Villas with a pool Caribbean | Apartments to rent with swimming facilities | Holiday Lettings

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17,061 Holiday homes

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

(10) Excellent 

18

Holiday villa with swimming pool in Caribbean

Tobago / Mount Irvine

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Mot Mot Lodge has an open plan living, dining and kitchen area, with double hight ceilings and full width sliding doors, opening out on to a large upper patio,with outdoor dining facilities. This dining area links the interior and the garden seamlessly.  …see more

from £230 / night

£1610 / week

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from £230 / night

(2) Excellent 

12

Bermuda holiday apartment rental

Southampton Parish / South Shore

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Southampton has the distinct advantage of being close to ferry stops, and the charming village of Somerset where shops and cafes makes lingering for a while a very pleasant diversion. The remarkable renovated installation at the Naval Dockyard property (a British Navy  …see more

from £235 / night

£1639 / week

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from £235 / night

(10) Excellent 

16

Holiday townhouse with swimming pool in Caribbean

Enterprise / Cottonbay

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
“Repeat guest - many times over” This holiday villa has been our yearly destination for 6 years in a row. After our first encounter we knew we've found the right destination for our young family. What drew us to the property was the safety for our to  …see more

from £108 / night

£750 - £850 / week

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from £108 / night

(18) Excellent 

20

Caribbean holiday villa rental

Castara / Englishman's Bay

5 8 Min stay varies

  • 5 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Very peaceful and spacious home in a great location.” Everything was well prepared when we arrived. Jango (the master gardener and our greeter when we arrived) was very patient and waited for 4 hours as our flight was delayed. The house was well equi  …see more

from £114 / night

£800 - £1450 / week

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from £114 / night

(5) Excellent 

14

Holiday villa with swimming pool, golf nearby in Caribbean

Saint James Parish / Sunset Crest

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Barbados Villa with Private Pool and Beach Club Access. Walking Distance to the Beach and Duty Free Shopping. Sleeps 6 (3 Bedrooms).  …see more

from £278 / night

£1667 - £2143 / week

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from £278 / night

(17) Excellent 

35

Holiday apartment with swimming pool in Caribbean

Saint Peter Parish / Mullins

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Excellent apartment, lovely location.” Really lovely apartment equipped with all you need for a relaxing holiday. Location excellent for beach and restaurants. Property manager Angela and cleaner Brenda were both so helpful. We had such a good holiday  …see more

from £165 / night

£1150 - £2475 / week

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from £165 / night

(25) Very Good 

19

Holiday apartment with shared pool in Saint Ann Parish

Saint Ann Parish / Ocho Rios

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Ideal location!” A friend of mine goes to Jamaica every year and since I hadn’t visited for quite some time, so I decided why not. From the initial communication with Jacqueline I was put at ease. Communication was always prompt and pleasant and  …see more

from £80 / night

£560 - £630 / week

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from £80 / night

(1) Excellent 

22

Arrondissement of Fort-de-France / Le Lamentin

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning

 …see more

from £187 / night

£594 / week

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from £187 / night

(14) Excellent 

23

Holiday townhouse with shared pool in Caribbean

Saint James Parish / Fitts

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.25 km
  • Swimming pool
“easy, relaxing, wonderful” Organisation - Roz handled the booking really nicely and was helpful in arranging the extra kid-related equipment we needed. We were met on our arrival at the villa, and everything was explained to us - couldn't have been sm  …see more

from £70 / night

£590 / week

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from £70 / night

(12) Excellent 

24

Holiday apartment with shared pool in Caribbean

Saint James Parish / Holetown

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
Stunning new apartments 4 minutes walk to the fabulous settlers beach.There are numerous bars/restaurants within walking distance for a variety of budgets. There are restaurants specialising in Italian, Indian or Thai as well as traditional Bajan food.Holetown is approx  …see more

from £81 / night

£567 - £800 / week

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from £81 / night

(24) Excellent 

24

Holiday villa with swimming pool in Antigua and Barbuda

Willikies / The Peninsula

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Delightful villa with a tranquil view” Turtle View was an amazing place to stay. We loved the house, well equipped, clean and comfortable. It was homely with out being cluttered and also had a well brilliant kitchen. We could have sat on the deck all  …see more

