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$165 -- Bermuda: Fairmont's Biggest Annual Sale: 50% Off
 
Source: Fairmont Southampton | By Camille Lamb Guzman

The AAA 4-Diamond Fairmont Southampton is cutting rates in half for year-round stays, and including daily continental breakfast as an added perk.
All year

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Source: BookIt.com

For $109 per person, per night, book a deluxe junior suite at this all-inclusive beach resort.
Through December; best rates in Spring & Fall

 
Source: Hilton Aruba Caribbean Resort & Casino

Half off rates and the option to double dollars for resort credit make this an excellent deal for travel to one of the Caribbean's safest islands.
Discounts from May to mid-December

 
Source: Member Only Deal

Make winter a distant memory with this sale at a beachfront Cancun resort that's family-friendly and all-inclusive.
Through March; deeper discounts April - early July

 
Source: Four Seasons Resort Punta Mita

Frommer's calls it "one of the world's most spectacular resorts."
May 12, 2016 - Oct. 16, 2016

100% (265 ratings)
 
Source: Villa del Palmar Cancun

Experience an upscale gem that's "a world away from the city's party scene" (Travel + Leisure) with 30% off rooms at Villa Del Palmar resort
April 1 - July 12

86% (7 ratings)
 
Source: Aloft Cancun

The stylish Aloft Cancun is a great spot to stay for exploring Cancun's nightlife
March 30 - April 20

 
Source: BookIt.com

For $125 per guest per night, take advantage of 30% savings and unlimited golf at this oceanfront resort.
Through 2016; best rates in Spring-Summer

 
Source: BookIt.com

Save 55% on a Caribbean escape for two at this high-end all-inclusive resort in Montego Bay.
Travel through December

 
Source: BookIt.com

Save up to 65% on all-inclusive beach vacations. Most deals also include flight or resort credits.
Through December; Best rates in Spring-Summer

 
Source: BookIt.com

Score up to 65% savings at these all-inclusive beach resorts. Book your flight at the same time for additional savings.
Through December; best rates in Spring-Summer

 
Source: El Cid Castilla Beach

Escape the winter blues at El Cid Castilla Beach with all-inclusive and room-only deals during peak season
Through Aug. 31

 
Source: Westin Resort & Spa Cancun

This ocean front resort has a private, white sand beach, the Nichupte Lagoon and the "best waters for snorkeling" (Frommer's).
Many dates through April

 
Source: Member Only Deal

Stay in Cabo this winter and get $45 worth in extras with beautiful views of the harbor.
Daily through February

 
Source: Colony Club by Elegant Hotels

The nightly rate at this amenity-packed luxury resort includes freebies like tours, fitness classes and more.
June-August; 3-night stay required

 
Source: Rosarito Beach Hotel, Baja

Bask in the sun and relax by the beach with a 50%-off deal that includes daily mimosa breakfast, two 60-minute massages, a border FastPass and more.
Arrivals through June 28

96% (1139 ratings)
 
Source: Harlequin Hotels & Resorts

Sneak off to the lush rain forests and idyllic beaches of St. Vincent & the Grenadines -- "the Caribbean's best kept secret" (Travel + Leisure).
Arrival options April 16 - Dec. 15, 2016

 
Source: The Crane Residential Resort

Includes a swanky 750-square-foot Junior Suite
April-August; March for $260 per night

 

More Deals on Caribbean & Mexico Hotels

 
 
Through December; best rates in Spring
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Travel through December; best rates in Spring
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Travel through 2016; best rates in Spring
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Travel options through December
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