Cheap Vacations in Portland

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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 $685, price is now $546 per person
$546
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $2,658, price is now $1,350 per person
$1,350
per person
Apr 7 - Apr 15
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,193, price is now $919 per person
$919
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,149, price is now $894 per person
$894
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,123, price is now $1,784 per person
$1,784
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $987, price is now $852 per person
$852
per person
Apr 20 - Apr 23
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 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 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,265, price is now $1,111 per person
$1,111
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 1 day 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.
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 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
The Emrald of the North

The Emrald of the North

3.5 out of 5
Price was $2,006, price is now $1,483 per person
$1,483
per person
Apr 9 - Apr 12
found 2 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 $1,130, price is now $938 per person
$938
per person
Apr 18 - Apr 21
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $987, price is now $852 per person
$852
per person
Apr 20 - Apr 23
found 20 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Panoramic Cliffside Luxe Villa

Panoramic Cliffside Luxe Villa

2 out of 5
Save 100% on your flight
Price was $5,085, price is now $4,437 per person
$4,437
per person
Apr 21 - Apr 24
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 1 day 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 1 day 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 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Teal Horizon OceanfrontCaribbean Escape

Teal Horizon OceanfrontCaribbean Escape

2 out of 5
Price was $864, price is now $777 per person
$777
per person
Apr 27 - Apr 30
found 11 hours ago
Roundtrip 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 $772, price is now $698 per person
$698
per person
Apr 21 - Apr 24
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 $3,647, price is now $3,379 per person
$3,379
per person
Apr 4 - Apr 7
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,117, price is now $1,035 per person
$1,035
per person
Apr 17 - Apr 20
found 6 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)

4-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 $1,149, price is now $894 per person
$894
per person
Apr 18 - Apr 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 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 $4,793, price is now $3,952 per person
$3,952
per person
Apr 5 - Apr 9
found 1 day 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 $2,123, price is now $1,784 per person
$1,784
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,311, price is now $1,138 per person
$1,138
per person
Apr 9 - Apr 13
found 1 day ago
Roundtrip flight included
New York (JFK) 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 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 $6,054, price is now $5,273 per person
$5,273
per person
Apr 21 - Apr 25
found 1 day 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 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,265, price is now $1,111 per person
$1,111
per person
Apr 4 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 1 day 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 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 $1,192, price is now $1,054 per person
$1,054
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) 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 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
Save 100% on your flight
Price was $2,146, price is now $1,330 per person
$1,330
per person
Apr 27 - May 2
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,320, price is now $1,005 per person
$1,005
per person
Apr 18 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 day 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 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,165, price is now $936 per person
$936
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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 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 $1,468, price is now $1,232 per person
$1,232
per person
Apr 7 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,241, price is now $1,054 per person
$1,054
per person
Apr 9 - Apr 14
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
3 Bedroom Beachfront Cozy House

3 Bedroom Beachfront Cozy House

2 out of 5
Price was $2,711, price is now $2,312 per person
$2,312
per person
Apr 7 - Apr 12
found 24 hours ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Sea Shell Palms

Sea Shell Palms

2.5 out of 5
Price was $1,093, price is now $944 per person
$944
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,127, price is now $977 per person
$977
per person
Apr 9 - Apr 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)

6-7 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 $685, price is now $546 per person
$546
per person
Apr 15 - Apr 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
GC Resort

GC Resort

3 out of 5
Price was $1,193, price is now $919 per person
$919
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Whispering Seas

Whispering Seas

3.5 out of 5
Price was $1,642, price is now $1,267 per person
$1,267
per person
Apr 18 - Apr 24
found 21 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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 $1,735, price is now $1,462 per person
$1,462
per person
Apr 9 - Apr 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Seapalms

Seapalms

3 out of 5
Price was $809, price is now $687 per person
$687
per person
Apr 27 - May 3
found 16 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Cozy Cove Villa in Drax Hall

Cozy Cove Villa in Drax Hall

2 out of 5
Price was $1,570, price is now $1,348 per person
$1,348
per person
Apr 9 - Apr 15
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Ocho Rios (OCJ)
Paradisiac Euphoria Beach Access Pool 24hr Gated

Paradisiac Euphoria Beach Access Pool 24hr Gated

2 out of 5
Price was $1,633, price is now $1,429 per person
$1,429
per person
Apr 5 - Apr 11
found 1 day 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 $11,823, price is now $10,423 per person
$10,423
per person
Apr 11 - Apr 18
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Morgans cliff

Morgans cliff

3.5 out of 5
Price was $1,096, price is now $981 per person
$981
per person
Apr 21 - Apr 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Ocho Rios (OCJ)
Blue Berry Hills Villa

Blue Berry Hills Villa

3 out of 5
Price was $5,325, price is now $4,770 per person
$4,770
per person
Apr 4 - Apr 11
found 1 day ago
Roundtrip flight included
New York (JFK) to Ocho Rios (OCJ)
Apartment E6

Apartment E6

3.5 out of 5
Price was $959, price is now $862 per person
$862
per person
Apr 20 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Ocho Rios (OCJ)
Tuscany Sun Villa at Legacy Townhouse

Tuscany Sun Villa at Legacy Townhouse

2 out of 5
Price was $3,212, price is now $2,909 per person
$2,909
per person
Apr 9 - Apr 15
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 2 days ago
$265
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Fri, Apr 24 from Fort Lauderdale to Kingston, returning Mon, Apr 27, priced at $265 found 2 days ago
Thu, Mar 12 - Fri, Mar 27
MIA
Miami
KIN
Kingston
$319 Roundtrip, found 18 hours ago
$319
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Thu, Mar 12 from Miami to Kingston, returning Fri, Mar 27, priced at $319 found 18 hours ago
Tue, Mar 17 - Tue, Mar 31
MCO
Orlando
KIN
Kingston
$326 Roundtrip, found 4 days ago
$326
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Tue, Mar 17 from Orlando to Kingston, returning Tue, Mar 31, priced at $326 found 4 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.
Pool
Free WiFi
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.
Pool
Breakfast included
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 8 - Mar 9
Total with taxes and fees
Located in Port Antonio, Geejam is a 3-minute drive from Trident Castle and 9 minutes from Rio Grande.
Pool
Spa
Don't see what you're looking for?
See all available properties in Portland
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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.