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Family Friendly Holidays in Caribbean - Holiday Lettings

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15,301 family friendly properties

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Holiday villa in Trinidad and Tobago

Grande Riviere villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 12

from £235 / night

£1,642 / week

1 / 19

Holiday home with swimming pool in Caribbean

Las Galeras house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from £422 / night

£2,814 / week

1 / 27

Holiday villa in Caribbean

Cap Estate villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £446 / night

£3,119 - £4,432 / week

1 / 16

Holiday apartment in Caribbean

Palm - Eagle Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

from £657 / night

£4,596 / week

1 / 25

Holiday home in Trinidad and Tobago

Crown Point house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £118 / night

£821 / week

1 / 38

Caribbean holiday villa rental

Philipsburg villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £429 / night

£3,283 - £5,745 / week

1 / 18

Holiday villa rental

Sosua villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Amazing Villa” The property was better than advertised. I completely enjoyed my stay at this property it was very clean, safe, and close to all activities. The property was serviced well, and the pool was awesome. Honestly, there was not one thing about it that I didn't like. The property manager and staff provided great service, and was very knowledgable of the area. I greatly recommend this property.

from £168 / night

£1,116 / week

1 / 19

Holiday apartment accommodation

Ocho Rios apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £93 / night

£610 - £774 / week

1 / 6

Home rental in Caribbean

Guayama house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £165 / night

£1,173 / week

1 / 10

St Martin / St Maarten holiday villa rental

Terres Basses villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,273 / night

£8,910 / week

1 / 42

Holiday cottage with swimming pool in Caribbean

Nevis cottage

  • 2 bedrooms
  • 6 bathrooms
  • sleeps 4

from £244 / night

£1,689 / week

1 / 6

Holiday home rental

Juan Dolio house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £66 / night

£282 / week

1 / 33

Holiday apartment in Jamaica

Montego Bay apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £65 / night

£453 / week

1 / 60

Holiday cottage in Caribbean

Deshaies cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £141 / night

£764 / week

1 / 16

Caribbean holiday villa rental

Rincon villa

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 18

from £1,084 / night

£7,583 / week

1 / 42

Holiday villa in Curaçao

Willemstad villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

from £164 / night

£1,145 - £1,552 / week

1 / 27

Villa accommodation in Caribbean with shared pool

Punta Cana villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 5

from £113 / night

£657 / week

1 / 26

Caribbean holiday apartment rental

Calibishie apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £66 / night

£394 / week

1 / 11

Holiday apartment in Bahamas

Nassau apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £211 / night

£1,313 / week

1 / 31

Holiday villa with shared pool in Caribbean

Saint Peter Parish villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £704 / night

£5,909 / week

1 / 12

Holiday apartment with golf nearby in Caribbean

Humacao apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £169 / night

£1,501 - £2,158 / week

1 / 15

Caribbean holiday b&b rental

Buccoo b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £188 / night

£1,313 / week

1 / 47

Holiday home with golf nearby in Caribbean

Frigate Bay house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

“Relaxing! Memorable! Close to the Beach!” This villa is close to everything in the resort area- Frigate Bay. It is walking distance to the beach and close to the local strip which is filled with local restaurants. This villa is alot bigger than we thought, the rooms are huge. We all had a peaceful rest at nights. We hope to go back by the end of this year.

from £263 / night

£1,839 / week

1 / 8

Holiday apartment in Caribbean

Santiago Rodriguez Province apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

from £57 / night

£376 / week

1 / 12

Villa rental in Caribbean with swimming pool

Punta Cana villa

  • 6 bedrooms
  • 7 bathrooms
  • sleeps 14

“Juanillo 25” We had the pleasure of staying in this beach paradise for 10 days during the Christmas holidays. The house is beautiful and the staff could not have been more accommodating. We loved every minute of our stay from the sumptuous meals to the tranquility of the endless beach. Every aspect of the holiday was perfect. jackie rose

from £5,628 / night

£32,826 / week

1 / 28

Caribbean holiday cottage rental

Calibishie cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £57 / night

£338 - £404 / week

1 / 11

Holiday villa in Caribbean

Cabarete villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £159 / night

£979 / week

1 / 9

Caribbean holiday villa rental

Puerto Plata villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £188 / night

