Highland Vacation Rentals & Ski-in/Ski-out Homes
Villa
10.0Exceptional
(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
1054 ft²
Fireplace/Heating
Pool
Kitchen
Parking
US $130/Night
7 Nights - US $907
House
10.0Exceptional
(3 Reviews)
4 Bedrooms
3 Baths
8 Guests
2335.77 ft²
- Pool
Balcony/Terrace- Parking
Internet
US $317/Night
7 Nights - US $2,217
House
5 Bedrooms
3 Baths
12 Guests
4700 ft²
- Fireplace/Heating
- Pool
Ocean View- Balcony/Terrace
US $532/Night
7 Nights - US $3,721
Villa
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $169/Night
7 Nights - US $1,185
House
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
7 Guests
1560.77 ft²
- Balcony/Terrace
- Parking
Air Conditioner- Internet
US $175/Night
7 Nights - US $1,225
Villa
10.0Exceptional
(4 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $141/Night
7 Nights - US $984
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
- Parking
US $144/Night
7 Nights - US $1,009
House
10.0Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $124/Night
7 Nights - US $866
House
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $223/Night
7 Nights - US $1,561
Luxury Places to Stay in Highland
Over 106+ Luxury Places to Stay in or Near Highland
House
9.8Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $2,837/Night
7 Nights - US $19,856
House
10.0Exceptional
(11 Reviews)
6 Bedrooms
7 Baths
14 Guests
3245 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,781/Night
7 Nights - US $12,469
House
10.0Exceptional
(6 Reviews)
5 Bedrooms
5 Baths
16 Guests
4995 ft²
- Hot Tub
- Fireplace/Heating
- Kitchen
- Parking
US $938/Night
7 Nights - US $6,563
House
9.6Exceptional
(4 Reviews)
5 Bedrooms
5 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $917/Night
7 Nights - US $6,418
House
10.0Exceptional
(13 Reviews)
5 Bedrooms
3 Baths
14 Guests
5000 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $704/Night
7 Nights - US $4,928
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $502/Night
7 Nights - US $3,517
House
9.0Exceptional
(2 Reviews)
4 Bedrooms
4 Baths
9 Guests
3498.27 ft²
- Fireplace/Heating
- Balcony/Terrace
View- Parking
US $466/Night
7 Nights - US $3,262
New
Resort
1 Bath
12 Guests
161.46 ft²
Oceanfront- Hot Tub
Spa- Pool
US $454/Night
7 Nights - US $3,177
House
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $450/Night
7 Nights - US $3,150
Top-Rated Vacation Rentals with a Pool in Highland
Over 26+ Top-Rated Vacation Rentals with a Pool in or Near Highland
House
10.0Exceptional
(44 Reviews)
3 Bedrooms
2 Baths
6 Guests
2656 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $287/Night
7 Nights - US $2,008
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1151.74 ft²
- Spa
- Pool
- Balcony/Terrace
- View
US $149/Night
7 Nights - US $1,043
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
957.99 ft²
- Pool
- Balcony/Terrace
- Parking
- Internet
US $137/Night
7 Nights - US $959
Condo
9.8Exceptional
(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
1188 ft²
- Pool
- Kitchen
- Parking
- Air Conditioner
US $139/Night
7 Nights - US $970
Condo
9.8Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $194/Night
7 Nights - US $1,361
House
9.4Exceptional
(33 Reviews)
4 Bedrooms
3 Baths
8 Guests
2335 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $262/Night
7 Nights - US $1,833
Villa
9.4Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
6 Guests
1000 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $132/Night
7 Nights - US $921
House
9.3Exceptional
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
1184.03 ft²
- Pool
- Balcony/Terrace
- Parking
- Internet
US $159/Night
7 Nights - US $1,115
Villa
9.2Exceptional
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $130/Night
7 Nights - US $909
Pet-Friendly Vacation Rentals in Highland
Over 25+ Pet-Friendly Vacation Rentals in or Near Highland
Villa
8.2Excellent
(11 Reviews)
2 Bedrooms
2 Baths
4 Guests
1100 ft²
- Pool
- Ocean View
- View
- Pet Friendly
US $167/Night
7 Nights - US $1,170
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
4 Guests
1496.18 ft²
- Balcony/Terrace
- View
- Pet Friendly
- Parking
US $106/Night
7 Nights - US $744
Cottage
2 Bedrooms
1 Bath
6 Guests
- Pet Friendly
- Air Conditioner
- Internet
Child Friendly
US $299/Night
7 Nights - US $2,092
House
2 Bedrooms
2 Baths
6 Guests
1302.43 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $261/Night
7 Nights - US $1,825
Villa
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $174/Night
7 Nights - US $1,221
Apartment
1 Bedroom
2 Baths
4 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,083
House
10.0Exceptional
(9 Reviews)
4 Bedrooms
3 Baths
10 Guests
2000 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Air Conditioner
US $272/Night
7 Nights - US $1,907
Villa
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $152/Night
7 Nights - US $1,062
House
9.4Exceptional
(45 Reviews)
4 Bedrooms
2 Baths
7 Guests
1456 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $274/Night
7 Nights - US $1,918
Large Vacation Homes & Villas in Highland
Over 19+ Large Vacation Homes & Villas in or Near Highland
Villa
2 Bedrooms
2 Baths
4 Guests
1150 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Parking
US $197/Night
7 Nights - US $1,378
House
7.9Very Good
(9 Reviews)
6 Bedrooms
6 Baths
12 Guests
328.3 ft²
- Fireplace/Heating
- Balcony/Terrace
- Parking
- Air Conditioner
US $85/Night
7 Nights - US $595
Villa
2 Bedrooms
2 Baths
4 Guests
954 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $133/Night
7 Nights - US $934
Villa
2 Bedrooms
2 Baths
6 Guests
1001.04 ft²
- Oceanfront
- Spa