from £171 / night

£1200 - £2400 / week

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from £171 / night

(23) Excellent 

24

Villa rental in Caribbean with swimming pool, golf nearby

Jolly Harbour / Jolly Harbour Villas

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Very relaxing place to stay” Property provides a great base for a relaxing stay and has everything you need for a great holiday. Bart the property manager welcomed us in and waved us good bye and I'm sure would have been available if needed during th  …see more

from £150 / night

£900 - £1350 / week

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from £150 / night

(4) Excellent 

12

Holiday studio with shared pool, golf nearby in Caribbean

Saint James Parish / Sunset Crest

Studio 3 5 nights min

  • Studio
  • Sleeps 3
  • 5 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Car not necessary
“Fantastic” Thankyou Helen for yet another fantastic stay in your apartment , it's our home from home and look forward to seeing you again later this year.x  …see more

from £48 / night

£334 - £362 / week

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from £48 / night

(9) Excellent 

23

Holiday villa accommodation

Saint James Parish / Holder's Hill

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“Beautiful Villa with that personal touch from the cleaner” Prior to arrival the owner was very helpful with car hiring and attention to detail as we needed a divider in one of the rooms as we had brother and sister teenagers of different sexes sharing  …see more

from £107 / night

£750 - £900 / week

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from £107 / night

17

Holiday home in Caribbean

St. Kitts and Nevis / Nevis

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+
Description from the ownerClifton Gardens offer beautiful cottages that are a great alternative to staying in a hotel. The cottages are located close to the large selection of outdoor and indoor amenities, such as an equestrian center, RV facility, restaurants a  …see more

from £100 / night

£635 - £912 / week

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from £100 / night

(4) Excellent 

20

Barbados holiday apartment rental

Saint James Parish / Holetown

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
Boutique complex of 10 apartments, all with air conditioning, communal pool and dedicated parking. beach & bars 4 minutes walk  …see more

from £74 / night

£515 - £775 / week

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from £74 / night

(9) Very Good 

23

Caribbean holiday apartment accommodation

Saint Peter Parish / Gibbes

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“For us this has EVERYTHING!! Totally brilliant!!” On our 5th visit to Barbados - a glorious island which never disappoints and where there's always plenty to do - we discovered Ashanti Apt. 5 and we got a fabulous self-catering experience at very reas  …see more

from £100 / night

£500 - £575 / week

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from £100 / night

(6) Very Good 

21

Holiday villa with swimming pool in Caribbean

Saint James Parish / Weston

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.001 km
  • Swimming pool
“Wonderful Property” Our stay was a pleasure from start to finish. We were greeted at the airport by the recommended taxi driver and again at the villa by Julianna and Lianna. Julianna ran us through all of the basics of the property on arrival and ev  …see more

from £400 / night

£2500 - £5000 / week

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from £400 / night

20

Grande-Terre Island / Saint Francois

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £84 / night

£306 - £394 / week

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from £84 / night

(9) Excellent 

21

Antigua and Barbuda holiday villa rental

Saint Phillip Parish / Long Bay

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“A fantastic holiday destination, where nothing more can be asked for” Brightside is an amazing place to stay on holiday - clean, spacious, wonderful views and perfect for a relaxing time away. I stayed out there with some friends and we had an excelle  …see more

from £454 / night

£3175 - £5000 / week

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from £454 / night

(15) Excellent 

15

Holiday villa with swimming pool in Barbados

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.7 km
  • Swimming pool
“Perfect haven for a fabulous holiday” My Wife and I and our dear friends stayed at Beija Flor for our first Bajan holiday. The house is wonderfully relaxing, in a near perfect location, is fully equipped to satisfy your every need and the pool is a jo  …see more

from £199 / night

£1390 - £2604 / week

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from £199 / night

(15) Excellent 

16

Holiday apartment with swimming pool in Caribbean

Mullins / Beacon Hill

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Condo is kept at a very high specification and standard” Had a very relaxing 9 days in a lovely garden apartment with pool. John & Sheila who own it helped a great deal before we went. Kerry the local manager was also very professional & helpful, as  …see more

