Hemingway Vacations from $262

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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
Price was $593, price is now $262 per person
$262
per person
Feb 26 - Mar 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
La habitacion muy buena y limpia expaciosa recomendaria cambiar ollas y sartenes estan muy viejos y quemados

Reviewed on Dec 4, 2025

Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was $1,887, price is now $701 per person
$701
per person
Jan 30 - Feb 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
Great room very clean and comfortable.

Reviewed on Nov 30, 2025

Florida Hotel & Conference Center in the Florida Mall

Florida Hotel & Conference Center in the Florida Mall

3.5 out of 5
Price was $910, price is now $352 per person
$352
per person
Jan 12 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9.2/10 Wonderful! (2,232 reviews)
Clean room, friendly staff and great facilities

Reviewed on Dec 8, 2025

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was $1,450, price is now $593 per person
$593
per person
Jan 27 - Feb 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
The outside of the building could use some tlc but inside was clean and updated. Staff was attentive, polite, & helpful. Breakfast was surprisingly better than I anticipated with hot options outside of the traditional continental options. Furniture around pool was pressure washed every morning and plentiful. There are no seating options for the beach however we would definitely stay here again.

Reviewed on Nov 30, 2025

Westgate Cocoa Beach Resort

Westgate Cocoa Beach Resort

4 out of 5
Price was $1,531, price is now $682 per person
$682
per person
Jan 18 - Jan 24
found 1 hour ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (500 reviews)
No Beach view but beach is an10m walk so not too bad. Beach chairs falling apart. The pools and tiki bar were awesome. The two room suite was okay and for the most part pretty clean. But there were some dead bugs which is not what I expected for the price point.

Reviewed on Nov 6, 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
$129 nightly
The price is $138 total per night from Dec 10 to Dec 11
$138 total
Dec 10 - Dec 11
Total with taxes and fees
9/10 Wonderful! (1,276 reviews)
Great place

Reviewed on Dec 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
$149 nightly
The price is $159 total per night from Jan 1 to Jan 2
$159 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.6/10 Exceptional! (1,071 reviews)
Front desk check in staff very friendly, room spotless and comfortable.

Reviewed on Dec 8, 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
$73 nightly
The price is $81 total per night from Dec 14 to Dec 15
$81 total
Dec 14 - Dec 15
Total with taxes and fees
8.2/10 Very Good! (1,007 reviews)
yes

Reviewed on Dec 8, 2025

Microtel Inn & Suites by Wyndham Leesburg/Mt Dora
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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.