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Highland City Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Highland City vacation rentals

A living room with a large mural of marine life, a ceiling fan, a flat-screen TV, and a dining area in the background.

1. 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
The price is CA $83
CA $349 total
includes taxes & fees
Sep 27 - Sep 28
BlockHaven near Legoland & Disney
A modern kitchen with stainless steel appliances, a microwave, and a refrigerator.

2. Studio Signature

Studio Signature
Lakeland
10.0 out of 10, Exceptional, (11 reviews)
"Clean cute friendly quiet neighborhood really enjoyed this stay and will likely stay again in future"
United States
Mel B.
The price is CA $94
CA $243 total
includes taxes & fees
Sep 25 - Sep 26
Studio Signature
A compact, well-lit room with a kitchenette, a bed, and a small seating area.

3. 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.
The price is CA $140
CA $271 total
includes taxes & fees
Sep 25 - Sep 26
Suite Escape in Family friendly area
A residential driveway leading to a garage with a white garage door, surrounded by lush greenery and trees.

4. Private Studio Suite

Private Studio Suite
Lakeland
9.6 out of 10, Exceptional, (19 reviews)
"Excellent stay. Would definitely book again."
United States
Heather
The price is CA $57
CA $170 total
includes taxes & fees
Sep 29 - Sep 30
Private Studio Suite
A hotel room with a bed, a sofa, a bedside table, a mirror, and a window with curtains.

5. 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, (26 reviews)
"Room was clean and comfortable. Close to lots of stores and restaurants. Would definitely stay here again. "
United States
Melissa R.
The price is CA $107
CA $226 total
includes taxes & fees
Sep 27 - Sep 28
Enjoy in this beautiful and serene south Lakeland area Perfect for 4 traveler
A living room with a sofa, a kitchen area with a counter and chairs, and a TV mounted on the wall.

6. RED DOOR HOUSE!

RED DOOR HOUSE!
South Lake Morton
9.6 out of 10, Exceptional, (66 reviews)
"Conveniently located and clean"
United States
Rachel
The price is CA $143
CA $353 total
includes taxes & fees
Oct 1 - Oct 2
RED DOOR HOUSE!
A modern living room with a TV, bookshelves, a dining area with chairs and a table, and a kitchen with a microwave.

7. Charming Suite In The Heart Of Lakeland

Charming Suite In The Heart Of Lakeland
Lakeland
8.8 out of 10, Excellent, (80 reviews)
"very nice place"
United States
Benjamin P.
The price is CA $76
CA $199 total
includes taxes & fees
Sep 25 - Sep 26
Charming Suite In The Heart Of Lakeland
A reception area with a check-in counter, two red chairs, and a tiled floor.

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 traveller
The price is CA $108
CA $137 total
includes taxes & fees
Sep 25 - Sep 26
2 Full Beds|Non-Smoking
A modern hotel room with a bed, a desk, a chair, and a sofa.

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.
The price is CA $107
CA $227 total
includes taxes & fees
Sep 23 - Sep 24
Cozy studio in enjoyable Lakeland with AC, WiFi
A swimming pool with a fence, lounge chairs, and a palm tree.

10. Lake Ida Beach Resort

Lake Ida Beach Resort
3.0 star property
Winter Haven
7.2 out of 10, Good, (196 reviews)
"Clean room and private area loved it"
United States
Heather
The price is CA $95
CA $106 total
includes taxes & fees
Sep 23 - Sep 24
Lake Ida Beach Resort
A compact kitchen with white cabinets, a stainless steel refrigerator, a coffee bar, and a tiled backsplash.

11. 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.
The price is CA $113
CA $249 total
includes taxes & fees
Sep 25 - Sep 26
Charming 1-bedroom apartment with AC, WiFi in enchanting Lakeland
A hotel room with a bed, a framed picture on the wall, and a view of the outside.

12. King Bed|Non smoking

King Bed|Non smoking
Bartow FL
10.0 out of 10, Exceptional, (120 reviews)
"Location is key when you're busy exploring, it was easy getting back after sightseeing all day!"
United States
Anonymous traveller
The price is CA $153
CA $188 total
includes taxes & fees
Sep 25 - Sep 26
King Bed|Non smoking
A hotel room with a bed, a TV, a desk, a chair, and a mirror.

