Head of The Bay Vacation Rentals

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Vacation Rentals in Head of The Bay

The Lighthouse Villas
Beach nearby
The Lighthouse Villas
3.5 star property
8.8 out of 10, Excellent, (148)
"The property was in perfect location so close to the beach restaurants thay yoi dont need car we love it, the bedroom super clean kitchen we didnt use but need a little update but people there and cleaning is perfect! Definitely recommended and I will return "
The Lighthouse Villas
Amazing Water Front Villa West End Tortola
Property grounds
Amazing Water Front Villa West End Tortola
10.0 out of 10, Exceptional, (65)
"We enjoyed 3 lovely days at this beautiful home. Ivet is a wonderful host and prepared dinner for us on the night of arrival. We would certainly stay here again."
Amazing Water Front Villa West End Tortola
Coconut Breeze Villas
Boating
Coconut Breeze Villas
3.5 star property
10.0 out of 10, Exceptional, (2)
"The view was spectacular from Ocean View Villa! The villa has been has been nicely renovated with many amenities. We were delighted to find coffee, milk and fresh baked banana bread for our first morning breakfast. We learned the bananas were grown on the properties. We would encourage using drivers recommended by the property as the driveway is step especially to the top."
The price is $243
$267 total
includes taxes & fees
Jun 2 - Jun 3
Coconut Breeze Villas
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Mango Bay Resort
On the beach, white sand, sun loungers, beach umbrellas
Mango Bay Resort
3.5 star property
9.4 out of 10, Exceptional, (54)
"Nala was awesome, very helpful and responsive, and advised me on a good restaurant when I arrived. Beautiful beach and great location... Great Sunset!!!! Only comments: It be good to have a Restaurant there, and a Gym room. Also, better coffee in the room."
Mango Bay Resort
Ocean and Island Views with Spectacular Sunsets and Alfresco Atmosphere
Pool | Outdoor pool
Ocean and Island Views with Spectacular Sunsets and Alfresco Atmosphere
10.0 out of 10, Exceptional, (102)
"Property manager was easy to contact, communicated well, and was pleasant to deal with. The property itself was beautiful, everything worked well. This was a great place for us to relax before we all went on excursions. Would recommend to anyone looking for a remote place to just enjoy the natural beauty and property."
The price is $550
$684 total
includes taxes & fees
Jun 3 - Jun 4
Ocean and Island Views with Spectacular Sunsets and Alfresco Atmosphere
VERY Private, Spectacular, Waterfront Location
Pool
VERY Private, Spectacular, Waterfront Location
10.0 out of 10, Exceptional, (59)
"We had a group of 10 adults that stayed at this villa in February 2024. The villa was clean and just a little dated. Chico and his wife were so easy to deal with and very helpful throughout our 10 day stay. The road to the villa was a bit hard to find and we probably should have rented 4x4 vehicles instead of vans. The beach area was lacking due to the trash, broken glass, cows, and goats everywhere. However, we were able to take a very short drive to a beach where we had a picnic and soaked up...
VERY Private, Spectacular, Waterfront Location
CASA CARIBE SEA LEVEL OCEANFRONT VILLA, Air Conditioning, Beautiful Views!
Property grounds
CASA CARIBE SEA LEVEL OCEANFRONT VILLA, Air Conditioning, Beautiful Views!
9.8 out of 10, Exceptional, (73)
"From the time we booked to our actual stay, we have only good things to say. The property is absolutely charming with ocean views and the sound of surf to the calm surroundings of the interiors. Location central between Long Bay and Apple Bay with great restaurants within walking distance. Loved it!"
CASA CARIBE SEA LEVEL OCEANFRONT VILLA, Air Conditioning, Beautiful Views!
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
Property grounds
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
10.0 out of 10, Exceptional, (7)
"This is an easy place to stay. It’s as advertised - new and very clean. When we booked we were trying to decide between a place in road town on the hill or this location. As we went through the week - we were so happy to stay on the West end of the island. Sopers Hole is a short 10-15 drive, Smuggler’s Cove is 10 minutes, Long Bay Beach is literally over the hill and Cane Garden bay is about 20-25 minutes. So, there are plenty of restaurants and awesome beaches close by. Val, the property...
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
Stylish, Secluded Villa with Pool, Hot tub and Stunning Views
Pool | Outdoor pool
Stylish, Secluded Villa with Pool, Hot tub and Stunning Views
9.8 out of 10, Exceptional, (93)
"4th stay... I here the internet service will be poppin' by the time we return : ) Thanks Ben!"
The price is $200
$364 total
includes taxes & fees
Jun 18 - Jun 19
Stylish, Secluded Villa with Pool, Hot tub and Stunning Views
Ke Villas
View from property
Ke Villas
3.0 star property
9.4 out of 10, Exceptional, (92)
"Very clean and well maintained. Great breakfast."
Ke Villas
Prettyview Villa above Wyndham Lambert Beach Resort
A heated pool
Prettyview Villa above Wyndham Lambert Beach Resort
10.0 out of 10, Exceptional, (45)
