Hemingway Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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Top Holiday Package Deals in Hemingway

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,262, price is now CA $642 per person
CA $642
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
The room was spotless!

Reviewed on Feb 8, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was CA $2,328, price is now CA $762 per person
CA $762
per person
Apr 23 - Apr 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.2/10 Very Good! (5,145 reviews)
the facility felt safe with the automatic gates. the hotel was really clean and even had different entertainment options for the kids on top of the pool. it's very family friendly and we loved all the posters that talked about family and faith.

Reviewed on Feb 6, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,212, price is now CA $1,072 per person
CA $1,072
per person
Apr 16 - Apr 23
found 9 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,085 reviews)
Clean, amazing staff. Very happy with the stay

Reviewed on Feb 7, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,361, price is now CA $673 per person
CA $673
per person
Apr 16 - Apr 23
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
Room was amazing, all though the jacuzzi jets were dirty so once i turned them on the water got really gross. They need to do better at cleaning. I was certainly disappointed because i got the room for the jacuzzi and didn’t get to use it because it was filthy.

Reviewed on Feb 5, 2026

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was CA $1,357, price is now CA $683 per person
CA $683
per person
Mar 23 - Mar 30
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
Everything was wonderful! I will stay again!

Reviewed on Feb 6, 2026

Where to stay in Hemingway

Find the best Hemingway areas and neighborhoods for the activities you enjoy most. Learn more about Hemingway
The Villages, 120K active adults... and their toys! 😬

Lake Sumter Landing

1 out of top 10 points of interest in this area

Though Lake Sumter Landing might not have many top sights, you can venture to the surrounding area to see attractions like The Villages Market Square and Cane Garden Country Club.

Find hotels in Lake Sumter Landing

Hemingway Hotel Deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
9.2/10 Wonderful! (1,312 reviews)
Nice staff, view of lake.

Reviewed on Feb 1, 2026

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The Waterfront Inn
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
9.6/10 Exceptional! (1,105 reviews)
Clean. Courteous staff. Great location

Reviewed on Feb 6, 2026

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Brownwood Hotel & Spa
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

2 out of 5
9700 Us Highway 441 Leesburg FL
Fully refundableReserve now, pay when you stay
The price is CA $119 per night from Feb 16 to Feb 17
CA $119
CA $132 total
Feb 16 - Feb 17
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
Big room, clean

Reviewed on Feb 2, 2026

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
See all 2,241 properties in Hemingway
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.
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Frequently asked questions

How much does a Hemingway vacation package cost?
Go from wondering to wandering with our Hemingway vacation packages, which start from a low CA $642. Select the hotels and flights that suit your plans. Then, add on a couple of activities or tours for an amazing escape.
How do I get a cheap travel package to Hemingway?
Book everything in the one place with our Hemingway vacation packages. You'll find deals on flights, hotels and more that'll keep your pocket happy and your adventurous spirit alive. And, with more than 550 air carriers and 1,000,000 properties around the world to select from, you'll have endless opportunities to mix and match however you please.
Where should I stay in Hemingway?
An escape to Hemingway isn't complete without stopping by The Villages Market Square. Why not choose a hotel within walking distance of this fantastic attraction?
What are the top hotels in Hemingway?
If this will be your first visit to Hemingway, book a room at Welcome To The Life or Vacation Home With Golf Cart - 2 Bed 2 Bath. Both offer comfy beds and are popular options with lots of travelers.
How far in advance should I book my Hemingway vacation?
Reward yourself with the biggest variety and the lowest prices by booking your Hemingway adventure nice and early. Airlines generally publish flights anywhere up to 12 months before departure, so start your planning as soon as possible. That being said, Expedia is committed to giving you the best deals around, so it's always a good time to book your dream vacation!
What does an Expedia Hemingway travel package include?
From flights and hotels to rental cars, Expedia can help you shape a Hemingway package that's ideal for you. Vacationing for a few weeks? Check out a rental car, hotel and flight bundle. If you're taking a quick break, a flight and hotel deal could be more your style. Experiences can also be added once you've made your booking. Our packages make it easy to plan and save.
What should I know before booking a Hemingway travel package?
Our prices are always low. However, you'll pick up even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Hemingway Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Just choose your preferred air carrier and create the perfect Hemingway trip.
If I'm not able to travel, can I cancel my Hemingway vacation package?
Whether it's your hotel or flight, you can cancel or change it. Booked your Hemingway vacation package in the last 24 hours? You may be able to make any changes for free. If it's been longer than that, you may be charged a fee by your hotel, airline or car rental company. For further information, head to our Customer Service Portal. We'll help you every step of the way.

Discover the most popular places to visit in Hemingway

The Villages Market Square

You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.

The Villages Market Square

Things to do

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

CA $75
per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in The Villages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.