Hemingway Vacations from $220

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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.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Save 100% on your flight
Price was $490, price is now $220 per person
$220
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,171 reviews)
Gould be a good idea to provided some info how to open the gate

Reviewed on Aug 24, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $605, price is now $276 per person
$276
per person
Oct 3 - Oct 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (3,048 reviews)
Our second visit to this property. Was very clean and convenient location for our trip. Only thing that needs improvement would be mattresses.

Reviewed on Aug 23, 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 $514, price is now $236 per person
$236
per person
Oct 24 - Oct 27
found 2 days ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,254 reviews)
Will refer to every one

Reviewed on Aug 24, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,297, price is now $616 per person
$616
per person
Oct 11 - Oct 15
found 15 hours ago
Roundtrip flight included
New York (NYC) to Orlando (MCO)
8.8/10 Excellent! (481 reviews)
Decent place. Spacious 2/2 with full kitchen and living room. A bit dated but clean. No room service and food stops at 830. Drinks are overpriced, overall a decent experience. Walking distance to the beach. Great location! Great for kids!

Reviewed on Jul 29, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $1,066, price is now $525 per person
$525
per person
Oct 25 - Nov 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.6/10 Exceptional! (1,000 reviews)
Very spacious hotel, great staff and nice location

Reviewed on Aug 23, 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
$124 nightly
The price is $133 total per night from Sep 1 to Sep 2
$133 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (1,193 reviews)
"This was our second time staying here and just like last time, everything was perfect."

Reviewed on Aug 23, 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
$139 nightly
The price is $149 total per night from Sep 1 to Sep 2
$149 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (1,007 reviews)
"I have stayed here a dozen times since 2020 and love this place. I highly recommend it!"

Reviewed on Aug 22, 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
$88 nightly
The price is $94 total per night from Sep 1 to Sep 2
$94 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,004 reviews)
Great Hotel but..
"Everything was perfect, but I would recommend to clean the carpet in the room, it looks like dirty"

Reviewed on Aug 22, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,050 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

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.