Holiday Rentals in Head of The Bay

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Head of The Bay

Apartment in Virgin Gorda

3.5 star property
9.4 out of 10, Exceptional, (57)
"Nice property with beautiful beach just steps away from your door. "
United States
Wendy
The price is €619
includes taxes & fees
1 Dec - 2 Dec
Mango Bay Resort

Holiday Home in Tortola

2.0 star property
10.0 out of 10, Exceptional, (3)
"We were very pleased with our friendly accommodating host. The house provided everything we needed plus more! It is very spacious and cleanliness was top notch. I would definitely return and plan to stay longer next time!"
Canada
Carmen S.
The price is €288
includes taxes & fees
25 Nov - 26 Nov
Family Friendly, centrally located - modern & spacious 2 bed 2 bath retreat.

Aparthotel in Cane Garden Bay

2.5 star property
9.8 out of 10, Exceptional, (19)
"Excellent staff service. Room is big, bed is very good and view amazing!"
United States
Lisandra
The price is €224
includes taxes & fees
24 Nov - 25 Nov
Coconut Breeze Villas

Apartment in Tortola

9.4 out of 10, Exceptional, (8)
"We had a fabulous time!! Plenty to do & see - all within walking distance. It was perfect for our trip. "
United States
Sue T.
The price is €145
includes taxes & fees
1 Dec - 2 Dec
Sailors Gem II: Experience Caribbean Life at this Spacious Apartment!

Holiday Home in Parham Town

9.8 out of 10, Exceptional, (10)
"What an awesome view we loved this place and it’s the only place I will stay the host was awesome !"
United States
john
The price is €302
includes taxes & fees
24 Nov - 25 Nov
Top of the Hill Blue Sunshine

Apartment in Scrub Island

Spacious Family Base Near Sandy Beach and Scenic Island Walking Trails | 3 Units

Apartment in Tortola

2.0 star property
10.0 out of 10, Exceptional, (2)
"Francis and Simone were the best hosts. Everett hung was really clean and nice and the view was amazing. Would stay there every time. "
United States
Kami M.
The price is €327
includes taxes & fees
24 Nov - 25 Nov
Ocean Breeze Comfort

Apartment in Tortola

8.6 out of 10, Excellent, (15)
"Location was great! We were only there for one night before taking a sailing trip so it was perfect for us. "
United States
Anonymous traveller
The price is €145
includes taxes & fees
22 Dec - 23 Dec
Sailor's Gem I: Feel the Real Caribbean Life and Live Local at this Apartment!

Apartment in Tortola

9.8 out of 10, Exceptional, (6)
"Great host safe quiet and clean apartment "
United States
Sovill
The price is €217
includes taxes & fees
24 Nov - 25 Nov
#6 One Bedroom with AC and Bathroom - 10 Minutes from two beaches

Apartment in Tortola

The price is €221
includes taxes & fees
24 Nov - 25 Nov
#7 Studio sunset islands view, queen bed, bath & kitchen 10 min to town & beach

Apartment in Road Town

8.4 out of 10, Very good, (6)
"Felt vey safe and seccure"
United States
Albeadea
The price is €269
includes taxes & fees
24 Nov - 25 Nov
SALE$Abigail's Entire 2 Bedroom Apartments SALE, SALE$$

Holiday Home in Tortola

8.4 out of 10, Very good, (5)
"Great accommodations, clean well provision, and the views were spectacular. Best of all Justin was so accommodating and helpful as well as his father Brian. Thank you very much we appreciate everything and we will be back."
United States
Brenda B.
The price is €477
includes taxes & fees
24 Nov - 25 Nov
Fort Recovery Beachfront Villa and Suites Hotel luxury 2BR

Apartment in Tortola

The price is €269
includes taxes & fees
6 Dec - 7 Dec
5 Studio with queen bed & bathroom - 10 min to beach & town

Villa in Tortola

9.6 out of 10, Exceptional, (15)
"Such a beautiful house. Very clean and spacious. "
United States
Brenda v.
The price is €968
includes taxes & fees
24 Nov - 25 Nov
Private Luxury Villas

Villa in Leonards

10.0 out of 10, Exceptional, (2)
"Our host was awesome and really accommodating. 10 out of 10. We will stay again."
United States
Najla D.
The price is €277
includes taxes & fees
24 Nov - 25 Nov
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola

Holiday Home in Road Town

9.8 out of 10, Exceptional, (14)
"We had a quick one night stay, but would definitely recommend. The secluded beach is so beautiful. Definitely coming back to explore more."
United States
Braxton H.
The price is €601
includes taxes & fees
25 Nov - 26 Nov
Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!

Villa in Buck Island

The price is €2,233
includes taxes & fees
24 Dec - 25 Dec
Secluded Beachfront Teepee Villa w/ Ocean Views

Holiday Home in Greenbank Estate

Eyrie Guest Cottage, Greenbank

Apartment in Tortola

The price is €213
includes taxes & fees
24 Nov - 25 Nov
Cozy Studio4 in serene Tortola with AC, WiFi. Enjoyable getaway with Sunset View

Aparthotel in Buck Island

The Dream | Private 360° View Suite in Buck 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Head of The Bay Hotel Reviews

Find out more about Head of The Bay

Everything you need to know about Head of The Bay holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Head of The Bay holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Head of The Bay holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Head of The Bay holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Head of The Bay. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Head of The Bay holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Head of The Bay holiday rentals we have selected for you start as low as €224 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Head of The Bay rentals

At Expedia, we put the best Head of The Bay holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Head of The Bay rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Head of The Bay holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Head of The Bay. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Head of The Bay?

Yes, there are holiday rentals close to the most popular sights in Head of The Bay, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Head of The Bay has to offer?

"Your Caribbean Haven: Where Comfort Meets Local Charm": This holiday home rental outside of Head of The Bay has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

What’s there to see and do in Head of The Bay?

While you're exploring the area, Little Dix Bay Beach and Savannah Beach are a couple of picturesque spots to get outside and enjoy nature. Spring Bay Beach and Mahoe Bay Beach are a couple of places you'll find in the wider area.

What’s a holiday rental in Head of The Bay like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Head of The Bay. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and bustling concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.