Head of The Bay Vacation Rentals

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Our top choices for Head of The Bay vacation rentals

Coconut Breeze Villas

Coconut Breeze Villas
2.5 star property
Cane Garden Bay
9.4 out of 10, Exceptional, (33 reviews)
"Staff was great. Place was clean. Outside seating was perfect. "
United States
Kathryn
The price is CA $247
CA $308 total
includes taxes & fees
May 27 - May 28
Coconut Breeze Villas

#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 CA $136
CA $300 total
includes taxes & fees
Jun 4 - Jun 5
#6 One Bedroom with AC and Bathroom - 10 Minutes from two beaches

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 CA $149
CA $351 total
includes taxes & fees
May 19 - May 20
5 Studio with queen bed & bathroom - 10 min to beach & town

Fort Recovery Beachfront Resort

Fort Recovery Beachfront Resort
4.0 star property
West End
The price is CA $308
CA $363 total
includes taxes & fees
May 28 - May 29
Fort Recovery Beachfront Resort

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)
"Views, Views, Views! And great accomodations"
United States
Renato Bruno dos Santos
The price is CA $401
CA $458 total
includes taxes & fees
Jun 4 - Jun 5
Zafira Luxe 1-bedroom villa with sauna, steam, sunset views, AC, WIFI in Tortola

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, (14 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 CA $273
CA $446 total
includes taxes & fees
May 18 - May 19
Sailors Gem II: Experience Caribbean Life at this Spacious Apartment!

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 $274
CA $469 total
includes taxes & fees
May 16 - May 17
Top of the Hill Blue Sunshine

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 CA $134
CA $299 total
includes taxes & fees
May 15 - May 16
Cozy Studio4 in serene Tortola with AC, WiFi. Enjoyable getaway with Sunset View

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 CA $197
CA $225 total
includes taxes & fees
May 15 - May 16
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 CA $281
CA $576 total
includes taxes & fees
May 16 - May 17
SUNFLOWER LANE APARTMENT #5 - OCEAN VIEW 7 mins from Capital

#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 CA $149
CA $312 total
includes taxes & fees
May 15 - May 16
#7 Studio sunset islands view, queen bed, bath & kitchen 10 min to town & beach

Fort Recovery Oceanfront 2 Bedroom Signature Villa

Fort Recovery Oceanfront 2 Bedroom Signature Villa
Tortola
8.4 out of 10, Very good, (7 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 CA $603
CA $749 total
includes taxes & fees
May 21 - May 22
Fort Recovery Oceanfront 2 Bedroom Signature Villa

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 CA $377
CA $492 total
includes taxes & fees
May 15 - May 16
Charming 1-bedroom apartment in welcoming Tortola with WiFi, AC

Endless Caribbean Views from a Luxury Villa Near Kayak & Dive Spots | 2 Units

Endless Caribbean Views from a Luxury Villa Near Kayak & Dive Spots | 2 Units
Scrub Island
The price is CA $7,332
CA $10,047 total
includes taxes & fees
Jun 3 - Jun 4
Endless Caribbean Views from a Luxury Villa Near Kayak & Dive Spots | 2 Units

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, (18 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 CA $670
CA $922 total
includes taxes & fees
May 25 - May 26
Family-sized villa- 5 mins from secluded beach! 10 mins from city centre!

Entire home with Mesmerizing Sea Views

Entire home with Mesmerizing Sea Views
Virgin Gorda
The price is CA $467
CA $635 total
includes taxes & fees
May 21 - May 22
Entire home with Mesmerizing Sea Views

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 $212
CA $241 total
includes taxes & fees
May 15 - May 16
Peaceful Studio Retreat w/ Full Kitchen near Great Mountain • 5 Min to Road Town

Victotia Silver Suite

Victotia Silver Suite
Hodges Creek Marina
The price is CA $432
CA $725 total
includes taxes & fees
May 16 - May 17
Victotia Silver Suite

Discover the Beauty of BVI from a Villa with Pools & Snorkel Access | 2 Units

Discover the Beauty of BVI from a Villa with Pools & Snorkel Access | 2 Units
Scrub Island
The price is CA $7,332
CA $10,047 total
includes taxes & fees
Jun 3 - Jun 4
Discover the Beauty of BVI from a Villa with Pools & Snorkel Access | 2 Units

Caribbean Oasis with Pools & Views Near World-Famous Snorkeling Sites | 3 Units

Caribbean Oasis with Pools & Views Near World-Famous Snorkeling Sites | 3 Units
Scrub Island
The price is CA $8,239
CA $11,284 total
includes taxes & fees
Jun 3 - Jun 4
Caribbean Oasis with Pools & Views Near World-Famous Snorkeling Sites | 3 Units
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Head of The Bay. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Top of the Hill Blue Sunshine: This vacation home rental outside of Head of The Bay offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. You can relax into your vacation with a selection of games and a hot tub.

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 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.