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Winter Vacations

Be Live Collection Marien

Hotel rating 4.0 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Deluxe Gardenview Double

Dec 08, 2026 (7 days)
Book with Deposit
~~was $2750~~ Save 55%

$1247 PP incl. taxes & fees
Viva Wyndham Tangerine

Hotel rating 4.0 out of 5 stars

Toronto to Cabarete, Dominican Republic

All Inclusive

Superior Room

Dec 10, 2026 (7 days)
Book with Deposit
~~was $2004~~ Save 37%

$1257 PP incl. taxes & fees
Blue Bay Villas Doradas

Hotel rating 4.0 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Room

Dec 15, 2026 (7 days)
Book with Deposit
~~was $1881~~ Save 33%

$1257 PP incl. taxes & fees
Vik Arena Blanca

Hotel rating 4.0 out of 5 stars

Toronto to Punta Cana, Dominican Republic

All Inclusive

Room Gardenview

Dec 06, 2026 (7 days)
Book with Deposit
~~was $2899~~ Save 56%

$1279 PP incl. taxes & fees
Viva Wyndham V Heavens

Hotel rating 4.0 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Bliss Room

Dec 01, 2026 (7 days)
Book with Deposit
~~was $2771~~ Save 53%

$1306 PP incl. taxes & fees
Whala Boca Chica

Hotel rating 3.0 out of 5 stars

Toronto to Santo Domingo, Dominican Republic

All Inclusive

Room

Dec 05, 2026 (7 days)
Book with Deposit
~~was $1865~~ Save 30%

$1313 PP incl. taxes & fees
Senator Puerto Plata Spa Resort

Hotel rating 4.5 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Senator Junior Suite 1 King

Dec 01, 2026 (7 days)
Book with Deposit
~~was $2981~~ Save 55%

$1336 PP incl. taxes & fees
Vh Gran Ventana

Hotel rating 4.5 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Superior Room

Dec 15, 2026 (7 days)
Book with Deposit
~~was $2024~~ Save 33%

$1365 PP incl. taxes & fees
Cofresi Palm Beach and Spa Resort

Hotel rating 3.5 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Superior Room

Jan 31, 2027 (7 days)
Book with Deposit
~~was $1975~~ Save 30%

$1392 PP incl. taxes & fees
Whala Bavaro

Hotel rating 4.0 out of 5 stars

Toronto to Punta Cana, Dominican Republic

All Inclusive

Room

Dec 16, 2026 (7 days)
Book with Deposit
~~was $2095~~ Save 32%

$1422 PP incl. taxes & fees

Bahia Principe Grand Jamaica

Hotel rating 4.5 out of 5 stars

Toronto to Runaway Bay, Jamaica

All Inclusive

Deluxe Junior Suite Double

Dec 13, 2026 (7 days)
Book with Deposit
$1822 PP incl. taxes & fees
Samsara Cliff Resort and Spa

Hotel rating 3.0 out of 5 stars

Toronto to Negril, Jamaica

All Inclusive

Gardenview Room

Feb 02, 2027 (7 days)
Book with Deposit
$1875 PP incl. taxes & fees
Bahia Principe Luxury Runaway Bay

Hotel rating 5.0 out of 5 stars

Toronto to Runaway Bay, Jamaica

All Inclusive

Deluxe Junior Suite King

Dec 08, 2026 (7 days)
Book with Deposit
$1881 PP incl. taxes & fees
Legends Beach Resort

Hotel rating 3.0 out of 5 stars

Toronto to Negril, Jamaica

All Inclusive

Room Garden Side

Dec 10, 2026 (7 days)
Book with Deposit
$1910 PP incl. taxes & fees
Iberostar Rose Hall Beach

Hotel rating 4.0 out of 5 stars

Toronto to Montego Bay, Jamaica

All Inclusive

Premium Room

Dec 13, 2026 (7 days)
Book with Deposit
$2068 PP incl. taxes & fees
Seagarden Beach Resort

Hotel rating 3.5 out of 5 stars

Toronto to Montego Bay, Jamaica

All Inclusive

Room

Dec 09, 2026 (7 days)
Book with Deposit
$2099 PP incl. taxes & fees
Riu Montego Bay

Hotel rating 5.0 out of 5 stars

Toronto to Montego Bay, Jamaica

All Inclusive

Room

Dec 08, 2026 (7 days)
Book with Deposit
$2141 PP incl. taxes & fees
Riu Ocho Rios

