Title: Portland Vacation Rentals from $96: Search Short-Term Rentals | Expedia.com [Portland Travel Guide](https://expedia.com/Portland.dx6159622)[Portland Hotels](https://expedia.com/Destinations-In-Portland.d6159622.Hotel-Destinations)[Portland Flights](https://expedia.com/Destinations-In-Portland.d6159622.Flight-Destinations)[Car Rentals in Portland](https://expedia.com/Destinations-In-Portland.d6159622.Car-Rental-Destinations)[Portland Vacations](https://expedia.com/Portland.d6159622.Destination-Travel-Guides) ![#lifeatexpedia That blue, it just doesn’t stop! ](https://images.trvl-media.com/place/319626250106701481/3a4fc553-fc35-4cdc-9aaf-279302394926.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Kristi Miller ![](https://images.trvl-media.com/place/319626250106701481/3a4fc553-fc35-4cdc-9aaf-279302394926.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Top Cities in Portland ![Winnifred Beach which includes general coastal views as well as a small group of people](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/110000/110325-Winnifred-Beach.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Port Antonio [](https://expedia.com/Port-Antonio-Vacation-Rentals.d2855.Travel-Guide-VacationRentals) ## Our top choices for Portland vacation rentals ![Villa, 1 King Bed, Non Smoking | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/33000000/32730000/32724300/32724294/7740d0e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 King Bed, Non Smoking | Living room | Flat-screen TV](https://images.trvl-media.com/lodging/33000000/32730000/32724300/32724294/c462ecc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32730000/32724300/32724294/ff5a1fe0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/33000000/32730000/32724300/32724294/eacc5e3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Grand Sinopia Inn Portland [](https://www.expedia.com/Port-Antonio-Hotels-The-Grand-Sinopia-Inn-Portland.h32724294.Hotel-Information) Port Antonio $571 nightly $624 total Mar 12 - Mar 13 Total with taxes and fees [](https://www.expedia.com/Port-Antonio-Hotels-The-Grand-Sinopia-Inn-Portland.h32724294.Hotel-Information) ![Exclusive Cabin | Terrace/patio](https://images.trvl-media.com/lodging/103000000/102900000/102894900/102894828/1dccee7e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, 4 Bedrooms | Free WiFi](https://images.trvl-media.com/lodging/103000000/102900000/102894900/102894828/040d803d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite Suite | Living area](https://images.trvl-media.com/lodging/103000000/102900000/102894900/102894828/865be3ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exclusive Cabin | Free WiFi](https://images.trvl-media.com/lodging/103000000/102900000/102894900/102894828/be0a8ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Reggae Legends Estate [](https://www.expedia.com/Kingston-Hotels-Reggae-Legends-Estate.h102894828.Hotel-Information) Jack's Hill 9.8/10 Exceptional (6 reviews) "A really amazing find! Stunning location with fantastic views. Quiet and relaxing. The cabin was a great experience and we were so well looked after by Anne-Marie." ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) Nicola $264 nightly $305 total Feb 18 - Feb 19 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Reggae-Legends-Estate.h102894828.Hotel-Information) ![Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/138c4d2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House, Garden View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/6ed00de2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House, Garden View | Living area](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/caef3e00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House, Garden View | Living area](https://images.trvl-media.com/lodging/110000000/109990000/109981200/109981158/cfe793d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Phoenix Park Villas Portmore [](https://www.expedia.com/Portmore-Hotels-Phoenix-Park-Villas-Portmore.h109981158.Hotel-Information) Portmore 10/10 Exceptional (5 reviews) "I will definitely recommend that you stay here is so peaceful security are strictly on point with everything and the comfort of the home is great will be staying back for sure ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimoya $218 nightly $252 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Portmore-Hotels-Phoenix-Park-Villas-Portmore.h109981158.Hotel-Information) ![House | Beach](https://images.trvl-media.com/lodging/96000000/95700000/95697700/95697634/95d71285.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95700000/95697700/95697634/w2400h1594x0y0-5acf6d7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Exterior](https://images.trvl-media.com/lodging/96000000/95700000/95697700/95697634/ca73843e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | Living area | TV](https://images.trvl-media.com/lodging/96000000/95700000/95697700/95697634/6a86c449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### House - Sleeps 6 - Patio - Parking [](https://www.expedia.com/Port-Morant-Hotels-Stunning-5-Bed.h95697634.Hotel-Information) Port Morant $148 nightly $172 total Mar 2 - Mar 3 Total with taxes and fees [](https://www.expedia.com/Port-Morant-Hotels-Stunning-5-Bed.h95697634.