Vacation Rentals in Highlands, FL

PRICE PER NIGHT

ACCOMMODATION TYPES

3B/2Ba Home with Commmunity Pool. 30min from Universal Studios
9.4

Excellent

·
Highlands
·
3 br
·
Sleeps 8
·
Pool · Air Conditioning · Furnished ·
From
$230/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Pool
Air Conditioning
Furnished
In Unit Laundry
Wifi
Swimming Pool
Other spaces
Kitchen
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1x1 Guest Suite 15 mins from UCF
10

Excellent

·
Winter Springs
·
1 br
·
Sleeps 2
·
Smoking Allowed · Pool · Air Conditioning ·
From
$41/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Smoking Allowed
Pool
Air Conditioning
Furnished
Wifi
Swimming Pool
Cozy 3/2 with Pool, Hot Tub, Patio + 5* Location!
10

Excellent

·
Winter Springs
·
3 br
·
Sleeps 11
·
Fitness Center · Dishwasher · Hot Tub ·
From
$209/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Fitness Center
Dishwasher
Hot Tub
Oven
Pool
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Workspace, Kitchen
Paradise in a country setting . ( Note this an upstairs apartment 1100 sq ft )
10

Excellent

·
Lake Mary
·
2 br
·
Sleeps 4
·
Outdoor Space · Balcony · Private Pool ·
From
$159/night
Check availability
Property
Apartment · 2 Beds · 1 bath
Amenities
Private Pool
Oven
Pool
Air Conditioning
Furnished
In Unit Laundry
Wifi
Swimming Pool
Other spaces
Balcony, Kitchen
The Suite at Lake Mary
10

Excellent

·
Lake Mary
·
1 br
·
Sleeps 2
·
On Site Laundry · Waterfront · Walk In Closets ·
From
$55/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Waterfront
Walk In Closets
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Resort like Lake House on 2+ acres, Golf Course, pool, fishing dock, pool table
10

Excellent

·
Casselberry Country Club
·
3 br
·
Sleeps 8
·
Outdoor Space · Fitness Center · Fireplace ·
From
$400/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Fitness Center
Fireplace
Dishwasher
Private Pool
Lake
Waterfront
Oven
Pool
Other spaces
Kitchen
Beautiful Renovated Home - Peaceful Location60
10

Excellent

·
Casselberry
·
3 br
·
Sleeps 6
·
Dishwasher · Workspace · Oven ·
From
$186/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
New Modern Home- Perfect for your next vacation.66

No reviews

·
Casselberry
·
3 br
·
Sleeps 5
·
Dishwasher · Workspace · Oven ·
From
$181/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Peace and quiet
10

Excellent

·
Longwood
·
2 br
·
Sleeps 5
·
Fitness Center · Dishwasher · Workspace ·
From
$102/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Fitness Center
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Wheelchair Accessible
Other spaces
Workspace, Kitchen

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Peaceful and Private Orlando Getaway | Game Garage + Hot tub + fenced in yard
9

Excellent

·
Longwood
·
3 br
·
Sleeps 10
·
Dishwasher · Smoking Allowed · Private Pool ·
From
$163/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Dishwasher
Smoking Allowed
Private Pool
Oven
Pool
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Beautiful 2 bed townhome 35 minutes from Disney
10

Excellent

·
Casselberry
·
2 br
·
Sleeps 6
·
Furnished ·
From
$200/night
Check availability
Property
House · 2 Beds · 2 baths
Amenities
Furnished
Cozy Lakeside Cottage
9.9

Excellent

·
Lake Mary
·
1 br
·
Sleeps 4
·
On Site Laundry · Dishwasher · Lake ·
From
$62/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
On Site Laundry
Dishwasher
Lake
Waterfront
Oven
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Cozy and picture perfect Little house on the Lake
9.6

Excellent

·
Lake Mary
·
3 br
·
Sleeps 5
·
Outdoor Space · Fitness Center · Fireplace ·
From
$116/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Fitness Center
Fireplace
Dishwasher
Lake
Waterfront
Oven
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Florida Vacation with pool fun for families
9.6

Excellent

·
Casselberry Country Club
·
3 br
·
Sleeps 7
·
Outdoor Space · Private Pool · Oven ·
From
$190/night
Check availability
Property
House · 3 Beds · 2 baths
Amenities
Private Pool
Oven
Pool
Air Conditioning
Furnished
In Unit Laundry
Wifi
Swimming Pool
Other spaces
Kitchen
The Tiny Cottage in the Springs!

No reviews

·
Hickory Square
·
2 br
·
Sleeps 4
·
Outdoor Space · Ceiling Fan · Fireplace ·
From
$129/night
Check availability
Property
House · 2 Beds · 1 bath
Amenities
Ceiling Fan
Fireplace
Smoking Allowed
Air Conditioning
Furnished
In Unit Laundry
Wifi
Wheelchair Accessible
Other spaces
Kitchen
Affordable, convenient and pet-friendly family space
10

Excellent

·
Maitland
·
1 br
·
Sleeps 4
·
Fitness Center · Dishwasher · Balcony ·
From
$100/night
Check availability
Property
Condo · 1 Bed · 1 bath
Amenities
Fitness Center
Dishwasher
Oven
Pool
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Balcony, Kitchen
Entire House - King Bed Suite & Golf Course View
10

