Hemingway Vacations from ￥257,443

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 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

The Latest Hemingway Vacation Packages

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

Palazzo Lakeside Hotel

3 out of 5
Price was ￥388,456, price is now ￥257,443 per person
￥257,443
per person
Sep 5 - Sep 10
found 6 hours ago
Roundtrip flight included
Sapporo (CTS) to Orlando (MCO)
8.2/10 Very Good! (5,209 reviews)

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was ￥673,188, price is now ￥413,245 per person
￥413,245
per person
Sep 5 - Sep 11
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Orlando (MCO)
9.2/10 Wonderful! (1,010 reviews)
Per my stay found pots and pans old and burnt , AC was not cooling well in the first floor master also I have never heard that you have to buy your own toilet paper once you run out.... Also we had to use the same towels over and over again I never heard a that unacceptable for the amount that I paid. The unit it self was outdated. It was definitely not worth the price that I paid. I will think twice before ever booking there. VERY DISAPPOINTED

Reviewed on Jul 21, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was ￥472,465, price is now ￥296,231 per person
￥296,231
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Orlando (MCO)
9.6/10 Exceptional! (1,150 reviews)
This was such a nice place to stay. The staff were all so nice and friendly. The room was lovely and had great little touches (like bottles of water). The restaurant next door was a nice addition as well. Overall would recommend this place and would stay here again.

Reviewed on Jul 20, 2026

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was ￥417,408, price is now ￥262,052 per person
￥262,052
per person
Sep 5 - Sep 10
found 1 day ago
Roundtrip flight included
Sapporo (CTS) to Orlando (MCO)
9/10 Wonderful! (3,711 reviews)
The AC worked very well. The parking area and surrounding property gave a good sense of security.

Reviewed on Jul 20, 2026

Monumental Hotel Orlando

Monumental Hotel Orlando

3.5 out of 5
International Drive District
Price was ￥410,326, price is now ￥268,101 per person
￥268,101
per person
Sep 5 - Sep 10
found 6 hours ago
Roundtrip flight included
Sapporo (CTS) to Orlando (MCO)
7.2/10 Good! (1,167 reviews)

Where to stay in Hemingway

Find the best Hemingway areas and neighborhoods for the activities you enjoy most. Learn more about Hemingway
A yellow golf cart on a paved road with palm trees and a body of water in the background.

Lake Sumter Landing

1 out of top 10 points of interest in this area

While visiting Lake Sumter Landing, you might make a stop by sights like The Villages Market Square and Lake Sumter.

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 ￥18,757 per night from Jul 27 to Jul 28
￥18,757
￥20,070 total
Jul 27 - Jul 28
includes taxes & fees
9.8/10 Exceptional! (1,301 reviews)
"This hotel is beautiful. Love the pool. Having bar and restaurant is convenient. Less then 5 minute drive to brownwood town center. Couple places are easy walkable. Would definitely stay in there again. Only complaint pillows were little flat. The breakfast Buffett is to pricey."

Reviewed on Jul 21, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is ￥18,222 per night from Jul 29 to Jul 30
￥18,222
￥19,498 total
Jul 29 - Jul 30
includes taxes & fees
9.2/10 Wonderful! (1,446 reviews)
"Very clean, tranquility an a lot to do near the surrounding area of property."

Reviewed on Jul 21, 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 ￥20,330 per night from Jul 23 to Jul 24
￥20,330
￥21,754 total
Jul 23 - Jul 24
includes taxes & fees
9.6/10 Exceptional! (243 reviews)
"The hotel has just recently opened. Everything about our stay was very comfortable. We did not use the pool or fitness center, but both looked nice. We did eat at Yamas which is a Mediterranean restaurant on site. This was our second time dining there and each time we thought the food was very ..."

Reviewed on Jul 21, 2026

Hotel Eastport
See all 2,247 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.

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 ￥257,443. 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.

Things to do

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

￥8,940
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.