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/37000000/36470000/36462700/36462638/2ec4f3fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room, 1 Queen Bed | Blackout drapes, iron/ironing board, bed sheets](https://images.trvl-media.com/lodging/37000000/36470000/36462700/36462638/e57be092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/37000000/36470000/36462700/36462638/dbfd266b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kingvilla [](https://www.expedia.com/Port-Morant-Hotels-Kingvilla.h36462638.Hotel-Information) Port Morant $85 nightly $95 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Port-Morant-Hotels-Kingvilla.h36462638.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9678900/9678841/51dab38b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 2 Bedrooms, 2 Bathrooms, City View | 1 bedroom, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/10000000/9680000/9678900/9678841/a8faef2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 2 Bedrooms, 2 Bathrooms, City View | Living area | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/10000000/9680000/9678900/9678841/c9d2f08c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 2 Bedrooms, 2 Bathrooms, City View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/10000000/9680000/9678900/9678841/76d83379.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Tianna Guest Apartments [](https://www.expedia.com/Kingston-Hotels-Casa-Tianna-Guest-Apartments.h9678841.Hotel-Information) Havendale 9.4/10 Exceptional (53 reviews) "We had a three night stay here and it was magnificent! We had a quiet night just drinking a couple of beers on the master balcony. Damian was an attentive, host Excellent place to stay in Kingston!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.com/Kingston-Hotels-Casa-Tianna-Guest-Apartments.h9678841.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/17000000/16730000/16727600/16727540/b3e5ba01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchen, Mountain View | Living room | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/17000000/16730000/16727600/16727540/e57449a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchen, Mountain View | In-room dining](https://images.trvl-media.com/lodging/17000000/16730000/16727600/16727540/1ef3c839.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Kitchen, Mountain View | 1 bedroom, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/17000000/16730000/16727600/16727540/026784c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Kingston Apt at Wellington Cove [](https://www.expedia.com/Kingston-Hotels-New-Kingston-Apt-At-Wellington-Cove.h16727540.Hotel-Information) Liguanea 8.8/10 Excellent (8 reviews) "I rented this apartment for about a week during business presentation in Kingston. The staff were helpful, detailed and kind. Also, the location and general layout is very safe and well-kept. I appreciated having laundry appliances and a full kitchen with pots and pans so that I could cook, too. Security guards at gate 24/7 plus staff on WhatsApp made me feel like everything was always taken care of. Also, I was concerned about mosquitos, but the apartment is set up so that they basically... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melanie $221 nightly $234 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-New-Kingston-Apt-At-Wellington-Cove.h16727540.Hotel-Information) ![2 outdoor pools](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/d4bcfe9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Villa, 3 Bedrooms, Accessible, Hill View | View from room](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/e1aaba74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Bedrooms, Pool Access, Garden View | Living room | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/aa5a177a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Bedrooms, Pool Access, Garden View | In-room dining](https://images.trvl-media.com/lodging/20000000/19110000/19105500/19105425/15ff1fcd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Country Club Villa I [](https://www.expedia.com/Kingston-Hotels-The-Country-Club-Villa-I.h19105425.Hotel-Information) Kingston 9.0/10 Wonderful (10 reviews) "The management team was awesome, the AC didn’t work in the main room on the first night but Ms Vicki made sure that I didn’t go a second night without it." