Holiday Rentals in Head of The Bay

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Holiday Rentals in Head of The Bay

The Lighthouse Villas
3.5 star property
8.8 out of 10, Excellent, 148 reviews
"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
10.0 out of 10, Exceptional, 65 reviews
"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
Mango Bay Resort
3.5 star property
9.4 out of 10, Exceptional, 54 reviews
"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
10.0 out of 10, Exceptional, 102 reviews
"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."
Ocean and Island Views with Spectacular Sunsets and Alfresco Atmosphere
VERY Private, Spectacular, Waterfront Location
10.0 out of 10, Exceptional, 59 reviews
"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
Coconut Breeze Villas
3.5 star property
10.0 out of 10, Exceptional, 3 reviews
"Amazing views in a great location. The staff was very friendly and helpful. The villa was nice and had everything you need. Great kitchen and living spaces. We lived watching the sun set from the deck. "
The price is €247
per night
21 Jun - 22 Jun
Coconut Breeze Villas
Villa Matija - Eco-Friendly, Luxurious Getaway
9.6 out of 10, Exceptional, 80 reviews
"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
Stylish, Secluded Villa with Pool, Hot tub and Stunning Views
9.8 out of 10, Exceptional, 94 reviews
"4th stay... I here the internet service will be poppin' by the time we return : ) Thanks Ben!"
The price is €347
per night
2 Jul - 3 Jul
Stylish, Secluded Villa with Pool, Hot tub and Stunning Views
Spectacularly situated Beach Front High Tide@ The Tides at Little Apple Bay.
10.0 out of 10, Exceptional, 15 reviews
"This was a very comfortable place with beach access. Very clean and our host was always available. I did miss having a TV but we definitely didnt need one. I would love to stay there again!"
Spectacularly situated Beach Front High Tide@ The Tides at Little Apple Bay.
CASA CARIBE SEA LEVEL OCEANFRONT VILLA, Air Conditioning, Beautiful Views!
9.8 out of 10, Exceptional, 73 reviews
"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!
Prettyview Villa above Wyndham Lambert Beach Resort
10.0 out of 10, Exceptional, 45 reviews
"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
New Construction Oceanfront Home/Pool Private Walk To Beach
9.8 out of 10, Exceptional, 16 reviews
"We had an amazing view from the villa and Mindy met us at the dock and helped with our baggage. There was supposed to be a crib for my granddaughter but Mindy was able to get a pack n play which worked out well. Sugarcane Restaurant was just a short walk away with good food and we enjoyed every minute especially the private pool and beach."
New Construction Oceanfront Home/Pool Private Walk To Beach
Private two bedroomed villa within Long Bay Beach Resort on Tortola, BVI
9.8 out of 10, Exceptional, 28 reviews
"Our host, Caroline, was by far the best host we have ever encountered anywhere!! She went out of her way, literally, to make sure we had what we needed. From helping to get groceries delivered, to refilling propane to grill, to arranging transportation…we could not have asked for more. And the villa was absolutely perfect. Amazing views, equipped with everything we needed and very comfortable and relaxing. "
Private two bedroomed villa within Long Bay Beach Resort on Tortola, BVI
Ke Villas
3.0 star property
9.6 out of 10, Exceptional, 94 reviews
"A lovely, laid back and relaxing BVI experience. As frequent visitors to Tortola I’m sure we will be back at KE Villas next time again. Charles was a friendly and wonderful host. "
Ke Villas
Luxury 7BR waterfront villa w/ instaviews & boat
9.6 out of 10, Exceptional, 5 reviews
"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 €3,165
per night
22 Jun - 23 Jun
Luxury 7BR waterfront villa w/ instaviews & boat
Breathtaking views , Jacuzzi , open plan house , 5 min to Nanny Cay Beach & Bar
10.0 out of 10, Exceptional, 22 reviews
"We were very fortunate enough to select this house to stay in for a week during our trip to BVI and Tortola. This place sits high above the ocean with magnificent views, steady breezes flowing throughout and almost no outside noises which provides perfect tranquility. The owners, Chris and Karen, were gracious hosts and went above and beyond expectations to make sure we were comfortable and had everything we needed for our stay. They even lent us a vehicle to drive to a restaurant for dinner...
Breathtaking views , Jacuzzi , open plan house , 5 min to Nanny Cay Beach & Bar
'Tortola Adventure' Private Villa: Ocean-View Pool
9.6 out of 10, Exceptional, 43 reviews
"Everything about the Tortola Adventure Villa was perfect for our family of 5 adults. The beautiful views make it all worth it. The location to the ferry ports, wonderful beaches and restaurants was very convenient. We enjoyed sipping our cocktails in the pool while taking in the breathtaking views. The air conditioning in the 2 bedrooms worked great and cooled us off each evening after our days of exploring Tortola and the nearby island, while the open air great room on the top floor received...
'Tortola Adventure' Private Villa: Ocean-View Pool
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
10.0 out of 10, Exceptional, 8 reviews
"Great property. Well equipped, even had some bug spray, in addition to beach chairs, umbrellas and everything you could need for the kitchen. Beds were comfy. I do wish there were fans on the porch, but everything else was perfect."
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
Stylish, newly renovated and upgraded Beach house steps from the water
10.0 out of 10, Exceptional, 52 reviews
"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
The Beach House - stylish beach-chic 4 bedroom villa at Long Bay beach
10.0 out of 10, Exceptional, 17 reviews
"Overall, the property is exactly as listed. The one thing that was not included was the telescope which you can see in the pictures. We were a little disappointed when we arrived that it was not there. And we could not get the outdoor speakers to work. That would’ve been nice to have the music by the pool, the portable speaker provided wouldn’t hold a charge. Tortola is a very beautiful island. It was our second trip. This home is amazing. The location is wonderful. We were able to walk to...
The Beach House - stylish beach-chic 4 bedroom villa at Long Bay beach
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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
4.5 star property
8.8 out of 10, Excellent, 420 reviews
"Always love it here!"
The price is €188
per night
21 Jun - 22 Jun
Wyndham Tortola BVI Lambert Beach Resort
Village Cay Hotel and Marina
3.5 star property
8.2 out of 10, Very good, 456 reviews
"Nice hotel with a great view of the marina. Not a resort if that is what you are looking for but they do have a nice small pool and bar/restaurant. "
The price is €180
per night
23 Jun - 24 Jun
Village Cay Hotel and Marina
Maria's By the Sea Hotel
3.5 star property
8.8 out of 10, Excellent, 684 reviews
"Great locatio"
The price is €227
per night
29 Jun - 30 Jun
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 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 €247 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?

Stylish, newly renovated and upgraded Beach house steps from the water: This holiday home rental outside of Head of The Bay is located on the beach, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Make the most of games in this rental home to help you unwind.

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 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.

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