£1,220 / week

1 / 6

Holiday apartment with shared pool in Caribbean

Punta Cana apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

from £235 / night

£1,595 / week

1 / 34

Holiday apartment with tennis court in Caribbean

Orient Bay apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Wake up to beautiful ocean views and warm trade winds” My wife and I stayed in this studio for a week in early January 2014 and we were extremely pleased with every aspect. The owners are very responsive and friendly. When we arrived, the caretaker was awaiting our arrival with a smile and offered reserved parking and an efficient check in. Very friendly and happy to accomodate us in whatever we needed. When we walked in, there were no suprises, except the amazing view! The pictures are exact and the view in person is even better. Wi-fi and TV are good. Decoration and style is chic and European. Great use of space. Ac is good if you need it. The old vacated hotel building adds some romance to the grounds, and the small stores in Mont Vernon were a convenience, even though the Simply Market was an easy 5 minute drive. We found a new restaurant every night very close by, and every meal was delicious. The full service in-studio kitchen allowed us to eat breakfast and lunch in, enjoying the beach, then just dining out once a day in the evening for dinner. The pool is very nice, and the beach is irresistable. Short walk to dine, drink, and enjoy just down the beach. Everyone was very friendly and happy. All in all, we enjoyed this relaxing vacation and studio so much, we've already booked a stay next January.

from £71 / night

£460 - £920 / week

1 / 28

Holiday villa with swimming pool in Dominican Republic

Puerto Plata villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £160 / night

£1,116 / week

1 / 25

Villa rental in St. Kitts and Nevis with shared pool

New Castle villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £469 / night

£3,283 / week

1 / 10

Holiday apartment with shared pool in Dominican Republic

Cabarete apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“Great condo in a convenient location.” The condo was great...everything went smoothly from the time we arrived. The condo is lovely, the bed super comfortable and everything works well. Has everything you need. Location is great...just a 5 minute walk on the beach to the restaurants and. 10 minutes walk to Janet's if you need groceries. The street can be a little noisy on the weekends but if you leave the bathroom window and door shut, you can hardly hear it. Overall, our stay was fantastic! I would definitely go back. Just a heads up, condo is on the second floor and there are no elevators...we had to lug our stroller up and down which was fine, I need the exercise, but it would not work out for a wheelchair or anything like that.

from £57 / night

£394 / week

1 / 20

Holiday cottage with shared pool in St. Vincent and the Grenadines

Bequia cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £371 / night

£2,594 / week

1 / 35

Holiday apartment in Trelawny Parish

Duncans apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £141 / night

£985 - £1,248 / week

1 / 29

Caribbean holiday villa rental

Mount Pleasant villa

  • 8 bedrooms
  • 8 bathrooms
  • sleeps 16

from £1,607 / night

£11,247 / week

1 / 49

Holiday apartment rental

Scarborough apartment

  • 3 bedrooms
  • 1 bathroom
  • sleeps 4

“The best possible welcome & stay that we could've imagined.” My family and I recently rented the entire guesthouse [upper & lower], and have only praise for the treatment we received while there. The house was even more lovely than in the photos - as were Tina, Lion, and Spice. In fact, we now consider them part of our extended family, and send our warmest wishes to them always. Our stay lasted for an entire month, and we completely loved our experience...from the happy moment that we arrived, right through until the sad one when we departed.

from £43 / night

£254 - £319 / week

1 / 16

Holiday cottage with shared pool in Caribbean

Vieux Fort cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £94 / night

£657 - £1,051 / week

1 / 8

Holiday villa with swimming pool in Saint Ann Parish

Mammee Bay villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Riviera Villa is like living in paradise with beautiful people.” My party and I have been visiting our holiday home as we like to call it for the last 13 years. In recent years we have gone twice. The staff have become apart of our own family. Need l say more. The villa is spacious inviting and very clean, with air conditioning in each room. The pool is cleaned daily and is situated just of the veranda, easy to keep an eye on the young ones. It also has its own gate which can be locked to keep the younger child out if not supervised. The food which is prepared in the spacious kitchen is cooked to perfection. Some of the ingredients are taken off the property including herbs, mangos, bananas and other lustrous fruits and provisions. My party and l look forward to going to our home in the beautiful island of Jamaica. The private beach is just a short walk away where you can mingle and enjoy various cocktails and relax and enjoy the beautiful sunshine.

from £171 / night

£1,426 - £1,886 / week

1 / 14

Holiday villa with shared pool in Caribbean

Rio San Juan villa

  • 18 bedrooms
  • 19 bathrooms
  • sleeps 36

from £5,159 / night

£36,109 / week

1 / 7

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