Caroline Vacations from $226

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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.

The Latest Caroline Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Palazzo Lakeside Hotel

Palazzo Lakeside Hotel

3 out of 5
Price was $615, price is now $226 per person
$226
per person
Dec 8 - Dec 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,210 reviews)
Professional and efficient Front Desk Agent…Clean rooms and nice to walk outside the property….

Reviewed on Oct 31, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $941, price is now $358 per person
$358
per person
Dec 5 - Dec 10
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (1,037 reviews)
Room was good size. Had a great view. It was like having a small condo with everything you need. Staff was unbelievably awesome. Marilyn, the front desk who checked us in took care of us throughout the whole duration and was absolutely fantastic. Facility lacked activities for kids but if you want something quiet, safe, and roomy this is the place. Would definitely recommend this place.

Reviewed on Oct 27, 2025

Seasons Florida Resort

Seasons Florida Resort

2 out of 5
Price was $620, price is now $252 per person
$252
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (3,197 reviews)
The room was only cleaned once, we had to ask for clean towels and toilet paper.

Reviewed on Oct 31, 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
Price was $557, price is now $234 per person
$234
per person
Jan 9 - Jan 13
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.8/10 Excellent! (589 reviews)
Clean nice beach very close clean room friendly staff

Reviewed on Oct 31, 2025

The Delaney Hotel

The Delaney Hotel

3.5 out of 5
South Orange
Price was $1,229, price is now $528 per person
$528
per person
Jan 5 - Jan 12
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.6/10 Exceptional! (1,019 reviews)
This was such a great location, so nice and clean. Very happy I chose The Delaney. 💯

Reviewed on Oct 31, 2025

Where to stay in Caroline

Find the best Caroline areas and neighborhoods for the activities you enjoy most. Learn more about Caroline
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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

Caroline Hotel Deals

Walk or Cart to Lake Sumter Landing! Our Village Gem - 5 Star - w/ Golf Cart

Walk or Cart to Lake Sumter Landing! Our Village Gem - 5 Star - w/ Golf Cart

The Villages
9.8/10 Exceptional! (114 reviews)
Loved it

Reviewed on Oct 8, 2025

Get rates
Walk or Cart to Lake Sumter Landing! Our Village Gem - 5 Star - w/ Golf Cart
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive, The Villages, FL
$127 nightly
The price is $136 total per night from Nov 30 to Dec 1
$136 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (1,235 reviews)
We thought with what we paid for the room we should have had water front view

Reviewed on Oct 27, 2025

The Waterfront Inn
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
$103 nightly
The price is $110 total per night from Nov 9 to Nov 10
$110 total
Nov 9 - Nov 10
Total with taxes and fees
9.2/10 Wonderful! (1,053 reviews)
Very clean and roomy. Staff very friendly.

Reviewed on Oct 30, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,146 properties in Caroline
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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All Inclusive Vacations
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Discover the most popular places to visit in Caroline

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.