Villa holiday rentals in Portland Parish

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Popular amenities for Portland Parish villa rentals

Private villa rentals

Villa in Long Bay
4.2 out of 5 average rating, 5 reviews

Rose Garden Pool & Villa

DomoniekRating, 5 stars70 months ago
This is an great little country oasis in the hills of portland. Quiet and private.
Superhost
Villa in Portland Parish
4.88 out of 5 average rating, 57 reviews

Serendipity Beach Villa A Beachfront Escape

VanessaRating, 5 stars6 months ago
The property was breath taking, perfect location for a getaway/hideaway. The staff were very friendly and accommodating in addition I kept in communication with Delroy, who was very charming and quick to respond to my queries. I would recommend the Serendipity to anyone who wants a hideaway. I would recommend that the owners invest in air condition throughout the house, not only in the bedroom units. Must recommend that visitors to the property take the owners suggestion on a chef since there is no eateries near the property and the nearest town is miles away. I would definitely revisit the Serendipity, great accommodation💕
Guest favourite
Villa in Port Antonio
4.95 out of 5 average rating, 56 reviews

Inn The Town - Room #5

RomaineRating, 5 stars5 days ago
We intend to book this place again because it was perfect. We parked the car and walked to everywhere in the town. This is the perfect location if u want to explore port Antonio. The check in was easy… same with the check out. I will definitely be back
Villa in Drapers District
4.61 out of 5 average rating, 28 reviews

Search-Me-Heart Entire Villa

SimoneRating, 5 stars1 month ago
This was a great stay for our family as we had a larger group, each person could get private space and come together in the shared space! It's near Natural Mystic so you're right next to the night vibes but if you don't mind then the location is worthwhile because it's also very conveniently located to the beautiful Frenchman's Cove.

Luxury villa rentals

Guest favourite
Villa in Ocho Rios
5 out of 5 average rating, 15 reviews

"Zyani Boutique Resort: Luxury Villa by the Sea"

BillRating, 5 stars11 months ago
ZYANI was recommended by dear friends. Our group of 7 rented the entire villa for 3 nights, and we'd all go back in a heartbeat. The focal point is the patio, directly on the ocean—it's stunning. The soothing sound of the ocean is a constant. The saltwater pool is perfect. Each bedroom is spacious, all with their own bathroom and nice little touches. If the ocean breeze isn’t enough, the ceiling and floor fans are good. We opted to hire a chef for our stay, and the meals they cooked for us were all fantastic. Stephanie and her team are friendly, attentive, and detail-oriented. The place is full of love and tranquility. I recommend you either drive or use Uber, as there's not much within walking distance. Stephanie recommended a small secluded beach nearby, and is less than a 10-minute drive. Other area attractions are 30 to 60 minutes away; Stephanie guided us on what to do (and, equally important, what to skip). Much love to Stephanie for creating a peaceful oasis in Ocho Rios! ♥️
Guest favourite
Villa in Kingston
4.93 out of 5 average rating, 55 reviews

Unique & Private 6-bedroom Villa

CrystalRating, 5 stars1 month ago
The stay at Joanna’s place was beautiful, comfortable, and was very clean . Miss Carline was helpful and friendly. My family and I loved the atmosphere, and would definitely come back. Thanks Joanna for your prompt response when we had questions and for your hospitality.
Villa in Old Fort Bay
4.62 out of 5 average rating, 13 reviews

SunsVilla on the Beach- Ocho Rios

DanielleRating, 5 stars10 months ago
The stay was amazing. My team felt they were treated like family. The chef and caretaker were warm and wonderful. 10/10 will stay there again.
Guest favourite
Villa in Ocho Rios
4.87 out of 5 average rating, 46 reviews

Luxury White Sand Beach Cottage 3bd w Chef

BhusanRating, 5 stars7 months ago
We stayed for 1 week in the 3 bedroom house. Location was good, near downtown Ochi which meant lots to do and walk to like restaurants and shopping. The house is part of a 3 building complex with its own beach sandwiched in between 2 larger hotels. We had a good stay and the staff were great. Between Milo, Diana, Lileth, and Sheryl, they provided a welcoming vibe. And the dogs were very friendly as well. Would stay here again.
Villa in Ocho Rios
4.5 out of 5 average rating, 36 reviews

Oceanview Villa w/ Chef & Butler Near Attractions

BeverleyRating, 5 stars41 months ago
I loved my stay in this house the staff was amazing the food was amazing the atmosphere was amazing not once did I have to think about anything I can’t wait to be back.
Villa in St. Mary Parish
5 out of 5 average rating, 3 reviews

Bespoke Vacation Villa near Ocho Rios

AshleyRating, 5 stars25 months ago
Cannot say enough good things about Cedars. Wasi and his staff were attentive from beginning to end. Definitely more of a curated experience, reminiscent of a real bed and breakfast. We had a lot of time to break off and do our own thing, but Wasi was always there when issues arose. Highly recommend for anyone looking to relax and let their hair down for a few days.
Superhost
Villa in Oracabessa
5 out of 5 average rating, 4 reviews

