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

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1,263 Holiday homes

Filters applied: Swimming pool (1,275)

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

(1) Excellent 

16

Holiday villa in Ironshore

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

(5) Very Good 

10

St James, Montego Bay holiday condo rental

Montego Bay / St James, Montego Bay

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 km
  • Swimming pool
condo, apartment in montego bay , montego bay condo, one bedroom condo in jamaica<br />Guests have full access to the Palmyra Resort grounds with onsite fitness facility  …see more

from £113 / night

£791 / week

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from £113 / night

(6) Very Good 

21

Villa rental in Negril Beach with shared pool

Negril / Negril Beach

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
******** Our $450. per week special ends December 31, 2016 ********** Located on Norman Manley Blvd, Negril hip strip, directly across the street from Negril's famous 7 miles white sand beach. Access to the beach right across the street just a few steps away. We  …see more

from £53 / night

£323 - £621 / week

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from £53 / night

(1) Excellent 

41

Ocho Rios holiday apartment let

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Fishermans point resort is a one Bedroom beach apartment (living room, bedroom, kitchen, bath room), beach 3 minutes walk, with ocean view, located in Ocho Rios Turtle Street Mahogany Beach. The spacious apartments sleeps 4, Cable TV. The living and dining area a  …see more

from £70 / night

£350 - £590 / week

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from £70 / night

(6) Very Good 

27

Negril 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 £560 / night

£3920 / week

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from £560 / night

(2) Very Good 

29

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
The Resort is situated on 19 acres of lush landscaped gardens with 90 story residences surrounding a freshwater swimming pool, swim-up bar, whirlpool and bar. There are also two tennis courts and a Spa. Beach 7 minutes walk from apartment. We also have rentals at S  …see more

from £75 / night

£350 - £590 / week

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from £75 / night

(1) Very Good 

5

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Swimming pool
  • Air conditioning
The apartment is elegantly furnished and has an awesome viewing balcony overlooking the Caribbean sea. the car park is very spacious, the bed sitting room is also spacious and has a separate kitchen and bathroom area. The apartment is 5 minutes drive from the famous Dun  …see more

from £33 / night

£162 / week

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from £33 / night

(8) Very Good 

37

Runaway Bay holiday apartment rental

Saint Ann Parish / Runaway Bay

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Swimming pool
“Perfect Vacation Apt!!!” This vacation apt is the best that I have stayed. It was ideally situated near all attractions, stores, day and night activities, beaches, restaurants. I could literally walk to the nearest beach and restaurant. the apt was co  …see more

from £57 / night

£396 / week

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from £57 / night

(3) Average 

18

Holiday condo with shared pool in Negril

Westmoreland Parish / Negril

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Negril' absolute beachfront studios, Carib Beach Apartments, for less than the cost of a hotel room, offer swimming-pool, Jacuzzi, choice of beach styles (one is clothing optional), on to uninterrupted beach over 4 miles with atmospheric bars, carvings, cafes etc.&  …see more

from £81 / night

£404 - £726 / week

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from £81 / night

(25) Very Good 

19

Holiday apartment with shared pool in Ocho Rios

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 / week

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from £80 / night

12

Holiday home in Oracabessa

Saint Mary Parish / Oracabessa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Your room is a spacious king size or twin room with private shower room and access to huge balcony and dining space shared with one other room! Stunning panoramic views of the mountains, ocean and golden eye island! Fantastic in the mornings! Access to shared pool area  …see more

from £32 / night

£198 / week

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from £32 / night

(6) Very Good 

34

Ocho Rios holiday condo rental

Saint Ann Parish / Ocho Rios

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Most Relaxing Holiday Ever” My son & I had never been to Jamaica before... traveled with friends that were born in Jamaica. People in Jamaica are the most genuine people on earth. They are so kind, helpful and always happy. I definitely will be goi  …see more

from £90 / night

£600 / week

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from £90 / night

(10) Excellent 

40

Runaway Bay holiday bungalow rental

Saint Ann Parish / Runaway Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Nearest beach 2 km
  • Swimming pool
  • Child friendly
Contemporary stylish beach villa located along Jamaica's picturesque north coast Runaway Bay :) Villa is located in a secure upmarket gated community called Richmond. The community is quiet and safe with 24 hour security. There is also a supermarket located on th  …see more

from £64 / night

£446 / week

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from £64 / night

12

Holiday private room rental

Saint Mary Parish / Oracabessa

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Private garden
Your room is a spacious and bright queen size room with private shower room facilities. Amazing ocean and mountain views! Access to shared pool area, lounge/TV area and kitchen if you like to cook! Of course we can offer breakfast and dinner freshly cooked to order! Fre  …see more

