COVID-19 Update

The impact of COVID-19 on travel is unprecedented. Like you, we’re monitoring the situation. Rest assured, we’re here to help with questions about your plans. Learn more here: About the coronavirus outbreak (COVID-19)

Middleton Rentals

Updating...

age 0-16
439 Results

Relevance

Price: low to high

Price: high to low

Number of reviews

439 Houses

Reggae Legends Villa - Skyline Drive (Villa 1)

Middleton villa

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$455

Nomadic Escapes Getaway!

Middleton house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$218

The Hidden Oasis / 2 Bedroom hillside getaway!

Middleton condo

2 bedrooms / 3 bathrooms / sleeps 4

Price per night from

$114

THE GREEN JEWEL

Middleton house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 59 minutes

Price per night from

$230

Crowne Gardens Retreat

Middleton house

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$1,832

Great rentals within 20 miles that match your search

Tranquility Villa~Port Antonio

Port Antonio villa

2 bedrooms / 1 bathroom / sleeps 5

“Fabulous, relaxing, beautiful, private...” This was my second time staying at Tranquility, (15th trip to Jamaica), My stays at Tranquility, were by far the best! Each stay gets better and better! I love the home, it's beautiful, spacious, clean, private, and the view is priceless! It's far enough away from everything, that you have the privacy you desire, but it's close enough to experience everything Jamaica has to offer. The food the cook made was fabulous, it was wonderful to have exactly what we wanted for our meals. (Helpful if your'e vegetarian, or have special dietary needs- one of us is vegetarian and the other, not). Can't pinpoint what I like most. Meals outside with a beautiful view and flower decorations on the table, lots of sun on both sides of the house, the food, swimming pool...? I loved, loved, loved everything! All of my vacation needs were met, and then some! Can't wait to get back!

Price per night from

$304

The Dorchester

Kingston apartment

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$109

Shotover Gardens Estate - cottage with pool

Port Antonio log cabin

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$58

2 Bedroom Luxury Apartment, (Casa Tianna Kingston)

Kingston apartment

2 bedrooms / 4 bathrooms / sleeps 4

Responds fast! avg. 1 hour 52 minutes

Price per night from

$132

1 Bedroom Luxury Apartment, (Casa Tianna Kingston)

Kingston apartment

1 bedroom / 3 bathrooms / sleeps 2

“Very good” The accommodation was very good. Very Luxurious and safe.Being that it was my first time to Kingston I was naturally nervous about safety but Kevin went out of his way to make sure I felt very safe. I was picked up by a driver once I landed at the airport and taken straight to the beautiful accommodation. I will definitely be staying there every time I come to Jamaica

Responds fast! avg. 1 hour 52 minutes

Price per night from

$79

Signature's 21 @ the Country Club

Kingston apartment

1 bedroom / 1 bathroom / sleeps 3

“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 rented this beautiful treasure the week of my wedding to host a moderate group for our wedding rehearsal brunch and for me to have a place to relax away from the packed family home prior to the big day. The location was so breath taking that it was the ideal spot for us to film our pre-wedding video and take pictures as my bridesmaids and myself got ready for the main event. The garden was nicely manicured and looked beautiful. What I enjoyed best was sitting on the patio for breakfast enjoying the beautiful garden scenery as well as looking out at Kingston from the vantage point of this hidden treasure. At night the location took on a magical ambience as I enjoyed the lights of the city from standing on the patio and the stars in the sky while listening to music softly in the background. The neighborhood is quiet and at times you can forget that anyone else lives around you as Signature's 21 makes you feel like you are on your own island paradise. My guests who came for the rehearsal brunch all fell in love with Signature's 21. I hope to visit again soon and I am sure that a few of my guests will too. Thank you Bancroft for sharing your garden treasure with us. I wish you continued success with Signature's 21 @ the Country Club!

Price per night from

$97

Affordable Vacation in St. Catherine Jamaica

Spanish Town apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$172

Morgan's Retreat 2 BR House Gated Community near KGN and Portmore

Portmore house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$98

Kingston Vacation Rental Call 1876-631-2910

Kingston cottage

1 bedroom / 1 bathroom / sleeps 2

“FIVE STARS” This place have pass my expectation very clean,comfortable & cozy i was more than comfortable and the host Andrea is the sweetest doll ever me personally i prefer to stay some where so that i can cook my own meals so a hotel was a no for me i will with a doubt book again this place is worth every penny home away from home oh yea Andrea have the best curry EVER:)

Responds fast! avg. 13 minutes

Price per night from

$69

Hill Top Kingston Jamaica

Kingston b&b

1 bedroom / 2 bathrooms / sleeps 2

“Awesome place” I went to Hill Top with my Family last year and it was awesome, the staff were so nice to my kids, the place was clean and nice. The view there was spectacular, especially in the nights.

Price per night from

$114

Kingsworth BnB

Kingston b&b

5 bedrooms / 5 bathrooms / sleeps 13

Price per night from

$241

The Oasis- by JamCan (with a/c)

Kingston apartment

1 bedroom / 2 bathrooms / sleeps 2

Price per night from

$79

Suite 205 at The Strathairn - by JamCan

Kingston apartment

1 bedroom / 3 bathrooms / sleeps 2

“very comfortable.” I stayed for 12 days. It was very comfortable. big king size bed and room very airy. sat on the balcony nice fresh Jamaican breeze. all my quest were announced.( security camera, elevator, gym, - worked well) roof top balcony lovely at night to overlook Kingston. pick up to and from airport was on time. management return call promptly. only thing I never had was a personal aide/helper but I am sure management could arrange that. lol.

