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Anguilla Holiday Vacation with Pools

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45 rentals in Anguilla.
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Oceana Villa Anguilla - Private Panoramic View with Heated Pool, vacation rental in Anguilla
Oceana Villa Anguilla - Private Panoramic View with Heated Pool, vacation rental in Anguilla
Oceana Villa Anguilla - Private Panoramic View with Heated Pool, vacation rental in Anguilla

Oceana Villa Anguilla - Private Panoramic View with Heated Pool

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps, All pools
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LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS, vacation rental in Anguilla
LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS, vacation rental in Anguilla
LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS, vacation rental in Anguilla

LUXURY VILLA 'B ON THE SEA' IN ANGUILLA, 5 ENSUITE BEDROOMS, 2 DECKS, 2 POOLS

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Nevaeh Villa Anguilla, 9 bedroom beachfront villa (5, 6, 8 bed rates on request), vacation rental in Anguilla
Nevaeh Villa Anguilla, 9 bedroom beachfront villa (5, 6, 8 bed rates on request), vacation rental in Anguilla
Nevaeh Villa Anguilla, 9 bedroom beachfront villa (5, 6, 8 bed rates on request), vacation rental in Anguilla

Nevaeh Villa Anguilla, 9 bedroom beachfront villa (5, 6, 8 bed rates on request)

Holiday Rental House
9 bedrooms
12 bathrooms
Sleeps 20
Match: Sleeps, All pools
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Ocean Terrace Luxury 2BR Condos, Spectacular Views, vacation rental in Anguilla
Ocean Terrace Luxury 2BR Condos, Spectacular Views, vacation rental in Anguilla
Ocean Terrace Luxury 2BR Condos, Spectacular Views, vacation rental in Anguilla

Ocean Terrace Luxury 2BR Condos, Spectacular Views

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, All pools
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Spyglass Hill Villa, vacation rental in Anguilla
Spyglass Hill Villa, vacation rental in Anguilla
Spyglass Hill Villa, vacation rental in Anguilla

Spyglass Hill Villa

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps, All pools
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Mainstay Villa at Elsie Bay, vacation rental in Anguilla
Mainstay Villa at Elsie Bay, vacation rental in Anguilla
Mainstay Villa at Elsie Bay, vacation rental in Anguilla

Mainstay Villa at Elsie Bay

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Alegria Villa: Barefoot elegant luxury villa with effortless beach access, vacation rental in Anguilla
Alegria Villa: Barefoot elegant luxury villa with effortless beach access, vacation rental in Anguilla
Alegria Villa: Barefoot elegant luxury villa with effortless beach access, vacation rental in Anguilla

Alegria Villa: Barefoot elegant luxury villa with effortless beach access

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Three Dolphins  Lockrum Bay, Anguilla  BWI, vacation rental in Anguilla
Three Dolphins  Lockrum Bay, Anguilla  BWI, vacation rental in Anguilla
Three Dolphins  Lockrum Bay, Anguilla  BWI, vacation rental in Anguilla

Three Dolphins Lockrum Bay, Anguilla BWI

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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BestValue1300/5bd/night. Rent 1 bdr or more,  rates adjusted on a sliding scale, vacation rental in Anguilla
BestValue1300/5bd/night. Rent 1 bdr or more,  rates adjusted on a sliding scale, vacation rental in Anguilla
BestValue1300/5bd/night. Rent 1 bdr or more,  rates adjusted on a sliding scale, vacation rental in Anguilla

BestValue1300/5bd/night. Rent 1 bdr or more, rates adjusted on a sliding scale

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps, All pools
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Location, Location, Location! Stunning Villa Azure, vacation rental in Anguilla
Location, Location, Location! Stunning Villa Azure, vacation rental in Anguilla
Location, Location, Location! Stunning Villa Azure, vacation rental in Anguilla

Location, Location, Location! Stunning Villa Azure

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Tequila Sunrise Villa in Anguilla, vacation rental in Anguilla
Tequila Sunrise Villa in Anguilla, vacation rental in Anguilla
Tequila Sunrise Villa in Anguilla, vacation rental in Anguilla

Tequila Sunrise Villa in Anguilla

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Coconut Palm Villa -Twin Palms Villas at Meads Bay, vacation rental in Anguilla
Coconut Palm Villa -Twin Palms Villas at Meads Bay, vacation rental in Anguilla
Coconut Palm Villa -Twin Palms Villas at Meads Bay, vacation rental in Anguilla

Coconut Palm Villa -Twin Palms Villas at Meads Bay

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Anguilla Bow Green Villa on Rendezvous Bay Beach , vacation rental in Anguilla
Anguilla Bow Green Villa on Rendezvous Bay Beach , vacation rental in Anguilla
Anguilla Bow Green Villa on Rendezvous Bay Beach , vacation rental in Anguilla

