Caroline Vacations from $192

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to $1,045 when you book a flight and hotel together*

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

    Rest easy

    Plan, book, and manage your trip all in one place

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 $862, price is now $192 per person
$192
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,210 reviews)
Room. Very clean, front desk staff very friendly. However, the resort fee is ridiculous!

Reviewed on Oct 29, 2025

Hilton Orlando

Hilton Orlando

4 out of 5
International Drive District
Price was $926, price is now $344 per person
$344
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,005 reviews)
Nice hotel, but all the added fees and prices kill the enjoyment.

Reviewed on Oct 23, 2025

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was $1,259, price is now $509 per person
$509
per person
Jan 3 - Jan 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

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was $622, price is now $258 per person
$258
per person
Dec 4 - Dec 9
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,395 reviews)
The room was clean, the staff was friendly and very helpful. The resort has everything you need, you never have to leave! We did have an issue with hot water and the manager took care of us right away. My son really enjoyed the waterpark stayed until it closed. We will stay here again.

Reviewed on Oct 30, 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)
Very friendly staff. A lot of amenities. Cute and peaceful hotel.

Reviewed on Oct 29, 2025

Where to stay in Caroline

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

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
$123 nightly
The price is $132 total per night from Nov 16 to Nov 17
$132 total
Nov 16 - Nov 17
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 2 to Nov 3
$110 total
Nov 2 - Nov 3
Total with taxes and fees
9.2/10 Wonderful! (1,043 reviews)
Great location!

Reviewed on Oct 23, 2025

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 2,148 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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.