"Fantastic time!!! Bananakeete and Brandywine both amazing, cool hike Sage Mountain, enjoyed Cane Garden Bay beach swim(don’t miss Indigo Beach House). Scrub Island(Ixora Spa) and Virgin Gorda(Saba Rock) were awesome day trips. So nice to come back to the pool at Prettyview and enjoy …. The View. Gorgeous property!!!"
Prettyview Villa above Wyndham Lambert Beach Resort
Villa Matija - Eco-Friendly, Luxurious Getaway
Pool | Outdoor pool
Villa Matija - Eco-Friendly, Luxurious Getaway
9.6 out of 10, Exceptional, (80)
"Loved the property/location! 5 min drive to the beach at Brewers Bay. Great outside space at the house with amazing views- particularly sunset! Tom was a great host- our plane in was late and he was great about meeting us later to take us up to the house. We like to cook and the kitchen was well equipped! Pool was awesome as well! Easy to get into Road Town for provisions/shopping. Perfect location if you like quiet and peaceful!"
Villa Matija - Eco-Friendly, Luxurious Getaway
Spectacularly situated Beach Front High Tide@ The Tides at Little Apple Bay.
Property grounds
Spectacularly situated Beach Front High Tide@ The Tides at Little Apple Bay.
10.0 out of 10, Exceptional, (14)
"Good location to sopers hole, cane garden bay and smugglers cove. There some water and ice in the fridge for our first round of drinks great place"
Spectacularly situated Beach Front High Tide@ The Tides at Little Apple Bay.
New Construction Oceanfront Home/Pool Private Walk To Beach
On the beach, sun loungers, beach towels
New Construction Oceanfront Home/Pool Private Walk To Beach
9.8 out of 10, Exceptional, (15)
"We loved Drake’s View … that view! We loved the home, the pool, the grounds and that fabulous beach! Mindy was fabulous and took great care of us! A true gem!"
New Construction Oceanfront Home/Pool Private Walk To Beach
Luxury 7BR waterfront villa w/ instaviews & boat
An infinity pool
Luxury 7BR waterfront villa w/ instaviews & boat
9.6 out of 10, Exceptional, (5)
"We needed a place to escape the cold and found this paradise that could accommodate our large group. There is not much to do on Camanoe itself but that is exactly what we wanted. We could use the boats to skip to nearby islands for food/bars but the property has more than enough amenities to keep you happy. Richard our host was unbelievable. He helped us navigate the area, hire an incredible chef (Elke) , acquire a catamaran day trip, coordinate logistics seamlessly, and so much more. I can’t...
The price is $2,200
$3,345 total
includes taxes & fees
Jun 12 - Jun 13
Luxury 7BR waterfront villa w/ instaviews & boat
Spectacularly situated beachfront Apple Tide @ The Tides at Little Apple Bay
Property grounds
Spectacularly situated beachfront Apple Tide @ The Tides at Little Apple Bay
10.0 out of 10, Exceptional, (3)
"great view and right on the ocean. Very clean will stay there next time we are on the island. I am pretty sure this property is brand new. Loved it."
Spectacularly situated beachfront Apple Tide @ The Tides at Little Apple Bay
'Tortola Adventure' Private Villa: Ocean-View Pool
Property grounds
'Tortola Adventure' Private Villa: Ocean-View Pool
9.6 out of 10, Exceptional, (42)
"The home was not far from things to do, however, it afforded us complete privacy. We loved sitting on the outside decks at all times of the day sipping coffee or drinks and taking in the view. There was a good supply of nice furniture on the deck. The home had a somewhat eclectic style, was open and airy, had everything we needed, and was quite comfortable. To get to the bedrooms, you had to go outside and down the stairs to the lower level but that didn't bother us. Especially loved the outdoor...
'Tortola Adventure' Private Villa: Ocean-View Pool
In the Prestigious Belmont Estates just above Smugglers Cove
Pool
In the Prestigious Belmont Estates just above Smugglers Cove
8.0 out of 10, Very Good, (1)
"While planning a last minute getaway, We were lucky enough to find Villa Del Mar!! The owners were great to work with and the caretaker was always available to take care of any needs!!! A beautiful island built home with everything you could ask for (except a dishwasher) Amazing views from almost every room! Hope we get to visit again soon!!"
The price is $800
$1,255 total
includes taxes & fees
Jun 2 - Jun 3
In the Prestigious Belmont Estates just above Smugglers Cove
Coastin' A-Long - Exceptional Views and Great Long Bay Location!
Aerial view
Coastin' A-Long - Exceptional Views and Great Long Bay Location!
9.8 out of 10, Exceptional, (14)
"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 - Exceptional Views and Great Long Bay Location!
Stylish, newly renovated and upgraded Beach house steps from the water
Outdoor dining
Stylish, newly renovated and upgraded Beach house steps from the water
10.0 out of 10, Exceptional, (52)
"The location of this property is stunning! The pelican "show" was fun to watch every day. Its a bit of an adventure getting to the property (especially when it rains!) but no problem with 4wd vehicle. Easy drive to Cane Garden Bay, Long Bay Beach and Smugglers Cove."
Stylish, newly renovated and upgraded Beach house steps from the water
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See all available properties in Head of The Bay
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.