13. 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 traveller
The price is CA $153
CA $188 total
includes taxes & fees
Sep 25 - Sep 26
2 Full Bed|non smoking
Two doors with hanging robes, one pink and one blue, in a hallway.

14. Hidden Ruby-Apartment with Kitchen and Laundry

Hidden Ruby-Apartment with Kitchen and Laundry
Cleveland Heights
9.8 out of 10, Exceptional, (7 reviews)
"The place was excellent and the host was very friendly."
United States
Jim J.
The price is CA $73
CA $204 total
includes taxes & fees
Sep 23 - Sep 24
Hidden Ruby-Apartment with Kitchen and Laundry
A two-story building with a flat roof, large windows, and a balcony.

15. Two Bedroom Home in Beautiful downtown Lakeland

Two Bedroom Home in Beautiful downtown Lakeland
South Lake Morton
9.6 out of 10, Exceptional, (19 reviews)
"Great location and a short walk to downtown "
United States
Mark S.
The price is CA $138
CA $382 total
includes taxes & fees
Sep 23 - Sep 24
Two Bedroom Home in Beautiful downtown Lakeland
A house with a grey door, two exterior wall-mounted lights, and a stone baseboard.

16. 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
The price is CA $91
CA $145 total
includes taxes & fees
Oct 18 - Oct 19
Charming 1-bedroom apartment in wonderful Lakeland with AC
A hallway with a white door, a staircase with a black railing, and a bed in the background.

17. Modern 4-Bedroom Pool House w/ King Beds– 5 Minutes from Downtown!

Modern 4-Bedroom Pool House w/ King Beds– 5 Minutes from Downtown!
Lakeland
10.0 out of 10, Exceptional, (15 reviews)
"We lived our stay and the host was fantastic to work with. "
United States
Melissa B.
The price is CA $126
CA $468 total
includes taxes & fees
Sep 27 - Sep 28
Modern 4-Bedroom Pool House w/ King Beds– 5 Minutes from Downtown!
A covered outdoor patio area with brick walls, potted plants, and a white fence in the background.

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.
The price is CA $112
CA $224 total
includes taxes & fees
Sep 28 - Sep 29
Blue Dream Sunrise "Your Journey, Our Passion" Cozy retreat in lovely Lakeland
A hotel room with a bed, a chair, a nightstand, a lamp, and a painting on the wall.

19. 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 traveller
The price is CA $111
CA $310 total
includes taxes & fees
Oct 1 - Oct 2
Blue Door House " Grande Studio"
A modern living room with a brown leather sofa, a flat-screen TV, and a dining area with wooden cabinets and a kitchen in the background.

20. Heart of Downtown Lakeland - Urban Luxury Loft. Studio + Memory Foam Sofa Bed

Heart of Downtown Lakeland - Urban Luxury Loft. Studio + Memory Foam Sofa Bed
Downtown Lakeland
9.8 out of 10, Exceptional, (18 reviews)
"Great property....great location"
United States
Terry E.
The price is CA $164
CA $385 total
includes taxes & fees
Oct 1 - Oct 2
Heart of Downtown Lakeland - Urban Luxury Loft. Studio + Memory Foam Sofa Bed
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

Best Western Plus Winter Haven Inn & Suites 

Best Western Plus Winter Haven Inn & Suites 

10/10 Excellent
"Large clean modern room, very nice toiletries. The breakfast was great, a different hot option each day."
Krystal 2-night trip
Posted 3 hours ago
Best Western Plus Winter Haven Inn & Suites 

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Highland City vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Highland City vacation rentals we have selected for you start as low as CA $106 per night. Entering your travel dates in the search wizard 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?

Great quiet and comfortable, South Central Lakeland location.: This vacation home rental outside of Highland City is located on a lake and offers an outdoor pool, air-conditioning, and a Smart TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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. The Club at Eaglebrooke and Southgate Shopping Center 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.