Vacation Rentals with Pool in Jamaica

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Filtering by: Swimming pool

1,342 vacation rentals

(21) Excellent 

33

Cozy Cove - 5 Bdrm Villa w/Pool, Gated Community

St. James Parish / Montego Bay

Montego Bay villa

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool
“Jamaican Paradise!” Cannot truly express how fabulous this trip has been, Jaime from the very beginning has been gracious, warm and very accommodating. Her rental has been nothing but spectacular! It is exactly and more than what the pictures convey.
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Price per night from

$901

Price per night from

$901

(2) Excellent 

34

Seven Seas

Jamaica / St. Ann Parish

Saint Ann Parish villa

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Fantastic!” What a fantastic time we all just had at Seven Seas! Our whole family enjoyed the trip from young to old. Not only was the estate gorgeous, but activities abounded on the property. The snorkeling we were able to enjoy in our own backyard w
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Price per night from

$1,001

Price per night from

$1,001

(1) Very Good 

13

Sunrise Supreme

St. Ann Parish / Runaway Bay

Runaway Bay apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$59

Price per night from

$59

(4) Excellent 

22

Sugar Bay - Jamaica

St. Ann Parish / Discovery Bay

Discovery Bay villa

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Sugar Bay” I have been to Sugar Bay twice with my all girls tennis and bridge group. Sugar Bay is a gorgeous, upscale villa where you feel right at home! Reds, the wonderful houseman, is a delight and makes sure you have everything you need. The cook
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Price per night from

$2,035

Price per night from

$2,035

(8) Excellent 

15

Pavilion Villa

Jamaica / St. James Parish

Saint James Parish villa

6 14 min stay varies

  • 6 bedrooms
  • sleeps 14
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,216

Price per night from

$1,216

13

The Marley manor

Kingston Parish / Kingston

Kingston apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Air conditioning

Price per night from

$126

Price per night from

$126

(1) Excellent 

37

Spanish Cove

Jamaica / St. Ann Parish

Saint Ann Parish villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$881

Price per night from

$881

27

Tangerine Villa, Exclusive With Full Staff, Members Beach, Fabulous Ocean Views

St. Ann Parish / Runaway Bay

Runaway Bay villa

7 16 1 night min

  • 7 bedrooms
  • sleeps 16
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$997

Price per night from

$997

(31) Excellent 

35

Signature's 21 @ the Country Club

Kingston Parish / Kingston

Kingston apartment

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Signature's 21 @ the Country Club was the icing on the cake for my Simply Elegant Wedding Celebration.” The owner and caretaker of Signature's 21 @ the Country Club were both patient, kind and accommodating to our needs from booking to departure. I r
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Price per night from

$79

Responds fast!
avg. 1 hour 19 minutes

Price per night from

$79

34

Bolt House

Jamaica / St. Mary Parish

Saint Mary Parish villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$2,403

Price per night from

$2,403

(5) Very Good 

14

Shotover Gardens Estate - cottage with pool

Portland Parish / Port Antonio

Port Antonio log cabin

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 16 mi
  • Swimming pool
  • Child Friendly

Price per night from

$58

Price per night from

$58

(5) Very Good 

14

Beach Studio with European Country Charm 15 Minute

Montego Bay / Rose Hall

Rose Hall apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$81

Price per night from

$81

(2) Very Good 

19

Sun Kissed - Rio Bueno 4 Bedroom Beachfront

St. Ann Parish / Discovery Bay

Discovery Bay house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$787

Price per night from

$787

(15) Very Good 

Certificate of Excellence

20

Villa @ Richmond Estate with Private Beach

St. Ann Parish / Priory

Priory house

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool

Certificate of Excellence

Price per night from

$184

Responds fast!
avg. 3 hours 6 minutes

Price per night from

$184

(9) Excellent 

35

Grande Haven Villa - Oracabessa, St Mary Jamaica

St. Mary Parish / Oracabessa

Oracabessa villa

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$451

Responds fast!
avg. 3 hours 41 minutes

Price per night from

$451

(2) Excellent 

35

The Artiste's Boutique by Bohemian Lodges

Kingston Parish / Kingston

Kingston house

5 11 min stay varies

  • 5 bedrooms
  • sleeps 11
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$212

Responds fast!
avg. 3 hours 52 minutes

Price per night from

$212

14

Jamaica Luxury near the Beach

St. Andrew Parish / Bull Bay

Bull Bay house

11 34 1 night min

  • 11 bedrooms
  • sleeps 34
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$86

Responds fast!
avg. 44 minutes

Price per night from

$86

(16) Excellent 

19

Sol Mar Villa

Trelawny Parish / Silver Sands

Silver Sands villa

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$296

Responds fast!
avg. 1 hour 13 minutes

Price per night from

$296

17

Chilling on the Estate

Kingston Parish / Kingston

Kingston house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$80

Price per night from

$80

15

Valhalla Villa

St. Mary Parish / Boscobel

Boscobel villa

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

Price per night from

$453

Price per night from

$453

(2) Excellent 

31

Selah - Runaway Bay 4 Bedroom Beachfront

St. Ann Parish / Runaway Bay

Runaway Bay house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$1,430

Price per night from

$1,430

(1) Very Good 

42

Contemporay Central Spacious 2bdrm/2bth/Pool/Toni Comfort Suites

Kingston Parish / Kingston

Kingston apartment

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$161

Responds fast!
avg. 2 hours 6 minutes

Price per night from

$161

(1) Excellent 

22

Sea Haven

St. Ann Parish / Discovery Bay

Discovery Bay villa

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“We fell in love with all of it” This message just to thank you for the wonderfull holiday we had at Sea Haven. Your choice was the absolute perfect one. We have found such a peace in that house that it didn\'t seem real. The whole week was like walkin
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Price per night from

