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Highland City Vacation Rentals

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Highland City vacation rentals

Private kitchen

1. Studio Signature

Studio Signature
Lakeland
10.0 out of 10, Exceptional, (10 reviews)
"Clean cute friendly quiet neighborhood really enjoyed this stay and will likely stay again in future"
United States
Mel B.
$158 nightly
The price is $174
Sep 7 - Sep 8
Total with taxes and fees
Studio Signature
Property grounds

2. Private Studio Suite

Private Studio Suite
Lakeland
9.6 out of 10, Exceptional, (19 reviews)
"Excellent stay. Would definitely book again."
United States
Heather
$111 nightly
The price is $121
Sep 7 - Sep 8
Total with taxes and fees
Private Studio Suite
Dining

3. Charming Suite In The Heart Of Lakeland

Charming Suite In The Heart Of Lakeland
Lakeland
8.8 out of 10, Excellent, (78 reviews)
"very nice place"
United States
Benjamin P.
$129 nightly
The price is $142
Sep 7 - Sep 8
Total with taxes and fees
Charming Suite In The Heart Of Lakeland
Luxury House, 3 Bedrooms, Garden View | Living area

4. BlockHaven near Legoland & Disney

BlockHaven near Legoland & Disney
3.5 star property
Winter Haven
10.0 out of 10, Exceptional, (6 reviews)
"We loved this place! It was perfect for all of us! It was nice and clean as well!"
United States
Ericka
$230 nightly
The price is $258
Sep 9 - Sep 10
Total with taxes and fees
BlockHaven near Legoland & Disney
Exterior detail

5. Charming 1-bedroom apartment in wonderful Lakeland with AC

Charming 1-bedroom apartment in wonderful Lakeland with AC
Edgewood
9.4 out of 10, Exceptional, (9 reviews)
"Very clean, nice kitchenette area, comfy bed"
United States
amanda
$89 nightly
The price is $97
Sep 8 - Sep 9
Total with taxes and fees
Charming 1-bedroom apartment in wonderful Lakeland with AC
Interior

6. Suite Escape in Family friendly area

Suite Escape in Family friendly area
Lakeland
9.4 out of 10, Exceptional, (3 reviews)
"Great property for a weekend trip. Perfect for two people and a dog. The neighborhood was quiet and relaxing, making it easy to unwind. Would definitely stay again."
United States
Heather D.
$175 nightly
The price is $194
Sep 8 - Sep 9
Total with taxes and fees
Suite Escape in Family friendly area
Room

7. King Bed|Non smoking

King Bed|Non smoking
Bartow FL
10.0 out of 10, Exceptional, (120 reviews)
"Pleasantly surprised by how everything worked well during our stay here,definitely better than most budget options around!"
United States
Anonymous traveler
$84 nightly
The price is $93
Sep 7 - Sep 8
Total with taxes and fees
King Bed|Non smoking
Lobby

8. 2 Full Beds|Non-Smoking

2 Full Beds|Non-Smoking
Bartow FL
10.0 out of 10, Exceptional, (266 reviews)
"Great stay in Bartow."
United States
Anonymous traveler
$88 nightly
The price is $97
Sep 7 - Sep 8
Total with taxes and fees
2 Full Beds|Non-Smoking
Room

9. Cozy studio in enjoyable Lakeland with AC, WiFi

Cozy studio in enjoyable Lakeland with AC, WiFi
Lakeland Highlands
10.0 out of 10, Exceptional, (12 reviews)
"Great place to stay. It was very clean and large enough. Nice and quiet, away from the main roads. Plenty of good restaurants close by,"
United States
Brett L.
$147 nightly
The price is $162
Sep 7 - Sep 8
Total with taxes and fees
Cozy studio in enjoyable Lakeland with AC, WiFi
Interior

10. Charming 1-bedroom apartment with AC, WiFi in enchanting Lakeland

Charming 1-bedroom apartment with AC, WiFi in enchanting Lakeland
Lakeland
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and inviting place. The hosts are great people and always make sure guests are happy. Highly recommend "
United States
Jade E.
$161 nightly
The price is $178
Sep 11 - Sep 12
Total with taxes and fees
Charming 1-bedroom apartment with AC, WiFi in enchanting Lakeland
Room

11. 2 Full Bed|non smoking

2 Full Bed|non smoking
Bartow FL
10.0 out of 10, Exceptional, (93 reviews)
"Great spot if you're just passing through Bartow or need somewhere simple to stay overnight."
United States
Anonymous traveler
$84 nightly
The price is $93
Sep 7 - Sep 8
Total with taxes and fees
2 Full Bed|non smoking
Living area

12. RED DOOR HOUSE!

RED DOOR HOUSE!
South Lake Morton
9.6 out of 10, Exceptional, (66 reviews)
"Conveniently located and clean"
United States
Rachel
$184 nightly
The price is $203
Sep 8 - Sep 9
Total with taxes and fees
RED DOOR HOUSE!
Interior

