Photo by Vada Stevens
Open Photo by Vada Stevens
Estate Chocolate Hole and Great Cruz Bay long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz takes the hassle out of booking monthly rentals in Estate Chocolate Hole and Great Cruz Bay. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Stayz. Many long-term rentals in Estate Chocolate Hole and Great Cruz Bay are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Estate Chocolate Hole and Great Cruz Bay
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:15 June - 13 July
Image gallery for Eco Cabin in Paradise
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Eco Cabin in Paradise
St. John
13% off
Price is AU$11,681
AU$11,681
for 28 nights, 1 cabin
AU$417 per night
includes taxes & fees
Image gallery for Breathtaking Panoramic Views of the British Virgin Islands from hot tub & pool!
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Breathtaking Panoramic Views of the British Virgin Islands from hot tub & pool!
St. John
13% off
Price is AU$13,000
AU$13,000
for 28 nights, 1 home
AU$464 per night
includes taxes & fees
Image gallery for Family Glamping Site with AC
1010 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
Family Glamping Site with AC
St. John
8% off
Price is AU$9,311
AU$9,311
for 28 nights, 1 unit
AU$333 per night
includes taxes & fees
Image gallery for 2-bedroom condo with WiFi, AC View of water from deck Pool
9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
2-bedroom condo with WiFi, AC View of water from deck Pool
St. Thomas
13% off
Price is AU$8,779
AU$8,779
for 28 nights, 1 apartment
AU$314 per night
includes taxes & fees
Image gallery for PROMO Beach Walk<br>Beautiful 1 bedroom walking distance to Secret Harbor beach
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
PROMO Beach Walk<br>Beautiful 1 bedroom walking distance to Secret Harbor beach
St. Thomas
8% off
Price is AU$10,533
AU$10,533
for 28 nights, 1 apartment
AU$376 per night
includes taxes & fees
Image gallery for Couples Retreat, Sweeping VIEWS, Kayaks Await at the Beach!
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Couples Retreat, Sweeping VIEWS, Kayaks Await at the Beach!
St. John
8% off
Price is AU$19,438
AU$19,438
for 28 nights, 1 villa
AU$694 per night
includes taxes & fees
Image gallery for Affordable, oceanfront and walk to private beach gem
1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Affordable, oceanfront and walk to private beach gem
St. Thomas
8% off
Price is AU$13,965
AU$13,965
for 28 nights, 1 apartment
AU$499 per night
includes taxes & fees
Image gallery for On the Water with Style, 5 minute walk to Beach along the Marina
9.69.6 out of 10, Exceptional, (82 reviews)
Exceptional
(82 reviews)
On the Water with Style, 5 minute walk to Beach along the Marina
St. Thomas
8% off
Price is AU$7,533
AU$7,533
for 28 nights, 1 apartment
AU$269 per night
includes taxes & fees
Image gallery for Lovely, spacious upstairs condo at Crystal Cove, on Sapphire beach.
9.89.8 out of 10, Exceptional, (29 reviews)
Exceptional
(29 reviews)
Lovely, spacious upstairs condo at Crystal Cove, on Sapphire beach.
St. Thomas
8% off
Price is AU$9,810
AU$9,810
for 28 nights, 1 apartment
AU$350 per night
includes taxes & fees
Image gallery for Holiday Special Available! Escape to Island Oasis near Magens Bay—a getaway.
9.49.4 out of 10, Exceptional, (3 reviews)
Exceptional
(3 reviews)
Holiday Special Available! Escape to Island Oasis near Magens Bay—a getaway.
St. Thomas
24% off
Price is AU$10,188
AU$10,188
for 28 nights, 1 home
AU$364 per night
includes taxes & fees
Image gallery for New Listing! Island Bliss • 2BR • 3 Beds • 2 Baths
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
New Listing! Island Bliss • 2BR • 3 Beds • 2 Baths
St. Thomas
30% off
Price is AU$9,033
AU$9,033
for 28 nights, 1 apartment
AU$323 per night
includes taxes & fees
Image gallery for Perfect Romantic Getaway @Point Pleasant/3 Pools/Sun & Sea Grill! Book Now!
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
Perfect Romantic Getaway @Point Pleasant/3 Pools/Sun & Sea Grill! Book Now!
St. Thomas
8% off
Price is AU$10,732
AU$10,732
for 28 nights, 1 apartment
AU$383 per night
includes taxes & fees
Image gallery for Banana Sweet Top! 2 BEDROOM!! Hot Tub and Tesla back up power!
9.29.2 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
Banana Sweet Top! 2 BEDROOM!! Hot Tub and Tesla back up power!