$644

Price per night from

$644

33

Private Beach Condo, Pool, Jacuzzi, Private Chef and Housekeeping

St. Ann Parish / Ocho Rios

Ocho Rios apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 0.5 mi
  • Swimming pool
  • Air conditioning

Price per night from

$172

Price per night from

$172

(1) Excellent 

19

4 Bedroom Villa Across from Beach in Bluefields.

Westmoreland Parish / Bluefields

Bluefields house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.3 mi
  • Swimming pool

Price per night from

$70

Price per night from

$70

(2) Excellent 

25

Seagrapes - Jamaica

St. Ann Parish / Discovery Bay

Discovery Bay villa

6 10 min stay varies

  • 6 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Dream Vacation” We had a marvelous, fun-filled, and restful vacation in at Sea Grapes Everyone in our party was a little bit heartbroken when we had to go home I think! The accomadations were all that we had hoped for and the property and views were b
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Price per night from

$1,088

Price per night from

$1,088

13

Sundance - Tryall Club

Montego Bay / Hopewell

Hopewell villa

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Swimming pool

Price per night from

$3,147

Price per night from

$3,147

14

Karma Bay - Tryall Club

Montego Bay / Hopewell

Hopewell villa

6 12 min stay varies

  • 6 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Air conditioning

Price per night from

$2,217

Price per night from

$2,217

(1) Excellent 

11

Blissfull Bay View (Discovery Bay)

St. Ann Parish / Discovery Bay

Discovery Bay villa

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$135

Price per night from

$135

(2) Excellent 

17

Siesta

St. Ann Parish / Runaway Bay

Runaway Bay villa

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“"No problems..Irie!"” A large group of friends and myself have stayed here at Siesta several times. Although I have not been back since the late 80's, others of our group continue to go there just about every year. What I can say is that my time spent
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Price per night from

$830

Price per night from

$830

(14) Excellent 

14

Riviera Wellness Retreat, Mammee Bay villa, JM

St. Ann Parish / Mammee Bay

Mammee Bay villa

3 6 1 night min

  • 3 bedrooms
  • sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Riviera Villa is like living in paradise with beautiful people.” My party and I have been visiting our holiday home as we like to call it for the last 13 years. In recent years we have gone twice. The staff have become apart of our own family. Need l
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Price per night from

$253

Price per night from

$253

(35) Excellent 

44

Shakti Home-The villa you've been dreaming about

Saint Elizabeth Parish / Treasure Beach

Treasure Beach villa

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“The best the best the best” We traveled with our 4 children and my mother in law to Treasure Beach for the week. It was absolutely Phenomenal. It is perfectly situated On the beach with two magnificent beach coves 20 steps from the door. Our kids were
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Price per night from

$501

Price per night from

$501

(8) Excellent 

14

Coral Cove Cottage - Linga Awile

St. Ann Parish / Discovery Bay

Discovery Bay villa

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Perfect Vacation” What a fabulous time we all had at Coral Cove! We arrived and were welcomed by the whole staff and made to feel at home right away. The villa was absolutely beautiful. I have stayed at many different villas over the years but the ser
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Price per night from

$430

Price per night from

$430

(1) Excellent 

15

Shotover Gardens Estate - cabin with pool

Portland Parish / Port Antonio

Port Antonio log cabin

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 16 mi
  • Swimming pool
  • Child Friendly

Price per night from

$35

Price per night from

$35

(9) Excellent 

10

77 West Boutique Hotel (Cottage 1 of 5)

Saint Elizabeth Parish / Treasure Beach

Treasure Beach cottage

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$131

Price per night from

$131

(88) Excellent 

28

Award-winning villa with private beach and pool

Westmoreland Parish / White House

White House villa

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Wow!” We stayed as a family of 6 adults in September & had the time of our life! Andy the owner is really easy to do business with & communicates well. The location is superb with its own small private beach as well as an infinity pool. The grounds ar
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Price per night from

$626

Price per night from

$626

(14) Very Good 

57

Come Chill at Runaway Bays Silver Lime Villa 4Bed/4.5Bath/Pool/5min to Beach

St. Ann Parish / Runaway Bay

Runaway Bay house

4 10 3 nights min

  • 4 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
“Try it! You won't regret it.” My family and I had a great stay at Silver Lime Villa. There were 3 of us, two adults, and one ten years old. We were there for three weeks. The rooms had queen size beds, and the master bedroom had a full-size sofa bed.
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Price per night from

$441

Responds fast!
avg. 1 hour 6 minutes

Price per night from

$441

20

Twin Palms - Tryall Club

Montego Bay / Hopewell

Hopewell villa

7 14 7 nights min

  • 7 bedrooms
  • sleeps 14
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$3,511

Price per night from

$3,511