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveler [](https://www.expedia.com/Kingston-Hotels-The-Country-Club-Villa-I.h19105425.Hotel-Information) ![Economy Studio | 2 bedrooms, hypo-allergenic bedding, in-room safe, iron/ironing board](https://images.trvl-media.com/lodging/10000000/9680000/9678100/9678010/f0470347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Townhome, Multiple Bedrooms, Kitchen | Living area | 32-inch Smart TV with digital channels](https://images.trvl-media.com/lodging/10000000/9680000/9678100/9678010/7be7c3c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/10000000/9680000/9678100/9678010/a7fc400c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Studio | Private kitchen | Microwave, toaster, cookware/dishes/utensils, kitchen islands](https://images.trvl-media.com/lodging/10000000/9680000/9678100/9678010/edd91fa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Gardens [](https://www.expedia.com/Kingston-Hotels-The-Gardens.h9678010.Hotel-Information) Barbican 7.4/10 Good (58 reviews) "Safe and secure environment. Quiet and clean. Very comfy room for short stays. A little hard to locate based on gps (located off the main road, but my gps had me turn several times for no reason) but good otherwise. Would recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patra $95 nightly $96 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-The-Gardens.h9678010.Hotel-Information) ![Premium bedding, pillowtop beds, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/102000000/101090000/101081400/101081400/3d7ef1e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, individually furnished, blackout drapes](https://images.trvl-media.com/lodging/102000000/101090000/101081400/101081400/0cd6660b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LED TV with cable channels, Netflix, streaming services](https://images.trvl-media.com/lodging/102000000/101090000/101081400/101081400/09d4bd1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LED TV with cable channels, Netflix, streaming services](https://images.trvl-media.com/lodging/102000000/101090000/101081400/101081400/47d1ff0e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sweet Kensville [](https://www.expedia.com/Kingston-Hotels-Avant.h101081400.Hotel-Information) New Kingston 8.6/10 Excellent (4 reviews) "Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve $178 nightly $206 total Feb 22 - Feb 23 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Avant.h101081400.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/a95c9d31.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, Kitchen, Courtyard View | 2 bedrooms, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/efdcc75d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/14c9fd01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106080000/106074600/106074531/911349cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serenity Oasis Apartment [](https://www.expedia.com/Spanish-Town-Hotels-Serenity-Oasis-Apartment.h106074531.Hotel-Information) Spanish Town $115 nightly $133 total Mar 18 - Mar 19 Total with taxes and fees [](https://www.expedia.com/Spanish-Town-Hotels-Serenity-Oasis-Apartment.h106074531.Hotel-Information) ![City Apartment, 2 Bedrooms, Kitchen, Ground Floor | Living room | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/16000000/15880000/15875600/15875565/26cf0991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Apartment, 2 Bedrooms, Garden View, Executive Level | Living room | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/16000000/15880000/15875600/15875565/9a803c02.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Apartment, 2 Bedrooms, Garden View, Executive Level | Living room | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/16000000/15880000/15875600/15875565/bdd134b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Apartment, 1 Bedroom, Kitchen, Corner | In-room dining](https://images.trvl-media.com/lodging/16000000/15880000/15875600/15875565/8aea2fd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Kingston Guest Apartment at Donhead [](https://www.expedia.com/Kingston-Hotels-New-Kingston-Guest-Apartment-At-Donhead.h15875565.Hotel-Information) New Kingston 9.6/10 Exceptional (17 reviews) "Best value for money in Kingston. Safe, clean apartment with everything you need for self-catering and great air-conditioning and wi-fi. So close to the US Embassy, our trip went smoothly. Only issue is that check-in is very late and check-out is very early." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveler $288 nightly $307 total Feb 25 - Feb 26 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-New-Kingston-Guest-Apartment-At-Donhead.h15875565.Hotel-Information) ![Luxury Apartment, 2 Bedrooms, 2 Bathrooms, City View | 2 bedrooms, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/18000000/17510000/17507200/17507129/2031acde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Royale Guest Apartment [](https://www.expedia.com/Kingston-Hotels-Casa-Royale-Guest-Apartment.h17507129.Hotel-Information) Molynes Gardens 9.6/10 Exceptional (67 reviews) "Place was very clean and comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Demar $236 nightly $250 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Casa-Royale-Guest-Apartment.h17507129.Hotel-Information) ![Interior detail](https://images.trvl-media.com/lodging/13000000/12560000/12551900/12551865/3b1df887.