Highland City Holiday Rentals

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Holiday Rentals in Highland City

Lake Ida Beach Resort

3.0 star property
7.6 out of 10, Good, (159)
"Was a wonderful peaceful stay"
The price is AU$138
includes taxes & fees
3 Dec - 4 Dec
Lake Ida Beach Resort

Midway between Disney and the Gulf beaches

10.0 out of 10, Exceptional, (39)
"Nice comfortable home. Host very responsive and kind. Great quiet area. Was great for what we needed it for as a quick weekend getaway. "
The price is AU$301
includes taxes & fees
30 Nov - 1 Dec
Midway between Disney and the Gulf beaches

Modern Haines City Home w/ Pool & Lanai!

8.6 out of 10, Excellent, (24)
"Had to evacuate mobile home due to hurricane- this VRBO rental home made us feel safe and it was very clean"
Modern Haines City Home w/ Pool & Lanai!

Great quiet and comfortable, South Central Lakeland location.

9.8 out of 10, Exceptional, (119)
"excellent value. Very clean and private. Nice safe area. Only suggestion I have would be to have some disposable silverware available. Otherwise everything was as expected. "
The price is AU$146
includes taxes & fees
30 Nov - 1 Dec
Great quiet and comfortable, South Central Lakeland location.

Charming Suite In The Heart Of Lakeland

9.4 out of 10, Exceptional, (39)
"Great Place for A Quick weekend Stay One Single Room attached to a Home,Very well Kept "
The price is AU$232
includes taxes & fees
2 Dec - 3 Dec
Charming Suite In The Heart Of Lakeland

Villa Bonita. Southern Dunes 4 golf courses. Disney area!

9.6 out of 10, Exceptional, (145)
"We thoroughly enjoyed our family stay on our trip to Legoland and Orlando attractions. The property was very clean and met our needs perfectly. The pool was the icing on the cake for when kids got back or had some down time. The owner communication was top notch and very friendly and professional. Would stay here again!"
Villa Bonita. Southern Dunes 4 golf courses. Disney area!

Stay and Save! Stay now through December 20th and enjoy 20% off your stay 5 nights or more!

8.4 out of 10, Very good, (33)
"Great ply"
Stay and Save! Stay now through December 20th and enjoy 20% off your stay 5 nights or more!

The Blue House in Historic Downtown Lakeland

10.0 out of 10, Exceptional, (28)
"First time I have used a Vrbo location, and it was great. From booking the residence to checking out was a great experience. Tv was difficult to manage, but we didn’t stay indoors long. Thank you again."
The Blue House in Historic Downtown Lakeland

Plant City Home w/ Outdoor Pool!

9.2 out of 10, Wonderful, (15)
"We really enjoyed our stay here. We stayed here with our bridal party and some family members but there was enough space and things to do for everyone to enjoy. The backyard was the highlight we loved sitting out there and having the cows come up to us since we don’t get to see farm life like that often. The only downside I would say is for the money, there are some things that could’ve been updated or in better condition. Also, there were times when the hot tub would act a little funny, but for...
Plant City Home w/ Outdoor Pool!

The Lake Alfred Citrus Wood Guest Cabin

10.0 out of 10, Exceptional, (8)
"Very cozy, clean, host was very friendly."
The price is AU$232
includes taxes & fees
27 Nov - 28 Nov
The Lake Alfred Citrus Wood Guest Cabin

Vacation Home in Haines City, Fl

9.4 out of 10, Exceptional, (8)
"There was aunt in the kitchen bad The pool was dirty seemed like the pump wasn’t working properly "
Vacation Home in Haines City, Fl

Pet-Friendly Lakeland Escape w/ Private Pool!

9.8 out of 10, Exceptional, (24)
"My wife and I stayed for a week and couldn't ask for anything better. The property was in great shape after the hurricane. The neighborhood was quiet with a variety of restaurants all close to home. A grocery store just down the street which was convenient since my wife and I both love to cook. The host was easy to communicate with which made check in easy. The house was very clean and up to date and the pool was a nice added touch. Will definetely go back"
Pet-Friendly Lakeland Escape w/ Private Pool!

