50 Best Jamaica Estates on Holiday Lettings - Villas

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2,520 Vacation rentals

(34) Very Good 

19

Vacation 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
This accommodation is a fully air-conditioned two bedroom apartment situated on the 3rd floor, you may rent this apartment as a one, or two bedroom see table rates. FREE INTERNET ACCESS The Apartment is tastefully furnished to a high standard, within the …see more

from $123 / night

$862 / week

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avg. 2 hours 50 minutes

from $123 / night

(6) Very Good 

27

Negril Vacation 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 $695 / night

$4,864 / week

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from $695 / night

(1) Very Good 

39

Vacation guest house in Lucea

Hanover Parish / Lucea

3 12 1 night min

  • 3 bedrooms
  • sleeps 12
  • 1 night min
  • Nearest beach 24 mi
  • Child friendly
  • Air conditioning
This high-spec holiday home has a unique location in rural Jamaica with breath-taking views, stunning wildlife, forest, mountains and a chance to experience the real Jamaica. It is in the undiscovered village of Bessie Baker - a 45 minute drive from Montego Bay airport …see more

from $39 / night

$274 / week

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Responds fast!
avg. 18 minutes

from $39 / night

(5) Very Good 

12

Vacation apartment with shared pool in Tower Isle

Saint Mary Parish / Tower Isle

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Delicately designed, one bedroom apartment to rent in, Ocho Rios Jamaica. Turtle Beach Towers, is in the midst of all that is Ocho Rios, with the local beach opposite the rear gateway to the complex and popular attractions including The Hard Rock Cafe, Island Village an …see more

from $94 / night

$550 - $601 / week

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from $94 / night

37

Vacation apartment rental

Saint Catherine Parish / Old Harbour

4 12 3 nights min

  • 4 bedrooms
  • sleeps 12
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Enjoy the private pool is safe gardens. with safe area for children. We have hot water and wifi The house is a family home on a 3 acre small holding. The rooms are large and cool. There is a large lounge and kitchen with numerous balconies and verandas to relax on. Th …see more

from $84 / night

$588 / week

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from $84 / night

(13) Very Good 

26

Vacation villa with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Complimentary excursion for stays over two weeks. Ideal location for Rebel Solute in January 2018. Situated on Jamaica's north coast, Gated twenty four hour security. Nearby attractions include: Dunn's River Falls, Dolphin Cove and Mystic Mountain. Onsite pool, gym, …see more

from $149 / night

$1,042 / week

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avg. 2 hours 1 minutes

from $149 / night

12

Vacation home rental

Portland Parish / Port Antonio

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Private garden
Beautiful 2 floor house with big staircase around the house. You have a lot of privacy. Comfortable, pretty rooms and abeautiful garden between 2 Rivers where you can chill and relax. Very near to town and Near to beach. Come and enjoy. And also every sightseeing like b …see more

from $25 / night

$150 - $1,550 / week

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from $25 / night

34

Vacation villa with shared pool in Priory

Saint Ann Parish / Priory

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
3 bedrooms and 2 bathroom free Wi-Fi air con in all rooms constructed on the grounds of the historic green zone Richmond Estate comfortable, designed and beautiful landscaped villa in a gated community just 50mins to Montego bay and 15mins to Ocho Rios, with only10mins …see more

from $181 / night

$1,231 / week

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from $181 / night

(1) Excellent 

18

Vacation apartment rental

Kingston Parish / Kingston

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Car not necessary
  • Air conditioning
  • Private garden
Its a 2 level Apartment with bedroom upstairs. Private living room in the lower area. Private sitting area on lower level with private entrance. Kitchen and bathroom upstairs with a balcony nestled in the trees. Quiet and secure neighborhood. 24 Hour security service. C …see more

from $38 / night

$265 / week

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from $38 / night

(5) Good 

33

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
Beautiful Beachfront (Newly Updated Floor & Kitchen) 1B/1B Condo in Ocho Rios, Jamaica. Centrally located on the White Sand Ocho Rios Bay Beach. By the Cruise Ship Pier in Fishermans Point. With FREE WIFI & NETFLIX. Fully Equipped Kitchen with stove and oven, microwave, …see more

from $109 / night

$762 / week

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from $109 / night

32

Vacation condo with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
This accommodation is ideally located in close proximity to local attractions and amenities. Located on the ground floor, the apartment is very accessible and has its own garden area. Fresh bath towels and utensils are provided. The space This fully furnished, ground f …see more