13. Hidden Ruby-Apartment with Kitchen and Laundry

Hidden Ruby-Apartment with Kitchen and Laundry
Cleveland Heights
9.8 out of 10, Exceptional, (6 reviews)
"The place was excellent and the host was very friendly."
United States
Jim J.
$138 nightly
The price is $152
Sep 13 - Sep 14
Total with taxes and fees
Hidden Ruby-Apartment with Kitchen and Laundry
Room

14. Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler

Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler
Lakeland Highlands
10.0 out of 10, Exceptional, (25 reviews)
"Room was clean and comfortable. Close to lots of stores and restaurants. Would definitely stay here again. "
United States
Melissa R.
$147 nightly
The price is $162
Sep 15 - Sep 16
Total with taxes and fees
Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler
Laundry

15. PRIVATE GETAWAY

PRIVATE GETAWAY
South Lake Morton
9.8 out of 10, Exceptional, (17 reviews)
"Awesome property and host! The location was perfect within walking and driving distance of countless stores and restaurants. We will definitely stay again next time in Lakeland! "
United States
John D.
$164 nightly
The price is $182
Sep 7 - Sep 8
Total with taxes and fees
PRIVATE GETAWAY
Room

16. Blue Door House " Grande Studio"

Blue Door House " Grande Studio"
Cleveland Heights
8.6 out of 10, Excellent, (8 reviews)
"Very comfortable, great location (close to most things), quiet neighborhood."
United States
Anonymous traveler
$202 nightly
The price is $224
Sep 8 - Sep 9
Total with taxes and fees
Blue Door House " Grande Studio"
Outdoor pool

17. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (194 reviews)
"The cabins were great loved it there"
United States
Jennifer
$77 nightly
The price is $87
Sep 18 - Sep 19
Total with taxes and fees
Lake Ida Beach Resort
Terrace/patio

18. Blue Dream Sunrise "Your Journey, Our Passion" Cozy retreat in lovely Lakeland

Blue Dream Sunrise "Your Journey, Our Passion" Cozy retreat in lovely Lakeland
Lakeland
9.6 out of 10, Exceptional, (5 reviews)
"This place was so clean and perfect! Loved it! We would definitely stay here again!"
United States
Timothy S.
$170 nightly
The price is $170
Sep 8 - Sep 9
Total with taxes and fees
Blue Dream Sunrise "Your Journey, Our Passion" Cozy retreat in lovely Lakeland
Dining

19. Studio petite

Studio petite
South Lake Morton
9.6 out of 10, Exceptional, (39 reviews)
"Room was clean and met our needs. Not really lakefront, a little small but worked well for what we needed. "
United States
Steven J.
$155 nightly
The price is $171
Oct 1 - Oct 2
Total with taxes and fees
Studio petite
Room

20. The Loft at Raintree

The Loft at Raintree
Lakeland
8.8 out of 10, Excellent, (5 reviews)
"Very nice to stay at clean and spacious. Will definitely stay here again when in the area"
United States
German J.
$209 nightly
The price is $232
Sep 30 - Oct 1
Total with taxes and fees
The Loft at Raintree
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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Top Highland City Hotel Reviews

Staybridge Suites Winter Haven Auburndale by IHG

Staybridge Suites Winter Haven Auburndale by IHG

10/10 Excellent
"Our first time staying here. Good location in Winter Haven but at the same time, Disappointed to see homeless people right across the street from the hotel."
Penny 2-night trip
Posted 1 hour ago
Staybridge Suites Winter Haven Auburndale by IHG

Find out more about Highland City

Everything you need to know about Highland City vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Highland City vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Highland City vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Highland City vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Highland City. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Highland City in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $87 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Highland City rentals

At Expedia, we put the best Highland City vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Highland City rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Highland City vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Highland City. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Can I find a vacation rental in Highland City?

Yes, we have vacation rentals where you'll be just 11.5 mi (18.5 km) from LEGOLAND® Florida, offering you a more secluded option if you want a quiet place to stay.

What are some of the best vacation rentals that Highland City has to offer?

Lakeside Adventure Retreat | Heated Pool, Game Room & Private Dock | Optional Boat Cruise: This vacation home rental outside of Highland City is located on a lake and has a balcony, a pool table, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

What’s there to see and do in Highland City?

Explore the area and family-friendly sights such as LEGOLAND® Florida, or get out into nature at a spot like The Circle B Bar Reserve. Sanlan Bird and Wildlife Sanctuary and The Club at Eaglebrooke are a couple of places you'll find in the larger area.

What’s a vacation rental in Highland City like?

Vacation rentals are private properties you can book for a long or short time in Highland City. Vacation rentals provide amenities such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental a great option for a family trip.