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Head of The Bay Vacation Rentals

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Our top choices for Head of The Bay vacation rentals

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.
The price is CA $285
CA $487 total
includes taxes & fees
Oct 7 - Oct 8
Top of the Hill Blue Sunshine

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
The price is CA $321
CA $375 total
includes taxes & fees
Oct 7 - Oct 8
Fort Recovery Beachfront Resort

3. 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 CA $209
CA $238 total
includes taxes & fees
Oct 7 - Oct 8
Peaceful Studio Retreat w/ Full Kitchen near Great Mountain • 5 Min to Road Town

4. 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 CA $1,211
CA $1,739 total
includes taxes & fees
Oct 18 - Oct 19
British Virgin Islands Oasis with Pool, Spa & Easy Access to Dive Tours

5. Romantic Ocean Sunset Villa with Private Patio

Romantic Ocean Sunset Villa with Private Patio
Buck Island
The price is CA $2,260
CA $2,922 total
includes taxes & fees
Nov 1 - Nov 2
Romantic Ocean Sunset Villa with Private Patio

6. Caribbean Escape, Sunrise Oceanview Suite in BVI

Caribbean Escape, Sunrise Oceanview Suite in BVI
Buck Island
The price is CA $2,000
CA $2,571 total
includes taxes & fees
Oct 22 - Oct 23
Caribbean Escape, Sunrise Oceanview Suite in BVI

7. Oceanfront 2 Bedroom Premium Villa

Oceanfront 2 Bedroom Premium Villa
Tortola
The price is CA $584
CA $724 total
includes taxes & fees
Oct 9 - Oct 10
Oceanfront 2 Bedroom Premium Villa

8. 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
The price is CA $345
CA $392 total
includes taxes & fees
Oct 7 - Oct 8
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola

9. #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
The price is CA $141
CA $309 total
includes taxes & fees
Oct 7 - Oct 8
#4 One Studio with AC and Bathroom - 10 Minutes from two beaches

10. 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.
The price is CA $697
CA $959 total
includes taxes & fees
Oct 9 - Oct 10
Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!

11. Presence | Sunrise Ocean View in BVI

Presence | Sunrise Ocean View in BVI
Buck Island
The price is CA $2,260
CA $2,922 total
includes taxes & fees
Nov 1 - Nov 2
Presence | Sunrise Ocean View in BVI

12. 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.
The price is CA $428
CA $532 total
includes taxes & fees
Oct 22 - Oct 23
Beachfront 1-Bedroom Signature Villa

13. 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.
The price is CA $941
CA $1,169 total
includes taxes & fees
Oct 9 - Oct 10
Oceanfront 3 Bedroom Signature Villa

14. Luxury BVI Accommodations with Full-Service Spa & Nearby Snorkel Tours

Luxury BVI Accommodations with Full-Service Spa & Nearby Snorkel Tours
Scrub Island
The price is CA $1,148
CA $1,654 total
includes taxes & fees
Oct 18 - Oct 19
Luxury BVI Accommodations with Full-Service Spa & Nearby Snorkel Tours

15. A British Virgin Islands Oasis with Endless Caribbean Views & Marina Access

A British Virgin Islands Oasis with Endless Caribbean Views & Marina Access
Scrub Island
The price is CA $1,148
CA $1,654 total
includes taxes & fees
Oct 18 - Oct 19
A British Virgin Islands Oasis with Endless Caribbean Views & Marina Access

16. Secluded Private Island Paradise Suite with Ocean Views & Sailing Nearby

Secluded Private Island Paradise Suite with Ocean Views & Sailing Nearby
Scrub Island
The price is CA $1,211
CA $1,739 total
includes taxes & fees
Oct 18 - Oct 19
Secluded Private Island Paradise Suite with Ocean Views & Sailing Nearby

17. Private Island Paradise with Ocean Views, Spa Access & Beach Adventures

Private Island Paradise with Ocean Views, Spa Access & Beach Adventures
Scrub Island
The price is CA $764
CA $1,135 total
includes taxes & fees
Oct 18 - Oct 19
Private Island Paradise with Ocean Views, Spa Access & Beach Adventures

18. BVI Oasis with Pools & Marina Access Minutes to Snorkeling at The Caves

BVI Oasis with Pools & Marina Access Minutes to Snorkeling at The Caves
Scrub Island
The price is CA $764
CA $1,135 total
includes taxes & fees
Oct 18 - Oct 19
BVI Oasis with Pools & Marina Access Minutes to Snorkeling at The Caves

19. 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.
The price is CA $399
CA $495 total
includes taxes & fees
Oct 9 - Oct 10
Oceanfront 1-Bedroom Premium Corner Villa

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

Charming 2-bedroom vacation suite in beautiful East End Tortola!
Tortola
The price is CA $285
CA $475 total
includes taxes & fees
Oct 9 - Oct 10
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

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, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Head of The Bay vacation rentals we have selected for you start as low as CA $375 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 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.