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Head of The Bay Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Head of The Bay vacation rentals

A balcony with a view of a marina and the sea.

1. Top of the Hill Blue Sunshine

Top of the Hill Blue Sunshine
Parham Town
10.0 out of 10, Exceptional, (14 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.
$343 nightly
The price is $343
Oct 8 - Oct 9
Total with taxes and fees
Top of the Hill Blue Sunshine
A bedroom with a bed, a chair, a dresser, and a view of a balcony with a railing.

2. Fort Recovery Beachfront Resort

Fort Recovery Beachfront Resort
4.0 star property
West End
9.4 out of 10, Exceptional, (6 reviews)
"Enjoyed."
United States
Alberta
$225 nightly
The price is $248
Oct 9 - Oct 10
Total with taxes and fees
Fort Recovery Beachfront Resort
A covered outdoor area with a table and chairs, a potted plant, and two doors.

3. #4 One Studio with AC and Bathroom - 10 Minutes from two beaches

#4 One Studio 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
$208 nightly
The price is $218
Oct 8 - Oct 9
Total with taxes and fees
#4 One Studio with AC and Bathroom - 10 Minutes from two beaches
A wooden deck with wicker furniture and a view of the ocean.

4. Caribbean Escape, Sunrise Oceanview Suite in BVI

Caribbean Escape, Sunrise Oceanview Suite in BVI
Buck Island
$1,545 nightly
The price is $1,748
Oct 21 - Oct 22
Total with taxes and fees
Caribbean Escape, Sunrise Oceanview Suite in BVI
A spacious room with a large bed, a ceiling fan, and a view of the beach.

5. Secluded Beachfront Teepee Villa w/ Ocean Views

Secluded Beachfront Teepee Villa w/ Ocean Views
Buck Island
$2,154 nightly
The price is $2,437
Oct 21 - Oct 22
Total with taxes and fees
Secluded Beachfront Teepee Villa w/ Ocean Views
A modern building with a glass facade, outdoor seating area, and a view of the sunset over the water.

6. 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, (8 reviews)
"Perfect for both a little sightseeing and a lot of relaxing."
United States
Michael
$273 nightly
The price is $273
Oct 8 - Oct 9
Total with taxes and fees
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola
A two-story building with a light blue exterior, a white door, and a small balcony.

7. 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
$167 nightly
The price is $167
Oct 8 - Oct 9
Total with taxes and fees
Peaceful Studio Retreat w/ Full Kitchen near Great Mountain • 5 Min to Road Town
A balcony with a clear view of the ocean and hills.

8. 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, (19 reviews)
"Beautiful views, Roger is a gracious and helpful host. Nearby access to secluded and beautiful beaches."
United States
Melissa A.
$673 nightly
The price is $673
Oct 9 - Oct 10
Total with taxes and fees
Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!
Sink into a warm soak with sparkling sea views.

9. Endless Caribbean Views from a Suite with Pools Near Snorkeling Cays | 3 Units

Endless Caribbean Views from a Suite with Pools Near Snorkeling Cays | 3 Units
Scrub Island
$3,406 nightly
The price is $3,660
Oct 18 - Oct 19
Total with taxes and fees
Endless Caribbean Views from a Suite with Pools Near Snorkeling Cays | 3 Units
A hotel room with two beds, a red patterned rug, and a view of the sea through an open door.

10. Presence | Sunrise Ocean View in BVI

Presence | Sunrise Ocean View in BVI
Buck Island
$1,746 nightly
The price is $1,976
Oct 21 - Oct 22
Total with taxes and fees
Presence | Sunrise Ocean View in BVI
A room with a view of a beach, a wooden deck, and a sofa with a lamp.

11. Beachfront 1-Bedroom Signature Villa

Beachfront 1-Bedroom Signature Villa
Tortola
9.6 out of 10, Exceptional, (17 reviews)
"This property is beautiful. "
United States
Charles F.
$343 nightly
The price is $373
Oct 10 - Oct 11
Total with taxes and fees
Beachfront 1-Bedroom Signature Villa
A room with a sofa, dining table, chairs, and a view of the ocean.