from £29 / night

£170 / week

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from £29 / night

(5) Excellent 

26

Holiday villa with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Situated on Jamaica's north coast, in a gated community with twenty four hour security. Nearby attractions include: Dunn's River Falls, Dolphin Cove and Mystic Mountain. Onsite pool, gym, tennis courts, children's play area and park. Daily housekeeper  …see more

from £93 / night

£651 / week

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from £93 / night

(1) Very Good 

20

Ocho Rios 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.<  …see more

from £45 / night

£300 / week

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from £45 / night

(1) Excellent 

62

Villa rental in St. Ann's Bay with shared pool

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Gorgeous and affordable 3 bedroom Villa Ocho Rios St Ann Jamaica, perfect holiday getaway.  …see more

from £117 / night

£767 / week

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from £117 / night

(1) Excellent 

23

Holiday villa with swimming pool, golf nearby in Runaway Bay

Saint Ann Parish / Runaway Bay

4 8 2 nights min

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Whistling villa is one of the most affordable private villas with pool in Runaway Bay. Free access to public beach and shared private private beach for villa guests is just minutes away.Whistling villa is adjacentto Runaway bay's 18-hole, pga-quality golf course.  …see more

from £230 / night

£1609 / week

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from £230 / night

(1) Very Good 

26

Ocho Rios holiday studio rental

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Nearest beach 1 km
  • Swimming pool
  • Car not necessary
Pimento is a delightful spacious studio, one of three apartments overlooking the pool at Almond Tree Villa. Quiet upscale area, one of the nicest locations in Ocho Rios. Only 3 miles from the center of town and close to postcard perfect beaches. Lovely swimming pool and  …see more

from £40 / night

£250 - £315 / week

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from £40 / night

20

Holiday villa with swimming pool in White House

Westmoreland Parish / White House

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Palm Trees is an imposing hillside villa and guest house with a large private pool. It is located within it’s own grounds on the gated Anchor Estate on Jamaica’s South Coast. The villa is about 200 ft above sea level and 400 yards from the Beach. The views o  …see more

from £202 / night

£1412 - £1742 / week

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from £202 / night

(2) Excellent 

14

Ocho Rios holiday apartment let

Saint Ann Parish / Ocho Rios

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Chrisanns Beach Resort is a complex of beach front vacation apartments located four miles east of Ocho Rios that offer any holidaymaker an experience of Jamaica they could never forget. This enchanting property has its own private pool and beach with gazebo that overloo  …see more

from £76 / night

£550 - £560 / week

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from £76 / night

45

Holiday villa with swimming pool in Ocho Rios

Saint Ann Parish / Ocho Rios

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
A hidden gem located in Gibraltar Estate, surrounded by luscious greenery nestled in the hills, overlooking Oracabessa Bay, James Bond Beach and the world famous Golden Eye Resort. All rooms have private bathrooms AND private access! Oracabessa is the nearest village a  …see more

from £146 / night

£968 / week

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from £146 / night

(5) Very Good 

59

Holiday studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 3 Min stay varies

  • Studio
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
We offer additional extras such as Airport Transfer service Tour Guide service and extra Housekeeper service  …see more

from £80 / night

£560 - £896 / week

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from £80 / night

(5) Average 

32

Ski apartment to rent in Ocho Rios

Saint Ann Parish / Ocho Rios

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ski
FREE WIFIBeautiful beachfront apartment, villa, condo, vacation rental Ocho rios, Jamaica, cheap, affordable sea, sun, sunshine, fun, family, getaway<br />FREE WIFI, NETFLIX  …see more

from £72 / night

£503 / week

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from £72 / night

(10) Very Good 

25

Holiday studio with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
“Amazing” The apartment was wonderful!!! My partner and I felt comfortable inside the apartment which was fully equipped. It was definetly worth our time. Staff are also helpful and a delight to be around. You will not be disappointed upon your stay at  …see more

from £37 / night

£240 - £300 / week

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from £37 / 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 £2074 / night

£14517 - £25000 / week

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from £2074 / night

(2) Excellent 

33

Holiday townhouse rental

Westmoreland Parish / Negril

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This newly built two bedroom, two and a half bathroom townhouse, located on the cliffs, overlooking the ocean, is the perfect home away from home for your holiday, or stay in Negril, Jamaica. It easily sleeps 6 guests. The king bedroom can be separated into 2 twin bed  …see more

from £202 / night

£1412 - £2541 / week

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from £202 / night

37

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
This rental is in the fruited grounds off Villa Patiently Waiting, in the presitgious Mamme Bay Estate with 24 hours security. Located in Villa Patiently Waiting an established holiday rental This property consists of one large room with 2 double beds, TV, sound syste  …see more

