Caroline Vacations
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Your Caroline Vacation
Make planning your travels easier by snapping up a vacation package to Caroline. We'll look after the finer points, so you can focus on discovering everything this neighborhood can offer. Free up some time for sightseeing during your trip to Caroline. Nearby The Villages Market Square and Cane Garden Country Club are on the must-visit lists of most travelers. Whatever your dream Caroline vacation may look like, you can make it a reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
- Westgate Vacation Villas Resort
Jul 29 - Aug 4Westgate Vacation Villas Resort + Flight
Kissimmee6 nights8.2/10 - Very Good (1,934 reviews)"Great place for families and close to all parks"Reviewed May 24, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Westgate Palace Hotel / Universal / I-Drive
Jun 30 - Jul 5Westgate Palace Hotel / Universal / I-Drive + Flight
International Drive District5 nights8.8/10 - Excellent (1,255 reviews)"Ok"Reviewed May 20, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • Nonstop MCO - EWR • Nonstop - Westgate Town Center Resort
Jul 29 - Aug 4Westgate Town Center Resort + Flight
Kissimmee6 nights8.2/10 - Very Good (1,732 reviews)"I felt that it was very ghetto this time around. We used to come here every year, including this one, but this will be our last year. There was so many kids in the pool unattended parents nowhere to be found that used to be a place to relax now I don’t feel that way anymore."Reviewed May 20, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Westgate Lakes Resort & Spa Universal Studios Area
Jul 29 - Aug 4Westgate Lakes Resort & Spa Universal Studios Area + Flight
Orlando6 nights8.4/10 - Very Good (6,416 reviews)"Everything besides the spa and smoke house was wonderful and only because I had an itinerary already planned I didn’t get to enjoy those spaces so pls don’t take it as an insult or bad review. Water park and pools was great for kids and adults our room in our building was nice and clean and we were able to wash if needed to thanks to washer and dryer in our suite and sleep was beyond good no interruptions very peaceful and quiet when time to whine dwn and sleep thank you for being good to us we..."Reviewed May 24, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Westgate Towers Resort
Jun 29 - Jul 7Westgate Towers Resort + Flight
Kissimmee8 nights8.6/10 - Excellent (1,007 reviews)"The room was clean staff was nice.i was good for the weekend stay really enjoyed it."Reviewed May 24, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop
Where to stay in Caroline
Find the best Caroline areas and neighborhoods for the activities you enjoy most. Learn more about Caroline
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.
Caroline Hotel Deals
Walk to Lake Sumter Landing! Our Village Gem - 10 Star - w/ Golf Cart
The Villages FL
10/10 Exceptional! (123 reviews)
"My husband and I went to The Villages for a much needed break from the Michigan snow. Yes, there was still snow at home when we left on April 18th. We had booked this home a month ahead of time. Commuinication with the hosts was great and we were given the added bonus of a printout of tips for our ..."
Reviewed on Apr 29, 2026
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $123 total per night from Jun 23 to Jun 24
$123 total
Jun 23 - Jun 24
Total with taxes and fees
9.8/10 Exceptional! (1,192 reviews)
"This place was amazing, great restaurant and bar. The staff went out of their way to help with anything you needed. The room was above and beyond, huge shower, and super clean. I highly recommend this place to anyone coming to the area. We will be back."
Reviewed on May 24, 2026
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
$122 nightly
The price is $131 total per night from May 25 to May 26
$131 total
May 25 - May 26
Total with taxes and fees
9.2/10 Wonderful! (1,408 reviews)
"It was a pleasant surprise for us, exceeding our expectations."
Reviewed on May 22, 2026
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.
Discover the most popular places to visit in Caroline
The Villages Market Square
4.5/5(175 reviews)
You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.
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.
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.
Things to do
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.