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Winter Vacations

Blue Bay Villas Doradas

Hotel rating 4.0 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Room

Dec 03, 2026 (7 days)
Book with Deposit
~~was $2044~~ Save 39%

$1237 PP incl. taxes & fees
Be Live Collection Marien

Hotel rating 4.0 out of 5 stars

Toronto to Puerto Plata, Dominican Republic

All Inclusive

Deluxe Gardenview King

Dec 03, 2026 (7 days)
Book with Deposit
~~was $2750~~ Save 55%

$1237 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 07, 2026 (7 days)
Book with Deposit
~~was $2004~~ Save 38%

$1246 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 03, 2026 (7 days)
Book with Deposit
~~was $2183~~ Save 42%

$1256 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 01, 2026 (7 days)
Book with Deposit
~~was $3659~~ Save 65%

$1279 PP incl. taxes & fees
Emotions by Hodelpa

Hotel rating 4.0 out of 5 stars

Toronto to Santo Domingo, Dominican Republic

All Inclusive

Superior Room

Dec 15, 2026 (7 days)
Book with Deposit
~~was $3789~~ Save 65%

$1339 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 03, 2026 (7 days)
Book with Deposit
~~was $2044~~ Save 34%

$1344 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 07, 2026 (7 days)
Book with Deposit
~~was $2114~~ Save 36%

$1354 PP incl. taxes & fees
Coral Costa Caribe

Hotel rating 4.0 out of 5 stars

Toronto to Santo Domingo, Dominican Republic

All Inclusive

Superior Room

Dec 15, 2026 (7 days)
Book with Deposit
~~was $3839~~ Save 65%

$1359 PP incl. taxes & fees
Sunscape Coco Punta Cana

Hotel rating 4.0 out of 5 stars

Toronto to Punta Cana, Dominican Republic

All Inclusive

Deluxe Tropical View King

Dec 06, 2026 (7 days)
Book with Deposit
~~was $2114~~ Save 36%

$1363 PP incl. taxes & fees

Book a Stay at Royal Decameron Club Caribbean | redtag.ca

Hotel rating 3.0 out of 5 stars

Toronto to Runaway Bay, Jamaica

All Inclusive

Courtyard Room

Dec 15, 2026 (7 days)
Book with Deposit
$1492 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 02, 2026 (7 days)
Book with Deposit
$1751 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

Jan 19, 2027 (7 days)
Book with Deposit
$1813 PP incl. taxes & fees
Bahia Principe Luxury Runaway Bay

Hotel rating 5.0 out of 5 stars

Toronto to Runaway Bay, Jamaica

All Inclusive

Junior Suite Deluxe

Dec 02, 2026 (7 days)
Book with Deposit
~~was $2331~~ Save 22%

$1819 PP incl. taxes & fees
Legends Beach Resort

Hotel rating 3.0 out of 5 stars

Toronto to Negril, Jamaica

All Inclusive

Room

Jan 19, 2027 (7 days)
Book with Deposit
$1862 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
$2049 PP incl. taxes & fees
Book a Stay at Azul Fives Hotel Playa del Carmen | redtag.ca

Hotel rating 5.0 out of 5 stars

Toronto to Negril, Jamaica

All Inclusive

Deluxe Room

Dec 02, 2026 (7 days)
Book with Deposit
~~was $2570~~ Save 19%

$2082 PP incl. taxes & fees
Riu Montego Bay

Hotel rating 5.0 out of 5 stars

Toronto to Montego Bay, Jamaica

All Inclusive

Room

Dec 15, 2026 (7 days)
Book with Deposit
$2096 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 15, 2026 (7 days)
Book with Deposit
$2135 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 15, 2026 (7 days)
Book with Deposit
$2145 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 09, 2026 (7 days)
Book with Deposit
~~was $2382~~ Save 24%

$1819 PP incl. taxes & fees
Viva Wyndham Fortuna Beach

Hotel rating 3.5 out of 5 stars

Toronto to Freeport, Bahamas

All Inclusive

Superior Gardenview

Feb 06, 2027 (7 days)
Book with Deposit
~~was $2405~~ Save 15%

$2055 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 38%

$2079 PP incl. taxes & fees
Barbados Beach Club

Hotel rating 3.0 out of 5 stars

Toronto to Bridgetown, Barbados

All Inclusive

Deluxe Room

Jan 20, 2027 (7 days)
Book with Deposit
$2201 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 12, 2026 (7 days)
Book with Deposit
~~was $2952~~ Save 25%