Other types of properties in Head of The Bay you may be interested in

Wyndham Tortola BVI Lambert Beach Resort
On the beach, white sand, sun loungers, beach towels
Wyndham Tortola BVI Lambert Beach Resort
4.5 star property
8.8 out of 10, Excellent, (411)
"Absolutely fabulous property. Delicious restaurants and awesome location right on a spectacular beach. Loved this property and the staff were so kind and welcoming! Would definitely stay here again!"
The price is $185
$224 total
includes taxes & fees
Jun 2 - Jun 3
Wyndham Tortola BVI Lambert Beach Resort
Village Cay Hotel and Marina
Exterior
Village Cay Hotel and Marina
3.5 star property
8.2 out of 10, Very Good, (443)
"Very clean, nice area. Beautiful scenery. "
The price is $165
$195 total
includes taxes & fees
Jun 10 - Jun 11
Village Cay Hotel and Marina
Maria's By the Sea Hotel
In-room safe, individually decorated, desk, iron/ironing board
Maria's By the Sea Hotel
3.5 star property
8.8 out of 10, Excellent, (674)
"I wouldnt change anything. "
The price is $200
$245 total
includes taxes & fees
Jun 2 - Jun 3
Maria's By the Sea Hotel
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.

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

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Head of The Bay vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Head of The Bay vacation 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 low season months. For more hustle and bustle, you may prefer to visit Head of The Bay in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $200 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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 vacation 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 vacation.

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 vacation rentals in Head of The Bay?

Yes, you can find vacation rentals close to well known attractions in Head of The Bay, or you can go with a more secluded option if you're looking for a relaxing stay.

What are some of the best vacation rentals in Head of The Bay?

Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay: This vacation home rental outside of Head of The Bay offers a balcony, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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 and Mahoe Bay Beach are a couple of places you'll find in the larger area.

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

Vacation rentals are privately owned properties you can book for short or long periods in Head of The Bay. Vacation rentals feature amenities such as hot tubs, fire pits, and patios so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of privacy away from public hotel elevators and bustling concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive choice for families.

Recent reviews of Head of The Bay properties
Expedia verified reviews

Saba Rock Resort

Saba Rock Resort

5/5 Excellent
"We like everything!!!"
A verified traveler stayed at Saba Rock Resort
Posted 3 days ago
Saba Rock Resort