Best Vacation Homes in Portland
House
10.0(64 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
Hot Tub
Pool
Ocean View
Balcony/Terrace
£176/Night
7 Nights - £1,233
Apartment
10.0(3 Reviews)
1 Bedroom
1 Bath
4 Guests
3229.17 ft²
- Balcony/Terrace
Parking
Air Conditioner
Internet
£92/Night
7 Nights - £643
House
10.0(12 Reviews)
1 Bedroom
1 Bath
Oceanfront- Pool
- Ocean View
- Balcony/Terrace
£466/Night
7 Nights - £3,263
House
10.0(35 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Pool
- Ocean View
- Balcony/Terrace
View
£203/Night
7 Nights - £1,418
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
185.68 ft²
- Balcony/Terrace
Pet Friendly- Parking
- Air Conditioner
£93/Night
7 Nights - £650
House
10.0(26 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£210/Night
7 Nights - £1,470
Villa
10.0(15 Reviews)
5 Bedrooms
5 Baths
10 Guests
4500 ft²
- Oceanfront
- Hot Tub
- Ocean View
- Balcony/Terrace
£1,289/Night
7 Nights - £9,025
House
10.0(11 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£360/Night
7 Nights - £2,521
Portland Luxury Rentals
House
1 Bedroom
1 Bath
2 Guests
500 ft²
- Balcony/Terrace
Kitchen- Parking
- Internet
£4,420/Night
7 Nights - £30,942
Villa
6 Bedrooms
6 Baths
12 Guests
5800 ft²
Private Pool- Hot Tub
Spa- Pool
£3,978/Night
7 Nights - £27,847
£3,684/Night
7 Nights - £25,785
Villa
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
Breakfast
£3,094/Night
7 Nights - £21,659
Villa
4 Bedrooms
4 Baths
9 Guests
4499.31 ft²
Private Beach- Pool
- Ocean View
- Balcony/Terrace
£2,947/Night
7 Nights - £20,628
Hotel
1 Bath
608 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£1,705/Night
7 Nights - £11,933
Villa
6 Bedrooms
7 Baths
12 Guests
8611 ft²
- Private Pool
- Oceanfront
- Spa
Fireplace/Heating
£1,641/Night
7 Nights - £11,490
Hotel
1 Bath
608 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
£1,210/Night
7 Nights - £8,473
Portland Pet Friendly Vacation Rentals
Apartment
10.0(1 Review)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
£81/Night
7 Nights - £569
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
2 Guests
505.9 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£74/Night
7 Nights - £516
House
1 Bedroom
1 Bath
2 Guests
- Pet Friendly
- Parking
- Internet
Child Friendly
£75/Night
7 Nights - £527
House
9.6(28 Reviews)
2 Bedrooms
2 Baths
5 Guests
1160 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
£196/Night
7 Nights - £1,371
Apartment
10.0(1 Review)
1 Bedroom
1 Bath
3 Guests
- Pet Friendly
- Parking
- Child Friendly
£40/Night
7 Nights - £278
House
9.4(11 Reviews)
3 Bedrooms
2 Baths
12 Guests
900 ft²
- Balcony/Terrace
- Breakfast
- Pet Friendly
- Kitchen
£59/Night
7 Nights - £413
House
9.2(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£168/Night
7 Nights - £1,176
Villa
9.2(13 Reviews)
7 Bedrooms
5 Baths
14 Guests
1 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£1,000/Night
7 Nights - £6,998
Portland Large Vacation Homes
Villa
10.0(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Pool
- Ocean View
- Balcony/Terrace
- View
£210/Night
7 Nights - £1,469
House
10.0(1 Review)
5 Bedrooms
2 Baths
12 Guests
2400.35 ft²
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
£442/Night
7 Nights - £3,094
Villa
10.0(1 Review)
1 Bedroom
1 Bath
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£218/Night
7 Nights - £1,526
House
10.0(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
£1,030/Night
7 Nights - £7,209
Villa
10.0(1 Review)
2 Bedrooms
2 Baths
4 Guests
161.46 ft²
- Balcony/Terrace
- View
- Parking
- Air Conditioner
£195/Night
7 Nights - £1,367
Villa
10.0(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£144/Night
7 Nights - £1,006
Villa
10.0(3 Reviews)
4 Bedrooms
5 Baths
8 Guests
2500 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Parking
£1,169/Night
7 Nights - £8,186
Villa
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
525 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
£71/Night
7 Nights - £497
Why Choose Rent By Owner for your Portland Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Portland
When should you plan your Vacation Rentals stay?
