Island Hammock Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Island Hammock

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

Palazzo Lakeside Hotel

CA $653

per person

Nov 8 - Nov 13

found 1 day ago

Roundtrip flight included

Hamilton (YHM) to Orlando (MCO)

8.4/10 Very good! (5,314 reviews)

The clerk was helpful once we were there. Very friendly. But getting ahold of them before the stay was terrible. The room itself had many blemishes and the sealer around the shower was very discolored and looked moldy.

Reviewed on Sep 22, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Save 100% on your flight

CA $1,657

per person

Nov 2 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

9.2/10 Wonderful! (1,002 reviews)

Westgate Towers Resort

Save 100% on your flight

CA $882

per person

Nov 12 - Nov 19

found 14 hours ago

Roundtrip non-stop flight included

Montreal (YUL) to Orlando (MCO)

8.6/10 Excellent! (1,006 reviews)

Todo estuvo excelente. El personal muy atento y el cuarto muy comodo y limpio

Reviewed on Sep 20, 2026

Seasons Florida Resort

CA $793

per person

Dec 1 - Dec 8

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

9/10 Wonderful! (3,855 reviews)

The Delaney Hotel

South Orange

Save 100% on your flight

CA $1,140

per person

Dec 14 - Dec 19

found 1 day ago

Roundtrip non-stop flight included

Halifax (YHZ) to Orlando (MCO)

9.6/10 Exceptional! (1,202 reviews)

First impressions were great. The suite was huge! The Tavern was awesome, and management resolved concerns promptly. Its a bonus to have access to a fridge and microwave. The coffee makers were nice for making mini coffees. The only suggestion I'd have is to adjust the doors to not slam so loudly! I'd stay here again!

Reviewed on Sep 23, 2026

Where to stay in Island Hammock

Find the best Island Hammock areas and neighborhoods for the activities you enjoy most. Learn more about Island Hammock

A church with a clock tower and a red car parked in front.

St. Augustine Historic District

1 out of top 10 points of interest in this area

Explore the colonial heart of St. Augustine, featuring narrow streets and landmarks like Castillo de San Marcos and Cathedral Basilica. Discover the city's oldest residences, such as the González–Alvarez House.

A coastal town with a beach, ocean, and a pier.

Vilano Beach

1 out of top 10 points of interest in this area

Vilano Beach is beloved for its stunning beaches. Take some time to explore sights in the area like Vilano Beach and Castle Otttis.

A hammock between trees by a clear lake with a duck swimming nearby.

Crescent Beach

Crescent Beach is known for its beaches, and you can plan a trip to Fort Matanzas National Monument and Crescent Beach while you're in town.

A grand building with arched walkways and a fountain in the center.

Downtown Historic District

3 out of top 10 points of interest in this area

If you're spending some time in Downtown Historic District, Lightner Museum and Ponce de León Hall are top sights worth seeing.

A sunset over the ocean with birds flying.

Butler Beach

Butler Beach is popular for its beaches, and if you're looking for more to see and do, you might think about a trip to St. Augustine Beach or Butler Beach State Park.

Island Hammock Hotel Deals

Guy Harvey Resort on St Augustine Beach

860 A1A Beach Blvd St. Augustine FL

Fully refundableReserve now, pay when you stay

CA $188

CA $210 total

Oct 1 - Oct 2

includes taxes & fees

Best Western Seaside Inn

541 A1A Beach Boulevard St. Augustine FL

Fully refundableReserve now, pay when you stay

CA $135

CA $150 total

Oct 4 - Oct 5

includes taxes & fees

8.4/10 Very good! (1,000 reviews)

"The room was “wet”, sheets, floor, it was weird. I expect humidity in Florida but this was over the top. And it smelled musty. At breakfast the milk was spoiled. Manager was not much help when we told him he might want to check the room, the floors were wet, he said it humid."

Reviewed on Sep 21, 2026

DoubleTree by Hilton St. Augustine Historic District

116 San Marco Ave St. Augustine FL

Fully refundableReserve now, pay when you stay

CA $130

CA $145 total

Sep 27 - Sep 28

includes taxes & fees

8.6/10 Excellent! (1,100 reviews)

"The first room had a musty smell. They gave us new room there was no smell but a wad of hair was on the sprinkler head in the hallway of the room."

Reviewed on Sep 22, 2026

See all 6,237 properties in Island Hammock

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.