Caroline Vacations from $273

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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 $1,070, price is now $273 per person
$273
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,186 reviews)
Very beautiful place and clean. I loved the cabanas outside and the lighted walkway to another beautiful sitting area. Breakfast was provided and amazing with different breakfast stations. I would definitely recommend and would love to come back and stay longer.

Reviewed on Sep 6, 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 $738, price is now $351 per person
$351
per person
Nov 21 - Nov 25
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (5,303 reviews)
Las cimodidades limpieza todo excelente

Reviewed on Sep 7, 2025

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Save 100% on your flight
Price was $602, price is now $297 per person
$297
per person
Oct 17 - Oct 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8/10 Very Good! (1,361 reviews)
It’s an ok option if visiting but there are so many more family friendly options available with less price gouging on site, cleaner rooms, and better location. I would personally never stay here again.

Reviewed on Sep 3, 2025

Hilton Orlando

Hilton Orlando

4 out of 5
International Drive District
Save 100% on your flight
Price was $1,036, price is now $516 per person
$516
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,007 reviews)
Great place to stay at. Can’t go wrong.

Reviewed on Sep 1, 2025

Boardwalk Inn and Suites

Boardwalk Inn and Suites

2.5 out of 5
Davis
Save 100% on your flight
Price was $608, price is now $309 per person
$309
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.4/10 Very Good! (1,445 reviews)
Access underground, lodging, elevators that worked and the staff was very great and very efficient

Reviewed on Sep 6, 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

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square

The Villages
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Location! Our Village Gem-5 Star-3 min to Sumter Landing-Restaurants-Town Square
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 8 to Sep 9
$133 total
Sep 8 - Sep 9
Total with taxes and fees
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
$126 nightly
The price is $135 total per night from Sep 14 to Sep 15
$135 total
Sep 14 - Sep 15
Total with taxes and fees
Brownwood Hotel & Spa
See all 2,056 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.