Middleton Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

490 Houses

(4) Excellent 

5

Reggae Legends Villa - Skyline Drive (Villa 1)

St. Andrew Parish / Middleton

Middleton villa

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly

Price per night from

$570

Price per night from

$570

10

Jacks Hill Tropical Arcadia-Twin Room with Bathroom

St. Andrew Parish / Middleton

Middleton house

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$63

Price per night from

$63

10

Jacks Hill Tropical Arcadia-Double Room with Bathroom

St. Andrew Parish / Middleton

Middleton house

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Child Friendly
  • Private garden

Price per night from

$96

Price per night from

$96

10

Jacks Hill Tropical Arcadia - TWO Interconnected Bedrooms with Bathroom & Balcon

St. Andrew Parish / Middleton

Middleton guest house

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Pet Friendly
  • Private garden

Price per night from

$140

Price per night from

$140

Great rentals within 20 miles that match your search

Distance approx 2.78 km from Middleton Show on Map

14

Camelia´s Private Room

Kingston Parish / Kingston

Kingston apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Nearest beach 40 mi
  • Child Friendly
  • Car not necessary

Price per night from

$35

Responds fast!
avg. 1 hour 22 minutes

Price per night from

$35

Distance approx 4.84 km from Middleton Show on Map

(3) Excellent 

11

City Central Apartment

Kingston Parish / Kingston

Kingston apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Air conditioning

Price per night from

$65

Responds fast!
avg. 2 hours 45 minutes

Price per night from

$65

Distance approx 3.21 km from Middleton Show on Map

(12) Excellent 

19

Kozy Korner Studio Apartment, Home Away From Home

Kingston Parish / Kingston

Kingston apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Nearest beach 26 mi
  • Air conditioning
  • Private garden
“Excellent Accommodations!!!! The Best in Kingston!!!!” We absolutely enjoyed our stay at Kozy Korners! The apartment was just as described. It was perfect for me and my husband. The descriptions and pictures are a perfect testament to the propert
…see more

Price per night from

$60

Price per night from

$60

Distance approx 12.47 km from Middleton

(11) Excellent 

Certificate of Excellence

34

The Caymanas Villa

Saint Catherine Parish / Portmore

Portmore house

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 6 mi
  • Swimming pool
  • Child Friendly

Certificate of Excellence

Price per night from

$80

Responds fast!
avg. 1 hour 10 minutes

Price per night from

$80

Distance approx 4.38 km from Middleton Show on Map

34

A spacious property awaits you!

Kingston Parish / Kingston

Kingston apartment

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly

Price per night from

$70

Price per night from

$70

Distance approx 6.36 km from Middleton Show on Map

28

Lovely Jamaican Get-Away

Kingston Parish / Kingston

Kingston house

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 20 mi
  • Child Friendly
  • Air conditioning

Price per night from

$160

Price per night from

$160

Distance approx 7.15 km from Middleton Show on Map

(10) Excellent 

17

KIMOCHI Escape the rush! 20 min fr Kingston center

Kingston Parish / Kingston

Kingston apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Child Friendly
“Paradise” I recently stayed here for 2 nights at the end of a whirlwind working holiday. Panoramic views -clean -stunning decor -friendly and helpful. The best way to wind down before a 30 hour flight back home. Perfect to relax and to be creative too
…see more

Price per night from

$130

Price per night from

$130

Distance approx 5.18 km from Middleton Show on Map

10

Comfortable Suite 2

Kingston Parish / Kingston

Kingston apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 16 mi
  • Child Friendly
  • Car not necessary

Price per night from

$65

Price per night from

$65

Distance approx 6.36 km from Middleton Show on Map

(1) Very Good 

25

Lovely Jamaican Get-Away

Kingston Parish / Kingston

Kingston apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 20 mi
  • Child Friendly
  • Air conditioning

Price per night from

$140

Price per night from

$140

Distance approx 16.48 km from Middleton

(4) Excellent 

25

Pearl Ocean Villa

Portland Parish / Port Antonio

Port Antonio guest house

6 8 1 night min

  • 6 bedrooms
  • sleeps 8
  • 1 night min
  • Nearest beach 1 mi
  • Child Friendly
  • Car not necessary

Price per night from

$201

Responds fast!
avg. 2 hours 53 minutes

Price per night from

$201

Distance approx 3.13 km from Middleton Show on Map

(3) Excellent 

30

The Inn at 6

Kingston Parish / Kingston

Kingston townhouse

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$326

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$326

Distance approx 2.71 km from Middleton Show on Map

8

Paradise

Kingston Parish / Kingston

Kingston house

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$70

Price per night from

$70

Distance approx 13.93 km from Middleton

(1) Very Good 

23

SAFE COZY 1BR (Entire)HOUSE IN FULLY SECURED GATED CARIBBEAN ESTATE. Portmore!!

