Hemingway Vacation Packages

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Top Holiday Package Deals in Hemingway

Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8.2/10 Very Good! (5,097 reviews)
Best Resort hands down

Reviewed on Jul. 27, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.6/10 Excellent! (1,006 reviews)
This is our secons time sraying here. The proprty is spacious and clean. The room is always amazing and can accomodate our family of 6!

Reviewed on Jul. 27, 2025

Reunion Resort & Golf Club

Reunion Resort & Golf Club

5 out of 5
Reunion
per person
Sep 29 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8.8/10 Excellent! (1,331 reviews)
All the staff were friendly and welcoming. Room service was quick. The waterpark was great for little kids.

Reviewed on Jul. 26, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,277 reviews)
Our Air conditioner was not working as it should. The temp never moved from 77 degrees. We kept it cool with the ceiling fans. Also, the pool that is open until 10 water felt very dirty, and the bottom of the pool was slimy.

Reviewed on Jul. 26, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (1,649 reviews)
I liked everything about the property; however I did not get a balcony as it stated in my confirmation email and upon booking. I also did not like that the times available for the waterpark did not meet me needs at all, and it was closed as well as the pool whenever i wanted to go. I had a relative that stayed at the Westgate in Orlando, and their pool was open until 11pm and I enjoyed her balcony as I did not get one.

Reviewed on Jul. 22, 2025

Where to stay in Hemingway

Find the best Hemingway areas and neighborhoods for the activities you enjoy most. Learn more about Hemingway
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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
The price is CA $171 per night from Aug 3 to Aug 4
CA $171
CA $183 total
Aug 3 - Aug 4
includes taxes & fees
9/10 Wonderful! (1,190 reviews)
"Great location! Very nice restaurant with outdoor lakeview seating."

Reviewed on Jul. 21, 2025

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
The price is CA $178 per night from Aug 17 to Aug 18
CA $178
CA $190 total
Aug 17 - Aug 18
includes taxes & fees
9.6/10 Exceptional! (1,021 reviews)
Great Staycation
"Great place! Clean and spacious."

Reviewed on Jul. 26, 2025

Brownwood Hotel & Spa
Holiday Inn Express & Suites Wildwood The Villages by IHG

Holiday Inn Express & Suites Wildwood The Villages by IHG

3.5 out of 5
928 East State Road 44, Wildwood, FL
Fully refundableReserve now, pay when you stay
The price is CA $133 per night from Aug 10 to Aug 11
CA $133
CA $143 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,013 reviews)
Would stay again!
"We traveled for a tournament for our son. So glad we booked here. The staff was so friendly and helpful. The breakfast was fantastic and they worked hard to keep hot fresh food coming. Thank you so much for your hospitality!!"

Reviewed on Jul. 25, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,032 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 $547. 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.