Excellent

·
Sanford
·
2 br
·
Sleeps 6
·
Outdoor Space · Dishwasher · Workspace ·
From
$119/night
Check availability
Property
Apartment · 2 Beds · 2 baths
Amenities
Dishwasher
Air Conditioning
Furnished
In Unit Laundry
Wifi
Fitness Center
Other spaces
Workspace, Kitchen
Beautiful Resort like Chalet - North Of Orlando In Longwood, Florida
10

Excellent

·
Longwood
·
4 br
·
Sleeps 8
·
Outdoor Space · Fitness Center · Assigned Parking ·
From
$285/night
Check availability
Property
Apartment · 4 Beds · 3 baths
Amenities
Fitness Center
Assigned Parking
Dishwasher
Lake
Waterfront
Oven
Air Conditioning
Furnished
Other spaces
Workspace, Kitchen
Lakefront Luxury Furnished Split Floor Plan First Floor Condo

No reviews

·
Casselberry
·
3 br
·
Sleeps 4
·
Fitness Center · Dishwasher · Lake ·
From
$63/night
Check availability
Property
Condo · 3 Beds · 2 baths
Amenities
Fitness Center
Dishwasher
Lake
Waterfront
Hot Tub
Oven
Pool
Air Conditioning
Other spaces
Kitchen
Convenient Lake Mary Home Near Golf, Parks, Tennis and more

No reviews

·
Lake Mary
·
4 br
·
Sleeps 9
·
Private Pool · Pool · Air Conditioning ·
From
$249/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Private Pool
Pool
Air Conditioning
Furnished
In Unit Laundry
Wifi
Swimming Pool
Cozy House in Historic Longwood FL

No reviews

·
Longwood
·
3 br
·
Sleeps 30
·
Dishwasher · Lake · Waterfront ·
From
$198/night
Check availability
Property
House · 3 Beds · 1 bath
Amenities
Dishwasher
Lake
Waterfront
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Kitchen
Tiny Cottage
9.5

Excellent

·
Longwood
·
1 br
·
Sleeps 2
·
Fitness Center · Fireplace · Workspace ·
From
$95/night
Check availability
Property
Apartment · 1 Bed · 1 bath
Amenities
Fitness Center
Fireplace
Air Conditioning
Furnished
In Unit Laundry
Wifi
Other spaces
Workspace, Kitchen
Come and Enjoy our Clean and Spacious Home
9.5

Excellent

·
Sanford
·
4 br
·
Sleeps 12
·
Outdoor Space · Fireplace · Dishwasher ·
From
$332/night
Check availability
Property
House · 4 Beds · 2 baths
Amenities
Fireplace
Dishwasher
Private Pool
Oven
Pool
Air Conditioning
Furnished
In Unit Laundry
Other spaces
Kitchen
Spacious Lovely 2-bedroom vacation home with pool

No reviews

·
Winter Park
·
3 br
·
Sleeps 6
·
Dishwasher · Oven · Air Conditioning ·
From
$135/night
Check availability
Property
Apartment · 3 Beds · 2 baths
Amenities
Dishwasher
Oven
Air Conditioning
Furnished
In Unit Laundry
Wifi
Swimming Pool
Other spaces
Kitchen
Home > Florida Vacation Rentals > Winter Springs Vacation Rentals > Highlands Vacation Rentals
Updated: March 22, 2023

Learn about vacation rentals in

Highlands

Browse 1 vacation rentals near Highlands in Winter Springs, Florida. If you’re interested in touring around Winter Springs, and you want to stay in the Highlands neighborhood, use our interactive map to find your next rental. You can see pictures of Highlands vacation rentals, view amenities and features, browse by property types, and more. Whether you’re looking for a Highlands staycation, weekend getaway, or a long vacation, we’ve got you covered. The lowest vacation rental price in Highlands is $230 per night and goes up to as much as $230 per night. Use the date filters at the top to select your travel dates and view availability.
1 of the vacation rentals near Highlands are houses. The average bathroom count for a vacation house near Highlands is 2. The average price for vacation houses near Highlands is $230 per night. There are 1 vacation homes under this price. The most common amenities for vacation rentals near Highlands are: swimming pool, kitchen, and in-unit laundry. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.

3 bed rentals

1 available

Getting around Highlands

Walking

6/10
Some shops and stores are within a few minutes.

Car

9/10
Commuting is easy with multiple accessible routes and plenty of parking.

Transit

3/10
There are a few mass transit options within the area.

Points of interest in Highlands

Groceries

7/10
At least one grocery store within a 15-minute walk

Shopping

5/10
Some shops within walking distance

Cafes

4/10
Some cafés within walking distance

Restaurants

5/10
Some restaurants within walking distance

Parks

9/10
Large amount of park space nearby

Nightlife

3/10
Few or no bars within walking distance

Vacation Rentals in Highlands, FL FAQ

How many vacation rentals in Highlands are available?

There are currently 1 vacation rentals in Highlands available. Choose from nightly rentals, monthly rentals, weekend rentals, and weekly rentals to find your perfect stay in Highlands.

What types of vacation rental properties are available in Highlands, FL?

As of March 22, 2023, there are 1 vacation houses for rent in Highlands and no vacation condos and apartments for rent in Highlands, FL. Check each listing to view photos and get more details about pricing and available amenities.

Are there any vacation rentals in Highlands, FL with more than 1 bedroom?

Yes, there are 1 Highlands vacation rentals with more than 1 bedroom. To view a more detailed amenity list, click on the available properties on Vacations by Zumper.

How many pet friendly Highlands vacation rentals are available?

As of March 22, 2023, there are no pet friendly vacation rentals in Highlands, Florida available. For more information about pet policies regarding dogs and cats, view the property listing or contact the leasing agent.

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