Guana Island Vacations from $2,268

Book a Hotel + Flight or Car together to unlock savings

Your Guana Island Vacation

Lock in a Guana Island vacation package and prepare to experience the highlights of this city. Consider staying in the neighborhood of Wickhams Cay 1, which is good for views, dining and shopping. Eager to get out and explore? Long Bay Beach, Trellis Bay Beach and Marina Cay Beach are just a few of the most popular places to visit during your trip to Guana Island. Don't put off your visit to this city any longer. Your perfect Guana Island vacation is just a few clicks away with Expedia.

The Latest Guana Island vacation packages

Price found within the past 48 hours. Click for updated prices.
Coconut Tree Villa

Coconut Tree Villa

3.5 out of 5
Price was $3,030, price is now $2,268 per person
$2,268
per person
Nov 9 - Nov 16
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
8.6/10 Excellent! (37 reviews)
A Mixed Stay at Coconut Tree Villa Our recent stay at Coconut Tree Villa offered some enjoyable aspects, but it also had significant shortcomings that impacted our overall experience. While we appreciate the villa's potential, it felt more akin to a "poor college student's style" accommodation rather than a well-maintained vacation rental. The most notable issues were the broken couches indoors, which made relaxing comfortably quite difficult. Additionally, the outdoor furniture lacked cushions, which really detracted from our ability to enjoy the outdoor spaces and made them less inviting. With some much-needed updates and attention to comfort, Coconut Tree Villa could truly shine. However, as it stands, these issues prevented our stay from being as comfortable and enjoyable as we had hoped.

Reviewed on Jul 2, 2025

Bitter End Yacht Club

Bitter End Yacht Club

3.5 out of 5
Save 100% on your flight
Price was $4,526, price is now $3,183 per person
$3,183
per person
Nov 9 - Nov 16
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
9/10 Wonderful! (46 reviews)
it was amazing; the spot the beaches, the staff, the wifi and the activities are out of this world.

Reviewed on Jul 12, 2017

Oil Nut Bay

Oil Nut Bay

4 out of 5
Save 100% on your flight
Price was $5,215, price is now $3,815 per person
$3,815
per person
Nov 9 - Nov 16
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
10/10 Exceptional! (1 review)
Scrub Island Resort, Spa & Marina

Scrub Island Resort, Spa & Marina

5 out of 5
Price was $3,431, price is now $2,544 per person
$2,544
per person
Nov 9 - Nov 16
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
9/10 Wonderful! (171 reviews)
This was one of the best experiences we've ever had. The hotel is spectacular, as is the shuttle service and the hotel staff. The only thing I didn't like is that when you purchase the stay package, they don't tell you about the room and service fees, and then they charge you at the end of your stay, which are unavoidable. But the stay was truly spectacular!!!

Reviewed on Sep 1, 2025

Cane Garden Bay Beach Hotel

Cane Garden Bay Beach Hotel

3.5 out of 5
Price was $3,142, price is now $2,573 per person
$2,573
per person
Nov 9 - Nov 16
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
9.8/10 Exceptional! (150 reviews)
Absolutely spectacular! Definitely coming back.

Reviewed on Sep 1, 2025

Don't see what you're looking for?
See all available trips from Chicago to Guana Island
View all trips

Guana Island Hotel Deals

Village Cay Hotel and Marina

Village Cay Hotel and Marina

3.5 out of 5
Nibbs St, Road Town, Tortola
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $175 total per night from Sep 20 to Sep 21
$175 total
Sep 20 - Sep 21
Total with taxes and fees
8/10 Very Good! (774 reviews)
"Beautiful view of the marina from our room #1"

Reviewed on Sep 15, 2025

Village Cay Hotel and Marina
Nanny Cay Resort and Marina

Nanny Cay Resort and Marina

3 out of 5
Nanny Cay, Road Town, NA
$160 nightly
The price is $175 total per night from Sep 17 to Sep 18
$175 total
Sep 17 - Sep 18
Total with taxes and fees
8.4/10 Very Good! (6 reviews)
"Closer to my customers"

Reviewed on Sep 10, 2025

Nanny Cay Resort and Marina
Sebastian's on the Beach

Sebastian's on the Beach

3 out of 5
Apple Bay, West End, Tortola
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $91 total per night from Sep 17 to Sep 18
$91 total
Sep 17 - Sep 18
Total with taxes and fees
8.4/10 Very Good! (832 reviews)
"Great property with beach front and excelent views"

Reviewed on Sep 15, 2025

Sebastian's on the Beach
See all 444 properties in Guana Island
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.

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Guana Island vacation package cost?
You'll find cheap prices from $2,268 on Expedia for your Guana Island break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Guana Island costs.
What are the cheapest months to go to Guana Island?
You can typically find lower rates and greater availability in January, May and September. Browse our cheap Guana Island vacation packages and you could get some great off-season discounts.
How many days is enough for Guana Island?
With a well-organized travel plan, you can easily visit the top Guana Island sights in a few days. But if you want to venture off the beaten track or go on day trips, consider booking your Guana Island vacation for longer.
How to find the best Guana Island package deals?
Use Expedia's filter tool to find some terrific Guana Island package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Guana Island package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Guana Island vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can personalize your Guana Island escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Guana Island?
If you're considering a spontaneous Guana Island 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 find awesome deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Guana Island vacation packages?
Your Guana Island break is meant to be an escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.