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Hillcrest Heights Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Hillcrest Heights vacation rentals

A bedroom with a stone fireplace, a large bed, and a view of the outdoors through large windows.

1. Lake View•Gardens•Private Balcony Suite•Legoland

Lake View•Gardens•Private Balcony Suite•Legoland
Lake Wales
9.0 out of 10, Wonderful, (12 reviews)
"Great view, comfortable room for our one night stay."
United States
Vern H.
$139 nightly
The price is $154
Nov 1 - Nov 2
Total with taxes and fees
Lake View•Gardens•Private Balcony Suite•Legoland
A riverside cabin with a dock, surrounded by lush greenery and a cloudy sky.

2. Camp Mack Lodge, Marina & RV Resort

Camp Mack Lodge, Marina & RV Resort
3.0 star property
Lake Wales
9.0 out of 10, Wonderful, (224 reviews)
"Camp Mack is an awesome place for getting away for a few days or longer. The surroundings are beautiful, and the people are so friendly."
United States
Terri
$97 nightly
The price is $109
Oct 19 - Oct 20
Total with taxes and fees
Camp Mack Lodge, Marina & RV Resort
A modern hotel room with a bed, a sofa, a TV, and a fireplace.

3. Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake

Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
Lake Wales
8.0 out of 10, Very good, (4 reviews)
"Room was spotless. Private entrance, the shuffleboard table game was fun, coffee and creamer was awesome. Bedding was so soft. You could tell there was construction going on with in the property however there wasn’t any noice and the room was clean clean clean!!! "
United States
Barbara
$159 nightly
The price is $176
Nov 1 - Nov 2
Total with taxes and fees
Stylish Retreat/86`TV/King Bed/Spa Shower/Shuffleboard/Near the Lake
A wooden deck leading to a dock over water, surrounded by grass and trees with Spanish moss.

4. Stilt House on the Shore at Lake Reedy

Stilt House on the Shore at Lake Reedy
Frostproof
10.0 out of 10, Exceptional, (4 reviews)
"Great place to stay. It was perfect for our family. Great spot on the lake. Very quiet and peaceful. Will definitely return in the future. "
United States
Thomas C.
$255 nightly
The price is $282
Oct 5 - Oct 6
Total with taxes and fees
Stilt House on the Shore at Lake Reedy
A kitchen shelf with jars of spices, a bottle of cooking spray, and a white candle.

5. This old Florida feeling getaway is 420 friendly and a great place to just relax

This old Florida feeling getaway is 420 friendly and a great place to just relax
Avon Park
8.0 out of 10, Very good, (4 reviews)
"We were very fascinated by the farm animals and the dogs "
United States
Debi D.
$132 nightly
The price is $145
Oct 3 - Oct 4
Total with taxes and fees
This old Florida feeling getaway is 420 friendly and a great place to just relax
A spacious lobby with a seating area, a counter with a menu board, and a kitchen area in the background.

6. Dundee | King Bed Non Smoking

Dundee | King Bed Non Smoking
Dundee FL
10.0 out of 10, Exceptional, (122 reviews)
"Comfy beds really helped recharge after busy days at nearby attractions."
United States
Anonymous traveler
$88 nightly
The price is $97
Oct 3 - Oct 4
Total with taxes and fees
Dundee | King Bed Non Smoking
A modern kitchen with built-in appliances, a dining area with a table and chairs, and a hallway leading to a door.

7. Premium Lake Wales Getaway!

Premium Lake Wales Getaway!
Lake Wales
9.8 out of 10, Exceptional, (6 reviews)
"Jill & Kayla, thank you do mich for the wonderful stay. I look forward visiting again"
United States
Dawn H.
$303 nightly
The price is $335
Oct 24 - Oct 25
Total with taxes and fees
Premium Lake Wales Getaway!
Two lounge chairs with metal frames and grey fabric seats, positioned near a pool with a tiled edge.

8. Lake Front! Spacious Home w/heated pool & kayaks

Lake Front! Spacious Home w/heated pool & kayaks
Lake Wales
10.0 out of 10, Exceptional, (26 reviews)
"It’s a lovely, quiet location "
United States
Kathy M.
$467 nightly
The price is $516
Oct 5 - Oct 6
Total with taxes and fees
Lake Front! Spacious Home w/heated pool & kayaks
A compact living space with a loft bed, a TV mounted on the wall displaying streaming services, a small bathroom, and a wooden floor.

9. Lakefront Tiny Cottage 4 Miles to LEGOLAND.

Lakefront Tiny Cottage 4 Miles to LEGOLAND.
winter have
9.0 out of 10, Wonderful, (42 reviews)
"Awesome location, very nice"
United States
Kyle P.
$135 nightly
The price is $149
Oct 4 - Oct 5
Total with taxes and fees
Lakefront Tiny Cottage 4 Miles to LEGOLAND.
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

10. Cozy & Inviting 3BR and 2 Bath • Full Kitchen + Laundry

Cozy & Inviting 3BR and 2 Bath • Full Kitchen + Laundry
Lake Wales
9.0 out of 10, Wonderful, (4 reviews)
"Clean and nice"
United States
Antolin
$181 nightly
The price is $200
Oct 12 - Oct 13
Total with taxes and fees
Cozy & Inviting 3BR and 2 Bath • Full Kitchen + Laundry
An indoor swimming pool with a clear view of the sky through a metal roof structure.

11. Hotel Style Lakeview Cottage • 3BR • Heated Pool

Hotel Style Lakeview Cottage • 3BR • Heated Pool
Lake Wales
$253 nightly
The price is $280
Oct 3 - Oct 4
Total with taxes and fees
Hotel Style Lakeview Cottage • 3BR • Heated Pool
A modern reception area with a wooden panel design, a tiled floor, and a white door in the background.

