Head of The Bay Vacation Rentals

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Head of The Bay

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

Apartment in Tortola

9.8 out of 10, Exceptional, (6)
"Great host safe quiet and clean apartment "
United States
Sovill
The price is ￥14,585
￥36,360 total
includes taxes & fees
Dec 18 - Dec 19
#6 One Bedroom with AC and Bathroom - 10 Minutes from two beaches
Beach
Sailors Gem II: Experience Caribbean Life at this Spacious Apartment!

Apartment in Tortola

9.4 out of 10, Exceptional, (8)
"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 ￥20,005
￥25,107 total
includes taxes & fees
Dec 15 - Dec 16
Sailors Gem II: Experience Caribbean Life at this Spacious Apartment!
Property grounds
Family Friendly, centrally located - modern & spacious 2 bed 2 bath retreat.

Vacation Home in Tortola

2.0 star property
10.0 out of 10, Exceptional, (3)
"We were very pleased with our friendly accommodating host. The house provided everything we needed plus more! It is very spacious and cleanliness was top notch. I would definitely return and plan to stay longer next time!"
Canada
Carmen S.
The price is ￥27,914
￥46,058 total
includes taxes & fees
Dec 7 - Dec 8
Family Friendly, centrally located - modern & spacious 2 bed 2 bath retreat.
Interior
Top of the Hill Blue Sunshine

Vacation Home in Parham Town

9.8 out of 10, Exceptional, (10)
"What an awesome view we loved this place and it’s the only place I will stay the host was awesome !"
United States
john
Top of the Hill Blue Sunshine
Property grounds
5 Studio with queen bed & bathroom - 10 min to beach & town

Apartment in Tortola

The price is ￥16,904
￥46,044 total
includes taxes & fees
Dec 10 - Dec 11
5 Studio with queen bed & bathroom - 10 min to beach & town
Terrace/patio
Ocean Breeze Comfort

Apartment in Tortola

2.0 star property
10.0 out of 10, Exceptional, (2)
"Francis and Simone were the best hosts. Everett hung was really clean and nice and the view was amazing. Would stay there every time. "
United States
Kami M.
The price is ￥69,786
￥96,770 total
includes taxes & fees
Dec 5 - Dec 6
Ocean Breeze Comfort
Interior
SALE$Abigail's Entire 2 Bedroom Apartments SALE, SALE$$

Apartment in Road Town

8.4 out of 10, Very Good, (6)
"Felt vey safe and seccure"
United States
Albeadea
The price is ￥18,610
￥46,493 total
includes taxes & fees
Dec 7 - Dec 8
SALE$Abigail's Entire 2 Bedroom Apartments SALE, SALE$$
Dining
Nature's Hideaway

Apartment in Horsepath

The price is ￥24,037
￥34,582 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Nature's Hideaway
Terrace/patio
Coconut Breeze Villas

Aparthotel in Cane Garden Bay

2.5 star property
9.8 out of 10, Exceptional, (19)
"Excellent staff service. Room is big, bed is very good and view amazing!"
United States
Lisandra
Coconut Breeze Villas
On the beach, white sand, sun loungers, beach umbrellas
Mango Bay Resort

Apartment in Virgin Gorda

3.5 star property
9.4 out of 10, Exceptional, (57)
"Nice property with beautiful beach just steps away from your door. "
United States
Wendy
The price is ￥66,452
￥103,593 total
includes taxes & fees
Dec 8 - Dec 9
Mango Bay Resort
4 bedrooms, iron/ironing board, WiFi, bed sheets
Private Luxury Villas

Villa in Tortola

9.6 out of 10, Exceptional, (15)
"Such a beautiful house. Very clean and spacious. "
United States
Brenda v.
The price is ￥139,572
￥173,379 total
includes taxes & fees
Dec 5 - Dec 6
Private Luxury Villas
Pool
Fort Recovery Beachfront Villa and Suites Hotel luxury 2BR

Vacation Home in Tortola

8.4 out of 10, Very Good, (5)
"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 ￥66,981
￥78,975 total
includes taxes & fees
Dec 7 - Dec 8
Fort Recovery Beachfront Villa and Suites Hotel luxury 2BR
Property grounds
Cozy Studio4 in serene Tortola with AC, WiFi. Enjoyable getaway with Sunset View

Apartment in Tortola

The price is ￥15,213
￥37,360 total
includes taxes & fees
Dec 5 - Dec 6
Cozy Studio4 in serene Tortola with AC, WiFi. Enjoyable getaway with Sunset View
Terrace/patio
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola

Villa in Leonards

10.0 out of 10, Exceptional, (2)
"Our host was awesome and really accommodating. 10 out of 10. We will stay again."
United States
Najla D.
The price is ￥43,461
￥49,509 total
includes taxes & fees
Dec 5 - Dec 6
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola
Property grounds
SUNFLOWER LANE APARTMENT #5 - OCEAN VIEW 7 mins from Capital

Apartment in Road Town

The price is ￥31,791
￥65,505 total
includes taxes & fees
Jan 3 - Jan 4, 2026
SUNFLOWER LANE APARTMENT #5 - OCEAN VIEW 7 mins from Capital
Beach
Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!

Vacation Home in Road Town

9.8 out of 10, Exceptional, (15)
"We had a quick one night stay, but would definitely recommend. The secluded beach is so beautiful. Definitely coming back to explore more."
United States
Braxton H.
The price is ￥75,834
￥104,369 total
includes taxes & fees
Dec 8 - Dec 9
Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!
Marina
Spacious Family Base Near Sandy Beach and Scenic Island Walking Trails | 3 Units

Apartment in Scrub Island

The price is ￥874,186
￥1,187,665 total
includes taxes & fees
Dec 5 - Dec 6
Spacious Family Base Near Sandy Beach and Scenic Island Walking Trails | 3 Units
1 bedroom, in-room safe, free WiFi, bed sheets
Secluded Beachfront Teepee Villa w/ Ocean Views

Villa in Buck Island

The price is ￥316,053
￥406,728 total
includes taxes & fees
Dec 8 - Dec 9
Secluded Beachfront Teepee Villa w/ Ocean Views
1 bedroom, in-room safe, free WiFi, bed sheets
Joy Suite | Breakfast Included Caribbean Vacation

Aparthotel in Buck Island

The price is ￥165,781
￥209,258 total
includes taxes & fees
Dec 8 - Dec 9
Joy Suite | Breakfast Included Caribbean Vacation
Exterior
Charming 1-bedroom apartment in welcoming Tortola with WiFi, AC

Apartment in Tortola

The price is ￥38,382
￥50,788 total
includes taxes & fees
Dec 5 - Dec 6
Charming 1-bedroom apartment in welcoming Tortola with WiFi, AC
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

Wyndham Tortola BVI Lambert Beach Resort

Wyndham Tortola BVI Lambert Beach Resort

10/10 Excellent
"The room and the service at the hotel was fantastic. "
Cara 1-night trip
Posted 3 days ago
Wyndham Tortola BVI Lambert Beach Resort

Find out more about Head of The Bay

Search for holiday rentals in Head of The Bay on Expedia! You can easily find your home rentals, villas, holiday apartments in Head of The Bay using one of the methods below:

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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?

"Your Caribbean Haven: Where Comfort Meets Local Charm": This vacation home rental outside of Head of The Bay has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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 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.