Head of The Bay Holiday Rentals

  • 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

Our top choices for Head of The Bay holiday rentals

Coconut Breeze Villas

Coconut Breeze Villas
2.5 star property
Cane Garden Bay
9.4 out of 10, Exceptional, (30 reviews)
"Staff was great. Place was clean. Outside seating was perfect. "
United States
Kathryn
The price is NZ$385
includes taxes & fees
24 Apr - 25 Apr
Coconut Breeze Villas

Peaceful Studio Retreat w/ Full Kitchen near Great Mountain • 5 Min to Road Town

Peaceful Studio Retreat w/ Full Kitchen near Great Mountain • 5 Min to Road Town
Road Town
The price is NZ$301
includes taxes & fees
14 Apr - 15 Apr
Peaceful Studio Retreat w/ Full Kitchen near Great Mountain • 5 Min to Road Town

Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!

Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!
Road Town
9.8 out of 10, Exceptional, (17 reviews)
"Fantastic place to stay! Well organized and easy to access. The recommendation for a Taxi driver familiar with the property made getting there much more convenient. "
United States
Barrett W.
The price is NZ$1,137
includes taxes & fees
15 Apr - 16 Apr
Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!

Sailors Gem II: Experience Caribbean Life at this Spacious Apartment!

Sailors Gem II: Experience Caribbean Life at this Spacious Apartment!
Tortola
9.0 out of 10, Wonderful, (12 reviews)
"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 NZ$547
includes taxes & fees
15 Apr - 16 Apr
Sailors Gem II: Experience Caribbean Life at this Spacious Apartment!

Fort Recovery Oceanfront 2BR Signature Villa

Fort Recovery Oceanfront 2BR Signature Villa
Tortola
8.4 out of 10, Very good, (5 reviews)
"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 NZ$923
includes taxes & fees
15 Apr - 16 Apr
Fort Recovery Oceanfront 2BR Signature Villa

Top of the Hill Blue Sunshine

Top of the Hill Blue Sunshine
Parham Town
10.0 out of 10, Exceptional, (13 reviews)
"Great location with an amazing view, our host was really nice and helpful with places to go and visit. Super clean, we recommend this place 100% !"
United States
aurelie A.
The price is NZ$576
includes taxes & fees
14 Apr - 15 Apr
Top of the Hill Blue Sunshine

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

Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola
Leonards
10.0 out of 10, Exceptional, (7 reviews)
"Views, Views, Views! And great accomodations"
United States
Renato Bruno dos Santos
The price is NZ$561
includes taxes & fees
15 Apr - 16 Apr
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola

#6 One Bedroom with AC and Bathroom - 10 Minutes from two beaches

#6 One Bedroom with AC and Bathroom - 10 Minutes from two beaches
Tortola
9.8 out of 10, Exceptional, (7 reviews)
"Great host safe quiet and clean apartment "
United States
Sovill
The price is NZ$375
includes taxes & fees
14 Apr - 15 Apr
#6 One Bedroom with AC and Bathroom - 10 Minutes from two beaches

Nature's Hideaway

Nature's Hideaway
Horsepath
10.0 out of 10, Exceptional, (1 review)
"Naja is the best! "
United States
John
The price is NZ$281
includes taxes & fees
14 Apr - 15 Apr
Nature's Hideaway

SUNFLOWER LANE APARTMENT #5 - OCEAN VIEW 7 mins from Capital

SUNFLOWER LANE APARTMENT #5 - OCEAN VIEW 7 mins from Capital
Road Town
The price is NZ$715
includes taxes & fees
18 Apr - 19 Apr
SUNFLOWER LANE APARTMENT #5 - OCEAN VIEW 7 mins from Capital

