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Anguilla Family Villa Collection

Anguilla Family Villa Collection

The Caribbean is a great destination choice for families or multiple families traveling together. With a private kitchen and enough space for everyone, a Caribbean villa rental can be the most economical accommodation choice. Whether you are seeking a beachfront villa, a private island or a hillside villa with an amazing view, our favorite family villas section provides some of the best villas in the Caribbean for your family vacation.

If you do things with an all or nothing attitude, you'll flip over Le Bleu Villa. It's hard to think of anything this drop-dead gorgeous rental doesn't have. Aside from ...
Le Bleu Villa its on 2.5 acres of beachfront in Little Harbor
10 BR rate.

Le Bleu Villa

11 11

Anguilla

Beachfront | Pool | AC

Details
For large groups wanting extreme luxury, the oceanfront ÀNI Anguilla is a perfect choice. There are two separate villas, each with their own private pool, common areas, and five-star amenities. ...
ÀNI Anguilla
6-9 BR rates.

ANI Anguilla

10 10

Anguilla

Pool | AC

Details
If you’re looking for luxury, Nevaeh has it in abundance. Not only does it sit on a gorgeous, private piece of Long Bay, it also has 1.35 acres of lush, ...
Nevaeh is located on a beautiful stretch of Long Bay Beach
5-8 BR rates.

Nevaeh Villa - Fully Staffed

9 8+

Anguilla

Beachfront | Pool | AC

Details
"Cerulean" means "heaven," and this private resort attends to all the details of your stay to create your personal heaven. A full staff with butlers, a general manager, a culinary ...
Cerulean Villa is located on Barnes Bay

Cerulean Villa

9 9+

Anguilla

Beachfront | Pool | AC

Details
Santosha sits right on Long Bay Beach and is perfect for beach weddings, anniversaries, and any special event. You can't help but feel like you're at a resort here, since ...
Santosha is located along a beautiful stretch of Long Bay Beach
5-8 BR rates.

Santosha Villa Estate

9 9

Anguilla

Beachfront | Pool | AC

Details
“Nevaeh” is “heaven” backwards, and the villa's golf simulator, movie theater, media room, and gym are just a few of the reasons why this celestial name suits the property. The ...
Nevaeh is located on a beautiful stretch of Long Bay Beach
5-8 BR rates.

Nevaeh Villa

9 8+

Anguilla

Beachfront | Pool | AC

Details
Kandara is great if you're looking for space and privacy. The villa and guest house has 10,000 square feet of space, an acre of land and its own private beach cove. ...
Kandara Villa is located on Anguilla's West End
6 BR rate.

Kandara

8 8+

Anguilla

Near Beach | Pool | AC

Details
If you want to not only see the water from your villa but be able to step right into it, you'll love Beach Court Villa. Shoal Bay is a great ...
Beach Court Villa is settled at the western end of Shoal Bay Beach
2-7 BR rates.

Beach Court Villa

8 8

Anguilla

Beachfront | Pool | AC

Details
The Beach House's high-class architecture and contemporary style is enough to make you want to stay forever, but that's not even close to where its amazingness ends. In fact it's ...
The Beach House features an amazing pool and outdoor area

The Beach House

8 9+

Anguilla

Beachfront | Pool | AC

Details
Zenaida offers a great experience at an exceptional value. The beach is down a short, private path, and the villa has a private, night-lit tennis court with a soft Har-Tru ...
Zenaida Beach & Tennis Estate is located just above Sandy Hill Beach
3-6 BR rates.

Zenaida Beach & Tennis Estate

7 7

Anguilla

Beachfront | Pool | AC

Details
This seaside villa is 7,000 square feet and is on 3.5 acres of land with gorgeous panoramic views. Between the pool, hot tub, two hammocks, and snorkeling equipment, there's little reason to ...
Paradise Villa is located near Blowing Point
4, 5 BR rates.

Paradise Villa

7 5+

Anguilla

Pool | AC

Details
Triton Villa is nestled into its own hillside enclave above Lockrum Bay and Little Harbour. This villa shares a secluded cove and amazing snorkeling spots with two other villas in ...
Triton Villa is located on LockRum Bay
4, 5 BR rates.