from £150 / night

£1050 - £2295 / week

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from £150 / night

(20) Excellent 

20

Home rental in Caribbean with swimming pool

Saint Peter Parish / Maynards

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Lovely Villa, great location” Our party of family and friends had a lovely time at Palm Villa. The facilities are excellent, it was plenty big enough for all ten of us and Beverley was helpful and went out of her way to make our stay comfortable. We  …see more

from £125 / night

£875 - £2555 / week

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from £125 / night

(20) Excellent 

22

Holiday hotel apartment with shared pool in St. Lucia

Castries Quarter / Marigot Bay

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Brilliant Apartment in Marigot” The moment we arrived in St Lucia it was an incredible adventure. We rented a Jeep at the airport and drove to Marigot Bay. Coming from the US, driving was a thrill from the very beginning. The people of St Lucia are  …see more

from £200 / night

£1400 - £2400 / week

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from £200 / night

(11) Excellent 

17

Holiday home with swimming pool in Caribbean

Willikies / The Peninsula

3 6 5 nights min

  • 3 bedrooms
  • Sleeps 6
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool
“I cannot say enough good about this property” I am an experienced visitor of Antigua, coming three to five times a year on business for the past ten years or so. For the second time, I took my family along, and we decided to stay for three weeks in t  …see more

from £270 / night

£1800 - £1995 / week

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from £270 / night

(3) Very Good 

26

Holiday villa with swimming pool in Caribbean

Christ Church Parish / Oistins

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children
“Amazing villa” This could not be better. We love this villa. The pool was big and very nice and it was very good view of the atlantic. The villa was big with 3 bedrooms, and 3 bathrooms, and even a gym. Loved the kitchen. Margret was very helpful. We  …see more

from £175 / night

£1100 - £1680 / week

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from £175 / night

(15) Excellent 

21

Holiday lodge in Caribbean

Great Exuma / George Town

3 8 5 nights min

  • 3 bedrooms
  • Sleeps 8
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Seabreeze Lodge is ideal for 2 families or groups of fishermen. Its located on Bonefish Flats in Great Exuma. We offer 5-star, luxury private accommodation.Bonefish fishing, kayaking, deep water fishing, turtle watching, sailing, golf, lazing by our heated pool  …see more

from £334 / night

£2334 / week

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from £334 / night

(7) Very Good 

18

Studio rental in Caribbean with shared pool

Marigot / Nettle Bay Beach Club

Studio 2 7 nights min

  • Studio
  • Sleeps 2
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning
Completely renovated and refurbished, works finished in March 2015, great sized terrace with 2 lounge chairs and small dining table for 2, trendy new kitchen, zen style shower bathroom, upscale furniture, great value for the price. Close to beaches as 'Baie Rouge&#  …see more

from £71 / night

£492 - £678 / week

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from £71 / night

(44) Excellent 

23

Villa rental in St. Lucia with swimming pool, golf nearby

Castries / La Toc

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“It was a magical experience and we were reluctant to return home” We had a wonderful five night stay at this impressive newly built villa in a stunning location overlooking the Caribbean Sea, with the sandy beach of La Toc a short stroll away. The  …see more

from £239 / night

£1667 - £3917 / week

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from £239 / night

16

Gros Islet / Beausejour

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

 …see more

from £124 / night

£867 / week

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from £124 / night

(10) Excellent 

24

Grande-Terre Island / Sainte-Anne

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £170 / night

£721 - £1272 / week

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from £170 / night

(1) Very Good 

20

Barahona Province / Paraiso

11 28 1 night min

  • 11 bedrooms
  • Sleeps 28
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool

 …see more

from £43 / night

£212 - £1755 / week

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from £43 / night

(13) Excellent 

36

Holiday villa with swimming pool, golf nearby in Antigua and Barbuda

Antigua / Saint Mary's

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Cactus is a brand new property and first guests are due in January - 'real' photos will be available in Dec.  …see more

from £250 / night

£1750 - £3150 / week

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from £250 / night

(4) Excellent 

21

Holiday villa with swimming pool in Caribbean

Saint David Parish / Saint David's

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
“Great Spot - No AC as Advertised” This is a great spot with great amenities. Only disappointed about the fact of room advertised on TripAdvisor as air-condition but this is not the case.....  …see more

