Little Harbour Vacations from $1,597

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Your Little Harbour Vacation

An easy way to experience this city is with a custom-made Little Harbour vacation package. Stay in the neighborhood of Maho, which is good for dining, golfing and coastal beaches or go someplace else — our packages are all about you. Fill your spare time with tours of Crocus Bay Beach, Sandy Hill Beach and Little Bay, some of the top attractions you shouldn't miss during your trip to Little Harbour. Whoever you're going away with and whether your budget is big or small, your ultimate Little Harbour vacation is just clicks away with Expedia.

The Latest Little Harbour vacation packages

Price found within the past 48 hours. Click for updated prices.
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $2,049, price is now $1,597 per person
$1,597
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
8/10 Very Good! (255 reviews)
First let me say that Great House is not the Four Seasons. Or even the Three Seasons. But if you aren’t a snob and just baby to enjoy a beautiful beach, be served by wonderful people, sleep in a clean room and have foot access to 4 beach bars this is your place. We loved our stay and are most definitely coming back.

Reviewed on Dec 20, 2025

Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $23,229, price is now $14,961 per person
$14,961
per person
Feb 19 - Feb 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
No reviews
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $8,250, price is now $5,850 per person
$5,850
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.4/10 Exceptional! (89 reviews)
Beautiful pool and grounds, beach is so nice and staff at hotel were great.

Reviewed on Nov 25, 2025

Quintessence Hotel Anguilla

Quintessence Hotel Anguilla

4.5 out of 5
Save 100% on your flight
Price was $6,106, price is now $4,928 per person
$4,928
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.8/10 Exceptional! (27 reviews)
The property is beautiful and the best for a relaxing time. The rooms are so nice and when I arrived to my room they welcomed me with so many special details. The restaurant by the beach was so nice and staff is very welcoming. Definitely recommend especially if you just want peace

Reviewed on Jun 6, 2025

Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $3,307, price is now $2,690 per person
$2,690
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
9.2/10 Wonderful! (25 reviews)
Great staff and beautiful location! Highly recommend.

Reviewed on Dec 24, 2025

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Little Harbour Hotel Deals

Stunning 6 bedroom waterfront villa with wooden dock

Stunning 6 bedroom waterfront villa with wooden dock

Little harbour Anguilla
10/10 Exceptional! (2 reviews)
Fantastic
Was an absolute wonderful experience from beginning to end. Not a single complaint. Beautiful home with beautiful views. Would recommend

Reviewed on Jun 2, 2025

Get rates
Stunning 6 bedroom waterfront villa with wooden dock
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
$1,708 nightly
The price is $1,903 total per night from Jan 6 to Jan 7
$1,903 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
9.6/10 Exceptional! (243 reviews)
Everything was amazing!

Reviewed on Dec 9, 2025

Four Seasons Resort and Residences Anguilla
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Rendezvous Bay Rendezvous Bay
$327 nightly
The price is $365 total per night from Jan 2 to Jan 3
$365 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8/10 Very Good! (265 reviews)
First let me say that Great House is not the Four Seasons. Or even the Three Seasons. But if you aren’t a snob and just baby to enjoy a beautiful beach, be served by wonderful people, sleep in a clean room and have foot access to 4 beach bars this is your place. We loved our stay and are most definitely ...

Reviewed on Dec 20, 2025

Anguilla Great House Beach Resort
See all 328 properties in Little Harbour
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Little Harbour Vacation Packages

Little Harbour Essential Information

Language
English
Currency
East Caribbean dollars
Closest Airport
Clayton J. Lloyd Intl. Airport (AXA)
Top Sights
Crocus Bay Beach, Little Bay and Sandy Hill Beach

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Frequently asked questions

How much does a Little Harbour vacation package cost?
You'll find cheap prices from $1,597 on Expedia for your Little Harbour getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Little Harbour costs.
What are the cheapest months to go to Little Harbour?
You can generally find lower prices and better availability in July, August and December. Check out our cheap Little Harbour vacation packages and you could score some great off-season deals.
How many days is enough for Little Harbour?
With a well-organized travel plan, you can easily hit the main Little Harbour sights in a few days. But if you want to discover lesser-known spots or take day trips, think about booking your Little Harbour vacation for longer.
How to find the best Little Harbour package deals?
Begin your search for a Little Harbour package deal by entering your destination and preferred travel dates under our "Packages" tab. Then apply some filters, like "Property type" and "Amenities," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Little Harbour package deal straight away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Little Harbour escape underway.
Is it cheaper to book a Little Harbour vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll typically get a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Little Harbour vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Little Harbour?
If you're planning an impromptu Little Harbour adventure, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score awesome deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Little Harbour vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Little Harbour trip over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.