from £53 / night

£323 - £380 / week

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from £53 / night

(3) Average 

32

Ocho Rios holiday apartment rental

Saint Ann Parish / Ocho Rios

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.2 km
  • Swimming pool
Hotel Features. This 2bed Penthouse apartment in a resort, features a pool attached to a swim-up bar and an eight-person jetted tub. Beach 7 minutes away.One king bed, two-person jetted Jacuz tub, vanity sink in master bedroom located in loft with peaked wood ceili  …see more

from £100 / night

£540 - £680 / week

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from £100 / night

(3) Very Good 

20

Holiday apartment with shared pool, golf nearby in Runaway Bay

Saint Ann Parish / Runaway Bay

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
This one bedroom apartment comes with pool,wifi air condition, ceiling fan,and all amenities for self catering.  …see more

from £53 / night

£367 / week

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from £53 / night

(2) Excellent 

33

Tower Isle holiday apartment rental

Saint Mary Parish / Tower Isle

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Swimming pool
Sea Palms E3 is a delightful holiday apartment in the gated holiday complex of Seas Palms along the coastline between the town of Ocho Rios and Tower Isle. Free Wi-Fi broadband internet is included. The 1st floor (American 2nd floor) apartment offers three bedrooms, two  …see more

from £150 / night

£900 / week

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from £150 / night

(3) Very Good 

35

Holiday apartment rental

Saint Ann Parish / Ocho Rios

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Fishermans point resort is a one Bedroom beach apartment (living room, bedroom, kitchen, bath room), beach 3 minutes walk, with ocean view, located in Ocho Rios Turtle Street Mahogany Beach. The spacious apartments sleeps 4, Cable TV. The living and dining area a  …see more

from £70 / night

£350 - £520 / week

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from £70 / night

(6) Excellent 

49

Ocho Rios holiday apartment rental

Saint Ann Parish / Ocho Rios

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
“Ms” Beautiful gem in a great location, close to shops, restaurants and entertainment. Superbly clean and modern. The listing is exactly as the description. Suzzane and Ms. Theresa are a great team. They made every effort to make my stay a pleasant and  …see more

from £75 / night

£525 - £630 / week

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from £75 / night

20

Holiday villa with swimming pool in Mammee Bay

Saint Ann Parish / Mammee Bay

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Swimming pool
Fully staffed villa, set in private tropical gardens of Mammee Bay Estate. You choose, wonderful pool or Caribbean sea!. Lots of outdoor spots for relaxing. Great sea views from the spacious roof terrace with lounging area and wet bar. 5mins walk to the private beach. P  …see more

from £350 / night

£2500 / week

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from £350 / night

(2) Very Good 

24

Holiday condo with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
A song can always be heard in Ocho Rios.. Ochee as the locals call it..soak up the magical vibes in one of the most varied tourist hot spots in the Caribbean..Ocho Rios has everything for the discerning traveler...beach is on your doorstep..eateries..clubs...sports bars  …see more

from £60 / night

£370 / week

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from £60 / night

(1) Excellent 

15

Holiday studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Ocho Rios, Jamaica  …see more

from £72 / night

£484 / week

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from £72 / night

21

Villa rental in Silver Sands with swimming pool

Trelawny Parish / Silver Sands

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
Perfect for a relaxing vacation. You will be well looked after by the villa staff - cook, housekeeper and gardener,. The villa is also well located - halfway between Montego Bay (airport 40 mins) and Ocho Rios - to make excursions to other attractions in Jamaica. <  …see more

from £323 / night

£2017 / week

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from £323 / night

13

Holiday studio in Ocho Rios

Saint Ann Parish / Ocho Rios

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask owner if suitable for children
Fully equipped ,centrally located Studio Apartment in Ocho Rios Jamaica ,white sand beach ,outdoor pool ,Safe and secure with 24 hr security ,cozy accommodation ,walking distance to restaurants ,entertainment ,shopping ,attractions  …see more

from £81 / night

£565 / week

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from £81 / night

(2) Excellent 

7

Holiday apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Nearest beach 1 km
  • Swimming pool
  • Child friendly
Beautiful newly decorated one bedroom Suite. This is your home away from home. You can walk easily to the town for restaurants and entertainment. But, you really have no need as there is restaurant and pool onsite. The beaches are a short drive or walk away and many  …see more

from £65 / night

£390 - £450 / week

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from £65 / night

(7) Very Good 

34

Holiday villa rental

Saint Ann Parish / Runaway Bay

5 7 3 nights min

  • 5 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 7 km
  • Swimming pool
  • Child friendly
“Mrs” Myself and 6 other friends stayed at this villa in June and all I have to say is it was a great holiday the lady who owns the villa treated us like family from day one and as for the villa its self it was really nice and clean. All the rooms are  …see more

from £180 / night

£1100 - £1310 / week

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from £180 / night