Search 105,200+ Vacation Rentals

Jamaica Estates & Villas with Swimming Pool - 633 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

633 Vacation rentals

Filters applied: Swimming pool

(4)

1 / 12

Port Maria Villa

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Our first visit to Jamaica and we could not have hoped for a more perfect, comfortable place to stay than at the villa at Cabarita Outlook! Cutty, our driver and our man of all needs, and Sharon our fabulous cook were the frosting on the cake. We...”
- Review left on 03/13/2017

$355

Excellent (4 reviews)

Book

from $355 / night

(1)

1 / 29

Montego Bay Villa

  • 22
  • 36
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$90

Excellent (1 reviews)

Inquire

from $90 / night

(4)

1 / 26

St. Ann's Bay House

  • 4
  • 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$150

Excellent (4 reviews)

Book

from $150 / night

1 / 22

Discovery Bay Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$1935

Inquire

from $1935 / night

1 / 24

Tower Isle Apartment

  • 1
  • 3
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$98

Book

from $98 / night

1 / 12

Ocho Rios Villa

  • 6
  • 18
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$75

Book

from $75 / night

1 / 23

Montego Bay Villa

  • 22
  • 36
  • 1 night min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $90 / night

(8)

1 / 15

Montego Bay Townhouse

  • 2
  • 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“It was a nice stay at a really great location in Montego Bay. It was close to my family's house but also super close to hip strip and beaches and fun. Really nice place and the owner was helpful. The security at the gate can be annoying but you do...”
- Review left on 01/10/2017

$140

Excellent (8 reviews)

Inquire

from $140 / night

(1)

1 / 19

Runaway Bay Apartment

  • 2
  • 5
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$135

Excellent (1 reviews)

Book

from $135 / night

(7)

1 / 24

Ocho Rios House

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

$135

Very Good (7 reviews)

Book

from $135 / night

(34)

1 / 24

Montego Bay Apartment

  • 1
  • 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We stayed at the MBC last summer. Our condo was just as comfortable as home! In fact, we enjoyed staying there, we looked forward to returning to it's quiet, comfortable, and cozy haven after a day out and about sightseeing. Our stay in Montego Bay...”
- Review left on 09/05/2009

$90

Very Good (34 reviews)

Inquire

from $90 / night

1 / 13

Montego Bay Villa

  • 6
  • 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $118 / night

1 / 7

Montego Bay Villa

  • 4
  • 10
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $430 / night

1 / 19

Rose Hall House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1050

Inquire

from $1050 / night

1 / 54

Duncans House

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

from $500 / night

1 / 28

Montego Bay House

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $893 / night

1 / 24

Saint Mary Parish Villa

  • 9
  • 18
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$3429

Inquire

from $3429 / night

(1)

1 / 36

Wiltshire House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$855

Excellent (1 reviews)

Inquire

from $855 / night

1 / 44

Rose Hall Villa

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1543

Inquire

from $1543 / night

1 / 34

Ocho Rios House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $642 / night

1 / 22

Montego Bay Villa

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $858 / night

1 / 31

Saint James Parish Villa

  • 7
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1760

Inquire

from $1760 / night

1 / 1

Ocho Rios House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $861 / night

1 / 55

Mammee Bay House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1000

Inquire

from $1000 / night

1 / 23

Montego Bay Villa

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $929 / night

1 / 54

Duncans House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from $650 / night

(1)

1 / 20

Discovery Bay Villa

  • 3
  • 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$400

Excellent (1 reviews)

Inquire

from $400 / night

1 / 42

Ocho Rios Villa

  • 8
  • 18
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$8679

Inquire

from $8679 / night

1 / 25

Ocho Rios House

  • 6
  • 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$2000

Inquire

from $2000 / night

1 / 21

Ocho Rios Villa

  • 6
  • 16
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$2000

Inquire

from $2000 / night

(1)

1 / 34

Discovery Bay House

  • 5
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$985

Excellent (1 reviews)

Inquire

from $985 / night

1 / 32

Runaway Bay Villa

  • 8
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1929

Inquire

from $1929 / night

1 / 39

Rose Hall House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1550

Inquire

from $1550 / night

(1)

1 / 29

Runaway Bay House

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$880

Excellent (1 reviews)

Inquire

from $880 / night

(6)

1 / 38

Ironshore House

  • 8
  • 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1000

Excellent (6 reviews)

Inquire

from $1000 / night

1 / 20

Sandy Bay House

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

from $714 / night

1 / 25

Silver Sands House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly

from $465 / night

1 / 32

Hopewell House

  • 7
  • 14
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2727

Inquire

from $2727 / night

1 / 32

Hopewell House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$2727

Inquire

from $2727 / night

(1)

1 / 20

Ocho Rios House

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

$570

Excellent (1 reviews)

Inquire

from $570 / night