$2211 PP incl. taxes & fees
The Sands Barbados

Hotel rating 4.0 out of 5 stars

Toronto to Bridgetown, Barbados

All Inclusive

Sands Signature Room

Dec 07, 2026 (7 days)
Book with Deposit
~~was $3959~~ Save 42%

$2299 PP incl. taxes & fees
Breezes Resort

Hotel rating 3.0 out of 5 stars

Toronto to Nassau, Bahamas

All Inclusive

Classic Room

Jan 23, 2027 (7 days)
Book with Deposit
~~was $2499~~ Save 3%

$2436 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 30%

$2530 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 36%

$2530 PP incl. taxes & fees
The Club Barbados Resort and Spa

Hotel rating 4.0 out of 5 stars

Toronto to Bridgetown, Barbados

All Inclusive

Room Gardenview

Dec 13, 2026 (7 days)
Book with Deposit
~~was $3019~~ Save 14%

$2599 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%

$1517 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%

$1527 PP incl. taxes & fees
Occidental Tamarindo

Hotel rating 4.5 out of 5 stars

Toronto to Tamarindo, Costa Rica

All Inclusive

Superior Room

Dec 01, 2026 (7 days)
Book with Deposit
$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%

$1615 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 12, 2026 (7 days)
Book with Deposit
~~was $1995~~ Save 14%

$1712 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 Double Room

Dec 01, 2026 (7 days)
Book with Deposit
$1759 PP incl. taxes & fees
Occidental Papagayo

Hotel rating 4.5 out of 5 stars

Toronto to Liberia, Costa Rica

All Inclusive

Deluxe Room

Dec 01, 2026 (7 days)
Book with Deposit
$1819 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

Mar 03, 2027 (7 days)
Book with Deposit
~~was $4279~~ Save 53%

$2019 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 Tropical View Queen Standard

Dec 03, 2026 (7 days)
Book with Deposit
~~was $3529~~ Save 43%

$2019 PP incl. taxes & fees
Best Western Jaco Beach

Hotel rating 3.0 out of 5 stars

Toronto to Jaco beach, Costa Rica

All Inclusive

Room

Jan 20, 2027 (7 days)
Book with Deposit
~~was $2199~~ Save 4%

$2101 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 51%

$1089 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

Jan 18, 2027 (7 days)
Book with Deposit
~~was $1969~~ Save 39%

$1204 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

Jan 12, 2027 (7 days)
Book with Deposit
~~was $2159~~ Save 44%

$1219 PP incl. taxes & fees
Dos Playas Beach House by Faranda

Hotel rating 3.0 out of 5 stars

Toronto to Cancun, Mexico

All Inclusive

Room

Dec 02, 2026 (7 days)
Book with Deposit
~~was $2079~~ Save 41%

$1219 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 17, 2026 (7 days)
Book with Deposit
~~was $1979~~ Save 38%

$1229 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 43%

$1249 PP incl. taxes & fees
Royal Decameron Complex

Hotel rating 4.0 out of 5 stars

Toronto to Riviera Nayarit, Mexico

All Inclusive

Room Double

Jan 20, 2027 (7 days)
Book with Deposit
~~was $2529~~ Save 49%

$1293 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 42%

$1309 PP incl. taxes & fees
Krystal Grand Nuevo Vallarta

Hotel rating 4.0 out of 5 stars

Toronto to Riviera Nayarit, Mexico

All Inclusive

Deluxe Tropical View Double

Jan 20, 2027 (7 days)
Book with Deposit
~~was $2029~~ Save 35%

$1323 PP incl. taxes & fees
Decameron Isla Coral

Hotel rating 4.5 out of 5 stars

Toronto to Riviera Nayarit, Mexico

All Inclusive

Room King Balcony

Jan 18, 2027 (7 days)
Book with Deposit
~~was $2129~~ Save 37%

$1333 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.