Hotel rating 5.0 out of 5 stars

Toronto to Ocho Rios, Jamaica

All Inclusive

Room Gardenview

Dec 09, 2026 (7 days)
Book with Deposit
~~was $2555~~ Save 14%

$2190 PP incl. taxes & fees
Riu Negril

Hotel rating 5.0 out of 5 stars

Toronto to Negril, Jamaica

All Inclusive

Room Gardenview

Dec 09, 2026 (7 days)
Book with Deposit
~~was $2695~~ Save 19%

$2190 PP incl. taxes & fees
Ocean Coral Spring

Hotel rating 4.5 out of 5 stars

Toronto to Montego Bay, Jamaica

All Inclusive

Junior Suite Nature View

Dec 01, 2026 (7 days)
Book with Deposit
~~was $2528~~ Save 13%

$2196 PP incl. taxes & fees

Viva Wyndham Fortuna Beach

Hotel rating 3.5 out of 5 stars

Toronto to Freeport, Bahamas

All Inclusive

Superior Gardenview

Dec 05, 2026 (7 days)
Book with Deposit
~~was $2385~~ Save 24%

$1824 PP incl. taxes & fees
Starfish Jolly Beach Resort

Hotel rating 3.0 out of 5 stars

Toronto to Antigua, Antigua and Barbuda

All Inclusive

Room Double

Dec 01, 2026 (7 days)
Book with Deposit
~~was $2519~~ Save 27%

$1839 PP incl. taxes & fees
Ocean Point Resort and Spa

Hotel rating 3.0 out of 5 stars

Toronto to Antigua, Antigua and Barbuda

All Inclusive

Room Gardenview

Mar 30, 2027 (7 days)
Book with Deposit
~~was $3069~~ Save 36%

$1979 PP incl. taxes & fees
Island Inn Hotel

Hotel rating 3.0 out of 5 stars

Toronto to Bridgetown, Barbados

All Inclusive

Garden Courtyard Room

Dec 13, 2026 (7 days)
Book with Deposit
~~was $3329~~ Save 35%

$2159 PP incl. taxes & fees
Warwick Paradise Island Resort

Hotel rating 4.0 out of 5 stars

Toronto to Nassau, Bahamas

All Inclusive

Island View Room King

Dec 01, 2026 (7 days)
Book with Deposit
~~was $3787~~ Save 42%

$2208 PP incl. taxes & fees
Breezes Resort

Hotel rating 3.0 out of 5 stars

Toronto to Nassau, Bahamas

All Inclusive

Classic Room

Jan 14, 2027 (7 days)
Book with Deposit
$2239 PP incl. taxes & fees
Barbados Beach Club

Hotel rating 3.0 out of 5 stars

Toronto to Bridgetown, Barbados

All Inclusive

Deluxe Room

Dec 05, 2026 (7 days)
Book with Deposit
~~was $3122~~ Save 27%

$2286 PP incl. taxes & fees
Royalton Antigua Resort and Spa

Hotel rating 4.5 out of 5 stars

Toronto to Antigua, Antigua and Barbuda

All Inclusive

Luxury Junior Suite

Dec 09, 2026 (7 days)
Book with Deposit
~~was $3402~~ Save 26%

$2503 PP incl. taxes & fees
Pineapple Beach Club

Hotel rating 4.0 out of 5 stars

Toronto to Antigua, Antigua and Barbuda

All Inclusive

Pool Terrace Room

Dec 09, 2026 (7 days)
Book with Deposit
~~was $3611~~ Save 27%

$2643 PP incl. taxes & fees
The Verandah Resort and Spa

Hotel rating 4.0 out of 5 stars

Toronto to Antigua, Antigua and Barbuda

All Inclusive

Hillside Suite King

Dec 09, 2026 (7 days)
Book with Deposit
~~was $3982~~ Save 34%

$2643 PP incl. taxes & fees

Sheraton Bijao Beach Resort

Hotel rating 4.5 out of 5 stars

Toronto to Playa Blanca, Panama

All Inclusive

Deluxe Gardenview Room

Dec 12, 2026 (7 days)
Book with Deposit
~~was $1815~~ Save 16%

$1518 PP incl. taxes & fees
Playa Blanca Resort

Hotel rating 4.0 out of 5 stars

Toronto to Playa Blanca, Panama

All Inclusive

Room Gardenview

Dec 12, 2026 (7 days)
Book with Deposit
~~was $1795~~ Save 15%

$1528 PP incl. taxes & fees
Occidental Tamarindo

Hotel rating 4.5 out of 5 stars

Toronto to Tamarindo, Costa Rica

All Inclusive

Superior Room

Dec 09, 2026 (7 days)
Book with Deposit
~~was $2829~~ Save 44%

$1579 PP incl. taxes & fees
Royal Decameron Golf and Beach Rst

Hotel rating 4.0 out of 5 stars

Toronto to Playa Blanca, Panama

All Inclusive

Room Gardenview Double

Dec 12, 2026 (7 days)
Book with Deposit
~~was $2155~~ Save 25%

$1627 PP incl. taxes & fees
Riu Playa Blanca

Hotel rating 5.0 out of 5 stars

Toronto to Playa Blanca, Panama

All Inclusive

Tropical View Room

Dec 14, 2026 (7 days)
Book with Deposit
~~was $2035~~ Save 15%

$1725 PP incl. taxes & fees
Occidental Papagayo

Hotel rating 4.5 out of 5 stars

Toronto to Liberia, Costa Rica

All Inclusive

Deluxe Room

Dec 09, 2026 (7 days)
Book with Deposit
~~was $2309~~ Save 21%

$1819 PP incl. taxes & fees
The Westin Playa Bonita Panama

Hotel rating 4.5 out of 5 stars

Toronto to Panama City, Panama

All Inclusive

Deluxe Room Forest View

Dec 12, 2026 (7 days)
Book with Deposit
~~was $2165~~ Save 11%

$1922 PP incl. taxes & fees
Fiesta Resort Costa Rica | Book All Inclusive | redtag.ca

