Hemingway Vacations from $451

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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 Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $975, price is now $451 per person
$451
per person
Dec 3 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,012 reviews)
Fantastic property would stay there again. The elevators, hallways, and room could use a bit of a refresh. Only three or four elevators were working in tower B. The hallway ceilings where the popcorn style drop ceiling tiles. The room was nice; the couch was dated with patches and sun in, the dishes were from the 80s, the caulking in the bathrooms could use a refresh, but the rooms were quite clean and that was refreshing. Despite these comments, we would stay there again – it was a pleasant and comfortable stay.

Reviewed on Oct 13, 2025

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Save 100% on your flight
Price was $1,040, price is now $501 per person
$501
per person
Nov 12 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.2/10 Very Good! (5,346 reviews)
Free shuttles and close proximity to universal and sea world. Family friendly and a-lot of activities for the entire family. Fire pits, mini golf, bikes, pizza and ice cream all without leaving the property. Adults can enjoy yoga, Starbucks, the pool bar and drafts bar & grill. I would stay again in Orlando.

Reviewed on Oct 12, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $3,125, price is now $1,517 per person
$1,517
per person
Dec 25 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (486 reviews)
Excellent property to go too. Lazy river was night and the staff at the front desk was amazing. Very close to the beach with many restaurants and shops to walk too. Even saw Space X launch a rocket from this location. Perfect spot for a great price. Recommend especially if you're bring Children.

Reviewed on Oct 10, 2025

Bryan’s Spanish Cove

Bryan’s Spanish Cove

3 out of 5
Save 100% on your flight
Price was $1,013, price is now $504 per person
$504
per person
Dec 17 - Dec 23
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.4/10 Exceptional! (1,002 reviews)
Very clean well maintained quiet property in a great location. Very nice pool and hot tub on the lake. They have fishing tackle that we used. Also kayaks, paddle boats and pool toys. Was nice and quiet compared to the large larger resorts that charge for these activities but also have a ton of people. Highly recommend this place.

Reviewed on Oct 1, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $1,475, price is now $738 per person
$738
per person
Dec 22 - Dec 29
found 5 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,360 reviews)
Over All It Was Great Me And My Kids Had Wonderful Time And Wanna Go Back

Reviewed on Oct 1, 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 Spanish Springs Town Square.

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
$129 nightly
The price is $138 total per night from Nov 2 to Nov 3
$138 total
Nov 2 - Nov 3
Total with taxes and fees
9/10 Wonderful! (1,237 reviews)
"Room was too cool so we adjusted the temp to our needs."

Reviewed on Oct 11, 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
$140 nightly
The price is $150 total per night from Oct 16 to Oct 17
$150 total
Oct 16 - Oct 17
Total with taxes and fees
9.6/10 Exceptional! (1,029 reviews)
"10 out of 10"

Reviewed on Oct 7, 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 refundableReserve now, pay when you stay
$85 nightly
The price is $91 total per night from Oct 26 to Oct 27
$91 total
Oct 26 - Oct 27
Total with taxes and fees
9.2/10 Wonderful! (1,021 reviews)
"Clean, new holiday inn."

Reviewed on Oct 13, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,125 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.