Cheap Vacations in Island Harbour

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3-night Island Harbour 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 11 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 11 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 Island Harbour 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 Island Harbour 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 Island Harbour 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 $1,241, price is now $1,097 per person
$1,097
per person
Jan 15 - Jan 21
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 $27,697, price is now $18,254 per person
$18,254
per person
Jan 15 - Jan 21
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)
Coralito Bay Suites & Villas

Coralito Bay Suites & Villas

3.5 out of 5
Price was $1,554, price is now $1,245 per person
$1,245
per person
Jan 15 - Jan 21
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 $1,735, price is now $1,406 per person
$1,406
per person
Jan 15 - Jan 21
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 $2,802, price is now $2,326 per person
$2,326
per person
Jan 15 - Jan 21
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 $2,375, price is now $1,979 per person
$1,979
per person
Jan 15 - Jan 21
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)
Genesis Residences

Genesis Residences

2.5 out of 5
Price was $1,760, price is now $1,492 per person
$1,492
per person
Jan 15 - Jan 21
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 $5,243, price is now $4,489 per person
$4,489
per person
Jan 15 - Jan 21
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 $1,423, price is now $1,251 per person
$1,251
per person
Jan 15 - Jan 21
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 $12,558, price is now $11,239 per person
$11,239
per person
Jan 15 - Jan 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to The Valley (AXA)

Flight deals to Island Harbour

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 5 hours ago
$485
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Jan 21 from New York to The Valley, returning Tue, Jan 27, priced at $485 found 5 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 Island Harbour vacation

Lovely 6-bedroom Villa with Pool

Lovely 6-bedroom Villa with Pool

Island Harbor Anguilla
0.39 mi from city center
$3,741 nightly
The price is $4,041 total per night
$4,041 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Located in Island Harbour, this villa is within a 5-minute drive of Scilly Cay and Shoal Bay Beach.
Pool
Kitchen
Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Caribbean Rhapsody Villa, Oceanfront Island Harbour Anguilla!!

Island Harbour Anguilla
1 mi from city center
Get rates
When you stay at this villa in Island Harbour, you'll be by the ocean, within a 5-minute drive of Island Harbor Beach and Scilly Cay.
Pool
Kitchen
Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

Clearview Villas (UPPER): Casual, Bright, Affordable, Perfect for Families

Island Harbour Anguilla
1.05 mi from city center
Get rates
When you stay at this villa in Island Harbour, you'll be by the ocean, within a 5-minute drive of Island Harbor Beach and Scilly Cay.
Kitchen
Washer
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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.