Hotel rating 4.0 out of 5 stars

Toronto to Puntarenas, Costa Rica

All Inclusive

Fiesta Room

Mar 31, 2027 (7 days)
Book with Deposit
~~was $4229~~ Save 53%

$1969 PP incl. taxes & fees
Dreams Delight Playa Bonita Panama

Hotel rating 4.5 out of 5 stars

Toronto to Panama City, Panama

All Inclusive

Deluxe Partial Oceanview King

Feb 17, 2027 (7 days)
Book with Deposit
~~was $4279~~ Save 51%

$2079 PP incl. taxes & fees
Riu Guanacaste

Hotel rating 5.0 out of 5 stars

Toronto to Liberia, Costa Rica

All Inclusive

Room

Dec 05, 2026 (7 days)
Book with Deposit
~~was $2465~~ Save 8%

$2257 PP incl. taxes & fees

Flamingo Vallarta Hotel Marina | Book Your Stay | redtag.ca

Hotel rating 3.0 out of 5 stars

Toronto to Puerto Vallarta, Mexico

All Inclusive

Junior Suite

Dec 07, 2026 (7 days)
Book with Deposit
~~was $2239~~ Save 49%

$1139 PP incl. taxes & fees
Grand Palladium Colonial Resort | Book Your Stay | redtag.ca

Hotel rating 4.5 out of 5 stars

Toronto to Riviera Maya, Mexico

All Inclusive

Deluxe Gardenview Room

Dec 04, 2026 (7 days)
Book with Deposit
~~was $2399~~ Save 50%

$1189 PP incl. taxes & fees
Blue Bay Grand Esmeralda

Hotel rating 4.0 out of 5 stars

Toronto to Riviera Maya, Mexico

All Inclusive

Promo Room

Dec 14, 2026 (7 days)
Book with Deposit
~~was $1809~~ Save 31%

$1249 PP incl. taxes & fees
Krystal Vallarta

Hotel rating 4.0 out of 5 stars

Toronto to Puerto Vallarta, Mexico

All Inclusive

Superior Room

Dec 07, 2026 (7 days)
Book with Deposit
~~was $2269~~ Save 43%

$1289 PP incl. taxes & fees
Vamar Vallarta

Hotel rating 3.0 out of 5 stars

Toronto to Puerto Vallarta, Mexico

All Inclusive

Room

Dec 07, 2026 (7 days)
Book with Deposit
~~was $2189~~ Save 40%

$1309 PP incl. taxes & fees
Hacienda Buenaventura Vallarta | Book Your Stay | redtag.ca

Hotel rating 3.0 out of 5 stars

Toronto to Puerto Vallarta, Mexico

All Inclusive

Room King

Dec 07, 2026 (7 days)
Book with Deposit
~~was $2189~~ Save 39%

$1339 PP incl. taxes & fees
Flamingo Cancun Resort

Hotel rating 3.5 out of 5 stars

Toronto to Cancun, Mexico

All Inclusive

Lagoon View Room

Dec 02, 2026 (7 days)
Book with Deposit
~~was $2345~~ Save 42%

$1353 PP incl. taxes & fees
Viva Wyndham Maya

Hotel rating 4.0 out of 5 stars

Toronto to Riviera Maya, Mexico

All Inclusive

Superior Room

Dec 03, 2026 (7 days)
Book with Deposit
~~was $1969~~ Save 31%

$1359 PP incl. taxes & fees
Hilton Puerto Vallarta Resort

Hotel rating 5.0 out of 5 stars

Toronto to Puerto Vallarta, Mexico

All Inclusive

Resort Room Double

Mar 30, 2027 (7 days)
Book with Deposit
~~was $2019~~ Save 33%

$1359 PP incl. taxes & fees
Costa Club Punta Arena Vallarta | Book Your Stay | redtag.ca

Hotel rating 3.0 out of 5 stars

Toronto to Puerto Vallarta, Mexico

All Inclusive

Room

Dec 07, 2026 (7 days)
Book with Deposit
~~was $2249~~ Save 39%

$1379 PP incl. taxes & fees

Cuba - Varadero

Mexico - Cancun

Jamaica - Montego Bay

Mexico - Riviera Nayarit

Mexico - Riviera Maya

Dominican - Punta Cana

Dominican - Puerto Plata

Cuba - Holguin

Why book

January and February Vacation Packages on Sale! Book you Winter Vacation now to Caribbean, Mexico, Dominican Republic and Cuba, Choose your departure city and Get the Best prices on your Winter Vacations.