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:10 Aug - 7 Sept
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$6,050
AU$6,050
for 28 nights, 1 cottage
AU$216 per night
includes taxes & fees
Image gallery for Lameshur Bay Glamping Site with AC
9.89.8 out of 10, Exceptional, (30 reviews)
Exceptional
(30 reviews)
Lameshur Bay Glamping Site with AC
St. John
8% off
Price is AU$6,324
AU$6,324
for 28 nights, 1 unit
AU$226 per night
includes taxes & fees
Image gallery for Sunshine☀️House, with private water entry and high-speed Internet.
9.69.6 out of 10, Exceptional, (100 reviews)
Exceptional
(100 reviews)
Sunshine☀️House, with private water entry and high-speed Internet.
Rainbow Bay
9% off
Price is AU$9,769
AU$9,769
for 28 nights, 1 villa
AU$349 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, (43 reviews)
Exceptional
(43 reviews)
Casa Azul welcomes you to a stunning ocean view condo steps away from the beach
Alice Town
9% off
Price is AU$14,461
AU$14,461
for 28 nights, 1 apartment
AU$516 per night
includes taxes & fees
Image gallery for Wow ONLY 8 bed HOUSE 8MILE SJU Airport beach Corporate Team Wedding Dest Groups
7.47.4 out of 10, Good, (10 reviews)
Good
(10 reviews)
Wow ONLY 8 bed HOUSE 8MILE SJU Airport beach Corporate Team Wedding Dest Groups
Trujillo Alto
17% off
Price is AU$15,499
AU$15,499
for 28 nights, 1 home
AU$554 per night
includes taxes & fees
Image gallery for Fish Fever, Russell Island Bahamas
1010 out of 10, Exceptional, (57 reviews)
Exceptional
(57 reviews)
Fish Fever, Russell Island Bahamas
Russell Island
9% off
Price is AU$9,151
AU$9,151
for 28 nights, 1 home
AU$327 per night
includes taxes & fees
Image gallery for "Parrot 6" 37 Steps To The Ocean! Quiet, Ocean View
1010 out of 10, Exceptional, (102 reviews)
Exceptional
(102 reviews)
"Parrot 6" 37 Steps To The Ocean! Quiet, Ocean View
West Bay
8% off
Price is AU$11,075
AU$11,075
for 28 nights, 1 apartment
AU$396 per night
includes taxes & fees
Image gallery for Cozy Cove/Beach/FREE Golf Cart/Umbrella/Chairs/Kayak/Quiet Dead End Street
1010 out of 10, Exceptional, (68 reviews)
Exceptional
(68 reviews)
Cozy Cove/Beach/FREE Golf Cart/Umbrella/Chairs/Kayak/Quiet Dead End Street
Spanish Wells
14% off
Price is AU$13,067
AU$13,067
for 28 nights, 1 home
AU$467 per night
includes taxes & fees
Image gallery for OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!
1010 out of 10, Exceptional, (164 reviews)
Exceptional
(164 reviews)
OCEAN VIEW VILLA WITH PRIVATE POOL, STEPS FROM SECLUDED BEACH, GATED COMMUNITY!
Yabucoa
9% off
Price is AU$17,146
AU$17,146
for 28 nights, 1 home
AU$612 per night
includes taxes & fees
Image gallery for SAVE 20% at Coco Sands - 2 bed, beachfront, sea view condo
1010 out of 10, Exceptional, (23 reviews)
Exceptional
(23 reviews)
SAVE 20% at Coco Sands - 2 bed, beachfront, sea view condo
North Side
12% off
Price is AU$10,392
AU$10,392
for 28 nights, 1 apartment
AU$371 per night
includes taxes & fees
Image gallery for Elegant and Luxurious Villa on Gros Piton with a spectacular views of Caribbean
1010 out of 10, Exceptional, (89 reviews)
Exceptional
(89 reviews)
Elegant and Luxurious Villa on Gros Piton with a spectacular views of Caribbean
Soufrière
14% off
Price is AU$16,289
AU$16,289
for 28 nights, 1 villa
AU$582 per night
includes taxes & fees
Image gallery for Cayman Imperial Suite-Close to Beaches, Restaurants, Bus-stops & Stores
9.89.8 out of 10, Exceptional, (67 reviews)
Exceptional
(67 reviews)
Cayman Imperial Suite-Close to Beaches, Restaurants, Bus-stops & Stores
West Bay
8% off
Price is AU$5,063
AU$5,063
for 28 nights, 1 apartment
AU$181 per night
includes taxes & fees
Image gallery for Amazing Caribbean views!
