Caribbean Islands 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 Caribbean Islands. 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 Caribbean Islands 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 - Caribbean Islands
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:22 June - 20 July
Image gallery for Modern 1-bed studio in West Bay, with AC and private patio, short walk to beach!
9.89.8 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)
Modern 1-bed studio in West Bay, with AC and private patio, short walk to beach!
West Bay
9% off
Price is AU$6,296
AU$6,296
for 28 nights, 1 cottage
AU$225 per night
includes taxes & fees
Image gallery for Lameshur Bay Glamping Site with AC
1010 out of 10, Exceptional, (27 reviews)
Exceptional
(27 reviews)
Lameshur Bay Glamping Site with AC
St. John
8% off
Price is AU$6,552
AU$6,552
for 28 nights, 1 unit
AU$234 per night
includes taxes & fees
Image gallery for Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
9.89.8 out of 10, Exceptional, (101 reviews)
Exceptional
(101 reviews)
Beautiful Tree Frog Apartment! - South Sound - 5 min walk to Smith Cove
George Town
8% off
Price is AU$7,442
AU$7,442
for 28 nights, 1 apartment
AU$266 per night
includes taxes & fees
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$11,762
AU$11,762
for 28 nights, 1 cabin
AU$420 per night
includes taxes & fees
Image gallery for Gordon's Island Art Loft
9.89.8 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)
Gordon's Island Art Loft
St. Thomas
18% off
Price is AU$3,798
AU$3,798
for 28 nights, 1 home
AU$136 per night
includes taxes & fees
Image gallery for Casa Azul welcomes you to a stunning ocean view condo steps away from the beach
1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Casa Azul welcomes you to a stunning ocean view condo steps away from the beach
Alice Town
9% off
Price is AU$15,147
AU$15,147
for 28 nights, 1 apartment
AU$541 per night
includes taxes & fees
Image gallery for Relaxing Chalet with beautiful Sunrises & Sunsets!
9.69.6 out of 10, Exceptional, (62 reviews)
Exceptional
(62 reviews)
Relaxing Chalet with beautiful Sunrises & Sunsets!
San Juan
9% off
Price is AU$6,371
AU$6,371
for 28 nights, 1 chalet
AU$228 per night
includes taxes & fees
Image gallery for Beautiful Villa Near Culebra Wildlife Preserve
8.68.6 out of 10, Excellent, (57 reviews)
Excellent
(57 reviews)
Beautiful Villa Near Culebra Wildlife Preserve
Culebra
22% off
Price is AU$12,767
AU$12,767
for 28 nights, 1 villa
AU$456 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$19,572
AU$19,572
for 28 nights, 1 villa
AU$699 per night
includes taxes & fees
Image gallery for Charming Cottage in Rockley, Barbados only 5 mins Walk to Gorgeous Accra Beach!
9.69.6 out of 10, Exceptional, (64 reviews)
Exceptional
(64 reviews)
Charming Cottage in Rockley, Barbados only 5 mins Walk to Gorgeous Accra Beach!
Rockley
14% off
Price is AU$4,045
AU$4,045
for 28 nights, 1 cottage
AU$144 per night
includes taxes & fees
Image gallery for Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
9.29.2 out of 10, Wonderful, (43 reviews)
Wonderful
(43 reviews)
Isla Verde- Beach/Bar/Restaurants Near Airport For Same Day Booking Message me
Carolina
18% off
Price is AU$5,529
AU$5,529
for 28 nights, 1 home
AU$197 per night
includes taxes & fees
Image gallery for Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
9.09.0 out of 10, Wonderful, (37 reviews)
Wonderful
(37 reviews)
Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
Carolina
13% off
Price is AU$2,730
AU$2,730
for 28 nights, 1 home
AU$97 per night
includes taxes & fees
Image gallery for Ocean Front Divers Haven - World Class Diving & Snorkeling One Giant Stride Away
1010 out of 10, Exceptional, (72 reviews)
Exceptional
(72 reviews)
Ocean Front Divers Haven - World Class Diving & Snorkeling One Giant Stride Away
West Bay
8% off
Price is AU$11,166
AU$11,166
for 28 nights, 1 apartment
AU$399 per night
includes taxes & fees
Image gallery for SPECTACULAR BEACHFRONT 180° OCEANVIEW ORIENTBEACH POOL - YOU TOUCH THE SAND !
