Cheap Flights to Anguilla (2026/2027)

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Beautiful Rendez-Vous Bay beach in Anguilla

Rendezvous Bay

Flights
Rendezvous Bay
OriginDestinationTravel DatesFlights From*
SXMThe ValleyJune 17 to June 20$358
MIAThe ValleyAugust 19 to August 26$591
JFKThe ValleyJuly 21 to July 28$664
JFKThe ValleyJuly 21 to July 28$664
BOSThe ValleyJuly 25 to July 29$679
ATLThe ValleyJuly 17 to July 22$697
DCAThe ValleyJune 30 to July 8$708
LAXThe ValleyJuly 22 to July 27$825
SJUThe ValleyAugust 18 to September 8$846
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
BWIThe ValleyJune 7 to June 11$1,010
EWRThe ValleyJune 5 to June 21$1,517
JFKThe ValleyJune 7 to June 18$1,532
*Prices include taxes and fees

Best Anguilla Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Quintessence Hotel Anguilla
4.5-star property

Quintessence Hotel Anguilla

Jul 11 - Jul 18

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $4,274, price is now $3,456 per person
$3,456
per person
found 1 day ago
Aurora Anguilla Resort & Golf Club
5.0-star property

Aurora Anguilla Resort & Golf Club

Jul 11 - Jul 18

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $6,827, price is now $3,809 per person
$3,809
per person
found 1 day ago
Malliouhana Resort Anguilla
5.0-star property

Malliouhana Resort Anguilla

Jul 11 - Jul 18

7 night stay

Boston (BOS) to The Valley (AXA)

American Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $5,263, price is now $3,828 per person
$3,828
per person
found 1 day ago
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Travelers ❤️ These Anguilla 🏨

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
Book a stay at this luxury resort in West End Village. Enjoy free WiFi, free parking, and 3 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Meads Bay Beach are located nearby.
9.6/10 Exceptional! (251 reviews)
"Amazing location, great separation between the pools, very quiet."

Reviewed on Jun 1, 2026

Opens in a new windowFour Seasons Resort and Residences Anguilla
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Maundays Bay Maunday's Bay
Book a stay at this luxury resort in Maunday's Bay. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Meads Bay and Maundays Bay are located nearby.
9.6/10 Exceptional! (143 reviews)
"Beautiful scenery of miles of coastline and mountains and nearby islands!"

Reviewed on May 22, 2026

Opens in a new windowCap Juluca, A Belmond Hotel, Anguilla
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
Book a stay at this luxury resort in Rendezvous Bay. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Aurora International Golf Club are located nearby.
9.6/10 Exceptional! (197 reviews)
"This resort is beautifully laid out with gorgeous views and excellent food! The staff was so attentive that we felt special😊. The villas are luxurious with outdoor patio showers a spa tub and a separate dressing room for luggage and valuables . The view of the ocean from our villa was top tier! ..."

Reviewed on Jun 2, 2026

Opens in a new windowAurora Anguilla Resort & Golf Club
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Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Rendezvous Bay Rendezvous Bay
Book a stay at this beach hotel in Rendezvous Bay. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Meads Bay and Rendezvous Bay Beach are located nearby.
8.2/10 Very Good! (322 reviews)
"AC in the room was a mini split that kept the room very comfortable. Room and Bathroom were very clean. Housekeeping was there every day with fresh linens and towels. No complaints at all. Well, other than having to leave."

Reviewed on May 15, 2026

Opens in a new windowAnguilla Great House Beach Resort
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.

Frequently asked questions

How much is the cheapest flight to Anguilla?
A roundtrip flight to Anguilla cost as little as $358 over the last seven days. When you're ready to book, we'll help you find an amazing deal. This price was available on Travelocity for flights to Anguilla departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Anguilla?
Find your ideal fare with one of the 9 airlines that fly to Anguilla. If you're staying in The Valley, let Anguilla Air Services whisk you away to this lively city to explore its top sights. This popular carrier offers 30 flights there per month.
What is the cheapest month to fly to Anguilla?
If you've been dreaming of a break in Anguilla, June is the cheapest month to make your way there. This is according to Travelocity's direct return flight demand between January and December last year. Pick your preferred travel dates and lock in your seat today.
How can I check my flight status to Anguilla?
There are a couple of handy ways to look up your flight status. You can find all the necessary info in our "Trips" portal, which is located at the top right of our homepage. Log in or open a new account — you'll then be able to browse and manage your bookings whenever you need. If you're already on the go, the Travelocity app can also help you look up the status of your flight to Anguilla, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Anguilla?
Being flexible with your travel dates is one way to land an awesome deal. Travelocity makes it a piece of cake to find your ideal fare through the "Flexible dates" function. First, search for your flight to Anguilla, then compare prices for surrounding days by clicking the "Flexible dates" dropdown box above. Booking earlier and avoiding vacation periods are some other suggestions. In the last seven days, the best price for a return flight to Anguilla was $358. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Anguilla with Travelocity?
Pack your bags and get set for an awesome vacation with Travelocity. It's our job to track down fantastic deals on cheap flights to Anguilla. Whether you're seeking flexible airfares or cheap family flights from low-cost carriers, we've got you covered.
How much is a flight to Anguilla on average?
Passengers were picking up roundtrip flights to Anguilla for between $358 and $1,532 with Travelocity in the last seven days. Whether you're planning to fly economy or first class, we'll help you get a fantastic deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Anguilla?
This depends mostly on your carrier and the duration of your flight. Generally, most airlines provide warm meals, drinks and entertainment on long-haul journeys. Whether you're searching for first class flights to Anguilla or cheap flights for family vacations, you'll be well looked after from boarding to touchdown.

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