Hemingway Holidays

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    Save up to €185 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was €1,096, price is now €863 per person
€863
per person
5 Jan - 10 Jan
found 24 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
17.6/10 Exceptional! (3,229 reviews)
Staff was great. The room was clean

Reviewed on 19 Nov 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was €1,495, price is now €974 per person
€974
per person
5 Jan - 10 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
18.4/10 Exceptional! (2,232 reviews)
We had a great time.

Reviewed on 20 Nov 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was €1,456, price is now €1,048 per person
€1,048
per person
5 Jan - 10 Jan
found 1 day ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
19.2/10 Exceptional! (1,002 reviews)
Yes, great experience! Will book again.

Reviewed on 11 Nov 2025

Wyndham Grand Orlando Resort Bonnet Creek

Wyndham Grand Orlando Resort Bonnet Creek

4 out of 5
Price was €1,360, price is now €1,032 per person
€1,032
per person
26 Dec - 31 Dec
found 8 hours ago
Return flight included
Dublin (DUB) to Orlando (MCO)
17.6/10 Exceptional! (2,794 reviews)
The property is clean and well-organized, but the amenities are of poor quality.

Reviewed on 17 Nov 2025

Kapp and Kappy B&B

Kapp and Kappy B&B

3.5 out of 5
Historic Downtown Kissimmee
Price was €1,187, price is now €946 per person
€946
per person
5 Jan - 10 Jan
found 24 hours ago
Return direct flight included
Dublin (DUB) to Orlando (MCO)
19.6/10 Exceptional! (125 reviews)
Friendly host. Felt like home.

Reviewed on 11 Nov 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 may 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

Top hotels in Hemingway

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
9/10 Wonderful! (1,261 reviews)
Great stay!

Reviewed on 18 Nov 2025

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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
9.6/10 Exceptional! (1,056 reviews)
Hotel is beautiful, very clean and spacious rooms. Check in was a breeze, they had our room ready early. Nice staff, easy parking. Food at Wolfgang Puck restaurant was great. There are many other dining options 10 minute walk from the hotel.

Reviewed on 17 Nov 2025

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Brownwood Hotel & Spa
Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora

2 out of 5
9700 Us Highway 441 Leesburg FL
Fully refundableReserve now, pay when you stay
The price is €64 per night from 23 Nov to 24 Nov
€64
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
The gentleman at the front desk when I checked in was very polite and helpful. Not sure his name but I checked in late on Tuesday the 11th

Reviewed on 13 Nov 2025

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
See all 2,175 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 holiday package cost?
Go from wondering to wandering with our Hemingway holiday packages, which start from a low €863. 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 holiday 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 Holiday Home With Golf Cart - 2 Bed 2 Bath. Both offer comfy beds and are popular options with lots of travellers.
How far in advance should I book my Hemingway holiday?
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 holiday!
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. Holidaying 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 holiday 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 holiday package?
Whether it's your hotel or flight, you can cancel or change it. Booked your Hemingway holiday 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

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

€48
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.