Triton Villa at Kamique

6 6+

Anguilla

Near Beach | Pool | AC

Details
Antilles Pearl is a super luxurious beachfront villa in one of the best spots on Anguilla. There's a 50-foot skywalk that makes you feel like you're floating above the sea, ...
Antilles Pearl is located on Shoal Bay Beach
5 BR rate.
Specials.

Antilles Pearl Villa at Altamer

6 6

Anguilla

Beachfront | Pool | AC

Details
Villa Colibri has a sleek and modern design that belongs on a magazine cover. There's a swimming pool with different depths that any swimmer can enjoy, tons of outdoor space, ...
You'll find contemporary class at Colibri Villa.
2-5 BR rates.
Specials.

Colibri Villa

6 6

Anguilla

Pool | AC

Details
Three Dolphins isn't only gorgeous inside, it also has amazing sea views with St. Martin in the distance. The villa has all the modern amenities you want, like Roku TV ...
Three Dolphins sits in a beautiful location with great ocean views

Three Dolphins

5 4+

Anguilla

Near Beach | Pool | AC

Details
This waterfront villa would be great for a few couples or a large family. There's two queen suites upstairs and two twin suites downstairs, so adults can relax in solitude ...
Water's Edge Villa is located on Blowing Point
2, 4 BR rates.

Water's Edge

5 5

Anguilla

Near Beach | Pool | AC

Details
Vacationing will be as much fun for your kids as it is for you at Sand Castle Villa. It has everything you could possibly think of to keep the children ...
Sand Castle Villa is located on the North Shore of Anguilla with views of the Atlantic Ocean
3 BR rate.
Specials.

Sand Castle Villa

5 5+

Anguilla

Beachfront | Pool | AC

Details
If you want to be pampered, come to Sea Villa. In addition to its stunning common areas, you have access to an infinity pool, a Jacuzzi, outdoor space, and a ...
Sea Villa is situated facing the beach with amazing unobscured ocean views

Sea Villa at Long Bay Villas

5 5+

Anguilla

Beachfront | Pool | AC

Details
At Long Bay Villas, you can expect to be relaxed and pampered. There's a full staff, water sports, four king suites, and a bunk room, so everyone you travel with ...
The luxurious Sand Villa at Long Bay

Sand Villa at Long Bay Villas

5 4+

Anguilla

Beachfront | Pool | AC

Details
Rent the Two Palms property as a five-bedroom combo, or divide the units between groups of six and four. This rental is just off the waters of Meads Bay, and ...
Beach Palm

Twin Palms Villas

5 5+

Anguilla

Near Beach | Pool | AC

Details
If you like vibrant colors and great views, you'll love Villa Amarilla. Both the interiors and exteriors are done in a Caribbean style with an Italian vibe and Moroccan influences. ...
Beautiful Anguillan sunset from the back porch at Amarilla
3, 4 BR rates.

Villa Amarilla

5 5+

Anguilla

Near Beach | Pool | AC

Details
Blue Diamond's beachfront luxury leaves nothing out. There's a sound system, WiFi, and air-conditioning throughout the villa, a bar, a media room, a gym, a grand piano, and a huge ...
Blue Diamond Villa at Altamer is set on a prestigious location on Shoal Bay

Blue Diamond Villa at Altamer

5 7

Anguilla

Beachfront | Pool | AC

Details
If you want true pampering, come to Sky Villa. Things like daily housekeeping service are par for the course. Speaking of the course, this villa is very close to the ...
Sky Villa is the most private of the Long Bay Villas located just off the beach

Sky Villa at Long Bay Beach Villas

5 4+

Anguilla

Near Beach | Pool | AC

Details
Champagne Shores is the perfect villa rental for design lovers. The sea-facing wall is made up of huge panes of glass from top to bottom, and the terrace is made ...
Champagne Shores villa sits on a secluded beach near Pelican Bay

Champagne Shores

5 5+

Anguilla

Near Beach | Pool | AC

Details
Tamarind is perfect for two families to share, because each level has its own living area and balcony or terrace. Both living areas have a library and dining space. The ...
Tamarind Villa is located in Island Harbor just minutes from Shoal Bay East
2, 4 BR rates.