Studio petite

9.6 out of 10, Exceptional, (27)
"Excellent stay. Great location! Excellent communication."
The price is AU$233
includes taxes & fees
1 Dec - 2 Dec
Studio petite

3 bedroom 2 bath Ranch with pool

8.2 out of 10, Very good, (59)
"Great"
3 bedroom 2 bath Ranch with pool

Modernly updated open home with lake view, screened-in patio, grill, AC, & W/D

9.4 out of 10, Exceptional, (9)
"The property was very clean and comfortable. Very relaxing time on the screened patio with a view of the lake on cool nights."
Modernly updated open home with lake view, screened-in patio, grill, AC, & W/D

Cozy In-Law Suite in South Lakeland

10.0 out of 10, Exceptional, (10)
"Wonderful property and wonderful host! Absolutely perfect place for us when visiting grandkids in Lakeland. Very much looking forward to another visit! Thank you Natacha!!"
Cozy In-Law Suite in South Lakeland

Family-Friendly Winter Haven Home w/ Pool!

9.6 out of 10, Exceptional, (8)
"Property was clean. Was perfect for what we needed on a short notice. Definitely recommend staying. "
Family-Friendly Winter Haven Home w/ Pool!

Tropical oasis, centrally located, quiet street. Close to everything!

10.0 out of 10, Exceptional, (25)
"Very expensive. Beds were not comfortable at all. Pool was not warm enough to really enjoy. It shut off early so using the pool was limited. Drain in tub was blocked but homeowner responded and sent a plumber to correct. Unfortunately with 5 of us in the home plumber came in the evening so waited all day. Lot of extra charges"
Tropical oasis, centrally located, quiet street. Close to everything!

Cheerful New Construction Home

8.8 out of 10, Excellent, (27)
"11 minutes from Legoland! Super nice beautiful area. The beds were firm and hard I felt Like I was sleeping on the floor but I know every ones bed type is different I like softer bouncy like a cushion. But other than that everything was wonderful! "
The price is AU$684
includes taxes & fees
26 Nov - 27 Nov
Cheerful New Construction Home

Lake Whistler Hideaway - Come and enjoy this breathtaking lake front home!

10.0 out of 10, Exceptional, (24)
"This is a great place to stay if you’re in town for a baseball tournament. The pool is fantastic after melting at the fields. It’s a central location to Gulf side beaches or hitting up Orlando amusement parks. We appreciated that the kitchen had all things we needed and there were plenty of towels. Thanks for a great stay!"
Lake Whistler Hideaway - Come and enjoy this breathtaking lake front home!
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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Other types of properties in Highland City you may be interested in

La Quinta Inn & Suites by Wyndham Lakeland East

2.5 star property
6.8 out of 10, (1050)
"Everything ok "
The price is AU$132
includes taxes & fees
22 Dec - 23 Dec
La Quinta Inn & Suites by Wyndham Lakeland East

Best Western Plus Winter Haven Inn & Suites 

3.5 star property
9.4 out of 10, Exceptional, (598)
"Perfect "
The price is AU$213
includes taxes & fees
1 Dec - 2 Dec
Best Western Plus Winter Haven Inn & Suites 

Days Inn & Suites by Wyndham Lakeland

2.5 star property
7.6 out of 10, Good, (1000)
"Nice"
The price is AU$151
includes taxes & fees
16 Dec - 17 Dec
Days Inn & Suites by Wyndham Lakeland
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Can I find a holiday rental in Highland City?

Yes, we offer holiday rentals where you'll be just 11.5 mi (18.5 km) from LEGOLAND® Florida, providing a more remote option if you want a quiet place to stay.

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

Midway between Disney and the Gulf beaches: This holiday home rental outside of Highland City offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 wider area.

What’s a holiday rental in Highland City like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Highland City. Holiday rentals provide amenities such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for family gatherings.