Hemingway Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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The Latest Hemingway Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Terrace/patio
    Jul 30 - Aug 3

    Westgate Palace Hotel / Universal / I-Drive + Flight

    International Drive District
    4 nights
    4.0 star property
    9.0/10 - Wonderful (1,261 reviews)
    "Clean"
    Reviewed June 2, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $1,488
    CA $787
    per traveller
    found 1 hour ago
    Westgate Palace Hotel / Universal / I-Drive
  • Aerial view
    Aug 14 - Aug 28

    Westgate Vacation Villas Resort + Flight

    Kissimmee
    14 nights
    4.0 star property
    8.2/10 - Very good (1,981 reviews)
    "Room was clean and staff was friendly. The water park should be included in the price or you should make it more known that you have to pay per day. Also the water park should be open longer since it’s $25 dollars a person. 11-6pm is not enough time. Room was small. The room key worked for everything but our room door. The problem was solved quickly but when front desk was called, they told us that we were supposed to be in a different room. Parking was a nightmare."
    Reviewed June 10, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • 1 stop MCO - YYZ • 1 stop
    CA $2,235
    CA $1,021
    per traveller
    found 2 hours ago
    Westgate Vacation Villas Resort
  • Water park
    Aug 11 - Aug 22

    Westgate Town Center Resort + Flight

    Kissimmee
    11 nights
    4.0 star property
    8.2/10 - Very good (1,768 reviews)
    "Breaffast no bacon"
    Reviewed June 11, 2026
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • 1 stop MCO - YHM • 1 stop
    CA $2,112
    CA $1,070
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • Water park
    Aug 11 - Aug 22

    Westgate Lakes Resort & Spa Universal Studios Area + Flight

    Orlando
    11 nights
    4.0 star property
    8.4/10 - Very good (6,582 reviews)
    "Excellent service, facilities, near everything. Highly recommended!"
    Reviewed June 10, 2026
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • 1 stop MCO - YHM • 1 stop
    CA $2,218
    CA $1,198
    per traveller
    found 1 day ago
    Westgate Lakes Resort & Spa Universal Studios Area
  • Outdoor pool
    Aug 11 - Aug 22

    Element by Marriott Orlando Universal Blvd. + Flight

    International Drive District
    11 nights
    3.0 star property
    9.2/10 - Wonderful (2,241 reviews)
    "I enjoy my stay at element. Room was neat and clean. Well supply. Staff were friendly and kind. Breakfast was good. I will stay there again. Location is quiet and close to restaurants and parks."
    Reviewed June 10, 2026
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • 1 stop MCO - YHM • 1 stop
    CA $2,051
    CA $1,176
    per traveller
    found 1 day ago
    Element by Marriott Orlando Universal Blvd.

Where to stay in Hemingway

Find the best Hemingway areas and neighborhoods for the activities you enjoy most. Learn more about Hemingway
Lake Sumter Landing

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

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 $153 per night from Jun 16 to Jun 17
CA $153
CA $163 total
Jun 16 - Jun 17
includes taxes & fees
9.8/10 Exceptional! (1,220 reviews)
"Great stay, beds was soft and feel very nice"

Reviewed on Jun 11, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $137 per night from Jun 16 to Jun 17
CA $137
CA $146 total
Jun 16 - Jun 17
includes taxes & fees
9.2/10 Wonderful! (1,425 reviews)
"The hotel itself is absolutely beautiful. The staff were super helpful and friendly. It's within walking distance of tons of shopping and dining. The hotel bar looks out over the lake and is tastefully decorated. The bed was comfortable and the room was very clean. The fitness center has a universal ..."

Reviewed on Jun 10, 2026

The Waterfront Inn
Hotel Eastport

Hotel Eastport

2 out of 5
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
The price is CA $154 per night from Jul 1 to Jul 2
CA $154
CA $165 total
Jul 1 - Jul 2
includes taxes & fees
9.6/10 Exceptional! (192 reviews)
"Bar was right there in house"

Reviewed on Jun 5, 2026

Hotel Eastport
See all 2,213 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 . 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

4.5/5(2 reviews)

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

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

CA $76
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.