Tamarind Villa

5 5

Anguilla

Pool | AC

Details
Beaches Edge villa has a smart design that maximizes the ocean views. Of course there's a pool, daily maid service, and a concierge, but there's also full air-conditioning, an outside ...
Lounge by the pool and enjoy amazing ocean views at Beaches Edge East Villa

Beaches Edge

5 5+

Anguilla

Near Beach | Pool | AC

Details
Sandcastle Beach House is an action-packed choice for your next family vacation, anniversary, or celebration. With kayaks, paddle boards, bikes, and direct beach access, there's no shortage of things to ...
Sandcastle Beach House is located on on Limestone Bay
Specials.

Sandcastle Beach House

4 4+

Anguilla

Beachfront | Pool | AC

Details
Pelican Bay would be a great choice for a multi-generational family vacation. Three bedrooms are in the main house with exterior access, and the entire interior is extremely open and ...
Pelican Bay Villa has an ideal location in between Blowing Point and Pelican Bay
1-3 BR rates.

Pelican Bay

4 4+

Anguilla

Pool | AC

Details
Your hunt for beauty, solitude, and affordability near one of the world's best beaches is over. Okeanos is located 150 feet above the sea rocks with spectacular views. Whether you relax ...
Villa Okeanos sits in Shoal Bay East,
3 BR rate.

Okeanos

4 3+

Anguilla

Pool | AC

Details
Fiore villa is a beautiful, fully air-conditioned 4 bedroom villa just a short 2-3 minute walk to lovely Shoal Bay Beach. All four bedrooms have views of Shoal Bay East and 2 ...
Fiore Villa photo

Fiore Villa

4 4+

Anguilla

Near Beach | Pool | AC

Details
Villa Farina is the ultimate beachfront paradise in Anguilla! With 4 spacious bedrooms, each with interior access, and breathtaking sea views from the master bedrooms, this villa is perfect for a ...
Villa Farina in Anguilla
Specials.

Villa Farina

4 4

Anguilla

Beachfront | Pool | AC

Details
If you love outdoor showers, infinity pools, and a 20-second walk to the beach, stay at Alegria Villa. You'll find a spacious home with its own pool, gym, media room, ...
The beautiful pool and Caribbean views from Alegria Villa

Alegria Villa

4 4

Anguilla

Near Beach | Pool | AC

Details
Guests at Sandcastle Pointe get access to jaw-dropping ocean views, modern amenities, and luxurious design. Dive into the private infinity pool or take a shot on the manicured putting/croquet ...
Sandcastle Pointe Villa is located just west of Shoal Bay Beach
Specials.

Sandcastle Pointe at Shoal Bay

4 4+

Anguilla

Pool | AC

Details
If you like both contemporary and Caribbean styles, you'll love the beautiful browns, blues and whites at Seabird Villa. This villa is both soothing and classy, with a modern kitchen ...
Seabird Villa has beautiful sunset views
2, 3 BR rates.

Seabird Villa

4 4+

Anguilla

Near Beach | Pool | AC

Details
When ISLANDS magazine names you 'One of the Top 20 villas in the World', it's always a good sign. It has tons of outdoor space, a bed in a grove overlooking ...
The beautiful Bird of Paradise Villa
1-3 BR rates.

Bird of Paradise Villa

4 4+

Anguilla

Near Beach | Pool | AC

Details
Situated at the water's edge on the south end of Anguilla, Anani Villa takes advantage of its location to offer the best possible views of the island. The villa is ...
Anani Villa Kamique is one of three villas on Kamique Estate, situated directly on the Caribbean Sea
3 BR rate.

Anani Villa at Kamique

4 4

Anguilla

Beachfront | Pool | AC

Details
Villa Kai has water access to Sandy Hill Bay for exploring, and you can watch the waves crash onto the shore from the back door. The property is fenced in, ...
Villa Kai is located on Sandy Hill Bay
1, 2 BR rates.

Villa Kai

3 3

Anguilla

Pool | AC

Details
If you’re looking for an Anguilla beachfront rental, this resort villa is worth a look. It’s right on Meads Bay, one of the island’s most gorgeous beaches, ...
Tranquility Beach - Beachfront Penthouse Villa is located on Meads Bay Beach
Specials.

Tranquility Beach - Beachfront Penthouse

3 3+

Anguilla

Beachfront | AC | Resort Villa

Details
Modern design, beach access, and three bedrooms make this penthouse the perfect rental for your next vacation. It’s right on Meads Bay, which is one of the island’s ...
Tranquility Beach Anguilla is located on Meads Bay Beach
Specials.

