Hemingway Vacations from ￥203,008

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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 ￥265,675, price is now ￥203,008 per person
￥203,008
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9/10 Wonderful! (3,566 reviews)
By far the best place I stayed . Also like the resort was next to a Hawaiian restaurant and show was cool

Reviewed on May 17, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was ￥590,005, price is now ￥402,442 per person
￥402,442
per person
Jul 30 - Aug 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Orlando (MCO)
9.2/10 Wonderful! (1,011 reviews)
Loved the clean lesson the space. Loved how close o was to the pool and how friendly everyone was. Definitely 10/10

Reviewed on May 16, 2026

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was ￥416,836, price is now ￥294,268 per person
￥294,268
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
9.6/10 Exceptional! (1,102 reviews)
Wish there were more hotels like this one! The rooms, staff, bar, and overall experience is lovely. Parking is easy and free!

Reviewed on May 17, 2026

Mission to Mars

Mission to Mars

4 out of 5
Loughman
Save 100% on your flight
Price was ￥2,641,572, price is now ￥2,127,026 per person
￥2,127,026
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
No reviews
Landing Townhomes Davenport

Landing Townhomes Davenport

4 out of 5
Price was ￥314,160, price is now ￥262,964 per person
￥262,964
per person
Jul 8 - Jul 15
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Orlando (MCO)
8.4/10 Very Good! (15 reviews)
THE GOOD: The place is great, beautiful, and very clean. The neighborhood is very quiet. THE BAD: The check-in process is HORRIBLE because of the to may steps of registering with them. You have to go through a process that is like an exhaustive background investigation done by the FBI. Be prepared to provide a lot of PERSONAL INFORMATION. Additionally, too many steps to finally been able to check in.

Reviewed on Mar 23, 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 ￥18,304 per night from Jun 18 to Jun 19
￥18,304
￥19,586 total
Jun 18 - Jun 19
includes taxes & fees
9.8/10 Exceptional! (1,182 reviews)
Yes

Reviewed on May 17, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is ￥18,022 per night from May 25 to May 26
￥18,022
￥19,283 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (1,399 reviews)
Lovely hotel, great location for shopping, fun and dancing

Reviewed on May 17, 2026

The Waterfront Inn
Hampton Inn & Suites Lady Lake/The Villages

Hampton Inn & Suites Lady Lake/The Villages

3 out of 5
11727 Ne 63 Rd Dr Lady Lake FL
Fully refundableReserve now, pay when you stay
The price is ￥16,652 per night from Jun 7 to Jun 8
￥16,652
￥17,818 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
I have nothing but praise for the staff and rooms. Fix the parking and RIDICULOUS fee and you’d get six stars.

Reviewed on May 15, 2026

Hampton Inn & Suites Lady Lake/The Villages
See all 2,189 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 ￥203,008. 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

￥8,765
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.