Anguilla Group Villas


Vacation rentals that are large enough to accommodate a group are often hard to come by and renting multiple hotel rooms can break the bank. WhereToStay.com has searched all over the Caribbean to bring you a collection of villas large enough to accommodate groups on their Caribbean vacations. Unlike a hotel, villa rentals provide one cost for the entire home giving everyone their own space while still enjoying various amenities such as a private pool, chef services and housekeeping. Go on, take a look, the perfect villa for your group vacation is sure to be here!


High End Modern Elegance offers two swimming pools and two beaches on 2.5 acres 5 & 8 BR rates available

Anguilla

Beachfront | Pool | AC

From
$7750/Nt
Huge luxury estate features 2 separate villas, a full staff, and incredible ocean views

Anguilla

Pool

From
$8600/Nt
This private, beachfront villa has a full staff and five-star amenities for everyone in your party.

Anguilla

Beachfront | Pool | AC

From
$14286/Nt
Beachfront architectural masterpiece with butler, sports courts, and full entertainment system. Offers Specials.

Anguilla

Beachfront | Pool | AC

From
$3571/Nt
One of the Ultimate villas in Anguilla with over 20,000 square feet of enjoyment space! Offers Specials. 2, 3, 4, 5, 6 & 7 BR rates available

Anguilla

From
$1000/Nt
Ultra modern and fully staffed, the Beach House's amenities will have you living like 21st century kings

Anguilla

Beachfront | Pool | AC

From
$10714/Nt
Tropically high-tech, this 8-bedroom villa offers guests a multilevel pool, waterfall, golf simulator, tennis/basketball court, and signing privileges at nearby resorts. Offers Specials. 5 BR rates available

Anguilla

Beachfront | Pool | AC

From
$5980/Nt
Mini golf-course, an oceanfront beauty.

Anguilla

Pool

From
$1950/Nt
This property is fit for royalty (who have actually stayed here). Offers Specials. 3, 4 & 5 BR rates available

Anguilla

Pool

From
$1200/Nt
Luxury on Long Bay Beach! 4 BR rates available

Anguilla

Beachfront | Pool | AC

From
$8857/Nt
With 21,000 square feet at your disposal, you'll feel like you're at a resort but with all the comforts of home 3, 4 & 5 BR rates available

Anguilla

Near Beach | Pool

From
$2800/Nt
Sleek, Modern, Private, this 'fabulous' property just above Little Bay on Anguilla is the ultimate in vacation villas.

Anguilla

Pool

From
$6400/Nt
Don't lift a finger during your stay at Kishti Villa! Offers Specials. 4 BR rates available

Anguilla

Beachfront | Pool | AC

From
$4200/Nt
The largest of the Elements Villas, four couples can all have their own master suite with sea view terrace 3 & 4 BR rates available

Anguilla

Beachfront | Pool | AC

From
$2900/Nt
Beautifully and thoughtful designed for year-round solitude and relaxation. Offers Specials. 3 & 4 BR rates available

Anguilla

Near Beach | Pool

From
$2100/Nt
Want more than just a beachfront villa? This is it...theater, pool table and an exquisite gaming table! Offers Specials.

Anguilla

Beachfront | Pool | AC

From
$3357/Nt
Ultra-modern upscale Anguilla villa with glass walls that face the sea.

Anguilla

Near Beach | Pool

From
$1400/Nt
Super-Modern upscale Ocean Crest Villa with glass walls that are unlike anything you can imagine.

Anguilla

Near Beach | Pool

From
$1400/Nt
Luxurious, extremely modern villa with stunning sunset views, privacy, and lots of space. 3 BR rates available

Anguilla

Near Beach | Pool

From
$2650/Nt
A luxury retreat on Meads Bay Beach! Offers Specials. 4 BR rates available

Anguilla

Beachfront | Pool | AC

From
$4200/Nt
Striking 4-Story villa with a 50 foot skywalk over the sea! Offers Specials.

Anguilla

Beachfront | Pool | AC

From
$3214/Nt
Inviting villas, inviting atmosphere, inviting activities! 1, 2, 3 & 4 BR rates available

Anguilla

Near Beach | Pool

From
$595/Nt
Unparalleled Luxury, and access to the only golf course on Anguilla 1, 2 & 3 BR rates available

Anguilla

Beachfront | Pool | AC

From
$2200/Nt
Ultra Modern Design, a Private Concierge, Take your breath away Sunsets- all at Ani Viilla North on Anguilla

Anguilla

Pool

From
$5100/Nt
Observe the majesty of the sun setting over the ocean right from your balcony lounge chair. 1 & 3 BR rates available

Anguilla

Near Beach | Pool

From
$700/Nt
With easy beach access, incredible views, and lots of entertainment options, Pavilion Villa is the ideal getaway on Anguilla

Anguilla

Beachfront | Pool | AC

From
$2395/Nt