Highlands Vacations from $299

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Your Highlands Vacation

Your next great adventure is just around the corner with a vacation package to Highlands. Relaxation, entertainment and great times — you're sure to find it in this neighborhood. When it's time to explore the sights, you'll find loads of big-name attractions nearby including Jacksonville Zoo and Gardens, Oceanway Community Center and Florida State College North Campus. Tick off one, two or all during your trip to Highlands. Stop dreaming and start doing. When you're ready to lock in your vacation to Highlands, Expedia is here to help.

The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Hotel Jacksonville Riverfront

DoubleTree by Hilton Hotel Jacksonville Riverfront

4 out of 5
Downtown Jacksonville
Price was $426, price is now $299 per person
$299
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
6.6/10 (1,373 reviews)
The building is beautiful and is situated right by the St. John's Riverwalk and the Friendship Fountain, which are gorgeous. It was quiet and the room was clean. However, the bathroom was very small and the tub/shower was very awkward and difficult to get in and out of safely. There was no counter space and it was difficult to get hot water without losing water pressure. There was no refrigerator in the room and no streaming options on the TV. Overall, since we had other things to do in Jax and spent a limited amount of time in the room, we just dealt with it, but it was far from the best hotel experience I've had.

Reviewed on Aug 16, 2025

The Villas of Amelia Island

The Villas of Amelia Island

4 out of 5
Save 100% on your flight
Price was $700, price is now $483 per person
$483
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
8.4/10 Very Good! (1,071 reviews)
This resort is clean and well maintained. It was perfect to celebrate our anniversary! It’s right on the beach but still has a pool. It was very quiet and peaceful! The only downside is that it’s about 20 minutes away from downtown. We wanted to have dinner watching sunset, so we went to Brett’s Waterway Cafe at the marina by downtown. But there are restaurants on site. I would love to visit here again with my family. They have put put golf, pickleball courts, tennis courts and golf courses. The beach here is amazing! I definitely recommend this place!

Reviewed on Aug 30, 2025

Legacy Vacation Resorts Palm Coast

Legacy Vacation Resorts Palm Coast

3 out of 5
Save 100% on your flight
Price was $641, price is now $449 per person
$449
per person
Oct 12 - Oct 17
found 15 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Daytona Beach (DAB)
8.8/10 Excellent! (1,475 reviews)
This was a perfect place to stay, to get to know the area as we were looking for our new house around the community.

Reviewed on Aug 10, 2025

Omni Amelia Island Resort & Spa

Omni Amelia Island Resort & Spa

4 out of 5
Save 100% on your flight
Price was $2,399, price is now $1,725 per person
$1,725
per person
Oct 22 - Oct 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
8.6/10 Excellent! (1,014 reviews)
Service was top notch

Reviewed on Aug 31, 2025

The Ritz-Carlton, Amelia Island

The Ritz-Carlton, Amelia Island

5 out of 5
Save 100% on your flight
Price was $1,803, price is now $1,296 per person
$1,296
per person
Nov 6 - Nov 9
found 16 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Jacksonville (JAX)
9.2/10 Wonderful! (369 reviews)
Amazing property! Only needs better food

Reviewed on Jul 2, 2025

Where to stay in Highlands

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

3 out of top 10 points of interest in this area
4/5(912 area reviews)

If you're spending some time in Southside, St. Johns Town Center and The Avenues are top sights worth seeing.

Find hotels in Southside

Highlands Hotel Deals

Margaritaville Jacksonville Beach

Margaritaville Jacksonville Beach

2.5 out of 5
715 1st St N, Jacksonville Beach, FL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $197 total per night from Sep 2 to Sep 3
$197 total
Sep 2 - Sep 3
Total with taxes and fees
9/10 Wonderful! (3,011 reviews)
"Very nice ocean view and sunrise view"

Reviewed on Aug 28, 2025

Margaritaville Jacksonville Beach
Hyatt Regency Jacksonville

Hyatt Regency Jacksonville

4 out of 5
225 E Coastline Dr, Jacksonville, FL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $180 total per night from Sep 2 to Sep 3
$180 total
Sep 2 - Sep 3
Total with taxes and fees
Hyatt Regency Jacksonville
Omni Amelia Island Resort & Spa

Omni Amelia Island Resort & Spa

4 out of 5
39 Beach Lagoon Road, Fernandina Beach, FL
Fully refundableReserve now, pay when you stay
$257 nightly
The price is $288 total per night from Sep 7 to Sep 8
$288 total
Sep 7 - Sep 8
Total with taxes and fees
8.6/10 Excellent! (997 reviews)
"This is a great resort with beautiful pools and ocean views. The food was delicious and the wait staff were very friendly and attentive. The rooms were spacious and quiet. I highly recommend this resort."

Reviewed on Aug 31, 2025

Omni Amelia Island Resort & Spa
See all 3,574 properties in Highlands
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 Highlands

Pretty

Mayo Clinic Florida

Though Mayo Clinic Florida might be what brings you to town, perhaps you'll have a chance to explore more of Jacksonville while you are here.

Mayo Clinic Florida
Jacksonville Naval Air Station

Jacksonville Naval Air Station

After visiting Jacksonville Naval Air Station, make a plan to see the other sights and activities in Jacksonville. Experience the great live music or attend a sporting event in this family-friendly area.

Jacksonville Naval Air Station
EverBank Field which includes a lake or waterhole

EverBank Stadium

Capable of seating over 80,000 fans, this modern football stadium is the exciting home of the Jacksonville Jaguars, international soccer games and music events.

EverBank Stadium

Things to do

3 Hour Coastal Fun Cruise

3 Hour Coastal Fun Cruise

$150
per adult
3 Hour Coastal Fun Cruise
1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports

1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports

$140
per traveler
90% of travellers recommend
1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports
Chocolate Bar Class

Chocolate Bar Class - Hands on class

$20
per adult
Chocolate Bar Class - Hands on class
See all activities in Jacksonville
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.