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/13000000/12560000/12551900/12551865/b32a0072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, 1 Bedroom, City View, Ground Floor | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/13000000/12560000/12551900/12551865/977703ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12560000/12551900/12551865/19156df6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Eclipse Suite Guest Apartments [](https://www.expedia.com/Kingston-Hotels-Eclipse-Suite-Guest-Apartments.h12551865.Hotel-Information) Havendale 9.2/10 Wonderful (21 reviews) "Nice location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert [](https://www.expedia.com/Kingston-Hotels-Eclipse-Suite-Guest-Apartments.h12551865.Hotel-Information) ![Elite Apartment, 1 Bedroom, Ensuite | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/23000000/22650000/22650000/22649938/c6b11039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite Apartment, 1 Bedroom, Ensuite | Living area | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/23000000/22650000/22650000/22649938/ef5a9301.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Elite Apartment, 1 Bedroom, Ensuite | 1 bedroom, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/23000000/22650000/22650000/22649938/8f8fbe95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/23000000/22650000/22650000/22649938/0ea25f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### New Kingston Guest Apt at Kingsway [](https://www.expedia.com/Kingston-Hotels-New-Kingston-Guest-Apt-At-Kingsway.h22649938.Hotel-Information) New Kingston $300 nightly $321 total Feb 18 - Feb 19 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-New-Kingston-Guest-Apt-At-Kingsway.h22649938.Hotel-Information) ![50-inch LED TV with cable channels, TV](https://images.trvl-media.com/lodging/90000000/89820000/89810500/89810499/4c4a107d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89810500/89810499/af92f1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch LED TV with cable channels, TV](https://images.trvl-media.com/lodging/90000000/89820000/89810500/89810499/498e211e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89810500/89810499/ecdf732d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Guest Apartments at Border Crossings [](https://www.expedia.com/Kingston-Hotels-The-Guest-Apartments-At-Border-Crossings.h89810499.Hotel-Information) Havendale $189 nightly $206 total Mar 17 - Mar 18 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-The-Guest-Apartments-At-Border-Crossings.h89810499.Hotel-Information) ![Studio, Balcony | Free WiFi](https://images.trvl-media.com/lodging/119000000/118710000/118703600/118703555/w960h714x2y0-23302f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/119000000/118710000/118703600/118703555/bf9caeb6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Balcony | Bathroom](https://images.trvl-media.com/lodging/119000000/118710000/118703600/118703555/31c80576.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, Balcony | Private kitchen](https://images.trvl-media.com/lodging/119000000/118710000/118703600/118703555/06cb67d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stylish Studio in Chelsea Manor [](https://www.expedia.com/Kingston-Hotels-Stylish-Studio-In-Chelsea-Manor.h118703555.Hotel-Information) New Kingston 8.0/10 Very Good (2 reviews) "I loved that it was private and the staff was very welcoming everything was exactly what i wanted. I definitely would book agsin everything was so clean and neat" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) DONNA $265 nightly $306 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Kingston-Hotels-Stylish-Studio-In-Chelsea-Manor.h118703555.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92160000/92150500/92150486/7cc9a206.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92160000/92150500/92150486/4d51c78f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/93000000/92160000/92150500/92150486/498ea98c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/93000000/92160000/92150500/92150486/90431a70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tapioca Village Retreat [](https://www.expedia.com/Tapioca-Village-Retreat.h92150486.Hotel-Information) Castleton 6.0/10 (2 reviews) "There is so much nature and friendliness! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Günter $80 nightly $93 total Feb 17 - Feb 18 Total with taxes and fees [](https://www.expedia.com/Tapioca-Village-Retreat.h92150486.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110360000/110358400/110358371/c8728f4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110360000/110358400/110358371/ed574882.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Apartment, 1 Queen Bed, Non Smoking, Kitchen | 1 bedroom, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/111000000/110360000/110358400/110358371/719ef88e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/111000000/110360000/110358400/110358371/0ce809da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Apartment with roof top pool [](https://www.expedia.com/Kingston-Hotels-Apartment-With-Roof-Top-Pool.h110358371.Hotel-Information) Half Way Tree 8.0/10 Very Good (4 reviews) "Lovely " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Twana Melica [](https://www.expedia.com/Kingston-Hotels-Apartment-With-Roof-Top-Pool.h110358371.