Caribbean Islands holiday rentals

We found 71,198 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Caribbean Islands

Showing deals for:27 Nov - 4 Dec

Exterior
Pool
Room
Private kitchen
Exceptional
(132 reviews)

Lady Blue Sits On Beautiful Tar Bay Beach-Features Infinity pool/Outdoor Living

George Town

8% off
S$12,794
for 7 nights, 1 home
S$1,828 per night
includes taxes & fees
Lady Blue Sits On Beautiful Tar Bay Beach-Features Infinity pool/Outdoor Living
Pool or beach?
Property grounds
Lounge with amazing beach views. With high speed internet and 65" smart TV.
February Point Resort with Seacroft Villa (yellow) in the middle of the picture.
Exceptional
(123 reviews)

Beautiful Home - Perfect Beachfront Location - Spectacular Views - Gated Resort

George Town

5% off
S$6,218
for 7 nights, 1 villa
S$888 per night
includes taxes & fees
Beautiful Home - Perfect Beachfront Location - Spectacular Views - Gated Resort
Terrace/patio
Pool
Living area
Private kitchen
Exceptional
(40 reviews)

Casa de Campo 8 Bedroom Luxury Estate

La Romana

9% off
S$15,450
for 7 nights, 1 villa
S$2,207 per night
includes taxes & fees
Casa de Campo 8 Bedroom Luxury Estate
Interior
Beach
Exterior
Property grounds
Exceptional
(25 reviews)

Pool, Beachfront Villa, 16 ppl, Chef, Boat tours, Starlink, BBQ

William's Town

9% off
S$12,974
for 7 nights, 1 villa
S$1,853 per night
includes taxes & fees
Pool, Beachfront Villa, 16 ppl, Chef, Boat tours, Starlink, BBQ
Oceanside Bedroom facing East with exterior door onto the deck
Open living area with kitchen and French doors onto the back deck
ocean views from the kitchen and dinning area
Living area
Exceptional
(100 reviews)

Victoria's Island House -

Green Turtle Cay

8% off
S$3,015
for 7 nights, 1 home
S$431 per night
includes taxes & fees
Victoria's Island House -
View to dining area
Sun bathing on the deck while viewing the beautiful mountains
View of Side of Villa
Maison in the evening
Exceptional
(91 reviews)

Elegant and Luxurious Villa on Gros Piton with a spectacular views of Caribbean

Soufrière

9% off
S$4,910
for 7 nights, 1 villa
S$701 per night
includes taxes & fees
Elegant and Luxurious Villa on Gros Piton with a spectacular views of Caribbean
Room
Property grounds
Interior
Interior
Exceptional
(96 reviews)

Garden Suite near the Beach and restaurants!

Naguabo

8% off
S$1,281
for 7 nights, 1 home
S$183 per night
includes taxes & fees
Garden Suite near the Beach and restaurants!
View of villa from the beach.
Interior
Dining
The Beach Villas are to the right along the beach, and Beach Club is to the left
Exceptional
(93 reviews)

Boutique Villa steps away from the most beautiful beach in the Bahamas

Great Harbour Cay

12% off
S$2,860
for 7 nights, 1 villa
S$409 per night
includes taxes & fees
Boutique Villa steps away from the most beautiful beach in the Bahamas
Room
Pool
Property grounds
Exterior
Exceptional
(90 reviews)

High-end New Home - Large PRIVATE Pool, Snorkeling, Cliff Jumping, Kayaks & SUP

Governor's Harbour

7% off
S$5,264
for 7 nights, 1 home
S$752 per night
includes taxes & fees
High-end New Home - Large PRIVATE Pool, Snorkeling, Cliff Jumping, Kayaks & SUP
Children’s area
Interior
Exterior
Pool
Wonderful
(7 reviews)

San Juan, garden Cozy suite w/private pool, BBQ, nearby & peaceful

San Juan

9% off
S$1,251
for 7 nights, 1 villa
S$179 per night
includes taxes & fees
San Juan, garden Cozy suite w/private pool, BBQ, nearby & peaceful
Guest bedroom with comfy queen bedding and beautiful views of pool and Caribbean
Waterfront picnic area-canopy for shade provided that easily hooks to post clips
View from inside of swimming pool by deck
Living and dining area
Exceptional
(51 reviews)

Beautiful home in TOP location - PRIVATE HEATED POOL-Last minute XMAS deal!

Governor's Harbour

8% off
S$5,058
for 7 nights, 1 home
S$723 per night
includes taxes & fees
Beautiful home in TOP location - PRIVATE HEATED POOL-Last minute XMAS deal!
Kitchen island
Enjoy the infinity edge pool
Pool
Terrace/patio
Exceptional
(142 reviews)

Saltwater Sunrise at Exuma Beach Georgetown Ocean Front Vacation in Paradise

Moss Town

8% off
S$8,533
for 7 nights, 1 villa
S$1,219 per night
includes taxes & fees
Saltwater Sunrise at Exuma Beach Georgetown Ocean Front Vacation in Paradise
Breakfast table and kitchen
Las Cabezas de San Juan 20 minutes away, make reservations with one week ahead.
Family
Bedroom #3
Exceptional
(63 reviews)

A Beautiful Home Located Close To Beaches, Rain Forest, Golfing And Much More!

Luquillo

7% off
S$2,799
for 7 nights, 1 home
S$400 per night
includes taxes & fees
A Beautiful Home Located Close To Beaches, Rain Forest, Golfing And Much More!
Marina
Interior
Exterior
Interior
Exceptional
(19 reviews)

A boater's dream home with a private dock UP THE CREEK from Hope Town Harbor.

