Cheap Vacations in Anguilla

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Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
West End Bay Condos

West End Bay Condos

3.5 out of 5
Price was $1,985, price is now $1,805 per person
$1,805
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $29,471, price is now $21,964 per person
$21,964
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $8,375, price is now $6,275 per person
$6,275
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $11,604, price is now $10,498 per person
$10,498
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

3-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Edwards Guesthouse

Edwards Guesthouse

2.5 out of 5
Price was $691, price is now $642 per person
$642
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $12,706, price is now $9,454 per person
$9,454
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $3,576, price is now $2,687 per person
$2,687
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,130, price is now $936 per person
$936
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $2,784, price is now $2,416 per person
$2,416
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Price was $3,625, price is now $3,187 per person
$3,187
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,088, price is now $968 per person
$968
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,189, price is now $1,059 per person
$1,059
per person
Jan 22 - Jan 25
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Price was $5,149, price is now $4,690 per person
$4,690
per person
Jan 22 - Jan 25
found 13 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to The Valley (AXA)
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $932, price is now $850 per person
$850
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Price was $4,115, price is now $3,753 per person
$3,753
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Price was $2,802, price is now $2,802 per person
$2,802
per person
Jan 11 - Jan 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

4-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
West End Bay Condos

West End Bay Condos

3.5 out of 5
Price was $1,252, price is now $1,142 per person
$1,142
per person
Jan 4 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $17,174, price is now $12,973 per person
$12,973
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $5,000, price is now $3,851 per person
$3,851
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,740, price is now $1,488 per person
$1,488
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $4,049, price is now $3,541 per person
$3,541
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $4,665, price is now $4,083 per person
$4,083
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,393, price is now $1,219 per person
$1,219
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $2,112, price is now $1,873 per person
$1,873
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
6 BR Villa On Crocus Bay With Pool Concierge

6 BR Villa On Crocus Bay With Pool Concierge

2 out of 5
Price was $5,229, price is now $4,743 per person
$4,743
per person
Jan 13 - Jan 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,683, price is now $1,531 per person
$1,531
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Save 100% on your flight
Price was $15,153, price is now $13,858 per person
$13,858
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,462, price is now $1,360 per person
$1,360
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)

5-night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
West End Bay Condos

West End Bay Condos

3.5 out of 5
Price was $1,086, price is now $979 per person
$979
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $23,146, price is now $15,277 per person
$15,277
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $4,928, price is now $3,645 per person
$3,645
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $1,379, price is now $1,150 per person
$1,150
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $2,400, price is now $2,003 per person
$2,003
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $1,814, price is now $1,540 per person
$1,540
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $1,581, price is now $1,353 per person
$1,353
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $8,532, price is now $7,304 per person
$7,304
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Save 100% on your flight
Price was $4,420, price is now $3,793 per person
$3,793
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Coralito Bay Suites & Villas

Coralito Bay Suites & Villas

3.5 out of 5
Price was $1,644, price is now $1,415 per person
$1,415
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,520, price is now $1,309 per person
$1,309
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

5 out of 5
Save 100% on your flight
Price was $8,644, price is now $7,752 per person
$7,752
per person
Jan 24 - Jan 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

6-7 night Anguilla vacations

Price found within the past 48 hours. Click for updated prices.
Edwards Guesthouse

Edwards Guesthouse

2.5 out of 5
Price was $1,249, price is now $1,113 per person
$1,113
per person
Jan 7 - Jan 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to The Valley (AXA)
Sheriva Luxury Villas and Suites

Sheriva Luxury Villas and Suites

4 out of 5
Save 100% on your flight
Price was $29,471, price is now $21,964 per person
$21,964
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

5 out of 5
Save 100% on your flight
Price was $8,375, price is now $6,275 per person
$6,275
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Price was $2,462, price is now $2,014 per person
$2,014
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Coralito Bay Suites & Villas

Coralito Bay Suites & Villas

3.5 out of 5
Price was $2,140, price is now $1,793 per person
$1,793
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Paradise Cove Resort

Paradise Cove Resort

2.5 out of 5
Price was $2,002, price is now $1,683 per person
$1,683
per person
Jan 13 - Jan 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to The Valley (AXA)
Rendezvous Bay Hotel

Rendezvous Bay Hotel

3.5 out of 5
Price was $3,595, price is now $3,078 per person
$3,078
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Fountain Anguilla

Fountain Anguilla

3.5 out of 5
Price was $3,082, price is now $2,649 per person
$2,649
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

5 out of 5
Price was $6,425, price is now $5,548 per person
$5,548
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $2,363, price is now $2,087 per person
$2,087
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Save 100% on your flight
Price was $11,604, price is now $10,498 per person
$10,498
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)
La Vue Boutique Inn

La Vue Boutique Inn

3.5 out of 5
Price was $1,954, price is now $1,773 per person
$1,773
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

Top places to visit in Anguilla

FlightsFlightsHotelsHotels

West End Village

West End Village

Flight deals to Anguilla

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Wed, Jan 21 - Tue, Jan 27
EWR
New York
AXA
The Valley
$485 Roundtrip, found 7 hours ago
$485
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Wed, Jan 21 from New York to The Valley, returning Tue, Jan 27, priced at $485 found 7 hours ago
Thu, Feb 26 - Sun, Mar 1
MIA
Miami
AXA
The Valley
$485 Roundtrip, found 2 days ago
$485
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Feb 26 from Miami to The Valley, returning Sun, Mar 1, priced at $485 found 2 days ago
Mon, Jan 26 - Sat, Jan 31
IAD
Washington
AXA
The Valley
$506 Roundtrip, found 2 days ago
$506
Roundtrip
found 2 days ago
Select American Airlines flight, departing Mon, Jan 26 from Washington to The Valley, returning Sat, Jan 31, priced at $506 found 2 days ago

Top rated hotels for your Anguilla vacation

Four Seasons Resort and Residences Anguilla

Four Seasons Resort and Residences Anguilla

5 out of 5
Barnes Bay West End Village
6.06 mi from city center
$1,188 nightly
The price is $1,324 total per night
$1,324 total
Dec 10 - Dec 11
Total with taxes and fees
When you stay at Four Seasons Resort and Residences Anguilla in West End Village, you'll be on the beach and 10.9 mi (17.6 km) from Shoal Bay Beach.
Pool
Spa
Anguilla Great House Beach Resort

Anguilla Great House Beach Resort

4 out of 5
Rendezvous Bay Rendezvous Bay
4.66 mi from city center
Get rates
With a stay at Anguilla Great House Beach Resort in Rendezvous Bay, you'll be on the beach, just a 2-minute walk from Rendezvous Bay Beach and 12 minutes by foot from Aurora International Golf Club.
Pool
Spa
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

5 out of 5
Rendezvous Bay Rendezvous Bay
4.95 mi from city center
$1,123 nightly
The price is $1,246 total per night
$1,246 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
Located in Rendezvous Bay, Aurora Anguilla Resort & Golf Club is by the ocean, a 5-minute drive from Sandy Island and 8 minutes from Blowing Point Ferry Terminal.
Pool
Hot Tub
Don't see what you're looking for?
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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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.