Short city breaks Caribbean

Close

View larger map

Also consider

North America Holidays
178656 properties
Caribbean Holidays
28985 properties
Villas St. Barts
6,285 properties
Villas St. Maarten - Saint Martin
3,629 properties
Villas Barbados
3,406 properties
Villas Dominican Republic
3,172 properties
Villas Jamaica
2,456 properties
Apartments Puerto Rico
1,693 properties
Villas Guadeloupe
952 properties
US Virgin Isles
942 properties
Villas Bahamas
816 properties
Villas Aruba
611 properties
Villas St. Lucia
579 properties
Apartments Martinique
546 properties
Houses Antigua and Barbuda
504 properties
Villas British Virgin Isles
495 properties
Villas Anguilla
459 properties
Holiday rentals Turks and Caicos Islands
444 properties
Houses St. Vincent and the Grenadines
443 properties
Villas Curacao
348 properties
Villas Grenada
255 properties
Houses Trinidad and Tobago
231 properties

Caribbean

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

1,300 Holiday homes

Filters applied: City breaks (1,300)

Travellers going to Caribbean are booking December dates now. Secure your holiday home today and have the perfect trip.

(1) Excellent 

26

Holiday home with golf nearby in Caribbean

Great Abaco Island / Treasure Cay

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
“Great vacation home” Without a doubt this was one of our best family vacations so far. We met some wonderful people there especially Sue and George who took us out fishing and it was a great experience. we were really satisfied with our rental because  …see more

from £154 / night

£1072 / week

Book View

from £154 / night

26

Holiday villa accommodation

Saint Ann Parish / Discovery Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Welcome to Fortlands Point on the Beach, one of the world's most exquisite and luxurious 7 bedroom beachfront mansions located on a private promontory with its own private beach, swimming pool extensive gardens. Set amongst stunning landscaped gardens with tropical  …see more

from £2041 / night

£14286 - £24604 / week

Enquire View

from £2041 / night

22

Antigua and Barbuda holiday villa rental

Jolly Harbour / Jolly Harbour Villas

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Villa Oceana Breeze, a stunning 4 bedroom beach front villa is situated in Jolly Harbour Beach resort in Antigua. The villa is located in a private are on a beautiful white sand beach just a few steps away from the calm turquoise Caribbean Sea.• Holiday type Family, Hon  …see more

from £1701 / night

£11905 - £16667 / week

Enquire View

from £1701 / night

Featured properties

20

Holiday villa in Caribbean

Windward / Lorient

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Villa La Plage on St. Barts is one of the most sought after beachfront estates on the island. Located directly on Lorient Beach, this stunning villa offers 7 bedrooms, each with an ensuite bath. Discounts may apply for 2 week bookings or longer  …see more

from £5929 / night

£41500 - £127600 / week

Book View

from £5929 / night

(2) Very Good 

10

Tobago / Bon Accord

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary

 …see more

from £116 / night

£774 - £941 / week

Book View

from £116 / night

30

Saint Francois / Anse des Rochers

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 800 km
  • Swimming pool

 …see more

from £240 / night

£841 - £2866 / week

Book View

from £240 / night

28

Studio rental in Westmoreland Parish with shared pool

Westmoreland Parish / Negril

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Breath taking sea views and romantic sunsets are just part of what this Superior studio suite as to offer. Located on Negril's famous 7 mile suite, the sand and water is just a few steps away from your your feet. Enjoy the private beaches or venture on to the public 7 m  …see more

from £72 / night

£465 - £703 / week

Book View

from £72 / night

13

Holiday condo in Westmoreland Parish

Negril / Negril Beach

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Beautifully decorated one bedroom ocean view suite on the beach. Just a few steps away from the water, with the sound of the waves and the cool breeze flowing in its a great relaxation spot to be lazy and unwind. The suite sleeps up to four people comfortably, with a Qu  …see more

from £80 / night

£556 - £917 / week

Book View

from £80 / night

24

Holiday villa with golf nearby in St. Maarten-St. Martin

Sint Maarten / Beacon Hill, Sint Maarten

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Villa Encore, a luxury 5 bedroom villa located in the hill side of Terre Basses in St Martin. The villa is tasteful decorated offer a very spacious living area perfect for a large family. The nearest beach is Plum Bay beach which is a 3 minute drive f  …see more

from £891 / night

£6231 - £17461 / week

Enquire View

from £891 / night

53

Caribbean holiday apartment rental

Cabarete / Ocean Dream

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Beach, Cabarete,  …see more

from £79 / night

£536 - £1355 / week

Book View

from £79 / night

24

Apartment rental in Barbados with shared pool, golf nearby

Saint James Parish / James Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Experience one of Barbados's most luxurious 3 bedroom fully air conditioned vacation villa properties just steps away from one of the best beaches in the world. Old Trees 204 has been designed with privacy, space and total luxury in mind, Set on the second floor ov  …see more

