Cheap Vacations in Portland

Choose two or more items and save on your trip:

Portland vacations

Price found within the past 48 hours. Click for updated prices.
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $868, price is now $612 per person
$612
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Save 100% on your flight
Price was $2,971, price is now $2,382 per person
$2,382
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $8,351, price is now $6,980 per person
$6,980
per person
Apr 6 - Apr 12
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,018, price is now $1,696 per person
$1,696
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $741, price is now $637 per person
$637
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,025, price is now $890 per person
$890
per person
Apr 9 - Apr 13
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Coastal Escape in Riviera Tower Isle Beach Nearby

Coastal Escape in Riviera Tower Isle Beach Nearby

2 out of 5
Price was $1,282, price is now $1,119 per person
$1,119
per person
Apr 22 - Apr 26
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $4,687, price is now $4,098 per person
$4,098
per person
Apr 21 - Apr 24
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $5,290, price is now $4,680 per person
$4,680
per person
Apr 21 - Apr 24
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

3 out of 5
Price was $794, price is now $708 per person
$708
per person
Apr 16 - Apr 21
found 10 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)

3-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $732, price is now $534 per person
$534
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $741, price is now $637 per person
$637
per person
Apr 26 - Apr 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $4,687, price is now $4,098 per person
$4,098
per person
Apr 21 - Apr 24
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $777, price is now $685 per person
$685
per person
Apr 12 - Apr 15
found 1 hour ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Price was $5,199, price is now $4,584 per person
$4,584
per person
Apr 4 - Apr 7
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $5,290, price is now $4,680 per person
$4,680
per person
Apr 21 - Apr 24
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $936, price is now $837 per person
$837
per person
Apr 21 - Apr 24
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $779, price is now $705 per person
$705
per person
Apr 26 - Apr 29
found 18 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,191, price is now $1,078 per person
$1,078
per person
Apr 3 - Apr 6
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

3 out of 5
Price was $677, price is now $623 per person
$623
per person
Apr 21 - Apr 24
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $3,732, price is now $3,459 per person
$3,459
per person
Apr 4 - Apr 7
found 17 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $1,024, price is now $950 per person
$950
per person
Apr 4 - Apr 7
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)

4-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $595, price is now $506 per person
$506
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $1,926, price is now $1,276 per person
$1,276
per person
Apr 16 - Apr 20
found 8 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $868, price is now $612 per person
$612
per person
Apr 20 - Apr 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $4,793, price is now $3,952 per person
$3,952
per person
Apr 5 - Apr 9
found 7 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,018, price is now $1,696 per person
$1,696
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,025, price is now $890 per person
$890
per person
Apr 9 - Apr 13
found 20 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $6,584, price is now $5,725 per person
$5,725
per person
Apr 21 - Apr 25
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $6,054, price is now $5,273 per person
$5,273
per person
Apr 21 - Apr 25
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Coastal Escape in Riviera Tower Isle Beach Nearby

Coastal Escape in Riviera Tower Isle Beach Nearby

2 out of 5
Price was $1,282, price is now $1,119 per person
$1,119
per person
Apr 22 - Apr 26
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $2,922, price is now $2,572 per person
$2,572
per person
Apr 6 - Apr 10
found 14 hours ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
Coastal Escape Tower Isle Beach Nearby

Coastal Escape Tower Isle Beach Nearby

2.5 out of 5
Price was $1,052, price is now $926 per person
$926
per person
Apr 21 - Apr 25
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $6,857, price is now $6,049 per person
$6,049
per person
Apr 21 - Apr 25
found 7 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)

5-night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Seapalms

Seapalms

3 out of 5
Price was $774, price is now $673 per person
$673
per person
Apr 18 - Apr 23
found 6 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Save 100% on your flight
Price was $2,190, price is now $1,374 per person
$1,374
per person
Apr 9 - Apr 14
found 16 hours ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Save 100% on your flight
Price was $1,013, price is now $691 per person
$691
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $9,012, price is now $6,897 per person
$6,897
per person
Apr 9 - Apr 14
found 1 hour ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $9,353, price is now $7,227 per person
$7,227
per person
Apr 9 - Apr 14
found 1 hour ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $843, price is now $680 per person
$680
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $6,635, price is now $5,422 per person
$5,422
per person
Apr 9 - Apr 14
found 1 hour ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

Luxury Oceanfront Villa Fully Staffed Pool Jacuzzi Movie Theatre

3 out of 5
Save 100% on your flight
Price was $7,260, price is now $5,951 per person
$5,951
per person
Apr 28 - May 3
found 1 day ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Save 100% on your flight
Price was $2,299, price is now $1,891 per person
$1,891
per person
Apr 19 - Apr 24
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Sun-soaked Paradisiac Escape 3BR Private Beach Pool

Sun-soaked Paradisiac Escape 3BR Private Beach Pool

2 out of 5
Price was $1,559, price is now $1,286 per person
$1,286
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Ocho Rios (OCJ)
Teal Horizon Oceanfrontcaribbean Escape Tower Isle

