Hemingway Vacations from ￥271,552

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    Save up to ￥45,448 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.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was ￥356,536, price is now ￥271,552 per person
￥271,552
per person
May 21 - May 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9/10 Wonderful! (3,462 reviews)
Typical motel style establishment, we stayed one night before a morning flight home, was great for that, clean, check in staff was super friendly, lots of great communication prior to stay, I would totally recommend this for a night stay (or a few)

Reviewed on Mar 31, 2026

Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was ￥427,940, price is now ￥276,350 per person
￥276,350
per person
May 21 - May 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
8.2/10 Very Good! (5,182 reviews)
The bathroom was dirty when I got there. There was hair in the tub. I also didn’t like that there were barely any outlets to charge things.

Reviewed on Apr 2, 2026

Westgate Blue Tree Resort in Lake Buena Vista

Westgate Blue Tree Resort in Lake Buena Vista

3.5 out of 5
Price was ￥464,748, price is now ￥304,571 per person
￥304,571
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
8.6/10 Excellent! (1,005 reviews)
Its always a pleasure to stay at Westgate Bluetree! Clean rooms and property, friendly staff and very conveniently located near dusney, outlets, grocery stores and more!!

Reviewed on Apr 1, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was ￥557,908, price is now ￥369,520 per person
￥369,520
per person
May 5 - May 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.2/10 Wonderful! (1,008 reviews)
Friendly staff. Great location. Villa was amazing

Reviewed on Mar 28, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was ￥382,546, price is now ￥291,999 per person
￥291,999
per person
May 21 - May 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.6/10 Exceptional! (1,068 reviews)
great place , highly recommended

Reviewed on Mar 30, 2026

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
4.5/5(30 area reviews)

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 ￥21,881 per night from Apr 28 to Apr 29
￥21,881
￥23,413 total
Apr 28 - Apr 29
includes taxes & fees
9.8/10 Exceptional! (1,141 reviews)
Gina at the front desk was a doll. She was super personable and helpful. The rooms are comfortable.

Reviewed on Mar 31, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is ￥18,413 per night from May 3 to May 4
￥18,413
￥19,702 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (1,357 reviews)
Clean room, staff was very helpful and nice

Reviewed on Apr 1, 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 ￥22,449 per night from Apr 30 to May 1
￥22,449
￥24,021 total
Apr 30 - May 1
includes taxes & fees
9.6/10 Exceptional! (102 reviews)
Great place to stay. Staff is professional and informative. Hotel is new and really cool. Surrounding area has fun shops and live music all within walking distance. View is beautiful with lake and landscape. Only heads-up is… no gas station on the property so get gas before you leave the ...

Reviewed on Apr 2, 2026

Hotel Eastport
See all 2,264 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 ￥271,552. 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

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

￥8,728
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.