Anguilla Holiday Homes
2500 ft²
5 Guests
2 Bedrooms
1 Bathroom
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,007/Night
For 7 Nights CA $7,052
CA $177/Night
For 7 Nights CA $1,242
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Private Pool
- Spa
- Fireplace/Heating
CA $5,344/Night
For 7 Nights CA $37,410
5000 ft²
10 Guests
4 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,593/Night
For 7 Nights CA $11,154
2497.23 ft²
8 Guests
3 Bedrooms
3 Bathrooms
Ocean View
House
- Oceanfront
- Hot Tub
- Ocean View
CA $243/Night
For 7 Nights CA $1,701
2168 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $937/Night
For 7 Nights CA $6,558
484.38 ft²
2 Guests
1 Bedroom
1 Bathroom
Free Cancellation
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
CA $171/Night
For 7 Nights CA $1,194
6000 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $1,661/Night
For 7 Nights CA $11,629
1345.49 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Villa
- Pool
- View
- Parking
CA $3,923/Night
For 7 Nights CA $27,462
2 Guests
1 Bedroom
1 Bathroom
Ocean View
House
- Private Pool
- Pool
- Ocean View
CA $323/Night
For 7 Nights CA $2,265
753.47 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Free Cancellation
Apartment
- Balcony/Terrace
- Parking
- Air Conditioner
CA $205/Night
For 7 Nights CA $1,437
3500 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Ocean View
- Balcony/Terrace
- View
CA $622/Night
For 7 Nights CA $4,352
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
Sandy Hill
Island Harbour
East End Village
The Valley
The Quarter
West End Village
Shoal Bay
Blowing Point
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
- Great spot for family gatherings and romantic getaways.
- ON THE BEACH Luxury BeachHouse, sleeps 8, pool, hot-tub, fire-pit, …
- Escape the cold & snow in Anguilla at the ultimate vacation villa! Book today!
- Clubhouse Suite at Bellamare
- Fortune Rise. Car Rental available
- 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 534 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
3500 ft²
7 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,350/Night
For 7 Nights CA $9,447
3240 ft²
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,113/Night
For 7 Nights CA $7,794
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Villa
- Oceanfront
- Ocean View
- Balcony/Terrace
CA $697/Night
For 7 Nights CA $4,877
5000 ft²
10 Guests
5 Bedrooms
5 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Pool
CA $3,694/Night
For 7 Nights CA $25,857
4 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Condo
- Oceanfront
- Pool
- Ocean View
CA $756/Night
For 7 Nights CA $5,291
3500 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
CA $962/Night
For 7 Nights CA $6,736
6 Guests
3 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,474/Night
For 7 Nights CA $10,318
3500 ft²
10 Guests
4 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Pool
- Ocean View
CA $1,465/Night
For 7 Nights CA $10,258
4000 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Villa
- Private Pool
- Fireplace/Heating
- Pool
CA $918/Night
For 7 Nights CA $6,427
4000 ft²
10 Guests
5 Bedrooms
4 Bathrooms
Ocean View
Villa
- Private Pool
- Oceanfront
- Hot Tub
CA $3,444/Night
For 7 Nights CA $24,105
8 Guests
4 Bedrooms
2 Bathrooms
Ocean View
Villa
- Oceanfront
- Hot Tub
- Pool
CA $1,024/Night
For 7 Nights CA $7,166