9.69.6 out of 10, Exceptional, (71 reviews)
Exceptional
(71 reviews)
SPECTACULAR BEACHFRONT 180° OCEANVIEW ORIENTBEACH POOL - YOU TOUCH THE SAND !
Orient Bay
6% off
Price is AU$6,058
AU$6,058
for 28 nights, 1 apartment
AU$216 per night
includes taxes & fees
Image gallery for "Parrot 6" 37 Steps To The Ocean! Quiet, Ocean View
1010 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)
"Parrot 6" 37 Steps To The Ocean! Quiet, Ocean View
West Bay
8% off
Price is AU$17,571
AU$17,571
for 28 nights, 1 apartment
AU$628 per night
includes taxes & fees
Image gallery for Margaritaville Resort St Thomas Studio Deluxe
9.09.0 out of 10, Wonderful, (6 reviews)
Wonderful
(6 reviews)
Margaritaville Resort St Thomas Studio Deluxe
St. Thomas
9% off
Price is AU$10,419
AU$10,419
for 28 nights, 1 room
AU$372 per night
includes taxes & fees
Image gallery for Dawn Beach Club Villa. With Beach access.
7.67.6 out of 10, Good, (4 reviews)
Good
(4 reviews)
Dawn Beach Club Villa. With Beach access.
Oyster Pond
16% off
Price is AU$11,110
AU$11,110
for 28 nights, 1 home
AU$397 per night
includes taxes & fees
Image gallery for Fenced Property, Near all Beaches, Pool, Hot Tub, Sundeck, Firepit, Grill, Wi-Fi
1010 out of 10, Exceptional, (33 reviews)
Exceptional
(33 reviews)
Fenced Property, Near all Beaches, Pool, Hot Tub, Sundeck, Firepit, Grill, Wi-Fi
Governor's Harbour
9% off
Price is AU$11,556
AU$11,556
for 28 nights, 1 home
AU$413 per night
includes taxes & fees
Image gallery for Beach Villa
9.89.8 out of 10, Exceptional, (57 reviews)
Exceptional
(57 reviews)
Beach Villa
Luquillo
9% off
Price is AU$3,837
AU$3,837
for 28 nights, 1 apartment
AU$137 per night
includes taxes & fees
Image gallery for Romantic with Ocean Views - Sugar Beach Condos.
9.69.6 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
Romantic with Ocean Views - Sugar Beach Condos.
Christiansted
6% off
Price is AU$10,109
AU$10,109
for 28 nights, 1 apartment
AU$361 per night
includes taxes & fees
Image gallery for Luxury villa with sea view and Diamond swimming pool
9.89.8 out of 10, Exceptional, (82 reviews)
Exceptional
(82 reviews)
Luxury villa with sea view and Diamond swimming pool
Le Diamant
9% off
Price is AU$9,991
AU$9,991
for 28 nights, 1 villa
AU$357 per night
includes taxes & fees
Image gallery for VILLA SERENE—2 Bed, 2.5 Bath Villa with Beach Access just steps to Sapodilla Bay
9.89.8 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
VILLA SERENE—2 Bed, 2.5 Bath Villa with Beach Access just steps to Sapodilla Bay
Providenciales
8% off
Price is AU$20,768
AU$20,768
for 28 nights, 1 villa
AU$742 per night
includes taxes & fees
Image gallery for Cozy Corner ~Where Budget Meets Breathtaking Beach in a 1-bedroom studio with AC
8.08.0 out of 10, Very good, (1 review)
Very good
(1 review)
Cozy Corner ~Where Budget Meets Breathtaking Beach in a 1-bedroom studio with AC
East End
8% off
Price is AU$11,459
AU$11,459
for 28 nights, 1 apartment
AU$409 per night
includes taxes & fees
Image gallery for Villa Santorini 3-bedroom apartment in welcoming Bayamón with WiFi, AC. Enjoy
1010 out of 10, Exceptional, (11 reviews)
Exceptional
(11 reviews)
Villa Santorini 3-bedroom apartment in welcoming Bayamón with WiFi, AC. Enjoy
Bayamon
9% off
Price is AU$5,425
AU$5,425
for 28 nights, 1 apartment
AU$194 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 Caribbean Islands
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.
Caribbean Islands 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 Caribbean Islands 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 Caribbean Islands
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 Caribbean Islands 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 Caribbean Islands
Plans change. We get that. With Stayz, you can search, select 'free cancellation,' and see all rentals in Caribbean Islands with flexible cancellation policies.