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Mountain View | Private kitchen | Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/17000000/16790000/16781000/16780973/a82e5f72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Mountain View | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16790000/16781000/16780973/96c73b30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Mountain View | Living room | 50-inch flat-screen TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/17000000/16790000/16781000/16780973/7728605e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment, 2 Bedrooms, Mountain View | 1 bedroom, Egyptian cotton sheets, premium bedding, in-room safe](https://images.trvl-media.com/lodging/17000000/16790000/16781000/16780973/ea59cc5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Caribe Estate Guest Apartment I [](https://www.expedia.com/Portmore-Hotels-Caribe-Estate-Guest-Apartment-I.h16780973.Hotel-Information) Greater Portmore 10/10 Exceptional (5 reviews) "The entire set up was amazing and what i liked most was the communication and hospitality service..." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveler [](https://www.expedia.com/Portmore-Hotels-Caribe-Estate-Guest-Apartment-I.h16780973.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-02&endDate=2026-03-03®ionId=6159622&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_6159622) ## Find vacation rentals that suit your style Villas [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VILLA) Cabins [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=VACATION_HOME) Apartments [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APARTMENT) Cottages [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=COTTAGE) Condos [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CONDO) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=APART_HOTEL) Residences [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=RESIDENCE) Chalets [](https://www.expedia.com/Hotel-Search?destination=Portland%2C+Jamaica®ionId=6159622&latLong=18.176361%2C-76.445929&adults=2&startDate=2026-05-16&d1=2026-05-16&endDate=2026-05-19&d2=2026-05-19&lodging=CHALET) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Portland.d6159622.Vacation-Rental-Destinations)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FDestinations-In-Portland.d6159622.Vacation-Rental-Destinations) ## Top Portland Hotel Reviews ![ROK Hotel Kingston, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/72000000/71560000/71554900/71554883/3213ca97_y.jpg) ### ROK Hotel Kingston, Tapestry Collection by Hilton 10/10 Excellent "Clean rooms & great staff. Blessings to Sean at front desk for his helpfulness and clear understanding. Thank you to Miss Morgan and breakfast Crew for being helpful, friendly attentive and great at their jobs. Location was on point. Also cleaning staff was friendly and welcoming great at their jobs. Beds was comfortable. All Front desk staff was helpful & pleasant. Blessings to all loved my stay" [](https://expedia.com/Kingston-Hotels-Rok-Hotel-Kingston-Tapestry-Collection-By-Hilton.h71554883.Hotel-Information) ![The Courtleigh Hotel and Suites](https://images.trvl-media.com/lodging/1000000/480000/470200/470179/a412135d_y.jpg) ### The Courtleigh Hotel and Suites 10/10 Excellent "." [](https://expedia.com/Kingston-Hotels-The-Courtleigh-Hotel-And-Suites.h470179.Hotel-Information) ![R Hotel Kingston](https://images.trvl-media.com/lodging/19000000/18990000/18989600/18989524/a675b6b0_y.jpg) ### R Hotel Kingston 10/10 Excellent "Excellent check in. Friendly staff. Breakfast was amazing. Bed comfortable. " [](https://expedia.com/Kingston-Hotels-R-Hotel-Kingston.h18989524.Hotel-Information) ![S Hotel Kingston](https://images.trvl-media.com/lodging/3000000/2460000/2450100/2450088/57e4091f_y.jpg) ### S Hotel Kingston 10/10 Excellent "Great place. Clean rooms. Courteous staff. Nice breakfast." [](https://expedia.com/Kingston-Hotels-The-Spanish-Court-Hotel.h2450088.Hotel-Information) ![AC Hotel by Marriott Kingston, Jamaica](https://images.trvl-media.com/lodging/36000000/35560000/35559600/35559503/5af7ff9f_y.jpg) ### AC Hotel by Marriott Kingston, Jamaica 10/10 Excellent "Everything good " [](https://expedia.com/Kingston-Hotels-AC-Hotel-By-Marriott-Kingston.h35559503.Hotel-Information) ![Jamaica Colors Eco-Retreat Hotel and Spa](https://images.trvl-media.com/lodging/84000000/83770000/83764300/83764245/1de72ac7_y.jpg) ### Jamaica Colors Eco-Retreat Hotel and Spa 10/10 Excellent "Staff was friendly. My kids enjoyed the pool and the grounds. The room was clean and comfortable and the breakfast was delicious. The views from the pool is juat amazingly beautiful. Definitely recommend." [](https://expedia.com/Jamaica-Colors-Eco-Retreat-Hotel-And-Spa.h83764245.Hotel-Information) ![Geejam](https://images.trvl-media.com/lodging/3000000/2220000/2212000/2211904/48b4eb11_y.jpg) ### Geejam 