was spectacularlarge spacious well appointed and clean Close to one of the most beautiful beaches in Anguilla
4. Luxury house with private decks (from USD 99)
This luxurious 5,000 sq.ft. (465 square meters) 4-bedroom house with a private veranda, king and queen beds, blackout drapes, and marble tile floors, is a great vacation home that can easily fit up to 10 people. If you want to spend more time outdoors, the beaches are just a few minutes’ walk away. Or if you prefer to walk on foot, there are hiking trails around the house that lead to even more beautiful beaches. At the end of your hike or day at the beach, put your feet up on one of the many couches, indoor and outdoor, and let the constant breeze cool you down.
Top guest reviews
Host:
kid friendly Seabreeze cooled usWe enjoyed most our evenings star gazing with views of Mars Venus and Jupiter as well as the Southern CrossWhen we were in a pinch and our flight got cancelled they graciously helped us book another night and were very patient with us in extending our stayWe loved the location as with a car rentalWe found it very helpful that Pat came to meet us and direct us to the houseLocation:
especially Nat's Palm Grove in Junks Hole/There was also a local cell phone available that we paid a few bucks to activate - it did little but provide peace of mindAnswered every question within hours and have people on the island to call if you need anythingWe suspect it was either newly built or renovated; very classy beach villa that'sThe house is easy to locate however - move the map to show both East End Village and Sile Bay then visualize a straight line between themRead more reviewsAmenities & Room:
The ocean view was breathtakingThe kitchen was nicely outfittedEach room had a bathroom and three out of the four had there own verandaso well there was little use of the HVACIt was nicer than the pictures displayed
5. A Caribbean escape
This five-bedroom beachfront villa is a dream vacation rental. With ocean views all over, including the bedrooms, porch area, pool deck, and shaded veranda, it’s the perfect place for a week-long getaway. It’s a full-service, private villa with the main house and a guest house, with daily housekeeping and local concierge services available. Enjoy the open-plan full kitchen, living and dining area. The villa also has its own private pool and lounge area, a beach volleyball area, and a yard that leads straight to the beach.
Cul deSac
6. White Cedars Villa
White Cedars Villa was intricately designed to provide a calming and peaceful holiday for guests. Enjoy beautiful panoramic views of the Caribbean, the ocean, St. Martin, St. Barts, Saba and St. Kitts by the pool and on the patio. There are two living areas with a dining area in between plus a modern kitchen, a TV room, and a computer room. If you want to lounge by the beach, Crocus Bay Beach is nearby. The villa is good for a couple and if you want to stay with your family or friends, you can also rent Villa Colibri below, which has an additional nine bedrooms.
Crocus Hill, AI
7. Luxury villa for ten
Take a luxurious break in this majestic villa with five bedrooms and good for ten people. There are indoor and outdoor dining areas, a modern kitchen, WiFi, satellite TV in all rooms, a large heated pool, a roof deck, a game room with pool table, a family room, a media room, and a gym. And there’s also daily maid service and catering services available during your stay. When you stay here, you don’t need to worry about anything else but to enjoy yourself.
Sandy Hill Bay
8. Beach villa with two pools
One of the top 15 villas in the Caribbean, this 4.5-star villa has two living areas, one inside with a wet bar, and an outdoor one with a fireplace, sundeck, and a covered veranda. There are also beach bags, beach toys, a massive DVD library, flat screen TV and WiFi. Its got four master suites, with their own private veranda and Caribbean views. And the bathrooms have whirlpool tubs and indoor/outdoor showers. The kitchen is complete with a stove, microwave, with even a deep fryer, Kitchen aid mixer, and espresso machine. You can hire a chef, with the owners’ help, during your stay. Plus there are two lagoon-style heated pools surrounding the house or go to Sandy Hill Beach to soak up the sun. The owners can also help provide private concierge, daily housekeeping, and a car and driver. When you rent this house, you get the convenience of your own place with the amenities of a resort.
