Hemingway Vacations from $305

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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.
Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,274 reviews)
Great stay as always

Reviewed on Jul 6, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The protest has lots of amenities and activities, also nice spacious rooms

Reviewed on Jul 8, 2025

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

Ocean Sands Beach Boutique Inn - 1 Acre Private Beach

3.5 out of 5
Vilano Beach
Save 100% on your flight
per person
Sep 10 - Sep 15
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (540 reviews)
Nice Beach across the road, Very nice staff!

Reviewed on Jul 6, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
per person
Sep 12 - Sep 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,060 reviews)
When we arrived, instead of the 2 bedroom villa that I reserved and paid for, we got a one bedroom with a king bed and a sofa bed. They told me it was overbooked. Thankfully they moved us the next day.

Reviewed on Jul 8, 2025

Westgate River Ranch Resort & Rodeo

Westgate River Ranch Resort & Rodeo

3.5 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (354 reviews)
Nice place. Kids had a good time. Not encouraged to go there if you are a minority. You wont feel welcomed. The staff is great, but the type of people that go there arent really folks that likely share the same interests as you do. There are Confederate flags all over; etc. Hotel rooms are no bueno, old. IF you want something nice, you need to spend the money glamping or have your own trailer.

Reviewed on Jun 24, 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
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
$125 nightly
The price is $134 total per night from Jul 10 to Jul 11
$134 total
Jul 10 - Jul 11
Total includes taxes and fees
9/10 Wonderful! (1,176 reviews)
"Beautiful place to stay. Very peaceful."

Reviewed on Jul 7, 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
$144 nightly
The price is $154 total per night from Jul 13 to Jul 14
$154 total
Jul 13 - Jul 14
Total includes taxes and fees
9.6/10 Exceptional! (1,000 reviews)
"Class Hotel"

Reviewed on Jul 2, 2025

Brownwood Hotel & Spa
Holiday Inn Express & Suites Wildwood The Villages by IHG
Holiday Inn Express & Suites Wildwood The Villages by IHG
3.5 out of 5
928 East State Road 44, Wildwood, FL
Fully refundable
$87 nightly
The price is $93 total per night from Jul 13 to Jul 14
$93 total
Jul 13 - Jul 14
Total includes taxes and fees
9.2/10 Wonderful! (993 reviews)
"Enjoyed my stay. Wonderful staff."

Reviewed on Jul 6, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,018 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

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.