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

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16,353 Holiday homes

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

(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 - £1250 / week

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from £150 / night

(5) Excellent 

16

Villa rental in Caribbean with swimming pool, golf nearby

Punta Cana / Bavaro Beach

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
This spacious villa is ideal for large families or friends traveling together. With 4 complete bedrooms, each with their complete bathroom, and a maids quarter. This beautiful villa is situated in the gated residential Cocotal Golf & Country Club with a beautiful vi  …see more

from £242 / night

£1613 / week

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from £242 / 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.<br />Holeto  …see more

from £82 / night

£570 - £805 / week

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from £82 / night

Featured properties

(10) Excellent 

23

Holiday apartment with shared pool, golf nearby in Caribbean

Saint James Parish / Holetown

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
PLEASE NOTE: PRICES LISTED ARE FOR USING ONE BEDROOM -(2 PERSONS).EMAIL FOR THE COST OF USING 2 BEDROOMS. This privately owned, stunning new apartment is the largest in the complex, it can be booked with the choice of 1 or 2 bedrooms. It boasts a large spacious lounge  …see more

from £82 / night

£570 - £1088 / week

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from £82 / night

(5) Very Good 

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 £75 / night

£520 - £778 / week

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from £75 / night

(15) 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

£490 - £590 / week

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from £70 / 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

£1225 - £1680 / week

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from £175 / night

(7) Excellent 

25

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

Saint Mary Parish / Jolly Harbour

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“great place” We had a lovely time in villa 230b.very clean well equipped kitchen and a nice deck,and very close to the beach.  …see more

from £113 / night

£791 / week

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from £113 / night

6

Basse-Terre Island / Sainte Rose

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £39 / night

£250 - £457 / week

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from £39 / night

(17) Excellent 

35

Holiday apartment with swimming pool in Caribbean

Saint Peter Parish / Mullins

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • 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

(5) Very Good 

37

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

Saint Mary Parish / Jolly Harbour

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“NICE AND QUIET PLACE” We stayed almost two months in the villa and really appreciate it. The villa is very clean and updated. We specially appreciated having all our meals outside looking at the very nice view. The extended deck is fantastic and th  …see more

from £105 / night

£734 / week

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from £105 / night

(6) Very Good 

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 £283 / night

£1976 - £2178 / week

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from £283 / night

(8) Excellent 

19

Caribbean holiday apartment rental

Saint Peter Parish / Gibbes

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool
New self-catering Caribbean apartment with stunning sea views, only minutes away from the spectacular beaches at Gibbs and Mullins Bay in the parish of St. Peter. A large communal pool and balcony for al fresco dining. Ideal for families seeking relaxation.<br />F  …see more

from £115 / night

£800 - £960 / week

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from £115 / night

(11) Very Good 

22

Holiday villa accommodation

Bottom Bay / Apple Hall

3 6 6 nights min

  • 3 bedrooms
  • Sleeps 6
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.15 km
  • Swimming pool
Enjoy the cooling breezes of the Atlantic Ocean as you stroll along the secluded beaches. Then return to the villa, where you can enjoy a swim in the pool and a cocktail or glass of wine on the deck and watch the sunset over the ocean while listening to the sounds of cr  …see more

from £65 / night

£455 / week

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from £65 / 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

(12) Excellent 

26

Holiday villa rental

Gros Islet / La Brolette

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 km
  • Swimming pool
Mango Tree Villa is in an ideal position for families and is adjoining the Windjammer Landing Resort where you can relax, children can be booked into the children club (at the expense of the client). There are restaurants and bars. Water sports also at Windjammer avai  …see more

from £346 / night

£2420 - £2823 / week

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from £346 / night

(2) Excellent 

15

Holiday villa in Caribbean

Punta Cana / Bavaro

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Best vacation ever” We had an amazing stay on this villa! Perfect location with a private beach and great service - our villa was cleaned thoroughly everyday. I highly recommend taking the Day Pass - it costs $45 per day and gets you unlimited food  …see more

from £162 / night

£1049 - £1654 / week

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from £162 / night

(3) Very Good 

16

Arrondissement of Le Marin / Riviere-Salee

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £35 / night

£242 / week

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from £35 / night

(12) Very Good 

23

Holiday villa with swimming pool, golf nearby in St. Lucia

Cap Estate / Rodney Bay Heights

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
4 bedroom contemporary villa - amazing sea views swimming pool. Restaurants Marina Beach nearby  …see more

from £115 / night

£790 - £1210 / week

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from £115 / night

(2) Very Good 

15

Holiday apartment in Caribbean

Saint James Parish / Weston

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Lantana 24 is a stunning first floor 3 bedroom, 2 bathroom apartment. Located in the quieter block it enjoys fabulous sea views of the West Coast and is ideal for families or couples. This modern apartment is stylishly furnished and equipped for a very comfortable stay.  …see more

from £100 / night

£700 - £1037 / week

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from £100 / 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

(25) 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 - £1400 / week

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from £171 / 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 - £1100 / week