Teal Horizon Oceanfrontcaribbean Escape Tower Isle

2 out of 5
Price was $1,014, price is now $843 per person
$843
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,037, price is now $902 per person
$902
per person
Apr 22 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Ocho Rios (OCJ)

6-7 night Portland vacations

Price found within the past 48 hours. Click for updated prices.
Seapalms

Seapalms

3 out of 5
Price was $709, price is now $582 per person
$582
per person
Apr 26 - May 2
found 11 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Save 100% on your flight
Price was $1,221, price is now $834 per person
$834
per person
Apr 18 - Apr 24
found 1 day ago
Roundtrip flight included
New York (NYC) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Save 100% on your flight
Price was $2,971, price is now $2,382 per person
$2,382
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Sun-soaked Paradisiac Escape 3BR Private Beach Pool

Sun-soaked Paradisiac Escape 3BR Private Beach Pool

2 out of 5
Price was $1,971, price is now $1,617 per person
$1,617
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa Fully Staffed

Luxury Oceanfront Villa Fully Staffed

2 out of 5
Price was $8,351, price is now $6,980 per person
$6,980
per person
Apr 6 - Apr 12
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,604, price is now $1,377 per person
$1,377
per person
Apr 8 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Luxury Oceanfront Villa in Tower Isle

Luxury Oceanfront Villa in Tower Isle

2 out of 5
Save 100% on your flight
Price was $11,823, price is now $10,423 per person
$10,423
per person
Apr 11 - Apr 18
just found
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
3rd Floor Condo Tower Isle 24hr Security

3rd Floor Condo Tower Isle 24hr Security

2 out of 5
Price was $1,199, price is now $1,070 per person
$1,070
per person
Apr 3 - Apr 10
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $4,548, price is now $4,066 per person
$4,066
per person
Apr 6 - Apr 12
found 18 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
The Dream Nest At Csompo Silver Manor

The Dream Nest At Csompo Silver Manor

3 out of 5
Price was $2,130, price is now $1,933 per person
$1,933
per person
Apr 3 - Apr 9
found 7 hours ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Leisure Duplex At Csompo Silver Manor

Leisure Duplex At Csompo Silver Manor

2 out of 5
Price was $969, price is now $884 per person
$884
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Denver (DEN) to Ocho Rios (OCJ)
Apartment E6

Apartment E6

3.5 out of 5
Price was $1,206, price is now $1,103 per person
$1,103
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)

Top places to visit in Portland

Winnifred Beach which includes general coastal views as well as a small group of people
FlightsFlightsHotelsHotels

Port Antonio

Port Antonio

Flight deals to Portland

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Fri, Apr 24 - Mon, Apr 27
FLL
Fort Lauderdale
KIN
Kingston
$265 Roundtrip, found 15 hours ago
$265
Roundtrip
found 15 hours ago
Select Spirit Airlines flight, departing Fri, Apr 24 from Fort Lauderdale to Kingston, returning Mon, Apr 27, priced at $265 found 15 hours ago
Wed, Mar 11 - Sat, Mar 14
MIA
Miami
KIN
Kingston
$299 Roundtrip, found 1 day ago
$299
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Mar 11 from Miami to Kingston, returning Sat, Mar 14, priced at $299 found 1 day ago
Tue, Mar 17 - Tue, Mar 31
MCO
Orlando
KIN
Kingston
$326 Roundtrip, found 2 days ago
$326
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Mar 17 from Orlando to Kingston, returning Tue, Mar 31, priced at $326 found 2 days ago

Top rated hotels for your Portland vacation

Sea Cliff Resort

Sea Cliff Resort

3 out of 5
Ross Craig Long Bay Portland
Free Cancellation
11.75 mi from city center
Get rates
With a stay at Sea Cliff Resort in Long Bay, you'll be 2.1 mi (3.3 km) from Long Bay Beach and 7.3 mi (11.7 km) from Boston Bay Beach.
Jamaica Palace Hotel

Jamaica Palace Hotel

3.5 out of 5
Williamsfield Port Antonio Portland
Free Cancellation
Reserve now, pay when you stay
1.85 mi from city center
$169 nightly
The price is $188 total per night
$188 total
Mar 26 - Mar 27
Total with taxes and fees
Located in Port Antonio, Jamaica Palace Hotel is by the ocean, a 1-minute drive from Trident Castle and 7 minutes from Rio Grande.
Geejam

Geejam

4.5 out of 5
San San, Port Antonio Port Antonio Portland
2.48 mi from city center
$490 nightly
The price is $535 total per night
$535 total
Mar 5 - Mar 6
Total with taxes and fees
Located in Port Antonio, Geejam is a 3-minute drive from Trident Castle and 9 minutes from Rio Grande.
Don't see what you're looking for?
See all available properties in Portland
View all properties
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.

^Savings based on all package bookings with Flight + Hotel made on CheapTickets.com from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.