British Virgin Islands Oasis with Pool, Spa & Easy Access to Dive Tours

British Virgin Islands Oasis with Pool, Spa & Easy Access to Dive Tours
Scrub Island
10.0 out of 10, Exceptional, (1 review)
"Great stay. Staff were consistently friendly & professional. Governors Suite room was spacious, well-kept & very comfortable for a weeks’ stay. Five restaurant options provided plenty of choices. Good to very good food overall although I wish they had more bowls with veggie & protein options beyond salads. Decent gym. Easy to reach from the EIS airport & ferry service was prompt & convenient. Overall very nice facilities & we will consider returning next year. "
United States
Allison B.
The price is NZ$2,132
includes taxes & fees
14 May - 15 May
British Virgin Islands Oasis with Pool, Spa & Easy Access to Dive Tours

Charming 1-bedroom apartment in welcoming Tortola with WiFi, AC

Charming 1-bedroom apartment in welcoming Tortola with WiFi, AC
Tortola
10.0 out of 10, Exceptional, (1 review)
"Excellent!!! Took us in with almost no notice! They were exceptionally friendly and helpful. Place very comfortable and immaculate! Would definitely stay again . "
United States
Garth
The price is NZ$605
includes taxes & fees
14 Apr - 15 Apr
Charming 1-bedroom apartment in welcoming Tortola with WiFi, AC

5 Studio with queen bed & bathroom - 10 min to beach & town

5 Studio with queen bed & bathroom - 10 min to beach & town
Tortola
The price is NZ$435
includes taxes & fees
14 Apr - 15 Apr
5 Studio with queen bed & bathroom - 10 min to beach & town

#7 Studio sunset islands view, queen bed, bath & kitchen 10 min to town & beach

#7 Studio sunset islands view, queen bed, bath & kitchen 10 min to town & beach
Tortola
The price is NZ$387
includes taxes & fees
14 Apr - 15 Apr
#7 Studio sunset islands view, queen bed, bath & kitchen 10 min to town & beach

Secluded Villa | Caribbean Escape | Private Island

Secluded Villa | Caribbean Escape | Private Island
Buck Island
The price is NZ$3,233
includes taxes & fees
16 Apr - 17 Apr
Secluded Villa | Caribbean Escape | Private Island

“Villa Del Mar”, pairing high design with high altitude in Belmont, Tortola!

“Villa Del Mar”, pairing high design with high altitude in Belmont, Tortola!
Tortola
10.0 out of 10, Exceptional, (4 reviews)
"The house was as perfect as we could’ve imagined! Vic the host responded immediately with any questions and recommendations! Can’t wait to go back!"
United States
Greg F.
The price is NZ$2,842
includes taxes & fees
14 Apr - 15 Apr
“Villa Del Mar”, pairing high design with high altitude in Belmont, Tortola!

Caribbean Escape, Sunrise Oceanview Suite in BVI

Caribbean Escape, Sunrise Oceanview Suite in BVI
Buck Island
The price is NZ$2,861
includes taxes & fees
16 Apr - 17 Apr
Caribbean Escape, Sunrise Oceanview Suite in BVI

Cozy Studio4 in serene Tortola with AC, WiFi. Enjoyable getaway with Sunset View

Cozy Studio4 in serene Tortola with AC, WiFi. Enjoyable getaway with Sunset View
Tortola
6.0 out of 10, (1 review)
"Tough to find location even with the directions provided, poor signage overall. The bedding left some to be desired (one small blanket barely large enough for 1 person, the roosters and barking dogs made impossible to sleep without closing the windows making using the air conditioner necessary, communication was ok"
United States
Michael
The price is NZ$370
includes taxes & fees
14 Apr - 15 Apr
Cozy Studio4 in serene Tortola with AC, WiFi. Enjoyable getaway with Sunset View

Victotia Silver Suite

Victotia Silver Suite
Hodges Creek Marina
The price is NZ$889
includes taxes & fees
14 Apr - 15 Apr
Victotia Silver Suite

Joy Suite | Breakfast Included Caribbean Vacation

Joy Suite | Breakfast Included Caribbean Vacation
Buck Island
The price is NZ$2,115
includes taxes & fees
16 Apr - 17 Apr
Joy Suite | Breakfast Included Caribbean Vacation
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, 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 NZ$385 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?

Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay: 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 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 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.