from £675 / night

£4723 - £7500 / week

Enquire View

from £675 / night

24

Holiday villa with golf nearby in Caribbean

Antigua / Galley Bay

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Sugar Mill villa, a 7 bedroom villa located in Galley Bay Heights sits on a waterfront hillside with spectacular views overlooking the Caribbean Sea. Bordered by a roof-top garden, hand-crafted natural stone wall and split-level design.• Board: Self Catering  …see more

from £1701 / night

£11905 - £19842 / week

Enquire View

from £1701 / night

(1) Very Good 

20

Saint Ann Parish holiday apartment rental

Saint Ann Parish / Ocho Rios

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Ask owner if suitable for children
Wi-Fi, Pool, Private Car Park, Fully Equipped Kitchen, Bathroom, Hot Water, Large Balcony, Cool Pool, High Speed Broadband, Cable TV.This property is suited to a couple or friends sharing or a single traveler. Purpose built in block, your own front door and privacy.The  …see more

from £40 / night

£260 / week

Book View

from £40 / night

23

Caribbean holiday home rental

Simpson Bay / Simpson Bay Beach

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Our house is located in the most perfect blue beach of St Martin. This is the only private beach in a gated community in the entire Island. You have the best of both worlds here, calm and central with the incredible views of the beach from all the rooms. Private & f  …see more

from £335 / night

£2284 / week

Book View

from £335 / night

(1) Excellent 

17

Hanover Parish / Lucea

5 2 3 nights min

  • 5 bedrooms
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £60 / night

£417 / week

Book View

from £60 / night

(1) Average 

5

Arrondissement of Le Marin / Les Anses d'Arlet

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children

 …see more

from £69 / night

£478 / week

Book View

from £69 / night

24

Holiday villa with swimming pool, golf nearby in St. Maarten-St. Martin

Sint Maarten / Cupecoy Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Welcome to villa Ambiance, our luxurious 4 bedroom property located on the hillside of Terres Basses overlooking the Caribbean Sea. It is a fantastic family retreat and the perfect villa to spend a special occasion. The pool at Villa Ambiance is simply stunning and is t  …see more

from £851 / night

£5953 - £17461 / week

Enquire View

from £851 / night

15

Holiday villa with swimming pool in Caribbean

St. Barts / St. Jean

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Villa Zen is a luxury two bedroom villa located in the exclusive Pointe Milou area of St Barths. This romantic villa provides wonderful sea views and fantastic sunsets.• Board: Self Catering  …see more

from £738 / night

£5162 / week

Enquire View

from £738 / night

24

Holiday villa with swimming pool in Caribbean

Virgin Gorda / Mahoe Bay

5 20 Min stay varies

  • 5 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
Welcome to Villa Aquamare, one of the most luxurious and exquisite beach front villas in the British Virgin Island. Aquamare is a secluded enclave comprised of three 8,000 square-feet, five-bedroom villas, each situated on a different elevation with breath-taking ocean  …see more

from £2490 / night

£15516 - £52778 / week

Enquire View

from £2490 / night

8

Trinidad and Tobago holiday studio rental

Trinidad / Woodbrook

Studio 2 2 nights min

  • Studio
  • Sleeps 2
  • 2 nights min
  • Nearest beach 14 km
  • Car not necessary
  • Air conditioning
Well-appointed, self-catering private exterior apartment separate from main house. Easy access to downtown, shopping, beaches, tourist sites. Prime location for annual Carnival celebrations. Laundry and on-site parking available on premises for additional fee. Airport  …see more

from £36 / night

£227 / week

Book View

from £36 / night

25

Holiday villa with swimming pool, golf nearby in Caribbean

Sint Maarten / Beacon Hill, Sint Maarten

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
Welcome to La Perla Classic, a lovely one bedroom fully air-conditioned beachfront villa with private swimming pool located directly on Baie Rouge which is one of the most beautiful beaches in St Martin. Baie Rouge one of the most fabulous, intimate and quiet b  …see more

from £794 / night

£5556 - £8731 / week

Enquire View

from £794 / night

(1) Excellent 

11

Hotel apartment rental in Bahamas with shared pool

New Providence Island / Nassau

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
Apartment style hotel near airport. Banking and Dinning Nearby. Ocean Views and Beach access. Public Transportation to Night Life, Dinning, Casinos, Attractions, Shopping and much more.  …see more

from £143 / night

£794 / week

Book View

from £143 / night

(1) Excellent 

24

Holiday villa with swimming pool, golf nearby in Caribbean

Cap Estate / Smugglers Cove

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Smugglers Nest, a rustic and extraordinarily romantic 2 bedroom villa located on the St Lucia's water's edge with incredible views of Smugglers Beach.• Board: Self Catering  …see more

from £516 / night

£3612 / week

Enquire View

from £516 / night

17

Holiday studio in Caribbean

Negril / Negril Beach

Studio 2 1 night min

  • Studio
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Ask owner if suitable for children
  • Air conditioning
The studio is located inside the beach complex Point Village right on Jamaica's 7 mile beach in Negril. The suite as a beautiful ocean-view from inside the unit and balcony. There is a kitchenette with full appliances, Queen-size and two fold out futons. Located on o  …see more