Top guest reviews
Host:
we're friendly and helpful when needed and had the property in perfect condition Having traveled to Anguilla for 30years and experiencing many villas and hotelsBankie Banx for drinks and music Elvis for drinks and Blanchards Beach Bar and DaVida for lunch and the Pump Hose for music and dancingWe booked this home with several friends for a very special occasion (50th birthday) and had the absolutely most amazing vacationThe property managers are very attentive and helpful and the home comes with a chef that makes beautifully prepared mealsWe traveled with 3 other couples flew into St Martin and took a boat over to Anguilla arranged by the conciergeLocation:
our family is now spoiled by the Bird of Paradise and will not stay anywhere else on the islandand then we hopped around the island enjoying beaches beach bars and restaurants at Mead's Bay Sandy Ground Shoal Bay and Crocus BayPack lightly because it's a very casual islandThe Bird's beach is only a 5 minute walk and we were also happy to swim and lounge thereSt Bart's is only 15 minutes by private plane and makes a fun midweek day excursionCleanliness:
The rooms are spacious and well appointedRead more reviewsAmenities & Room:
The bedrooms are pretty evenly balancedAttention is paid to every detail from the Bulgari bath products to the cheerful and helpful staff
9. Affordable luxury accommodation for couples
This condo is a great getaway for couples who want to go on their second honeymoon or just to spend time together away from everyone else. The condo includes an outdoor and indoor living area, with a gourmet kitchen, a master bedroom with a king bed, and your own swimming pool. In case you want to enjoy the beach instead, you have your own access from the house to Shoal Bay. Beautiful ocean views are available, no matter where you are in or out of the house. And if you want to get out and enjoy the town, the house is a walking distance to restaurants, shops, and bars. Daily maid service and concierge service are available.
10. Great ocean views with lots of space
Are you looking for a condo in Anguilla with amazing views of the ocean that’s good for two to five people? This spacious two-bedroom condo is part of the 11 units inside Ocean Terrace, an intimate condo complex on a hill on the southeastern shore of Anguilla. The condo also offers beautiful panoramic views of St. Martin, St. Barths and St. Kitts. There is 1,500 sq.ft (139 square meters) of space, two private terraces, daily maid service, A/C in the entire house, ceiling fans, a complete gourmet kitchen, living and dining area, cable TV, and high-speed wireless internet access. And if you want to swim, you can swim on the oceans of Shoal Bay or the freshwater outdoor pool in the complex. It’s definitely the best place to stay when you’re looking for an accommodation where you can truly rest and recharge during your vacation.
Accommodates: 5
Minimum Nights: 2
Refund Policy :
Top guest reviews
Host:
He provided all the information we needed about the islandwe so warm welcoming and helpful during our entire stayHe went over and above for us and even made sure we had some snacks as well as breakfast and coffee for the next morning as we had arrived late at night Once we arrivedBob picked up some groceries for us before we arrived and helped us sort out a rental carAmbrose and Bob gave us wonderful restaurant recommendations -Location:
Ocean Terrace has easy access to many great beaches and restaurants and food shopsThe restaurants and local food scene are amazingbut it also has some of the best restaurantsAnguilla is by far the bestWe loved exploring many different beaches since it is so easy to navigate around the islandCleanliness:
Everything is very clean and well maintainedthe condo was beautifully decorated immaculately clean and had amazing views of the oceanwell appointed very quiet and immaculately cleanThe condo was very clean and well appointedI plan to return as soon as I possibly canRead more reviewsAmenities & Room:
The condo is on the top floor (one flight of stairs) and the view was just as spectacular as everyone describedThe fully equipped kitchen is great for making meals in tooThe casual comfortable surroundings are incredibly relaxingthe beds are amazingly comfortableThe condo is large and airy The balconies (one off of the master bedroom and one off the living room) facing St Martin are wonderfully large and private and are furnished with very comfortable ou...
Are you ready to go to Anguilla?
Are your bags packed and ready to go to Anguilla? You’re going to have so much fun for sure! Be sure to enjoy the most of what the island has to offer. And if you book one of the best Vrbo accommodations in Anguilla, you’re definitely going to have the best time of your life.
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