Anguilla Holiday Homes
Villa
10.0(68 Reviews)
2 Bedrooms
1 Bath
5 Guests
2500 ft²
Private Pool
Pool
Ocean View
Balcony/Terrace
R11,575/Night
7 Nights - R81,015
Apartment
10.0(8 Reviews)
1 Bedroom
1 Bath
2 Guests
- Balcony/Terrace
View
Parking
Air Conditioner
R2,142/Night
7 Nights - R14,997
Villa
10.0(7 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
Spa
Fireplace/Heating- Pool
R16,573/Night
7 Nights - R116,018
Villa
10.0(53 Reviews)
4 Bedrooms
3 Baths
10 Guests
5000 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R19,735/Night
7 Nights - R138,150
House
10.0(5 Reviews)
3 Bedrooms
3 Baths
8 Guests
2497.23 ft²
Oceanfront
Hot Tub- Ocean View
- Balcony/Terrace
R2,933/Night
7 Nights - R20,534
Villa
10.0(44 Reviews)
2 Bedrooms
2 Baths
4 Guests
2168 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R11,311/Night
7 Nights - R79,169
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
484.38 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
Internet
R2,060/Night
7 Nights - R14,420
Villa
10.0(38 Reviews)
4 Bedrooms
4 Baths
8 Guests
6000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R20,671/Night
7 Nights - R144,692
Villa
10.0(1 Review)
4 Bedrooms
4 Baths
8 Guests
1345.49 ft²
- Pool
- View
- Parking
- Air Conditioner
R47,363/Night
7 Nights - R331,540
House
10.0(35 Reviews)
1 Bedroom
1 Bath
2 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R3,894/Night
7 Nights - R27,258
House
10.0(1 Review)
1 Bedroom
3 Baths
6 Guests
2497.23 ft²
- Balcony/Terrace
Pet Friendly- Parking
- Air Conditioner
R4,944/Night
7 Nights - R34,608
Villa
10.0(31 Reviews)
4 Bedrooms
4 Baths
8 Guests
3500 ft²
- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
R7,449/Night
7 Nights - R52,142
Why Choose Rent By Owner for your Anguilla Holiday Homes?
What makes our Holiday Homes special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Weekly Weather Forecast for Anguilla
How to Book Your Anguilla Holiday Homes
What's our booking process?
Our platform allows you to browse a curated selection of holiday homes. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Anguilla
Common Holiday Homes Amenities
What amenities can you expect?
Our Holiday Homes are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Other Places to Stay in Anguilla
South Hill
Little Harbour
Rendezvous Bay
George Hill
Blowing Point
Shoal Bay
Sandy Hill
Island Harbour
East End Village
The Valley
The Quarter
West End Village
Frequently Asked Questions About Anguilla Holiday Rentals
1. What are the top Holiday Homes in Anguilla?
There are a lot of options in Anguilla. If you plan on staying in the Anguilla area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Holiday Homes in Anguilla:
- Tranquility Beach Anguilla
- Tranquility Beach Anguilla Resort
- exquisite, rejuvenating, charming, private, elegant, beautiful sunset, luxury
- Great spot for family gatherings and romantic getaways.
- Escape the cold & snow in Anguilla at the ultimate vacation villa! Book today!
- Fortune Rise. Car Rental available
- Clubhouse Suite at Bellamare
- LaVanda Cottage, Romantic Ocean Getaway
- ON THE BEACH - Ultra Luxury Villa, Sleeps 12, Pool, Hot-tub, Fire-Pit, Gym, …
- Stunning Ocean Front Shoal Bay Villa
2. How many Holiday Homes are available in Anguilla?
Currently, the total number of properties listed by RBO in 2026 is over 550 in the Anguilla area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Holiday Homes in Anguilla.
More Rentals You May Like Near Anguilla
Apartment
9.9(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
753.47 ft²
- Balcony/Terrace
- Parking
- Air Conditioner
- Internet
R2,479/Night
7 Nights - R17,353
Villa
10.0(28 Reviews)
3 Bedrooms
3 Baths
7 Guests
3500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R15,475/Night
7 Nights - R108,322
Villa
10.0(26 Reviews)
2 Bedrooms
2 Baths
4 Guests
3240 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R13,831/Night
7 Nights - R96,819
Villa
10.0(26 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
R8,413/Night
7 Nights - R58,882
Villa
10.0(25 Reviews)
5 Bedrooms
5 Baths
10 Guests
5000 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
R44,594/Night
7 Nights - R312,160
Villa
10.0(24 Reviews)
3 Bedrooms
3 Baths
6 Guests
3500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
R11,618/Night
7 Nights - R81,328
Condo
10.0(24 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
R9,125/Night
7 Nights - R63,876
Villa
10.0(22 Reviews)
3 Bedrooms
4 Baths
6 Guests
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R17,795/Night
7 Nights - R124,571
Villa
10.0(20 Reviews)
4 Bedrooms
4 Baths
10 Guests
3500 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
R16,815/Night
7 Nights - R117,699
Villa
10.0(18 Reviews)
3 Bedrooms
3 Baths
6 Guests
4000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
R10,530/Night
7 Nights - R73,714
Villa
10.0(17 Reviews)
5 Bedrooms
4 Baths
10 Guests
4000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
R39,223/Night
7 Nights - R274,553
Villa
10.0(16 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Hot Tub
- Pool
- Ocean View
R47,796/Night
7 Nights - R334,572
