Hemingway Holidays
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Our guide on 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
1 out of top 10 points of interest in this area
If you're spending some time in Lake Sumter Landing, The Villages Market Square and Lake Sumter are top sights worth seeing.
Virginia Trace
Virginia Trace might not have many top sights, but The Villages Market Square and Lake Sumter are two attractions nearby that you can check out.
Sunset Pointe
Though Sunset Pointe may not have many top sights, you can venture to the surrounding area to see attractions like Cane Garden Country Club and The Villages Market Square.
Duval
When in Duval, you can plan a visit to Cane Garden Country Club and The Villages Market Square, some noteworthy sights in the nearby area.
Bonita
Bonita might not have many top sights, but Cane Garden Country Club and The Villages Market Square are two attractions nearby that you can check out.
Our pick of the best Hemingway Hotel Deals
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
NZ$204
1 Sept - 2 Sept
includes taxes & fees
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
NZ$198
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (1,476 reviews)
"The hotel was clean and updated. Comfortable beds. Great lake view at hotel bar/restaurant. Staff was friendly and helpful. Excellent location a block from Sumtner Square with music , shopping and bars. Would stay here again. Highly recommend."
Reviewed on 10 Aug 2026
Hotel Eastport
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
NZ$215
26 Aug - 27 Aug
includes taxes & fees
9.6/10 Exceptional! (255 reviews)
"Hundreds of spiders everywhere plus roaches. $344 per room that should have been $225 in terms of construction and functionality."
Reviewed on 9 Aug 2026
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 . 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.
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.