Tranquility Beach - Penthouse

3 3+

Anguilla

Beachfront | AC | Resort Villa

Details
The Cottage at Meads Bay is a quiet, peaceful retreat for any vacationer. This villa offers three spacious bedrooms, gorgeous ocean views, and direct beach access to one of the ...
The Cottage at Meads Bay is located on Meads Bay, Anguilla’s most desirable beach

The Cottage at Meads Bay

3 3+

Anguilla

Beachfront | AC

Details
This villa is great for a few couples or a family. All three bedrooms have ensuite bathrooms, and two are kings while the third has two twins. There's a common ...
Sweet Return Villa is located near the golf course and Rendezvous Bay
2 BR rate.

Sweet Return Villa

3 3

Anguilla

Pool | AC

Details
Panarea Villa is truly beautiful, with a great housekeeper and lush gardens all around. I think this villa is ideal for a casual, laid-back Caribbean vacation, especially for young families ...
Panarea is located in Anguilla's West End, just minutes away from the island's most beautiful beache
1, 2 BR rates.

Panarea Villa

3 3

Anguilla

Near Beach | Pool | AC

Details
If you're looking for luxury and affordability at one of the world's greatest beaches, then quit searching because Shoal Bay East's Dreamcatcher Villa is it. It boasts 3 bedrooms/3.5 baths, an ...
Dreamcatcher Villa is located less than a mile from Shoal Bay Beach
1, 2 BR rates.

Dreamcatcher Villa

3 3+

Anguilla

Pool | AC

Details
This villa is only a 30 second walk up to the beach, which has plenty of beach chairs and umbrellas for lounging all day in the sun. The sand is feather ...
Beads Bay Beachside Villa 2 is in the Meads Bay Villas

Meads Bay Beachside 2

2 2+

Anguilla

Near Beach | AC

Details
This villa has everything you could want on a romantic vacation, and balances privacy and comfort. You'll have your own pool just steps away from the beautiful Meads Bay Beach, ...
Beads Bay Beachside Villa 3 is in the Meads Bay Villas
1 BR rate.

Meads Bay Beachside 3

2 2+

Anguilla

Near Beach | Pool | AC

Details
Your friends and family will love this beachfront rental on Meads Bay. It combines two units into one villa, so you get double the amenities, double the master suites, and ...
Tranquility Beach - Two Bedroom Beachfront Villa is located on Meads Bay Beach

Tranquility Beach - Beachfront 2 Bedroom

2 2

Anguilla

Beachfront | AC | Resort Villa

Details
Your friends and family will love staying in this Meads Bay villa. It combines two units into one, so everyone gets a luxurious master suite and ensuite bathroom. One suite ...
Tranquility Beach Anguilla is located on Meads Bay Beach

Tranquility Beach - 2 Bedroom

2 2

Anguilla

Beachfront | AC | Resort Villa

Details
If you want your own beach villa but still want the convenience of a front desk and concierge, beautiful Meads Bay Villa Resort is the perfect spot for you. This ...
Beads Bay Beachside Villa 1 is in the Meads Bay Villas

Meads Bay Beachside 1

2 2+

Anguilla

Near Beach | Pool | AC

Details
If you want a private pool and close proximity to the beach, Beach Palm Villa won't disappoint. It has one of the best values due to it's location, with just ...
Beach Palm Villa has a great patio and pool

Beach Palm Villa

2 2+

Anguilla

Near Beach | Pool | AC

Details
Oceana Villa only has two-bedrooms, but with over 5,000 square feet there is plenty of room to spread out. The outdoor furnishings on the upstairs balcony are super comfy and perfect ...
Oceana Villa is located on a hill above Crocus Bay
1 BR rate.

Oceana Villa

2 2

Anguilla

Near Beach | Pool | AC

Details
The beachfront villa at Meads Bay Beach Villas is the most popular property for an obvious reason... it sits steps away from the sand and waves. I love the fact ...
Meads Bay Beachfront Villa 1 is located on a beautiful stretch of Meads Bay Beach

Meads Bay Beachfront

2 2+

Anguilla

Beachfront | Pool | AC

Details

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