from $64 / night

$445 / week

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from $64 / night

7

Vacation home in Rose Hall

Montego Bay / Rose Hall

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 2 mi
  • Child friendly
  • Air conditioning
This property is a two bedroom cozy house, home away from home that is tastefully decorated. It is situated in a scenic community of Rosehall, Montego Bay. This beautiful home has seaview scenery, and is just 20 minutes from the airport. This house is a open plan wit …see more

from $80 / night

$558 / week

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from $80 / night

(5) Excellent 

24

Vacation villa in Mammee Bay

Saint Ann Parish / Mammee Bay

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Morning Glory Villas occupies 1.5 acres of beautifully manicured tropical garden is just a stroll (2 minute) from the beautiful private Mammee Bay beach with its powdery soft sands and beach club. This large property "Over the Moon" and "Sanora" offers 2 or 4 be …see more

from $152 / night

$1,064 / week

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from $152 / night

(4) Very Good 

8

Vacation home in Boscobel

Saint Mary Parish / Boscobel

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
Modern Large cool onsuite rooms with Amercian windjammer fans. . A relaxing through lounge lei, dining room and modern fitted kitchen. If you book all 3 rooms you will have the entire downstairs to yourself. You have a view of the sea from the front of house and lush g …see more

from $44 / night

$288 / week

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from $44 / night

14

Vacation condo with shared pool, golf nearby in Rose Hall

Montego Bay / Rose Hall

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Marriott SeaCastles Penthouse is a modern luxury condo overlooking the ocean. The property is peaceful and perfect for a relaxing vacation away from all the hustle and bustle found on many tourist resorts in the area. Our guests have the option of enjoying quiet relax …see more

from $171 / night

$1,363 / week

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Responds fast!
avg. 33 minutes

from $171 / night

(2) Very Good 

35

Mammee Bay Vacation villa rental

Saint Ann Parish / Mammee Bay

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
With the beauty of nature as its backdrop, Island Treasure Villas offer its guests a tranquil island escape that provides all the comfort of home with the flair and amenities of a 5 star hotel. A stay at this luxurious 3 bed, 2 baths villa provide guests with access to …see more

from $138 / night

$962 / week

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Responds fast!
avg. 1 hour 17 minutes

from $138 / night

(3) Excellent 

21

Vacation villa in Runaway Bay

Saint Ann Parish / Runaway Bay

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Child friendly
This two bedroom, sweet spot gem has spectacle views of the mountain on one side and the ocean on the other. There’s a gentle breeze with a large patio set in a tropical garden; the front lawn was used in the filming of the 2016 Season 20 finale of the Bachelor with Ben …see more

from $235 / night

$1,643 / week

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from $235 / night

(7) Excellent 

29

Vacation home in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
Located along Jamaica's scenic Northern Coast, Richmond St. Ann is an easy one hours drive from the Sangster International Airport in Montego Bay. Near by attractions: * Dunn's River * Mystic Mountains * Dolphin Cove * Cranbrook Flower Forest * Seville Great House * …see more

from $207 / night

$1,443 / week

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from $207 / night

(3) Very Good 

26

Vacation villa in Runaway Bay

Saint Ann Parish / Runaway Bay

4 6 3 nights min

  • 4 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Topaz Villa is situated in the quiet residential area of Cardiff Hall in Runaway Bay, St Ann's. The Villa boasts a large private swimming pool overlooking the golf club. The bedrooms are large and airy with ensuite and fans. There is a large lounge/diner for inside din …see more

from $87 / night

$522 / week

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from $87 / night

(12) Excellent 

54

Treasure Beach Vacation home rental

Saint Elizabeth Parish / Treasure Beach

5 8 2 nights min

  • 5 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Child friendly
The White House is located in Rose Hall St. Elizabeth, Jamaica. This holiday home is set 5km from Junction/Southfield. Lovers leap is 6km and 11km from Treasure beach. Be sure to check out the exclusive Pelican Bar and YS Falls as well as The Black River Safari Tours. T …see more

from $145 / night

$760 / week

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from $145 / night

(20) Very Good 

37

Vacation 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 mi
  • Swimming pool
Tamarind Apartment is one of three lovely studios sharing the grounds and swimming pool with Pimento and Cinnamon apartments together with Almond Tree Villa. Only 10 mins from Ocho Rios centre and close to some beautiful beaches. Tamarind is on the ground floor below P …see more