12. Elita Inn

Elita Inn
3.0 star property
Dundee
7.4 out of 10, Good, (35 reviews)
"Very nice accommadations..friendly staff"
United States
lance
$77 nightly
The price is $86
Oct 3 - Oct 4
Total with taxes and fees
Elita Inn
A swimming pool with lounge chairs and palm trees, surrounded by a modern building with large windows and string lights.

13. Lake Retreat w/Pool & Hot Tub near Bok Tower

Lake Retreat w/Pool & Hot Tub near Bok Tower
Lake Wales
9.8 out of 10, Exceptional, (76 reviews)
"Our family of 8 had a wonderful time! The space and amenities were perfect for our stay and we had excellent communication with the host. Would absolutely recommend this property. Thank you for everything! "
United States
Ali R.
$567 nightly
The price is $627
Oct 6 - Oct 7
Total with taxes and fees
Lake Retreat w/Pool & Hot Tub near Bok Tower
An outdoor hot tub area with a pool, surrounded by chairs and a table.

14. Legoland Splash Escape with pool and hot tub!

Legoland Splash Escape with pool and hot tub!
Winter Haven
10.0 out of 10, Exceptional, (74 reviews)
"We had a great time staying here. The house was well maintained. The kids enjoyed the pool."
United States
Amy
$302 nightly
The price is $333
Oct 6 - Oct 7
Total with taxes and fees
Legoland Splash Escape with pool and hot tub!
A reception area with a check-in counter, two red chairs, and a tiled floor.

15. 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
$82 nightly
The price is $90
Oct 3 - Oct 4
Total with taxes and fees
2 Full Beds|Non-Smoking
A modern kitchen with a stainless steel refrigerator, white cabinetry, a double sink, and a painting of flowers on the wall.

16. New Haven 5 mi to Legoland & 0.5 mi to dwntwn

New Haven 5 mi to Legoland & 0.5 mi to dwntwn
Winter Haven
10.0 out of 10, Exceptional, (1 review)
$252 nightly
The price is $276
Oct 3 - Oct 4
Total with taxes and fees
New Haven 5 mi to Legoland & 0.5 mi to dwntwn
A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a wooden floor.

17. Modern Dundee Townhome Near Lakes & Legoland!

Modern Dundee Townhome Near Lakes & Legoland!
Dundee
$308 nightly
The price is $342
Oct 3 - Oct 4
Total with taxes and fees
Modern Dundee Townhome Near Lakes & Legoland!
A compact living space with a dining area, kitchen, and a seating area with a sofa and a rug.

18. Family-Friendly 2BR Near LEGOLAND with Parking

Family-Friendly 2BR Near LEGOLAND with Parking
Winter Haven
8.6 out of 10, Excellent, (21 reviews)
"Absolutely great location for Legoland. The house had everything my family of 5 needed. Nice and quiet neighborhood. We would stay again! "
United States
Carolyn S.
$189 nightly
The price is $209
Oct 4 - Oct 5
Total with taxes and fees
Family-Friendly 2BR Near LEGOLAND with Parking
A spacious indoor area with a seating area, a counter, and a kitchen visible in the background.

19. Dundee | 2 Queen Bed Nmsk

Dundee | 2 Queen Bed Nmsk
Dundee FL
10.0 out of 10, Exceptional, (90 reviews)
"Location is close to Legoland, so perfect for families visiting with kids."
United States
Anonymous traveler
$99 nightly
The price is $109
Oct 3 - Oct 4
Total with taxes and fees
Dundee | 2 Queen Bed Nmsk
A building with a red door, numbered 132C, and a small porch area with a metal stool and a green bucket with a wooden stick.

20. Tiny Paradise

Tiny Paradise
Winter Haven
9.4 out of 10, Exceptional, (16 reviews)
"Check in was easy, this little house had everything we needed! Owner very responsive to needs very quickly through app. We would stay again!"
United States
Cheryl K.
$118 nightly
The price is $130
Oct 4 - Oct 5
Total with taxes and fees
Tiny Paradise
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 Hillcrest Heights Hotel Reviews

Home2 Suites By Hilton Winter Haven

Home2 Suites By Hilton Winter Haven

10/10 Excellent
"Rooms were clean, beds were comfortable, walking distance from Legoland and Publix, breakfast was ok."
Gustavo 2-night trip
Posted 8 hours ago
Home2 Suites By Hilton Winter Haven

Find out more about Hillcrest Heights

Everything you need to know about Hillcrest Heights 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 Hillcrest Heights 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 Hillcrest Heights vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Hillcrest Heights vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillcrest Heights. 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 Hillcrest Heights 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 $86 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 Hillcrest Heights rentals

At Expedia, we put the best Hillcrest Heights 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 Hillcrest Heights 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 Hillcrest Heights 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 Hillcrest Heights. 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 Hillcrest Heights?

Yes, we have vacation rentals close to popular local attractions in Hillcrest Heights, or you can select a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Hillcrest Heights?

Family Fun Haven: 3 Bed/2 Bath/6 Mi to Legoland/Pet Friendly!: This vacation home rental near Hillcrest Heights offers a patio, a garden, 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 you can cook with friends or family.

What’s there to see and do in Hillcrest Heights?

Explore the area and family-friendly sights such as LEGOLAND® Florida, or get out into nature at a spot like Crooked Lake. In the larger area, you’ll find Lake Wailes and Twin Lakes.

What’s a vacation rental in Hillcrest Heights like?

Vacation rentals are privately owned properties you can book for short or long periods in Hillcrest Heights. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy reception areas while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which makes a vacation rental an attractive choice for family gatherings.