10/10 Excellent "Our stay at Geejam was amazing, hotel rooms were large and really cool decor, the environment and views were spectacular and the food was incredible. Geejam team couldn’t have been more helpful, always on hand and delivering great customer care. Studio tour was also a great experience " [](https://expedia.com/Port-Antonio-Hotels-Geejam.h2211904.Hotel-Information) ![The Jamaica Pegasus Hotel](https://images.trvl-media.com/lodging/1000000/900000/891100/891006/ec7a53a5_y.jpg) ### The Jamaica Pegasus Hotel 10/10 Excellent "We arrived early and even though the room was not ready checking in was very courteous, friendly an professional. Our front desk person even traveled out to where we were relaxing near the pool bar lounge to let us know the room was ready and provided us with the room keys. The room was clean and comfortable. We enjoyed the balcony overlooking the pool area and the view of the Kingston downtown. The breakfast buffet was exceptional and more than we had expected with courteous staff. Overall a great stay and we plan on staying at the Pegasus on future trips." [](https://expedia.com/Kingston-Hotels-The-Jamaica-Pegasus-Hotel.h891006.Hotel-Information) ![Inn The Town](https://images.trvl-media.com/lodging/47000000/46100000/46092800/46092758/f9c44600_y.jpg) ### Inn The Town 10/10 Excellent "Next time I visit, I will definitely staying here again. The staff were nice and personable. We felt welcome the whole time. We got a great night sleep every night, as it was quiet and comfortable. The inn located in the perfect spot. I would recommend this accommodation to anyone. " [](https://expedia.com/Port-Antonio-Hotels-Inn-The-Town.h46092758.Hotel-Information) ## Find out more about Portland ## Discover your perfect Portland vacation rental with Expedia #### How many vacation rentals are available in Portland? Expedia has plenty of vacation rentals to choose from in and around Portland, so you’re guaranteed to find the right one for you. #### How much is a vacation rental in Portland? The selection of Portland vacation rentals we have selected for you start as low as $96 per night. Entering your travel dates in the search wizard you might find even better deals! #### What type of vacation rental can I get in Portland? Vacation rentals in Portland come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Portland vacation rentals to suit everyone. #### Why should I choose a vacation rental in Portland? Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Portland vacation rental often works out to be a fantastic, cost-effective option for [groups](https://www.expedia.com/lp/b/vr/large) and [families](https://www.expedia.com/lp/b/vr/family) visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. #### How do I find the best deal on a vacation rental in Portland? Find vacation rentals in Portland by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Portland. #### What amenities are available in a vacation rental in Portland? The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a [swimming pool](https://www.expedia.com/lp/b/vr/private-pool) is more your thing. Of course, there’s always the treat of having [your own hot tub](https://www.expedia.com/lp/b/vr/hot-tub). Expedia has a vast range of amenities in Portland vacation rentals designed to suit every budget and trip type. #### When is the best time to stay in a vacation rental in Portland? Everytime is a great time to head to Portland! Staying in a Portland vacation rentals you will always find lots going on to keep you entertained. #### Why book a vacation rental with Expedia? Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Portland. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Portland vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Portland, you can save even more. #### Can I cancel my vacation rental through Expedia? Yes, you can cancel or change your Portland vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted. ## Explore a world of travel with Expedia - Popular Portland Cities - All accommodation types in Portland - [Port Antonio Vacation Rentals ](https://expedia.com/Port-Antonio-Vacation-Rentals.d2855.Travel-Guide-VacationRentals) - [Long Bay Vacation Rentals ](https://expedia.com/Long-Bay-Vacation-Rentals.d6237109.Travel-Guide-VacationRentals) - [Rural Hill Vacation Rentals ](https://expedia.com/Rural-Hill-Vacation-Rentals.d6237272.Travel-Guide-VacationRentals) - [Buff Bay Vacation Rentals ](https://expedia.com/Buff-Bay-Vacation-Rentals.d553248635974804686.Travel-Guide-VacationRentals) - [Hope Bay Vacation Rentals ](https://expedia.com/Hope-Bay-Vacation-Rentals.d553248635942909793.Travel-Guide-VacationRentals) - [Vacation Homes in Portland ](https://expedia.com/Portland-Private-Vacation-Homes.d6159622-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Villas in Portland ](https://expedia.com/Portland-Villas.d6159622-aaVillas.Travel-Guide-Accommodation) - 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