from $55 / night

$377 - $493 / week

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avg. 1 hour 55 minutes

from $55 / night

20

Vacation b&b rental

Saint Thomas Parish / Yallahs

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child friendly
Ready to try something different? Need a quiet haven? Come to Jenny's Retreat the farm house on Black's Farm in Yallahs. You and your family and friends will always find a warm welcome waiting for you. You can watch the sun rise and set from our panoramic views, while s …see more

from $35 / night

$241 / week

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from $35 / night

(6) Very Good 

19

St James, Montego Bay Vacation 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 mi
  • Swimming pool
WELL APPOINTED LUXURY 1BEDROOM APARTMENT ON JAMAICA'S GOLD COAST, ROSE HALL IS WITHIN 5 MINUTES FROM MONTEGO BAY AIRPORT. AMENITES INCL GRANITE COUNTER TOPS IN KITCHEN & BATHROOMS, BREATHTAKING VIEW FROM BALCONIES OF THE CARIBBEAN SEA/POOL AREA, OTHER ON PROPERTY AMENIT …see more

from $172 / night

$1,203 / week

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from $172 / night

(12) Very Good 

41

Runaway Bay Vacation apartment rental

Saint Ann Parish / Runaway Bay

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Cozy Tropical Paradise Vacation Apt! Spend the summer vacation in paradise, or escape the cold winter at Dreamy Haven, where it is sunny all year round, and sunbathing on white sand beaches sipping margaritas in the middle of winter is the norm. Experience home away fro …see more

from $69 / night

$481 / week

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from $69 / night

(2) Excellent 

24

Runaway Bay Vacation villa rental

Saint Ann Parish / Runaway Bay

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
  • Private garden
It doesn’t get much better than this! Our new private 6000 square foot villa has been meticulously built and designed to ensure you have the best of the best with air conditioning in all of our sleeping areas. Boasting two full size bedrooms each with queen beds and one …see more

from $343 / night

$2,290 / week

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Responds fast!
avg. 1 hour 41 minutes

from $343 / night

(2) Very Good 

19

Runaway Bay Vacation guest house rental

Saint Ann Parish / Runaway Bay

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Richmond Estate Is Located On A Northern Coastal Property near the Resort Town Of St Anns Bay. It Is nestled between Runaway Bay and Priory, With A Breathtaking View Of The Caribbean Sea. Richmond St. Ann is an easy 50-minute drive from the Sangster International Ai …see more

from $160 / night

$1,216 - $4,459 / week

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from $160 / night

14

Vacation bungalow rental

Saint Ann Parish / Runaway Bay

3 4 3 nights min

  • 3 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
Householder with special breakfast service in a secure and clean accommodation. It is for very favourable cost and a central start point for many activities. Support from natives will be offered. Beach is 10 minutes walking away so as shops and bus stop. Diving school a …see more

from $33 / night

$228 - $911 / week

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from $33 / night

(2) Excellent 

27

Duncans Vacation villa rental

Trelawny Parish / Duncans

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Location: Things have changed at Yellow Canary Villa, the villa has just had a facelift with a cheerful entrance to the property. A double bedroom has been renovated and added, with a modern fresh decor. All bedrooms have been redecorated adding charm and colour to t …see more

from $172 / night

$1,203 - $1,323 / week

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from $172 / night

(1) Very Good 

6

Vacation apartment in Kingston

Kingston Parish / Kingston

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child friendly
  • Air conditioning
  • Private garden
Malia's Penthouse is fully furnished, has an amazing view of New Kingston and is within walking distance of Emancipation Park, Knutsford Blvd and Knutsford Express. Amenities include, King size bed, 3 piece sofa, a full kitchen, living room and bathroom. The apartment i …see more

from $87 / night

$579 / week

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Responds fast!
avg. 1 hour 59 minutes

from $87 / night

(1) Excellent 

38

Vacation home in Mandeville

Manchester Parish / Mandeville

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Nearest beach 24 mi
  • Child friendly
  • Private garden
A rustic space for you to unwind & rejuvenate in total tranquility & privacy. To quiet your mind, open your heart, and allow your body temple to return to a more relaxed state. Reconnect with the natural rhythms of nature and allow yourself this space to transform, a …see more

from $44 / night

$261 / week

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from $44 / night

15

Vacation apartment rental

Portland Parish / Buff Bay

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
Ray & Perry welcome you to The Windsor Retreat. A self catering luxury Guesthouse located in Portland on the Northeast coast side of Jamaica. The parish of Portland is well visited and borders the Blue Mountains National Park. There is plenty to explore in the surroundi …see more