To make the most of your stay, consider planning your vacation during the region's dry season when the weather in Portland, Jamaica, is ideal for exploring and relaxation.
Peak Season Highlights
December to April
During these months, you can enjoy warm and dry weather, ideal for exploring the scenic beauty of this destination.
Average Temperature Daytime: around 82°F to 85°F - Nighttime: approximately 70°F
July to August
This period marks the high tourist season with lively local events and vibrant atmospheres in the region.
Average Temperature Daytime: roughly 84°F to 87°F - Nighttime: about 72°F
Off-Season Highlights
May to June
The area experiences a quieter ambiance with fewer visitors, making it a peaceful time to book vacation rentals here.
Average Temperature Daytime: around 83°F to 86°F - Nighttime: roughly 71°F
September to November
As the rainy season tapers off, you may find more affordable rates and less crowded attractions in this part of the year.
Average Temperature Daytime: approximately 81°F to 84°F - Nighttime: about 69°F
Weekly Weather Forecast for Portland
How to Book Your Portland Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Portland
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private swimming pool surrounded by lush tropical landscapes
- Relax in your own outdoor lounge area with comfortable seating
- Take advantage of an expansive balcony or veranda offering scenic views
- Stroll through beautifully maintained tropical gardens
- Cook and dine al fresco in a fully equipped outdoor barbecue area
- Discover direct access to nearby beaches for sunbathing and water activities
- Utilize outdoor recreational spaces such as tennis courts or sports areas, if available
Top Attractions Around Portland
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of activities such as exploring local beaches, engaging in water sports, or experiencing the area's rich cultural heritage—all conveniently accessible from your nearby vacation rental.
Family Activities
- Portland Heritage Walks: Discover the rich history and vibrant culture of this region through guided tours that are perfect for family explorations.
- Blue Lagoon Island Excursion: Enjoy a day of snorkeling and swimming in the crystal-clear waters of the Blue Lagoon, offering a safe and engaging experience for kids and adults alike.
- Reach Falls Adventure: Visit this stunning waterfall where you can relax in natural pools and explore scenic trails suitable for all ages.
- Local Craft Markets: Immerse your family in the vibrant local crafts and flavors by browsing authentic markets that showcase the region's artistic talents.
Adult Activities
- Sightseeing along the Blue Lagoon: Discover the stunning turquoise waters and scenic views that make this destination a must-visit for relaxation and photography.
- Exploring the Boston Bay Beach: Enjoy the lively atmosphere and legendary jerk chicken, perfect for experiencing authentic local cuisine right on the sandy shores.
- Adventures at Somerset Falls: Embark on a tranquil boat ride or hike through lush surroundings to marvel at this picturesque waterfall nestled in the region's tropical landscape.
- Snorkeling and diving at the nearby coral reefs: Dive into clear waters to explore vibrant marine life and colorful coral formations that are easily accessible from here.
Other Places to Stay in Portland
Surrey County
Moore Town
Port Antonio
Drapers
Titchfield Peninsula
Fairy Hill
Orange Bay
Boston Bay
Snow Hill
Hope Bay
Long Bay
Buff Bay
Portland Travel Tips
How Can You Make the Most of Your Stay?
- Explore the local cuisine: Take advantage of the region's vibrant dining options to indulge in authentic Jamaican flavors during your stay.
- Visit off-the-beaten-path beaches: Discover secluded beaches that offer tranquility and natural beauty away from popular tourist spots.
- Engage with cultural experiences: Immerse yourself in the area’s rich heritage through local markets, music events, or art galleries.
- Plan outdoor adventures: Make the most of the tropical climate by arranging activities like hiking, snorkeling, or wildlife tours tailored to this destination.
Transportation Options
- Taxis and Private Transfers: Convenient for tailored travel around the region, offering flexible schedules for exploring local attractions from your vacation rental.
- Car Rentals: Ideal for those who prefer independence, allowing you to explore the area at your own pace with a variety of vehicles available nearby.
