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Top Holiday Rentals in Head of The Bay

Coconut Breeze Villas

2.5 star property
10.0 out of 10, Exceptional, (17)
"Excellent staff service. Room is big, bed is very good and view amazing!"
The price is £211
includes taxes & fees
4 Sept - 5 Sept
Coconut Breeze Villas

Ke Villas

3.0 star property
9.6 out of 10, Exceptional, (109)
"Great stay"
Ke Villas

VERY Private, Spectacular, Waterfront Location

10.0 out of 10, Exceptional, (61)
"This is a great place for a family vacation. The house is in great condition and has all the amenities you may need. It is located in a place to itself but at the same time, close to everything. Virgin Gorda is amazing. Owners were great in helping us get there, and with many tips that made our vacation great!"
VERY Private, Spectacular, Waterfront Location

Mango Bay Resort

3.5 star property
9.4 out of 10, Exceptional, (56)
"Nice property with beautiful beach just steps away from your door. "
Mango Bay Resort

Spectacularly situated Beach Front High Tide@ The Tides at Little Apple Bay.

10.0 out of 10, Exceptional, (33)
"the stay was amazing i would recommend the property to anyone "
Spectacularly situated Beach Front High Tide@ The Tides at Little Apple Bay.

Oceanfront - 3 Bedroom Villa - BEST VIEW IN TORTOLA

10.0 out of 10, Exceptional, (40)
"The house was perfect for our two families including two teenagers and 4 adults. Beach access and the beautiful view could not be beaten and the host and house manager were extremely helpful and responsive."
Oceanfront - 3 Bedroom Villa - BEST VIEW IN TORTOLA

Villa Sirenetta-Minutes from the beach!

9.8 out of 10, Exceptional, (117)
"Nice place, could use some minor u"
Villa Sirenetta-Minutes from the beach!

Endless Summer Villa - Luxury by the Sea

10.0 out of 10, Exceptional, (50)
"Great place to stay. A true highlight. Close to Cane Garden Bay which we felt was the ideal area to make our home base to travel from. Many restaurants and shops to visit. "
Endless Summer Villa - Luxury by the Sea

Ocean and Island Views with Spectacular Sunsets and Alfresco Atmosphere

10.0 out of 10, Exceptional, (123)
"From the moment we walked in to Limeberry Villa we were ecstatic about the location and home. Beautiful views, clean, and well-appointed. Jon and Jubi were extremely quick to respond to our questions and needs. We had one incident when an ac unit froze up in a BR and Jubi was there to fix it within 90 minutes. The location was great as well with multiple restaurants within a 15 minute drive. Highly recommend this villa. "
Ocean and Island Views with Spectacular Sunsets and Alfresco Atmosphere

Amazing Water Front Villa West End Tortola

10.0 out of 10, Exceptional, (98)
"Pleasant stay. Relaxing. Stocked with everything you would need from cooking to beaching. Loved the view and being on the water. Enjoyed our daily swims and sunsets. Convenient location. It was perfect!"
Amazing Water Front Villa West End Tortola

COASTIN' A-LONG - bright & breezy Caribbean vibes above beautiful Long Bay

10.0 out of 10, Exceptional, (21)
"The house is so beautiful and well maintained, all the bedrooms are outstanding in quality, and the house has everything you could possibly need for the beach or a night in. 10/10, this is THE place to stay on Tortola. Cant wait to come back!"
COASTIN' A-LONG - bright & breezy Caribbean vibes above beautiful Long Bay

The Lighthouse Villas

3.5 star property
9.0 out of 10, Wonderful, (177)
"We loved this property. It is conveniently located in Cane Garden Bay. The staff were very friendly and checked on us daily to make sure everything was perfect. We highly recommend staying here."
The Lighthouse Villas

SEVEN TEN bright coastal vibes & fun times above Long Bay & Smuggler's beaches

10.0 out of 10, Exceptional, (11)
"Very nice, highly recommend!"
SEVEN TEN bright coastal vibes & fun times above Long Bay & Smuggler's beaches

New Construction Oceanfront Home/Pool Private Walk To Beach

10.0 out of 10, Exceptional, (24)
"We absolutely luv’d it. The pool & view were incredible. Our host Mindy fantastic! Perfect for 2 couples staying upstairs. Great restaurant 5 min walk to Sugar Cane restaurant. "
New Construction Oceanfront Home/Pool Private Walk To Beach

Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola

10.0 out of 10, Exceptional, (1)
"Our host was awesome and really accommodating. 10 out of 10. We will stay again."
The price is £253
includes taxes & fees
4 Sept - 5 Sept
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola

STARGAZER - a tropical retreat & pool, above Long Bay & Smuggler's beaches

10.0 out of 10, Exceptional, (2)
"Loved this Villa! Gorgeous views and great accommodations!! Sharlene from the Villas of Tortola team took great care of us! Check in was very simple and all their recommendation on the guidebook they provide were spot on! The guidebook/app was extremely helpful!! We would definitely recommend this place and would love to go again!!"
STARGAZER - a tropical retreat & pool, above Long Bay & Smuggler's beaches

The best sunset view in the Bay

9.6 out of 10, Exceptional, (8)
"Simply the best stay in Tortola - the property was perfect with amazings views, easy access to best beaches and very helpful and kind owner. LOVE to stay again soon."
The best sunset view in the Bay

Paradiso Ocean View. A perfect getaway. 10 mins drive to Smugglers Cove Beach..

9.6 out of 10, Exceptional, (9)
"Beautiful property. 8 of us stayed before our charter SaiL The Villa was fabulous! Never felt crowed together. I recommend the Villa. "
Paradiso Ocean View. A perfect getaway. 10 mins drive to Smugglers Cove Beach..

The Blu-Edge - 3-bedroom Beach Villa • Oceanview + FREE Wyndham Resort Access

The Blu-Edge - 3-bedroom Beach Villa • Oceanview + FREE Wyndham Resort Access

Top of the Hill Blue Sunshine

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 !"
The price is £252
includes taxes & fees
5 Sept - 6 Sept
Top of the Hill Blue Sunshine
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.
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Top Head of The Bay Hotel Reviews

Find out more about Head of The Bay

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 £211 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?

New Construction Oceanfront Home/Pool Private Walk To Beach: This holiday home rental outside of Head of The Bay is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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.