from £236 / night

£1432 - £2533 / week

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from £236 / night

(8) Very Good 

37

Caribbean holiday tower rental

Saint George Parish / Lance aux Epines

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
Sugar Mill Tower — an alluring and lovely hideaway — ideal for honeymoons, anniversaries, proposals, & couple's retreat. An English 4-poster bed dominates the romantic round room. 2nd BR has a full-size bed. Both are en suite. Includes 3 levels of decks, private plu  …see more

from £286 / night

£2000 - £4000 / week

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from £286 / night

15

Caribbean holiday villa rental

St. Vincent and the Grenadines / Mustique

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Cottonwick Villa is a moderately sized but very comfortable three-bedroom villa on Mustique Island. A permanent staff of two are on hand to make your stay as idyllic as possible. Recently rebuilt in 2016 it offers everything that one could want to stay and enjoy M  …see more

from £636 / night

£4450 - £7500 / week

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from £636 / night

(6) Very Good 

27

Caribbean holiday villa rental

Westmoreland Parish / Negril

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Welcome to the Villa 3, your Jamaican vacation beach home. Just steps from the sea, Villa 3 sleeps and entertains groups of 2 to 10 comfortably.The villa is located in the gated Little Bay Country Club: an exquisite, brand new, beachfront community in Negril. Vi  …see more

from £420 / night

£2900 - £3250 / week

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from £420 / night

20

Caribbean holiday condo accommodation

Saint James Parish / Glitter Bay, St James Parish

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Our two bedroom two bathroom ground floor apartment is located on one of the best beaches on the west coast of Barbados. Fully air conditioned and fully furnished it is a perfect place for family holidays or for friends sharing. The kitchen is fully equipped with frid  …see more

from £300 / night

£2100 / week

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from £300 / night

(11) Excellent 

14

Apartment rental in Antigua and Barbuda with shared pool, golf nearby

Antigua / Friars Hill

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Great place to stay” Nice and easy transfer by taxi to the accommodation complex. Friendly reception staff on arrival. Very attractive and clean appartment, with a lovely balcony with sun loungers, table and chairs. Just a few hundred yards from a lo  …see more

from £79 / night

£550 - £875 / week

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from £79 / night

(10) Very Good 

10

Villa rental in Caribbean with swimming pool, golf nearby

Jolly Harbour / Harbour View

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
High quality 4 bedroom 3 bathroom property with private pool, Air-conditioning, wifi near excellent beach and golf course.This villa is unique in the neighbourhood with an extra outside dining gazebo that seats 8 people with views of the lagoon, mountains and pool. Anti  …see more

from £190 / night

£1330 - £1855 / week

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from £190 / night

Top Destination reviews

CoCoKreyol - Nevis
Excellent

The location is nice with great views. One needs a car though. There is a steep uphill drive to the street where the house is positioned. The apartment itself is clean and beautifully decorated. … see more
The wonderful waves of the sea F2 (3) 1-4 pers
great location, great value, very nice hosts

except for the AC and for the roosters, which I guess are universal problems on this island, everything was OK. the apartments are very spacious, very well located (proximity to a lot of beautiful beaches, a great botanical garden, the national park … see more
CoCoKreyol - Saint Kitts
Just perfect

Flat in the basement of owners house, but no Problem. He was really helpful and flexible. He drove me to the next car rental. Welcome Drinks, Food for the first breakfast and towels for the beach included! Well equipped flat with a huge terrace, nic … see more
Bluebayou
Fantastic

This is a beautifully maintained apartment in a brilliant location. The beach at Mullins is accessed by walking through the lovely gardens belonging to the complex which also contains a secluded and private pool. The property provides easy access to … see more
Sea Eagle, Beach Cottage, St.James
Great peaceful location that recharged our batteries.

I would rent again. As advertised, good local standard. Good value. Peaceful location. Good snorkeling. Near services and restaurants. Owner is very caring and attentive. … see more
Two Bays Villa at Cabier
DREAM HOLIDAY

There are so many things to tell you about our holiday in Grenada in December 2016 - first of all 'fabulous' is a word that I can use time and time again in my review. We arrived by taxi on our first day (car hire came the next day) and because th … see more