Anguilla Bow Green Villa on Rendezvous Bay Beach

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Bonne View Villa, vacation rental in Anguilla
Bonne View Villa, vacation rental in Anguilla
Bonne View Villa, vacation rental in Anguilla

Bonne View Villa

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Bow Green Rendezvous Anguilla, vacation rental in Anguilla
Bow Green Rendezvous Anguilla, vacation rental in Anguilla
Bow Green Rendezvous Anguilla, vacation rental in Anguilla

Bow Green Rendezvous Anguilla

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
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Beach Palm Villa - Twin Palms Villas at Meads Bay, vacation rental in Anguilla
Beach Palm Villa - Twin Palms Villas at Meads Bay, vacation rental in Anguilla
Beach Palm Villa - Twin Palms Villas at Meads Bay, vacation rental in Anguilla

Beach Palm Villa - Twin Palms Villas at Meads Bay

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps, All pools
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White Sands Anguilla - 5 min walk to beach, spacious, clean and comfortable, vacation rental in Anguilla
White Sands Anguilla - 5 min walk to beach, spacious, clean and comfortable, vacation rental in Anguilla
White Sands Anguilla - 5 min walk to beach, spacious, clean and comfortable, vacation rental in Anguilla

White Sands Anguilla - 5 min walk to beach, spacious, clean and comfortable

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
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SANDCASTLE VILLA - 11,500 sf Luxury Beachfront Villa + 2 Cars + Pool/Spa, vacation rental in Anguilla
SANDCASTLE VILLA - 11,500 sf Luxury Beachfront Villa + 2 Cars + Pool/Spa, vacation rental in Anguilla
SANDCASTLE VILLA - 11,500 sf Luxury Beachfront Villa + 2 Cars + Pool/Spa, vacation rental in Anguilla

SANDCASTLE VILLA - 11,500 sf Luxury Beachfront Villa + 2 Cars + Pool/Spa

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Champagne Shores Villa, vacation rental in Anguilla
Champagne Shores Villa, vacation rental in Anguilla
Champagne Shores Villa, vacation rental in Anguilla

Champagne Shores Villa

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Sea Villa at Long Bay Villas on Long Bay Beach. Ultra-Luxury Staffed Villa, vacation rental in Anguilla
Sea Villa at Long Bay Villas on Long Bay Beach. Ultra-Luxury Staffed Villa, vacation rental in Anguilla
Sea Villa at Long Bay Villas on Long Bay Beach. Ultra-Luxury Staffed Villa, vacation rental in Anguilla

Sea Villa at Long Bay Villas on Long Bay Beach. Ultra-Luxury Staffed Villa

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 11
Match: Sleeps, All pools
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Sand Villa at Long Bay Villas Anguilla: 5-Star Service on a Secluded Beach, vacation rental in Anguilla
Sand Villa at Long Bay Villas Anguilla: 5-Star Service on a Secluded Beach, vacation rental in Anguilla
Sand Villa at Long Bay Villas Anguilla: 5-Star Service on a Secluded Beach, vacation rental in Anguilla

Sand Villa at Long Bay Villas Anguilla: 5-Star Service on a Secluded Beach

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Mangrove Villa at Indigo Reef, vacation rental in Anguilla
Mangrove Villa at Indigo Reef, vacation rental in Anguilla
Mangrove Villa at Indigo Reef, vacation rental in Anguilla

Mangrove Villa at Indigo Reef

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Twin Palms Villas at Meads Bay, vacation rental in Anguilla
Twin Palms Villas at Meads Bay, vacation rental in Anguilla
Twin Palms Villas at Meads Bay, vacation rental in Anguilla

Twin Palms Villas at Meads Bay

Holiday Rental House
5 bedrooms
7 bathrooms
Sleeps 10
Match: Sleeps, All pools
More info
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Asha’s Place, vacation rental in Anguilla
Asha’s Place, vacation rental in Anguilla
Asha’s Place, vacation rental in Anguilla

Asha’s Place

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Stylish Place in Front of the Caribbean Sea - 3 Guests - Colonia furniture, vacation rental in Anguilla
Stylish Place in Front of the Caribbean Sea - 3 Guests - Colonia furniture, vacation rental in Anguilla
Stylish Place in Front of the Caribbean Sea - 3 Guests - Colonia furniture, vacation rental in Anguilla

Stylish Place in Front of the Caribbean Sea - 3 Guests - Colonia furniture

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps, All pools
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Sky Villa at Long Bay Villas Anguilla, Your Private Beach Oasis with Staff., vacation rental in Anguilla
Sky Villa at Long Bay Villas Anguilla, Your Private Beach Oasis with Staff., vacation rental in Anguilla
Sky Villa at Long Bay Villas Anguilla, Your Private Beach Oasis with Staff., vacation rental in Anguilla

Sky Villa at Long Bay Villas Anguilla, Your Private Beach Oasis with Staff.