from £54 / night

£606 / week

Book View

from £54 / night

30

Anguilla / The Valley

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

 …see more

from £239 / night

£953 / week

Book View

from £239 / night

24

Villa rental in Barbados with swimming pool, golf nearby

Saint James Parish / Paynes Bay

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to the luxury villa No. 1 Smugglers Cove, St JAMES, Barbados. Stretch out in complete luxury, in your stunning 3 bed-roomed ground floor luxury vacation rental in Barbados. Bask in near-perfect weather, literally 10 steps from one of the most beautiful white san  …see more

from £715 / night

£5000 - £11112 / week

Enquire View

from £715 / night

(2) Very Good 

23

Grande-Terre Island / Le Gosier

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £111 / night

£636 / week

Book View

from £111 / night

76

Holiday villa with swimming pool, golf nearby in Caribbean

Sint Maarten / Maho

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
Welcome to our luxurious Baie Longue Beach House villa. This wonderful villa is tastefully decorated in a West Indian style with lovely arches on the sea side is located directly on Baie Longue Beach. Baie Longue beach is really beautiful with over a mile of shimmering  …see more

from £590 / night

£4127 - £9524 / week

Enquire View

from £590 / night

42

Holiday villa with swimming pool in Caribbean

St. Barts / Gustavia

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
Located in gorgeous Gustavia, this bright villa is perfectly located for exploring the tropical island of St. Barths, promising an unforgettable holiday for up to 8 people. The plush living space is ideal for relaxing after a day in the sun. Enjoy a good book or one of  …see more

from £598 / night

£4182 - £14928 / week

Book View

from £598 / night

(17) Excellent 

28

Puerto Rico / Cabo Rojo

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 8 km
  • Swimming pool

 …see more

from £95 / night

£556 - £620 / week

Book View

from £95 / night

24

Caribbean holiday apartment rental

Saint James Parish / Holetown

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Welcome to Still Fathoms villa, our modern and stylish villa located directly on the ocean at Reed's Bay on the West Coast of Barbados. Still Fathoms is a luxurious 5 bedroom beach front villa with gorgeous views of the Caribbean Sea. This luxury villa feat  …see more

from £1405 / night

£9834 - £28056 / week

Enquire View

from £1405 / night

(4) Excellent 

65

Saint Ann Parish / Runaway Bay

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Swimming pool

 …see more

from £52 / night

£362 / week

Book View

from £52 / night

24

Villa rental in Caribbean with swimming pool, golf nearby

Saint James Parish / Montego Bay

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to Sunset on the Beach, a charming 5 bedroom private beach front villa located at the exclusively renowned Tryall Club in Montego Bay.• Board: Catered  …see more

from £1531 / night

£10715 - £22223 / week

Enquire View

from £1531 / night

(1) Excellent 

11

Cabrera / Orchid Bay Estates

8 20 Min stay varies

  • 8 bedrooms
  • Sleeps 20
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.4 km
  • Swimming pool

 …see more

from £2381 / night

£16667 - £27778 / week

Book View

from £2381 / night

(1) Very Good 

42

Las Terrenas / Las Ballenas

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.15 km
  • Child friendly

 …see more

from £30 / night

£178 - £314 / week

Book View

from £30 / night

23

Caribbean holiday apartment rental

Saint James Parish / Holetown

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 4 km
  • Swimming pool
Welcome to Ragamuffins House an exclusive 6 bedroom luxury villa in the renowned Royal Westmoreland Golf Resort on the West Coast of Barbados. This stunning villa is a truly unique villa offering both privacy and tranquillity while also boasting security and the incredi  …see more

from £1667 / night

£11667 - £18334 / week

Enquire View

from £1667 / night

26

Holiday condo in Westmoreland Parish

Westmoreland Parish / Negril

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child friendly
This wonderful one bedroom Queen suite as a glorious sea view's and is the perfect rental for a couple or small family. Located on the first floor the suite as a galley style kitchen, full appliances with utensils and coffee maker. Bathroom with tub, living room with 2  …see more

from £88 / night

£608 - £928 / week

Book View

from £88 / night

26

Holiday villa with swimming pool in Caribbean

St. Barts / St. Jean

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Welcome to Villa Diamond, one of the most exquisite villa rental in St Jean, St Barth. The newly built villa boasts a stunningly beautiful and stylish design with breath-taking views. The villa is centrally located on the St Jean hillside overlooking St. Jean Bay with a  …see more

from £850 / night

£5953 - £19842 / week

Enquire View

from £850 / night

24

Holiday villa with swimming pool in Caribbean

St. Barts / Gustavia

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
Welcome to Villa Ted, a luxury 2 bedroom villa located in the beautiful surroundings of Dévé in St Barths. The villa offers guests a beautiful outdoor terrace area with ample space and provides stunning panoramic view of the over Grand Cul de Sac and the island of Tor  …see more

from £547 / night

£3826 - £18016 / week

Enquire View

from £547 / night

17

Aruba / San Nicolas

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 km
  • Child friendly

 …see more

from £76 / night

£477 / week

Book View

from £76 / night