12. Oceanfront 2 Bedroom Premium Villa

Oceanfront 2 Bedroom Premium Villa
Tortola
$469 nightly
The price is $510
Oct 8 - Oct 9
Total with taxes and fees
Oceanfront 2 Bedroom Premium Villa
A neatly made bed with a white and maroon bedspread, two nightstands with potted plants, and a plain wall with a light switch.

13. Nature's Hideaway

Nature's Hideaway
Horsepath
10.0 out of 10, Exceptional, (1 review)
"Naja is the best! "
United States
John
$164 nightly
The price is $164
Oct 10 - Oct 11
Total with taxes and fees
Nature's Hideaway
A wooden deck with a wicker sofa and dining set overlooking a beach.

14. Oceanfront 3 Bedroom Signature Villa

Oceanfront 3 Bedroom Signature Villa
Tortola
9.4 out of 10, Exceptional, (11 reviews)
"Very nice place, great views and access to the beach. Host was very responsive and helpful as well!"
United States
Brian S.
$754 nightly
The price is $820
Oct 8 - Oct 9
Total with taxes and fees
Oceanfront 3 Bedroom Signature Villa
A spacious room with a thatched roof, a large bed, a dining area, and a view of the ocean.

15. Luxury Teepee Villa with Ocean Views in BVI

Luxury Teepee Villa with Ocean Views in BVI
Buck Island
$2,020 nightly
The price is $2,285
Oct 11 - Oct 12
Total with taxes and fees
Luxury Teepee Villa with Ocean Views in BVI
A room with a sofa, a lamp, a bookshelf, and a view of the sea through open doors.

16. Oceanfront 1-Bedroom Premium Corner Villa

Oceanfront 1-Bedroom Premium Corner Villa
Tortola
10.0 out of 10, Exceptional, (21 reviews)
"Our view, room and our host were amazing. We would stay here again. The king bed is very comfortable. "
United States
L H.
$320 nightly
The price is $348
Oct 8 - Oct 9
Total with taxes and fees
Oceanfront 1-Bedroom Premium Corner Villa
A balcony with a stone wall, a view of the sea, and a seating area with a cushion.

17. Romantic Ocean Sunset Villa with Private Patio

Romantic Ocean Sunset Villa with Private Patio
Buck Island
$1,746 nightly
The price is $1,976
Oct 21 - Oct 22
Total with taxes and fees
Romantic Ocean Sunset Villa with Private Patio
A stone wall with a view of the sea, a wooden chair, and a small table.

18. Secluded Villa | Caribbean Escape | Private Island

Secluded Villa | Caribbean Escape | Private Island
Buck Island
$1,746 nightly
The price is $1,976
Oct 21 - Oct 22
Total with taxes and fees
Secluded Villa | Caribbean Escape | Private Island
A bedroom with a black and white checkered floor, a wooden dresser, a mirror, a TV, a bed with patterned bedding, a ceiling fan, and an air conditioning unit.

19. #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
$219 nightly
The price is $227
Oct 8 - Oct 9
Total with taxes and fees
#7 Studio sunset islands view, queen bed, bath & kitchen 10 min to town & beach
Beach

20. Charming 2-bedroom vacation suite in beautiful East End Tortola!

Charming 2-bedroom vacation suite in beautiful East End Tortola!
Tortola
$315 nightly
The price is $335
Oct 8 - Oct 9
Total with taxes and fees
Charming 2-bedroom vacation suite in beautiful East End Tortola!
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

Fort Burt Hotel

Fort Burt Hotel

8/10 Good
"Clean room needs a table and microwave"
Ronald 7-night trip
Posted 3 days ago
Fort Burt Hotel

Find out more about Head of The Bay

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 $248 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 is located on the beach and has a balcony, a garden, and a barbecue grill 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. Virgin Gorda Harbor and Spring 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.