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Santosha Villa Estate Beachfront Private Resort All to Yourselves, vacation rental in Anguilla
Santosha Villa Estate Beachfront Private Resort All to Yourselves, vacation rental in Anguilla
Santosha Villa Estate Beachfront Private Resort All to Yourselves, vacation rental in Anguilla

Santosha Villa Estate Beachfront Private Resort All to Yourselves

Holiday Rental House
9 bedrooms
11 bathrooms
Sleeps 21
Match: Sleeps, All pools
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Octagon Villa, vacation rental in Anguilla
Octagon Villa, vacation rental in Anguilla
Octagon Villa, vacation rental in Anguilla

Octagon Villa

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps, All pools
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MODERN VILLA WITH POOL AND STUNING OCEAN VIEWS, vacation rental in Anguilla
MODERN VILLA WITH POOL AND STUNING OCEAN VIEWS, vacation rental in Anguilla
MODERN VILLA WITH POOL AND STUNING OCEAN VIEWS, vacation rental in Anguilla

MODERN VILLA WITH POOL AND STUNING OCEAN VIEWS

Holiday Rental House
1 bedroom
3 bathrooms
Sleeps 11
Match: Sleeps, All pools
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 7 bedroom Villa, vacation rental in Anguilla
 7 bedroom Villa, vacation rental in Anguilla
 7 bedroom Villa, vacation rental in Anguilla

7 bedroom Villa

Holiday Rental House
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps, All pools
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Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms, vacation rental in Anguilla
Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms, vacation rental in Anguilla
Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms, vacation rental in Anguilla

Enchanting, Family Friendly 3bdr, adjustable fee for more or less bedrooms

Holiday Rental House
3 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps, All pools
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COZY AND PRIVATE FOR TWO COUPLES TRAVELING TOGETHER, vacation rental in Anguilla
COZY AND PRIVATE FOR TWO COUPLES TRAVELING TOGETHER, vacation rental in Anguilla
COZY AND PRIVATE FOR TWO COUPLES TRAVELING TOGETHER, vacation rental in Anguilla

COZY AND PRIVATE FOR TWO COUPLES TRAVELING TOGETHER

Holiday Rental House
2 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps, All pools
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EXQUISITE FRIENDLY SPECTACULAR VIEWS 4BDRM VILLA , vacation rental in Anguilla
EXQUISITE FRIENDLY SPECTACULAR VIEWS 4BDRM VILLA , vacation rental in Anguilla
EXQUISITE FRIENDLY SPECTACULAR VIEWS 4BDRM VILLA , vacation rental in Anguilla

EXQUISITE FRIENDLY SPECTACULAR VIEWS 4BDRM VILLA

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 11
Match: Sleeps, All pools
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Heaven on Earth, Freshwater Infinity Pool, Tennis Court, Breakfast Daily, Media, vacation rental in Anguilla
Heaven on Earth, Freshwater Infinity Pool, Tennis Court, Breakfast Daily, Media, vacation rental in Anguilla
Heaven on Earth, Freshwater Infinity Pool, Tennis Court, Breakfast Daily, Media, vacation rental in Anguilla

Heaven on Earth, Freshwater Infinity Pool, Tennis Court, Breakfast Daily, Media

Holiday Rental House
8 bedrooms
8 bathrooms
Sleeps 18
Match: Sleeps, All pools
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Romantic Private Villa, Panoramic Ocean Views, Pool, Spectacular Outdoor Spaces., vacation rental in Anguilla
Romantic Private Villa, Panoramic Ocean Views, Pool, Spectacular Outdoor Spaces., vacation rental in Anguilla
Romantic Private Villa, Panoramic Ocean Views, Pool, Spectacular Outdoor Spaces., vacation rental in Anguilla

Romantic Private Villa, Panoramic Ocean Views, Pool, Spectacular Outdoor Spaces.

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps, All pools
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Luxury Beachfront Villa with Infinity Pool, Spa, Gym, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Villa with Infinity Pool, Spa, Gym, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Villa with Infinity Pool, Spa, Gym, Sauna, Mini Golf, vacation rental in Anguilla

Luxury Beachfront Villa with Infinity Pool, Spa, Gym, Sauna, Mini Golf

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps, All pools
More info
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Luxury Beachfront Condo with Infinity Pool, Hot Tub, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Condo with Infinity Pool, Hot Tub, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Condo with Infinity Pool, Hot Tub, Sauna, Mini Golf, vacation rental in Anguilla

Luxury Beachfront Condo with Infinity Pool, Hot Tub, Sauna, Mini Golf

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Villa Paradise - Waterfront 7 Bedroom Villa in Anguilla, Blowing Point, vacation rental in Anguilla
Villa Paradise - Waterfront 7 Bedroom Villa in Anguilla, Blowing Point, vacation rental in Anguilla
Villa Paradise - Waterfront 7 Bedroom Villa in Anguilla, Blowing Point, vacation rental in Anguilla