St. John
8% off
Price is AU$14,123
AU$14,123
for 28 nights, 1 home
AU$504 per night
includes taxes & fees
Image gallery for Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views
9.89.8 out of 10, Exceptional, (35 reviews)
Exceptional
(35 reviews)
Colorful Caribbean Cottage • King Bed, Pool, Lush Garden Views
St. John
13% off
Price is AU$13,581
AU$13,581
for 28 nights, 1 cottage
AU$485 per night
includes taxes & fees
Image gallery for New listing!! Amazing Views & Lovely Breezes! Remodeled 1BR/1BA Private Balcony!
9.89.8 out of 10, Exceptional, (14 reviews)
Exceptional
(14 reviews)
New listing!! Amazing Views & Lovely Breezes! Remodeled 1BR/1BA Private Balcony!
St. Thomas
6% off
Price is AU$12,686
AU$12,686
for 28 nights, 1 apartment
AU$453 per night
includes taxes & fees
Image gallery for Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
1010 out of 10, Exceptional, (86 reviews)
Exceptional
(86 reviews)
Breathtaking Panoramic Views Of The Caribbean Sea From This Luxury Villa
St. Thomas
8% off
Price is AU$16,871
AU$16,871
for 28 nights, 1 apartment
AU$603 per night
includes taxes & fees
Image gallery for ★★★★★Spectacular Water View-Private Wrap-Around Balcony-3 Pools-2 Restaurants ☼☼
1010 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
★★★★★Spectacular Water View-Private Wrap-Around Balcony-3 Pools-2 Restaurants ☼☼
St. Thomas
8% off
Price is AU$10,163
AU$10,163
for 28 nights, 1 apartment
AU$363 per night
includes taxes & fees
Image gallery for Fantastic Panoramic Views of The British Virgin Islands, Amazing Sunrises, Pool
1010 out of 10, Exceptional, (38 reviews)
Exceptional
(38 reviews)
Fantastic Panoramic Views of The British Virgin Islands, Amazing Sunrises, Pool
St. John
13% off
Price is AU$13,402
AU$13,402
for 28 nights, 1 apartment
AU$479 per night
includes taxes & fees
Image gallery for Cozy Condo 3 minutes away from Magens Bay beach!
1010 out of 10, Exceptional, (4 reviews)
Exceptional
(4 reviews)
Cozy Condo 3 minutes away from Magens Bay beach!
St. Thomas
11% off
Price is AU$9,293
AU$9,293
for 28 nights, 1 apartment
AU$332 per night
includes taxes & fees
Image gallery for Private cottage, private pool, great views !
9.49.4 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Private cottage, private pool, great views !
St. Thomas
17% off
Price is AU$18,182
AU$18,182
for 28 nights, 1 cottage
AU$649 per night
includes taxes & fees
Image gallery for Great Price on an Oceanview Suite on the Water. Near Beaches, Pools, Bar And Sun
8.88.8 out of 10, Excellent, (34 reviews)
Excellent
(34 reviews)
Great Price on an Oceanview Suite on the Water. Near Beaches, Pools, Bar And Sun
St. Thomas
12% off
Price is AU$8,189
AU$8,189
for 28 nights, 1 apartment
AU$292 per night
includes taxes & fees
Image gallery for Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Spectacular Oceanfront Villa: Stunning Views, Breezes, Serenity, and Pristine!
St. Thomas
16% off
Price is AU$9,568
AU$9,568
for 28 nights, 1 apartment
AU$342 per night
includes taxes & fees
Image gallery for 5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
1010 out of 10, Exceptional, (127 reviews)
Exceptional
(127 reviews)
5★ Sapphire Dream! Ocean & Marina Views-Sapphire Beach Condo-Luxury Reno!
St. Thomas
8% off
Price is AU$15,279
AU$15,279
for 28 nights, 1 apartment
AU$546 per night
includes taxes & fees
Image gallery for 1 Bedroom Condo w/ Mini Kitchen at Limetree Resort, Saint Thomas!!
8.08.0 out of 10, Very good, (1 review)
Very good
(1 review)
1 Bedroom Condo w/ Mini Kitchen at Limetree Resort, Saint Thomas!!
St. Thomas
9% off
Price is AU$18,821
AU$18,821
for 28 nights, 1 room
AU$672 per night
includes taxes & fees
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Estate Chocolate Hole and Great Cruz Bay
You’ll often find discounted rates for long stays of over 28 days on Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Estate Chocolate Hole and Great Cruz Bay Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Stayz with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Estate Chocolate Hole and Great Cruz Bay come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Estate Chocolate Hole and Great Cruz Bay
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Stayz offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Estate Chocolate Hole and Great Cruz Bay with pool
Stayz's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Estate Chocolate Hole and Great Cruz Bay
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Estate Chocolate Hole and Great Cruz Bay with flexible cancellation policies.