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from £79 / night

(1) Excellent 

27

Holiday apartment with shared pool in Caribbean

Punta Cana / Bavaro

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
My place is close to restaurants and dining, the beach, nightlife, family-friendly activities, and public transport. My place is good for couples, families (with kids), big groups, and furry friends (pets). Featuring an outdoor swimming pool surrounded by the extensive  …see more

from £122 / night

£732 / week

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from £122 / night

24

Holiday villa with swimming pool in Barbados

Saint Peter Parish / Gibbes

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Our 2 storey property consists of 3 large double air-conditioned bedrooms upstairs and a smaller twin bedroom downstairs. Upstairs is a large veranda that overlooks the tropical gardens with a comfy sofa and football table. The master bedroom also has its own private v  …see more

from £160 / night

£1600 / week

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from £160 / night

(6) Very Good 

24

Holiday villa with swimming pool in Caribbean

Saint James Parish / Weston

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“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 £767 / night

£5363 / week

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from £767 / night

(4) Excellent 

39

Saint-Martin / Anse Marcel

1 4 6 nights min

  • 1 bedroom
  • Sleeps 4
  • 6 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 km
  • Swimming pool

 …see more

from £95 / night

£604 - £664 / week

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from £95 / night

(20) Excellent 

24

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
  • Nearest beach 0.1 km
  • Swimming pool
“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

(1) Excellent 

16

Holiday villa in Jamaica

Montego Bay / Ironshore

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Welcome to Chateau Gloria Luxury Villa, your home away from home. Looking for place to relax? To enjoy the Jamaican spirit? Then this villa is perfect for you. The property offers its guests a private outdoor pool with bar, ocean view and is surrounded by a tropical g  …see more

from £588 / night

£4110 - £5375 / week

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from £588 / night

(8) Excellent 

29

Caribbean holiday villa rental

Saint James Parish / Fitts

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“FABULOUS” An absolute gem of a property!! Exactly as described. The house is fully equipped with everything you could possibly want to enjoy your holiday, fully equipped kitchen, washer dryer, microwave, toaster and air conditioning throughout, very c  …see more

from £67 / night

£475 - £625 / week

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from £67 / night

(16) Excellent 

17

Holiday townhouse with swimming pool in Caribbean

Saint James Parish / Holetown

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
“Excellent Facilities & Location” No 7. Hillside is an extremely high-end villa. The finish throughout the house is of a very high standard. With the accommodation running over 3 floors meant that we never felt like we were on top of each other, there  …see more

from £280 / night

£1960 - £3990 / week

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from £280 / night

(11) Very Good 

36

Saint Francois / Anse des Rochers

Studio 4 5 nights min

  • Studio
  • Sleeps 4
  • 5 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool

 …see more

from £48 / night

£311 - £397 / week

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from £48 / night

(4) Very Good 

24

Caribbean holiday apartment rental

Jolly Harbour / Hamilton Estate

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Swimming pool
“Loved it” Lovely apartment, had everything we need and spacious. Walking distance to valley church beach ( which you have to yourself if you get there early enough!) it is worth hiring a car though, which we did after one day of lugging water back fro  …see more

from £92 / night

£645 - £995 / week

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from £92 / night

(10) Excellent 

23

Apartment rental in Caribbean

Speightstown / Port St Charles

2 5 5 nights min

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Car not necessary
“An amazing time away, great location, beach literally on your doorstep and a stunning apartment.” This apartment is finished to the highest standard and boasts being born beach-front and marina-front - which is rare for this up-scale development... Ev  …see more

from £280 / night

£1960 - £6870 / week

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from £280 / night

29

Caribbean holiday villa rental

Saint James Parish / Holetown

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
Second home offered for selective holiday rental on the edge of the Sandy Lane Estate. Access to private Sandy Lane Property Owners beach. Completely refurbished 2016. 2.5 acres grounds. Roof Terrace with seating,sun loungers and hot tub, spectacular views ,gentle bree  …see more

from £400 / night

£2800 / week

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from £400 / night

(5) Very Good 

17

Basse-Terre Island / Sainte Rose

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool

 …see more

from £31 / night

£225 - £535 / week

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from £31 / night

37

Holiday home in Caribbean

Warrens / Arthur Seat

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
The property is a 2 bedroom 2 storey house set in three quartes acres of Gardens, with access to fruit trees depending on the time of year +Swimming pool, Ground floor:- Kitchen, dinner, Lounge, toilet , Patio balcony + First floor:- Bedroom 1, balcony, bedroo  …see more

from £80 / night

£440 - £490 / week

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from £80 / 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.<br />Bonefish fishing, kayaking, deep water fishing, turtle watching, sailing, golf, lazing by our heated p  …see more

from £339 / night

£2371 / week

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from £339 / night

(1) Excellent 

6

Holiday villa with swimming pool in Caribbean

Windward / Marigot

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Architectural Designers island hideaway overlooking beautiful Marigot Bay and its undiscovered beach, Villa Case et Cuis..  …see more

from £369 / night

£2580 / week

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from £369 / night

(3) Excellent 

16

Maria Trinidad Sanchez Province / Cabrera

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Swimming pool
  • Child friendly

 …see more

from £52 / night

£302 / week

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from £52 / night