Price per night from

$102

1 BD / 1 BR Luxury Apartment

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$103

Tropical Dreams: Sunny, picturesque, Large and Beautiful Frontroom

Kingston private room

1 bedroom / 1 bathroom / sleeps 2

“Wonderful place to be!” We were looking for more of a cultural experience and this was a wonderful place to start! Vivienne and Lloyd are amazing and we so enjoyed the time we had with them. We are already planning another vacation and will definitely be staying here again when in Kingston!! Our new home away from home!! Thanks again Viv and Lloyd for such great hospitality!!!

Price per night from

$52

Cozy Studio Apt- Kingston Jamaica

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

“You won't want to leave!” Its very rare to book a vacation rental and it actually exceeds your expectations... That's the case when i booked the La Rochelle apartment... I walked in and immediately said "Wow, Nice" - I was so pleased. I stayed in unit#3 - A very large 1 bedroom apartment, full kitchen, large living/dining area, large air conditioned bedroom with walk in closet... Clean, comfortable and felt like home. I cannot give this review without mentioning what a beautiful, warm and helpful person Faith Downie is... She was always accessible. If you call or text she answers right away or calls back very soon thereafter. She's always ready to assist your needs and give great suggestions. I felt like i was staying at my family's property, not just at an apartment/vacation rental. Ms Downie... a million thanks to you for a pleasant stay. I've told everyone i know about you and your vacation rentals. I will definitely be staying here on my next visit home. WONDERFUL! - Avery

Responds fast! avg. 2 hours 52 minutes

Price per night from

$92

Sea View Heights Villa Montego Bay

Rose Hall villa

16 bedrooms / 16 bathrooms / sleeps 36

Responds fast! avg. 15 minutes

Price per night from

$1,751

Strathairn110

Kingston house

1 bedroom / 1 bathroom / sleeps 2

“absolutley fantastic” very beautiful and quiet, atmosphere was too good to be true, I had the best time staying there, the staff and gate people were extraordinary, was truly a home away from home, will always be my first choice next time I am in Kingston Jamaica .

Price per night from

$97

Shotover Gardens Estate-Villa with Pool

Port Antonio villa

3 bedrooms / 2 bathrooms / sleeps 6

“My private piece of paradise” I have been to Jamaica several times before, and loved it, so I was expecting a great trip this time also. Shotover Gardens was just great! The views, the landscaped grounds, the pool, the privacy. After being there a few days I realized what I liked best: the complete comfort. No, this is not a high end luxury resort with people waiting on you; you will have to make your own drinks and open your own beers. But it is a terrific place to relax and soak up everything great about Jamaica. I stayed in the cottage. It is plenty roomy for 1 or 2 (hey, it's bigger than my apartment). It is modern and functional, with a full kitchen and hot shower. It is not fancy or pretentious. But the part of the cottage I enjoyed most was the back patio facing the Blue Mountains, or the azure ocean view, depending which way you turn the chair (there are some tough choices you have to make while staying here...). I wish I had a book to write, I would do it from this patio. Truth is, I didn't spend a lot of time in the cottage except for sleeping. I spent more time at the pool. (Is my elbow sore from opening the fridge at the pool?) The views are great from here too. I don't know how often the villa and cottage have guests at the same time, but I'd bet it's rare. For my stay I had Shotover Gardens to myself, not counting the hosts (and the sometimes groundskeepers). The hosts are friendly without being intrusive and can answer any local question, whether it's where to buy something or to recommend a day trip or the finer points of Jamaican culture. I also must comment on the cottage price. The grounds, pool, views are worth the price while sleeping under a tarp! And you get the cottage too. Unbelievable! I was very surprised to find high speed wireless internet. I will be back!

Price per night from

$172

Vacation & Short Term Rental

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$58

KIMOCHI Escape the rush! 20 min fr Kingston center

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

“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.

Price per night from

$149

Lunas guest house

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$126

Chester Apartment Complex

Spanish Town apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$92

Spanish Town Guesthouse

Spanish Town b&b

4 bedrooms / 2 bathrooms / sleeps 16

Price per night from

$52

Your Jamaica Vacation Home with Car

Spanish Town house

2 bedrooms / 3 bathrooms / sleeps 5

Price per night from

$119

NEW Kingston COOL SHADE HOLIDAYS

Kingston apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$109

Staycation - relaxing 1 bedroom with wi-fi & pool

Kingston apartment

1 bedroom / 3 bathrooms / sleeps 2

Price per night from

$98

3 Bedroom House Danishie's Place

Spanish Town private room

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$183

1 Bedroom Apartment Danishie's Place

Spanish Town b&b

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$63

dream vacation two bedroom unit

Spanish Town house

3 bedrooms / 1 bathroom / sleeps 4

Price per night from

$115

Light & Airy Living Space in Kingston Jamaica

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$79

Villa Yemayah

Port Antonio b&b

1 bedroom / 3 bathrooms / sleeps 2

Price per night from

$75

The Pentwood

Kingston apartment

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$86

Viewing 38 of 439
rentals in Middleton

×

Also consider