Villa Paradise - Waterfront 7 Bedroom Villa in Anguilla, Blowing Point

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, All pools
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Magnificent Island Luxury Villa, vacation rental in Anguilla
Magnificent Island Luxury Villa, vacation rental in Anguilla
Magnificent Island Luxury Villa, vacation rental in Anguilla

Magnificent Island Luxury Villa

Holiday Rental House
10 bedrooms
8 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Luxurious and Exclusive Beachfront Property, vacation rental in Anguilla
Luxurious and Exclusive Beachfront Property, vacation rental in Anguilla
Luxurious and Exclusive Beachfront Property, vacation rental in Anguilla

Luxurious and Exclusive Beachfront Property

Holiday Rental House
9 bedrooms
9 bathrooms
Sleeps 18
Match: Sleeps, All pools
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Prestigious Beachfront Property, vacation rental in Anguilla
Prestigious Beachfront Property, vacation rental in Anguilla
Prestigious Beachfront Property, vacation rental in Anguilla

Prestigious Beachfront Property

Holiday Rental House
8 bedrooms
10 bathrooms
Sleeps 16
Match: Sleeps, All pools
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Stunning Five Bedroom Villa, vacation rental in Anguilla
Stunning Five Bedroom Villa, vacation rental in Anguilla
Stunning Five Bedroom Villa, vacation rental in Anguilla

Stunning Five Bedroom Villa

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps, All pools
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Asha's Place Deluxe Studio, vacation rental in Anguilla
Asha's Place Deluxe Studio, vacation rental in Anguilla
Asha's Place Deluxe Studio, vacation rental in Anguilla

Asha's Place Deluxe Studio

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Luxury Beachfront Suite with Infinity Pool, Hot Tub, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Suite with Infinity Pool, Hot Tub, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Suite with Infinity Pool, Hot Tub, Sauna, Mini Golf, vacation rental in Anguilla

Luxury Beachfront Suite with Infinity Pool, Hot Tub, Sauna, Mini Golf

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, All pools
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Luxury Beachfront Estate with Infinity Pool, Hot Tub, Gym, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Estate with Infinity Pool, Hot Tub, Gym, Sauna, Mini Golf, vacation rental in Anguilla
Luxury Beachfront Estate with Infinity Pool, Hot Tub, Gym, Sauna, Mini Golf, vacation rental in Anguilla

Luxury Beachfront Estate with Infinity Pool, Hot Tub, Gym, Sauna, Mini Golf

Holiday Rental House
7 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps, All pools
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Private; panoramic views of Crocus Bay; heated pool, vacation rental in Anguilla
Private; panoramic views of Crocus Bay; heated pool, vacation rental in Anguilla
Private; panoramic views of Crocus Bay; heated pool, vacation rental in Anguilla

Private; panoramic views of Crocus Bay; heated pool

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 2
Match: Sleeps
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Beautiful 2 BR/2 BA Condo - Gorgeous Views of the Caribbean and St. Martin, vacation rental in Anguilla
Beautiful 2 BR/2 BA Condo - Gorgeous Views of the Caribbean and St. Martin, vacation rental in Anguilla
Beautiful 2 BR/2 BA Condo - Gorgeous Views of the Caribbean and St. Martin, vacation rental in Anguilla

Beautiful 2 BR/2 BA Condo - Gorgeous Views of the Caribbean and St. Martin

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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BellamareVilla, Shoal Bay East, Pool., vacation rental in Anguilla
BellamareVilla, Shoal Bay East, Pool., vacation rental in Anguilla
BellamareVilla, Shoal Bay East, Pool., vacation rental in Anguilla

BellamareVilla, Shoal Bay East, Pool.

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Shoal Bay Condo Penthouse for 2-4 Guests, vacation rental in Anguilla
Beautiful Shoal Bay Condo Penthouse for 2-4 Guests, vacation rental in Anguilla
Beautiful Shoal Bay Condo Penthouse for 2-4 Guests, vacation rental in Anguilla

Beautiful Shoal Bay Condo Penthouse for 2-4 Guests

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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BEACH HOUSE + CAR + POOL + HOT TUB + FIREPIT + VOLLEYBALL + ETC..., vacation rental in Anguilla
BEACH HOUSE + CAR + POOL + HOT TUB + FIREPIT + VOLLEYBALL + ETC..., vacation rental in Anguilla
BEACH HOUSE + CAR + POOL + HOT TUB + FIREPIT + VOLLEYBALL + ETC..., vacation rental in Anguilla

BEACH HOUSE + CAR + POOL + HOT TUB + FIREPIT + VOLLEYBALL + ETC...

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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