Saint Catherine Parish / Portmore

Portmore house

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$60

Price per night from

$60

Distance approx 12.61 km from Middleton

(3) Excellent 

16

The Greens at Caymanas (Modern 3 bdrm 2 bth home)

Kingston Parish / Kingston

Kingston house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 17 mi
  • Swimming pool
  • Child Friendly
“Trip” Wonderful, property. The owner, and host very helpfully and available for all needs. Will definitely book in future.
…see more

Price per night from

$180

Responds fast!
avg. 3 hours 7 minutes

Price per night from

$180

Distance approx 4.9 km from Middleton Show on Map

8

CeeJay's Apartment

Kingston Parish / Kingston

Kingston apartment

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Air conditioning

Price per night from

$90

Responds fast!
avg. 2 hours 29 minutes

Price per night from

$90

Distance approx 2.76 km from Middleton Show on Map

17

Olive's Nest

Kingston Parish / Kingston

Kingston house

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 24 mi
  • Child Friendly
  • Car not necessary

Price per night from

$60

Responds fast!
avg. 6 minutes

Price per night from

$60

Distance approx 4.89 km from Middleton Show on Map

38

Gated Apartment

Kingston Parish / Kingston

Kingston apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$80

Responds fast!
avg. 1 hour 14 minutes

Price per night from

$80

Distance approx 15.5 km from Middleton

(1)  

20

Hellshire Villas

Portmore / Hellshire

Portmore villa

2 2 1 night min

  • 2 bedrooms
  • sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Private garden

Price per night from

$40

Responds fast!
avg. 1 hour 15 minutes

Price per night from

$40

Distance approx 3.19 km from Middleton Show on Map

16

The Inn at 6 Deluxe

Kingston Parish / Kingston

Kingston room

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$140

Responds fast!
avg. 1 hour 21 minutes

Price per night from

$140

Distance approx 18.05 km from Middleton

43

JAZZY Glen's Place

St. Ann Parish / St. Ann's Bay

St. Ann's Bay house

4 6 3 nights min

  • 4 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 20 mi
  • Suitable for children age 5+
  • Ask about pets

Price per night from

$65

Price per night from

$65

Distance approx 4.77 km from Middleton Show on Map

34

New Kingston Guest Apt at Abbey

Kingston Parish / Kingston

Kingston apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$99

Price per night from

$99

Distance approx 12.41 km from Middleton

9

Modern Vacation Rental Awaits You

Saint Catherine Parish / Portmore

Portmore house

2 4 3 nights min

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

Price per night from

$90

Price per night from

$90

Distance approx 6.6 km from Middleton Show on Map

9

One32 Guest House Bejeweled - Apartment 4

Kingston Parish / Kingston

Kingston guest house

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 27 mi
  • Swimming pool
  • Child Friendly

Price per night from

$90

Price per night from

$90

Distance approx 15.73 km from Middleton

5

Villa Juanita - 2 Bedroom Suite #2

Portland Parish / Port Antonio

Port Antonio hotel apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Child Friendly

Price per night from

$696

Responds fast!
avg. 48 minutes

Price per night from

$696

Distance approx 5.26 km from Middleton Show on Map

4

Bella Vista Retreat, The Dorchester /Bedroom #1

Kingston Parish / Kingston

Kingston apartment

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Air conditioning

Price per night from

$100

Price per night from

$100

Distance approx 15.73 km from Middleton

16

Villa Juanita - Single Room 3

Portland Parish / Port Antonio

Port Antonio hotel apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly

Price per night from

$149

Responds fast!
avg. 48 minutes

Price per night from

$149

Distance approx 15.91 km from Middleton

33

'Heaven' Paradise Room

Saint Catherine Parish / Portmore

Portmore b and b

1 2 3 nights min

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

Price per night from

$70

Responds fast!
avg. 1 hour 16 minutes

Price per night from

$70

Distance approx 11.3 km from Middleton

31

Country Club Comfort

Saint Catherine Parish / Portmore

Portmore townhouse

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$90

Price per night from

$90

Distance approx 4.94 km from Middleton Show on Map

4

Beautiful & Convenient 1 Bedroom

Kingston / Port Royal

Port Royal apartment

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Child Friendly

Price per night from

$65

Price per night from

$65

Distance approx 8.77 km from Middleton

9

Rafjam Bed and Breakfast - Africa

Jamaica / Blue Mountains National Park

Blue Mountains National Park b and b

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child Friendly

Price per night from

$70

Price per night from

$70

Distance approx 19.8 km from Middleton

(30) Excellent 

11

Tranquility Villa~Port Antonio

Portland Parish / Port Antonio

Port Antonio villa

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
“Beautiful location with sweet views” visited this property with my wife and twin 3-year old girls. Girls loved the small pool - it was perfect for them. The views are just amazing. Property is just a few minutes drive from all the sites including
…see more

Price per night from

$266

Price per night from

$266

Distance approx 5.05 km from Middleton Show on Map

(3) Excellent 

28

Cozy Waterloo Apartment

Kingston Parish / Kingston

Kingston apartment

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child Friendly
  • Air conditioning

Price per night from

$59

Responds fast!
avg. 1 hour 59 minutes

Price per night from

$59

Distance approx 4.84 km from Middleton Show on Map

9

Comfortable Suite 376.8676

Kingston Parish / Kingston

Kingston apartment

1 2 1 night min

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

Price per night from

$100

Price per night from

$100

Distance approx 12.18 km from Middleton

17

Dream Vacation/ComfortzoneJamaica this for three bedroom

Saint Catherine Parish / Portmore

Portmore house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Air conditioning

Price per night from

$168

Price per night from

$168