Hemingway Vacations from $255

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Your Hemingway Vacation

Let our Hemingway vacation packages transport you to a destination where unforgettable memories are waiting to be made. While it's especially renowned for its golfing, there's plenty to love about this neighborhood. The Villages Market Square and Cane Garden Country Club are just a couple of the major attractions nearby to include on your itinerary during a trip to Hemingway. Stop daydreaming and start doing. When it's time to lock in your ideal vacation to Hemingway, Expedia will help get you there.

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 $602, price is now $255 per person
$255
per person
Jan 27 - Feb 3
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (3,229 reviews)
Great and clean also great location

Reviewed on Nov 25, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,889, price is now $565 per person
$565
per person
Jan 27 - Feb 3
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Clean room expected amenities

Reviewed on Nov 12, 2025

The Shores Resort & Spa

The Shores Resort & Spa

4 out of 5
Price was $1,017, price is now $370 per person
$370
per person
Jan 27 - Feb 3
found 2 days ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,681 reviews)
From the minute we checked in and Michelle greeted us, we knew we picked the right spot! Since it’s quiet season, they were able to upgrade our room to double balcony oceanfront. It felt like we were right over the beach! Very clean rooms and facilities. We were visiting my nephew who goes to school at DSC and the valet guys were so accommodating, allowing us to leave the car out front for a few hours here and there without charging us the parking fee. Sore isl shout out to Dom from valet. The pool area was great and we loved the tiki bar (shout out to Doug the bartender!) he even gave me a special drink for my bday!!! They give s’mores kits at night to use at the pool side fire pits too! When we come back to visit, we will definitely rebook at the Shores!!!

Reviewed on Nov 16, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $930, price is now $378 per person
$378
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,085 reviews)
Yes room was very nice and staff was super polite and helpful

Reviewed on Nov 22, 2025

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

Margaritaville Cottages Orlando with H2O Waterpark by Vstays

4 out of 5
Price was $1,576, price is now $693 per person
$693
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (1,001 reviews)
The place is exceptional and met all of our needs and then some

Reviewed on Nov 12, 2025

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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
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

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
$119 nightly
The price is $127 total per night from Dec 11 to Dec 12
$127 total
Dec 11 - Dec 12
Total with taxes and fees
9/10 Wonderful! (1,264 reviews)
I love the pool and hot tub. Room was v clean and the shower a real treat

Reviewed on Nov 24, 2025

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
$167 nightly
The price is $179 total per night from Dec 5 to Dec 6
$179 total
Dec 5 - Dec 6
Total with taxes and fees
9.6/10 Exceptional! (1,060 reviews)
We have stayed at the Brownwood multiple times. Its a great location for visiting relatives in the Villages. The whole facility is modern, up-to-date and well maintained. The staff is always helpful and polite. The rooms are nicely appointed and always clean.

Reviewed on Nov 25, 2025

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
$72 nightly
The price is $80 total per night from Nov 30 to Dec 1
$80 total
Nov 30 - Dec 1
Total with taxes and fees
8.4/10 Very Good! (1,014 reviews)
Room was clean and staff was friendly

Reviewed on Nov 23, 2025

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
See all 2,181 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.
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Discover the most popular places to visit in Hemingway

The Villages Market Square

4.5/5(174 reviews)

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

Nancy Lopez Legacy Golf & Country Club

Enjoy a round of golf in The Villages at Nancy Lopez Legacy Golf & Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Nancy Lopez Legacy Golf & Country Club

Glenview Champions Country Club

Enjoy a round of golf in The Villages at Glenview Champions Country Club. While in this family-friendly area, you can savor the top-notch restaurants.

Glenview Champions Country Club

Things to do

King William, a Gypsy Vanner Horse Stallion

Gypsy Gold Horse Farm Tour

$55
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.