Highlands Vacations from $236

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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.
Wyndham Garden Jacksonville

Wyndham Garden Jacksonville

3 out of 5
Southside
Price was $337, price is now $236 per person
$236
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
7.8/10 Good! (1,741 reviews)
Very modern and updated

Reviewed on Sep 8, 2025

DoubleTree by Hilton Hotel Jacksonville Riverfront

DoubleTree by Hilton Hotel Jacksonville Riverfront

4 out of 5
Downtown Jacksonville
Save 100% on your flight
Price was $497, price is now $328 per person
$328
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
6.6/10 (1,383 reviews)
No problems to comment about!!

Reviewed on Sep 7, 2025

The Ritz-Carlton, Amelia Island

The Ritz-Carlton, Amelia Island

5 out of 5
Save 100% on your flight
Price was $2,029, price is now $1,388 per person
$1,388
per person
Nov 13 - Nov 17
found 23 hours ago
Roundtrip flight included
New York (JFK) to Jacksonville (JAX)
9.2/10 Wonderful! (369 reviews)
Leticia at the front desk was fantastic! I had a health related attack on the way back from Atlanta and we decided to stay at the Ritz so I could rest. We stayed at this Ritz on our honeymoon over 30 years ago, had my 50th birthday party at Salt with guests for a weekend, stayed there for our 30th wedding anniversary and had dinner at Salt also (I highly recommend Salt), stayed many holidays with our children and friends, car shows, and it is still such a wonderful resort. You cannot go wrong staying at this beautiful resort. We have loved it for over 30 years and hope to keep going there for many more years to come. All of the staff is great, but a special shout out to Leticia. Thank you for helping us.

Reviewed on Sep 6, 2025

Hilton Jacksonville At Mayo Clinic

Hilton Jacksonville At Mayo Clinic

4.5 out of 5
Southside
Save 100% on your flight
Price was $611, price is now $427 per person
$427
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
No reviews
WaterWalk Extended Stay by Wyndham Jacksonville Deerwood Pk

WaterWalk Extended Stay by Wyndham Jacksonville Deerwood Pk

2 out of 5
Southside
Price was $382, price is now $271 per person
$271
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
8.8/10 Excellent! (638 reviews)
Pet friendly, clean room staff very pleasant

Reviewed on Sep 6, 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 9 to Sep 10
$197 total
Sep 9 - Sep 10
Total with taxes and fees
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
$182 nightly
The price is $206 total per night from Sep 18 to Sep 19
$206 total
Sep 18 - Sep 19
Total with taxes and fees
Hyatt Regency Jacksonville
Embassy Suites by Hilton Jacksonville Baymeadows

Embassy Suites by Hilton Jacksonville Baymeadows

3.5 out of 5
9300 Baymeadows Road, Jacksonville, FL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $124 total per night from Sep 14 to Sep 15
$124 total
Sep 14 - Sep 15
Total with taxes and fees
Embassy Suites by Hilton Jacksonville Baymeadows
See all 3,577 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

4.5/5(433 reviews)

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

4/5(300 reviews)

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

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

EverBank Stadium

4/5(386 reviews)

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.