Anguilla Adventure Vacations

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Flight and Adventure hotel deals in Anguilla

Price found within the past 48 hours. Click for updated prices.
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

CA $2,370
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (202 reviews)
The property is fantastic. The staff is super friendly. Breakfast at Chef's Table gave a lot of options. The spa is beautiful. It was the week before the property closes for the season, and half of the resort was closed. Dining options were limited. We had a car, so we went to a few local restaurants that were great. The beach is what we really enjoy, and it never disappoints at the Aurora.

Reviewed on Aug 17, 2026

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

CA $3,035
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (103 reviews)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

CA $2,814
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (279 reviews)
Overall a great stay. It’s a bit off the beaten path which is both nice and a little challenging to get around the rest of island. But with a rental car you get just about everywhere in under 30 minutes.

Reviewed on Aug 17, 2026

Cap Juluca, A Belmond Hotel, Anguilla

Cap Juluca, A Belmond Hotel, Anguilla

CA $6,052
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (158 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

CA $3,945
per person
Oct 31 - Nov 4
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
10/10 Exceptional! (8 reviews)
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5* Adventure holidays in Anguilla

Price found within the past 48 hours. Click for updated prices.
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

CA $2,370
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (202 reviews)
The property is fantastic. The staff is super friendly. Breakfast at Chef's Table gave a lot of options. The spa is beautiful. It was the week before the property closes for the season, and half of the resort was closed. Dining options were limited. We had a car, so we went to a few local restaurants that were great. The beach is what we really enjoy, and it never disappoints at the Aurora.

Reviewed on Aug 17, 2026

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

CA $3,035
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (103 reviews)
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

CA $2,814
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (279 reviews)
Overall a great stay. It’s a bit off the beaten path which is both nice and a little challenging to get around the rest of island. But with a rental car you get just about everywhere in under 30 minutes.

Reviewed on Aug 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Anguilla
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3 Night Adventure holidays in Anguilla

Price found within the past 48 hours. Click for updated prices.
Zemi Beach House, LXR Hotels & Resorts

Zemi Beach House, LXR Hotels & Resorts

CA $1,744
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.8/10 Exceptional! (279 reviews)
Overall a great stay. It’s a bit off the beaten path which is both nice and a little challenging to get around the rest of island. But with a rental car you get just about everywhere in under 30 minutes.

Reviewed on Aug 17, 2026

Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

CA $2,270
per person
Nov 2 - Nov 5
found 24 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to The Valley (AXA)
9.6/10 Exceptional! (202 reviews)
The property is fantastic. The staff is super friendly. Breakfast at Chef's Table gave a lot of options. The spa is beautiful. It was the week before the property closes for the season, and half of the resort was closed. Dining options were limited. We had a car, so we went to a few local restaurants that were great. The beach is what we really enjoy, and it never disappoints at the Aurora.

Reviewed on Aug 17, 2026

Don't see what you're looking for?
See all available trips from Columbus to Anguilla
View all trips

4 Night Adventure holidays in Anguilla

Price found within the past 48 hours. Click for updated prices.
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

CA $2,370
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (202 reviews)
The property is fantastic. The staff is super friendly. Breakfast at Chef's Table gave a lot of options. The spa is beautiful. It was the week before the property closes for the season, and half of the resort was closed. Dining options were limited. We had a car, so we went to a few local restaurants that were great. The beach is what we really enjoy, and it never disappoints at the Aurora.

Reviewed on Aug 17, 2026

Malliouhana Resort Anguilla

Malliouhana Resort Anguilla

CA $3,035
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to The Valley (AXA)
9.6/10 Exceptional! (103 reviews)
Ceblue Luxury Villas

Ceblue Luxury Villas

CA $3,888
per person
Nov 2 - Nov 6
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to The Valley (AXA)
10/10 Exceptional! (8 reviews)
Don't see what you're looking for?
See all available trips from Columbus to Anguilla
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Adventure Hotels in Anguilla

Frangipani Resort

Frangipani Resort

Meads Bay, middle of the beach West End Village
  • 19 min drive from Shoal Bay Beach
Book a stay at this luxury resort in West End Village. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Meads Bay and Meads Bay Beach ...
9.4/10 Exceptional! (75 reviews)
"This is a very nice place to stay with lovely people working here that make you feel welcome in Anguilla. Definitely recommend doing the boat ride if you can and all the water sports are great!"

Reviewed on Jul 11, 2021

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Frangipani Resort
Aurora Anguilla Resort & Golf Club

Aurora Anguilla Resort & Golf Club

Rendezvous Bay Rendezvous Bay
  • 17 min drive from Shoal Bay Beach
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. ...
9.6/10 Exceptional! (204 reviews)
"The property is fantastic. The staff is super friendly. Breakfast at Chef's Table gave a lot of options. The spa is beautiful. It was the week before the property closes for the season, and half of the resort was closed. Dining options were limited. We had a car, so we went to a few local restaurants ..."

Reviewed on Aug 17, 2026

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Aurora Anguilla Resort & Golf Club
Carimar Beach Club

Carimar Beach Club

Meads Bay West End Village
  • 18 min drive from Shoal Bay Beach
CA $640
CA $798 total
Aug 21 - Aug 22
includes taxes & fees
Book a stay at this beach hotel in West End Village. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Meads Bay and Meads Bay Pond are ...
9.4/10 Exceptional! (109 reviews)
"Great location, clean and perfect beach!"

Reviewed on Feb 23, 2026

Carimar Beach Club
See all 365 properties in Anguilla
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.

Things to do

High-Speed Ferry to St. Barths

High-Speed Ferry to St. Barths

CA $114
per adult
80% of travellers recommend
High-Speed Ferry to St. Barths
Colorful Species Of Birds

Colorful Species Of Birds

CA $69
per adult
94% of travellers recommend
Colorful Species Of Birds
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line

CA $190
per adult
90% of travellers recommend
Sky Explorer + Flying Dutchman + Schooner + Sentry Hill Line
See all activities in Anguilla

More vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.