from $51 / night

$353 / week

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from $51 / night

16

Vacation home with shared pool in St. Ann's Bay

Saint Ann Parish / St. Ann's Bay

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Close to the world famous attractions of Dunn's River and Mystic Mountain is this peaceful Villa in a gated community with 24 hour security. Ideal for individuals and families looking for a unique experience of the Caribbean in a relaxed, comfortable, secure environmen …see more

from $90 / night

$579 - $1,072 / week

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avg. 34 minutes

from $90 / night

23

Vacation apartment with shared pool in Ocho Rios

Saint Ann Parish / Ocho Rios

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Car not necessary
Columbus Heights in Ocho Rios is your own private luxury hillside condo overlooking the beautiful Bay and panoramic city views. Centrally located a solacios view and a very cooL natural sea breeze that hits you . Just walking distance to all the attractions of Ocho …see more

from $115 / night

$630 / week

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avg. 2 hours 0 minutes

from $115 / night

(7) Excellent 

15

Apartment rental in Ocho Rios with shared pool

Saint Ann Parish / Ocho Rios

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
This luxurious apartment comes with a super king size bed and 2 day beds which can accommodate up to 4 people comfortably; ideal for couples, families or a group of friends. You are moments from a sandy beach as well as the swimming pool, and the property it set within …see more

from $115 / night

$802 / week

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avg. 2 hours 6 minutes

from $115 / night

64

Vacation apartment rental

Kingston Parish / Kingston

2 12 3 nights min

  • 2 bedrooms
  • sleeps 12
  • 3 nights min
  • Child friendly
  • Air conditioning
A quiet retreat on Montcalm Drive over looking Havendale, St, Andrew is away from it all, yet only a 10 minutes from the heart of New Kingston and Half Way Tree. This is unique alternative vacation attraction. It gives easy access to the city, yet stands a world apart, …see more

from $138 / night

$745 - $1,706 / week

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from $138 / night

39

Vacation villa with golf nearby in Jamaica

Montego Bay / Rose Hall

2 50 1 night min

  • 2 bedrooms
  • sleeps 50
  • 1 night min
  • Child friendly
HUMMINGBIRD HALL JAMAICA has been hosting multi-award-winning weddings + events for over 10 years. We're a private mansion-villa nestled on an exclusive 5,000 acre private estate in Montego Bay. Our weddings have been featured in numerous blogs (including Style Me Prett …see more

from $1,718 / night

$12,023 / week

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from $1,718 / night

(11) Very Good 

22

Vacation villa in Treasure Beach

Saint Elizabeth Parish / Treasure Beach

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Modern spacious fully furnished 2 double bedrooms (sleeps up to six) villa to rent in the town of Junction, St Elizabeth, in Jamaica's Countryside on the South Coast of the Island. Light bright and airy. Located on a private hill with breath taking views all around. …see more

from $68 / night

$477 - $963 / week

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Responds fast!
avg. 1 hour 38 minutes

from $68 / night

(9) Excellent 

Certificate of Excellence

14

Vacation apartment in Tower Isle

Saint Mary Parish / Tower Isle

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 1 mi
  • Swimming pool
  • Air conditioning
Comfortable one bedroom apartment. Fully air conditioned and overlooking the warm waters of the aquamarine Caribbean Sea. Direct access to the beach or if you prefer ,a large swimming pool. Other amenities include water sports,Golf courses.boating and fishing. Within …see more

Certificate of Excellence

from $116 / night

$579 / week

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Responds fast!
avg. 1 hour 24 minutes

from $116 / night

(5) Excellent 

22

Vacation home rental

Kingston Parish / Kingston

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly
Get away from the hustle and bustle of modern day life.. Stay in a tranquil setting of sea breeze and foot hills Bec's Place is the best holiday rental property on the market for this price.. 1, 2 or 3 bedrooms available from $50 per night. The whole house is normally …see more

from $81 / night

$550 - $951 / week

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from $81 / night

(5) Excellent 

20

Vacation villa with swimming pool, golf nearby in Runaway Bay

Saint Ann Parish / Runaway Bay

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
Villa Pegasus is a stunning villa which can be found in the Upscale area of Cardiff Hall in the sleepy resort town of Runaway Bay. The property boasts 4 large bedrooms, 3 large reception rooms, a freeform swimming poo and a summer house (gazebo) with all the mod-cons o …see more

from $232 / night

$1,274 / week

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from $232 / night

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