- Buses and Minivans: An affordable option connecting key points within this destination, perfect for budget-conscious travelers staying in vacation rentals here.
- Motorbike Rentals: A nimble way to navigate narrower roads and enjoy scenic drives through the region’s lush landscapes and coastal areas.
Local Customs Options
- Gung-Ho Ceremonies: You might observe lively and colorful celebrations during local ceremonies that honor community heritage and traditions in this vibrant region.
- Music and Dance Etiquette: Engaging with authentic reggae rhythms and dance styles is common here, reflecting the area's deep cultural roots and lively spirit.
- Traditional Food Practices: Expect to encounter local customs around food preparation and communal meals that showcase the region’s rich culinary history.
- Market Trading Customs: Interacting with vendors at the local markets involves friendly bargaining and an appreciation for handmade crafts unique to the area.
Frequently Asked Questions About Portland?
1. What are the top vacation rentals in Portland?
There are a lot of options in Portland. If you plan on staying in the Portland area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Portland:
- Private Luxury Beachfront/Oceanfront Townhome in Beautiful Negril, Jamaica
- Private Oasis in Negril: Beachfront Luxury!
- 'Sunset Vista' - Negril Seafront Townhouse - W/Solar Power
- Port Antonio Seaside Villa in Jamaica SeaStar
- Stunning Ocean View
- Villa Sweet J - Run on Island Time
- Swim, Sleep and Exhale. Good for 1, perfect for 2 - 24hr security, Free Wifi
- The Sapphire | Negril Sunset Oceanfront Villa
- All Inclusive Negril Beachfront Family Villa located in a gated country club
- A beautiful villa with magnificent views of the Caribbean Sea in Negril, Jamaica
2. How many vacation rentals have private pools in Portland?
There are 23 vacation rentals with private pools near Portland. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Portland are best for families?
If you are looking for a family-friendly vacation home in Portland, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Portland:
4. How many Rentbyowner vacation rentals are available in Portland?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 545 in the Portland area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Portland.
5. What is the cancellation policy for vacation rentals in Portland, Jamaica?
Cancellation policies vary by property owner, so it's important to review the specific listing details before booking. You can also contact the host directly to clarify the cancellation terms and any potential fees.
6. Are there any special requirements or restrictions when booking a vacation rental in this area?
Certain properties may have specific requirements such as minimum stay durations, age restrictions, or approval processes. Be sure to check the listing details or reach out to the host for any special conditions.
7. How do I find the most accurate rates and availability for vacation rentals here?
Rates and availability are updated regularly on the listing pages. To ensure accuracy, book directly through the listing, and consider contacting the owner if you have specific dates or questions.
8. What amenities should I look for when booking a vacation rental in this destination?
Popular amenities include Wi-Fi, air conditioning, fully equipped kitchens, and private outdoor spaces. Review each property’s listing to confirm the amenities that meet your needs for a comfortable stay.
9. Is there a secure method to pay for my vacation rental reservation in this region?
Payments are typically processed through trusted platforms that offer secure methods for booking and payment. Check the listing for accepted payment options and contact the owner if you have concerns about the transaction security.
Portland Top Rated Vacation Rentals
Apartment
10.0(11 Reviews)
1 Bedroom
1 Bath
2 Guests
350 ft²
- Hot Tub
- Pool
- Ocean View
- Balcony/Terrace
£130/Night
7 Nights - £913
House
10.0(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
1160 ft²
- Private Pool
- Pool
- Ocean View
- Balcony/Terrace
£172/Night
7 Nights - £1,206
Apartment
10.0(4 Reviews)
1 Bedroom
1 Bath
3 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£95/Night
7 Nights - £662
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1163 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£424/Night
7 Nights - £2,968
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
9 Guests
3270 ft²
- Private Pool
- Oceanfront
- Pool
- Ocean View
£497/Night
7 Nights - £3,481
Condo
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Pool
- Ocean View
- View
- Kitchen
£118/Night
7 Nights - £825
Bed & Breakfast
10.0(2 Reviews)
1 Bedroom
1 Bath
2 Guests
- Pool
- Balcony/Terrace
- Breakfast
- Kitchen
£111/Night
7 Nights - £774
House
10.0(1 Review)
10 Bedrooms
10 Baths
20 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
£221/Night
7 Nights - £1,545