Oceanside Villa Oracabessa Access to Ocean & Pool

NicoleRating, 5 stars6 months ago
By far the best Villa I have ever stayed at. The staff here is phenomenal, they are friendly and attentive. The Chef was amazing, we had breakfast and dinner prepared for us during are stay, and it was so delicious! Also, the view of the ocean is beyond blissful! I highly recommend this villa.
Villa in Ocho Rios
4.58 out of 5 average rating, 71 reviews

Garden House Jamaica Pool, Chef & Housekeeping Inc

baRating, 5 stars1 month ago
Everything and every day was great and everyone had fun. The owner was upfront about the damage to the pool from previous guest but it was all good. We did put use the pool and had no issues with it, or anything else. And the housekeeper Marlene was lovely. Great meals, great conversation and lots of fun! If you are traveling with 10+ guests, I highly recommend renting this location. It was beautiful to wake up and see the ocean every morning, see new wildlife and just be at peace on the balcony and/or patio.

Villa rentals with a pool

Guest favourite
Villa in Boscobel
4.9 out of 5 average rating, 30 reviews

Catch My Drift Villa

VanessaRating, 5 stars1 week ago
Catch My Drift Villa made my birthday weekend absolutely unforgettable! From start to finish, this breathtaking villa exceeded all my expectations. The staff and host were incredibly kind, courteous, and responsive, ensuring every need was met. The facilities were spotless, spacious, and well-maintained, and the amenities were top-tier—everything was fully operational and ready for a seamless stay. The villa itself was both charming and luxurious, with a perfect blend of rural chic style that made the space feel uniquely special. It truly felt like the best of both worlds, thoughtfully designed to provide a relaxing, first-class experience. Just 15 minutes outside of Ocho Rios, this villa is now my new go-to getaway. I’ll definitely be back!
Superhost
Villa in Ocho Rios
5 out of 5 average rating, 6 reviews

*WinterSale *Skyview ~Modern/Spacious 3/3.5 Villa

LaurielRating, 5 stars19 months ago
Beautiful home. Lots of inside space. Kids enjoyed. Careful of the hot wata. 😂 well at least it’s hot. Close to activities. Quick and responsive host. We lost water pressure and a quick response showed how to get the reserve pump going. God bless
Guest favourite
Villa in Ocho Rios
4.97 out of 5 average rating, 29 reviews

Grand Island Villa - 3 BDRM

RayonRating, 5 stars4 months ago
This was an amazing experience that came with great recommendations for get restaurants and activities with in the area. We were also amazed by in home food delivery options that gives you the authentic Jamaican experience plus transportation. Truly in awe, definitely going back.
Guest favourite
Villa in Ocho Rios
4.84 out of 5 average rating, 55 reviews

TamrichTouchofParadise2

GabrielRating, 5 stars2 weeks ago
Such an understanding host that was communicative and accommodating. Had travel issues and she ensured that we weren’t further inconvenienced. Definitely will be looking to stay at her place if we come back. Amazing experience dealing with her.
Guest favourite
Villa in Ocho Rios
4.84 out of 5 average rating, 83 reviews

Serenity Retreat Villa Drax Hall w/Pool!

JessicaRating, 5 stars2 weeks ago
Thanks again we had a wonderful stay
Guest favourite
Villa in Ocho Rios
4.95 out of 5 average rating, 19 reviews

View 76 Villa- 3Br/King Bed/Gym, Infinity Pool

AlyssaRating, 5 stars1 month ago
We had an AMAZING time at Jermaine’s place! My group and I traveled in for my 30th birthday and everything was absolutely perfect! From Chef to the AMAZING Tracey, I couldn’t have asked for a better stay for the special day. The house was decorated to perfection and every meal was wonderful! The home itself if beautifully organized and smells like a tropical dream. We got to the Airbnb late and had some difficultly getting and Tracey left her home at 2 AM to help us! Then our flight was canceled and Tracey and Jermaine worked with us to ensure we were comfortable while we awaited updates from the airline. I can’t imagine a better team! Do yourself a favor and book!
Superhost
Villa in Ocho Rios
5 out of 5 average rating, 6 reviews

HiddenTreasure 4B/4B Pool Inc'd Detached Suites

KimieshaRating, 5 stars13 months ago
i will definitely stay again. Customer was on point , felt like i was home, neighborhood quiet and peaceful and safe. Shanique is a super host. House was clean and well kept and was just like what was on the profile pictures. Definitelywould recommend all to stay here.
Superhost
Villa in Ocho Rios
5 out of 5 average rating, 4 reviews

LUX 2BR Villa |5 Min to Beach|POOL|GYM |Gated Cmty

SanitaRating, 5 stars1 month ago
Beautiful home in a quiet and safe gated community. The views from our front door were amazing! Everything was as pictured. Came in a day late due to travel delays and Travis was very understanding and accommodating! Definitely recommend! You will not be disappointed!

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