8.88.8 out of 10, Excellent, (50 reviews)
Excellent
(50 reviews)
Amazing Caribbean views!
Vieques
17% off
Price is AU$9,225
AU$9,225
for 28 nights, 1 apartment
AU$329 per night
includes taxes & fees
Image gallery for A Beautiful Home Located Close To Beaches, Rain Forest, Golfing And Much More!
9.49.4 out of 10, Exceptional, (60 reviews)
Exceptional
(60 reviews)
A Beautiful Home Located Close To Beaches, Rain Forest, Golfing And Much More!
Luquillo
9% off
Price is AU$10,553
AU$10,553
for 28 nights, 1 home
AU$377 per night
includes taxes & fees
Image gallery for Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
9.29.2 out of 10, Wonderful, (23 reviews)
Wonderful
(23 reviews)
Luxury apartment stunning views /5 minutes from Saint Jean Beach/ swimming pool
St. Barthelemy
18% off
Price is AU$14,138
AU$14,138
for 28 nights, 1 apartment
AU$505 per night
includes taxes & fees
Image gallery for ! 8 minutes from the beach and tourist sites! Comfortable and central house.
9.89.8 out of 10, Exceptional, (46 reviews)
Exceptional
(46 reviews)
! 8 minutes from the beach and tourist sites! Comfortable and central house.
Fajardo
18% off
Price is AU$5,112
AU$5,112
for 28 nights, 1 home
AU$183 per night
includes taxes & fees
Image gallery for Toe's in the Sand-2 bed / 2 bath seaside condo - beach and pool.
9.49.4 out of 10, Exceptional, (58 reviews)
Exceptional
(58 reviews)
Toe's in the Sand-2 bed / 2 bath seaside condo - beach and pool.
Christiansted
12% off
Price is AU$8,734
AU$8,734
for 28 nights, 1 apartment
AU$312 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, (79 reviews)
Exceptional
(79 reviews)
Ocean Front Divers Haven - World Class Diving & Snorkeling One Giant Stride Away
West Bay
8% off
Price is AU$10,327
AU$10,327
for 28 nights, 1 apartment
AU$369 per night
includes taxes & fees
Image gallery for Private Studio with Pool in Downtown Punta Cana Self Check-In Long Stays Welcome
9.49.4 out of 10, Exceptional, (3 reviews)
Exceptional
(3 reviews)
Private Studio with Pool in Downtown Punta Cana Self Check-In Long Stays Welcome
Punta Cana
18% off
Price is AU$3,031
AU$3,031
for 28 nights, 1 apartment
AU$108 per night
includes taxes & fees
Image gallery for Luxury 2 Bedroom Home With Private Dock and Pool On The North End
1010 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)
Luxury 2 Bedroom Home With Private Dock and Pool On The North End
Hope Town
19% off
Price is AU$48,768
AU$48,768
for 28 nights, 1 home
AU$1,742 per night
includes taxes & fees
Image gallery for 2 bedroom / 2 bathroom, sleeps 8, interior designer condo with FREE dock space
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
2 bedroom / 2 bathroom, sleeps 8, interior designer condo with FREE dock space
Alice Town
9% off
Price is AU$9,391
AU$9,391
for 28 nights, 1 apartment
AU$335 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, (12 reviews)
Exceptional
(12 reviews)
Villa Santorini 3-bedroom apartment in welcoming Bayamón with WiFi, AC. Enjoy
Bayamon
9% off
Price is AU$5,216
AU$5,216
for 28 nights, 1 apartment
AU$186 per night
includes taxes & fees
Image gallery for Serenity by the Sea, beautiful condo sleeps up to 4!
9.89.8 out of 10, Exceptional, (97 reviews)
Exceptional
(97 reviews)
Serenity by the Sea, beautiful condo sleeps up to 4!
Christiansted
16% off
Price is AU$8,050
AU$8,050
for 28 nights, 1 apartment
AU$288 per night
includes taxes & fees
Image gallery for Beach Villa
9.89.8 out of 10, Exceptional, (66 reviews)
Exceptional
(66 reviews)
Beach Villa
Luquillo
9% off
Price is AU$3,762
AU$3,762
for 28 nights, 1 apartment
AU$134 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.