Hope Town

8% off
S$6,195
for 7 nights, 1 home
S$885 per night
includes taxes & fees
A boater's dream home with a private dock UP THE CREEK from Hope Town Harbor.
Room
Exterior detail
Dining
Exterior
Exceptional
(12 reviews)

Charming 2-Bedroom House in Tranquil Staniel Cay near Thunderball Grotto

Staniel Cay

13% off
S$2,710
for 7 nights, 1 home
S$387 per night
includes taxes & fees
Charming 2-Bedroom House in Tranquil Staniel Cay near Thunderball Grotto
Interior
Private kitchen
Room
Exterior detail
Exceptional
(37 reviews)

Cozy Corner w/ Private Pool, Pool Table, A/C, Wi-Fi, Laundry & Parking

Vega Baja

8% off
S$1,890
for 7 nights, 1 home
S$270 per night
includes taxes & fees
Cozy Corner w/ Private Pool, Pool Table, A/C, Wi-Fi, Laundry & Parking
Casa Delfin - View to the Dining Room from Living Room.
Casa Delfin - Swimming Pool and Bar.
Casa Delfin - Master Suite (3rd floor).
Casa Delfin - Living Room.
Exceptional
(18 reviews)

Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts

La Romana

9% off
S$25,465
for 7 nights, 1 villa
S$3,638 per night
includes taxes & fees
Casa Delfín by Luxe Haus™ – Butlered Villa, Staff, Pool, Golf Carts
Kitchen/Dining
Down Island View!
Bathroom
Ocean View from your deck
Exceptional
(9 reviews)

Remodeled Corner Unit D211 with washer & dryer. Sleeps 4

St. Thomas

7% off
S$4,938
for 7 nights, 1 apartment
S$705 per night
includes taxes & fees
Remodeled Corner Unit D211 with washer & dryer. Sleeps 4
Exterior detail
Outdoor dining
Room
Exterior
Wonderful
(50 reviews)

Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go

Carolina

8% off
S$696
for 7 nights, 1 home
S$99 per night
includes taxes & fees
Isla Verde Walk To Beach -Bars-Restaurants Near Airport Good for a Stop-N-Go
Room
Outdoor dining
Interior
Interior
Exceptional
(27 reviews)

Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop

Culebra

8% off
S$1,021
for 7 nights, 1 apartment
S$146 per night
includes taxes & fees
Studio en suite, king/twin beds sleep 3, multi-deck views, early access bag drop
Beach
Terrace looking east.
Exterior
Kitchen look towards front door.
Exceptional
(38 reviews)

Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay

West End

8% off
S$2,760
for 7 nights, 1 home
S$394 per night
includes taxes & fees
Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay
Exterior
Private kitchen
Interior
Terrace/patio
Exceptional
(42 reviews)

Anchor's Away, Russell Island

Russell Island

8% off
S$2,315
for 7 nights, 1 home
S$331 per night
includes taxes & fees
Anchor's Away, Russell Island
Playing Golf at Punta Espada Golf Course - the Best in the Caribbean
Ground-level apartment with an ocean view.
Concierge Building Rear View
Aquamarina Pool Area
Exceptional
(39 reviews)

Punta Cana, Capcana Resort - Luxury 5stars 2 Large Bedrooms Oceanfront Condo

Punta Cana

9% off
S$3,481
for 7 nights, 1 apartment
S$497 per night
includes taxes & fees
Punta Cana, Capcana Resort - Luxury 5stars 2 Large Bedrooms Oceanfront Condo
Entrance portico
Pool area
BBQ bar area at night
Dinning room area
Exceptional
(19 reviews)

Located close to Isabel Segunda Vieques, downtown 4 bedrooms with pool.

Vieques

8% off
S$2,886
for 7 nights, 1 home
S$412 per night
includes taxes & fees
Located close to Isabel Segunda Vieques, downtown 4 bedrooms with pool.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting friendly Caribbean Islands

The beaches and surrounding scenery provide a peaceful ambience to your holiday home in Caribbean Islands. Travellers appreciate the snorkelling in this welcoming city. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

How to get to and around Caribbean Islands

The nearest airport is in Santo Domingo (SDQ-Las Americas Intl.), located 47.8 mi (77 km) from the city centre.

You can see more of Caribbean Islands by catching a ride on the metro at Maria Montez Station, Pedro F. Bono Station or Francisco G. Billini Station.

Frequently asked questions

What is the best area to stay in Caribbean Islands when booking a holiday rental?
Sosúan is one of the more in-demand locations to book a holiday rental in Caribbean Islands. Looking for some cool things to do in this destination? Be sure to check out Sosua Beach and Playa Alicia.
How much does it cost to rent a holiday rental in Caribbean Islands?
The average price for a holiday rental in Caribbean Islands is determined by a number of factors, like property type, length of stay and season. Whether you're in search of a sprawling villa with lots of bedrooms or a cosy cabin for you and your other half, just enter your travel dates to discover stays with terrific value.
How much does it cost to rent a beach house in Caribbean Islands?
Prices for beach houses in Caribbean Islands differ depending on the size and type of the property and time of year you're travelling. Simply enter your dates of travel into Vrbo and how many guests to see available options and prices. From there you can use our filter tool to narrow your search results by amenities, ratings, nearby activities and more.
How old do you have to be to rent a holiday rental in Caribbean Islands?
You should check with the Caribbean Islands holiday rental you're considering on Vrbo as age restrictions differ. However, it's generally 16, 18 or 21.
How long can I rent a holiday rental in Caribbean Islands for?
It's really down to the Caribbean Islands property. To browse available options offering extended stays, just enter your travel dates and guest number into Vrbo's search page. Enjoy having the entire property to yourself, along with home comforts such as a kitchen, air conditioning and outdoor spaces where the kids can play. Keep an eye out for long-term stays that offer weekly or monthly discounts.