- Fireplace/Heating
- Ocean View
US $201/Night
7 Nights - US $1,409
House
3 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $308/Night
7 Nights - US $2,158
Villa
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1054 ft²
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $461/Night
7 Nights - US $3,224
Villa
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1054 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $150/Night
7 Nights - US $1,052
Villa
8.6Fabulous
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $198/Night
7 Nights - US $1,383
House
10.0Exceptional
(13 Reviews)
5 Bedrooms
3 Baths
10 Guests
1300 ft²
- Hot Tub
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $364/Night
7 Nights - US $2,550
Wheelchair Accessible Vacation Homes in Highland
Over 2+ Wheelchair Accessible Vacation Homes in or Near Highland
Cottage
5.0Average
(5 Reviews)
3 Bedrooms
2 Baths
2 Guests
900 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $144/Night
7 Nights - US $1,008
House
3 Bedrooms
3 Baths
6 Guests
3300 ft²
- Private Pool
- Pool
- Pet Friendly
- Kitchen
US $248/Night
7 Nights - US $1,736
Highland Resorts and Airbnb Homes Under $200
Over 33+ Highland Resorts and Airbnb Homes Under $200
House
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $184/Night
7 Nights - US $1,290
House
9.0Exceptional
(3 Reviews)
1 Bedroom
2 Baths
7 Guests
- View
- Parking
- Air Conditioner
- Internet
US $151/Night
7 Nights - US $1,059
Cottage
4.0Average
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Kitchen
- Parking
- Air Conditioner
- Internet
US $123/Night
7 Nights - US $860
Apartment
9.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
1151.74 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Breakfast
US $138/Night
7 Nights - US $966
New
House
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $180/Night
7 Nights - US $1,259
Condo
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
1421 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $193/Night
7 Nights - US $1,351
House
8.4Excellent
(6 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Child Friendly
US $197/Night
7 Nights - US $1,378
Cottage
8.0Excellent
(1 Review)
4 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $155/Night
7 Nights - US $1,086
House
9.6Exceptional
(5 Reviews)
2 Bedrooms
2 Baths
4 Guests
1800 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $172/Night
7 Nights - US $1,201
Instantly Bookable Vacation Homes in Highland
Over 38+ Instantly Bookable Vacation Homes in or Near Highland
House
9.6Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
7 Guests
1500 ft²
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $347/Night
7 Nights - US $2,432
House
10.0Exceptional
(13 Reviews)
4 Bedrooms
3 Baths
9 Guests
3500 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $428/Night
7 Nights - US $2,997
House
10.0Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
9 Guests
1800 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $240/Night
7 Nights - US $1,681
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
2 Baths
8 Guests
2356 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $367/Night
7 Nights - US $2,570
House
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Balcony/Terrace
- Kitchen
- Parking
- Air Conditioner
US $269/Night
7 Nights - US $1,884
House
9.6Exceptional
(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $277/Night
7 Nights - US $1,936
House
9.6Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
7 Guests
1671 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
US $231/Night
7 Nights - US $1,614
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $269/Night
7 Nights - US $1,882
RV Rental
1 Bedroom
1 Bath
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $240/Night
7 Nights - US $1,677
Book a Last Minute Place to Stay in Highland
About Highland Vacation Rentals
Explore over 115 vacation rentals in Highland with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Highland for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Highland. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Highland tailored to your preferences. On average, these rentals offer 1049.51 ft² of space, and are priced at an average of US $281 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Highland at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
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Top Types of Ski Accommodations in Highland
| Type | Count |
|---|---|
| Vacation Homes | 67 |
| Villas | 22 |
| Cottages | 8 |
| Holiday Apartments | 7 |
| Others | 2 |
| Unique Vacation Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Highland
★ Pro Tip: Discover Your Ideal Vacation Rental in Highland with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Highland, FL
View the weather forecast for Highland before booking your Highland Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Frequently Asked Questions About Highland?
What are the top vacation rentals in Highland?
When organizing your trip to Highland, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Highland. Peruse our collection of highly-rated properties and secure your reservation today.
- Welcome, enjoy your own PRIVATE POOL and LAKEFRONT Dock. Fish & Kayak
- Screened Patio & Grill at Sebring Resort Community
- 21-Acre Lakefront Paradise: Heated Pool, Private Beach, Animals, Fishing-Boating
- Waterfront Lake Placid Home with Private Dock!
- Enjoy this Natural Preserve.
- Lakehouse on lake Istokpoga. Separate inlaws quarters, 10 minutes from Raceway
- Lakehouse on Lake Francis with Huge Game Room next to Boat Ramp
- “Premier Host ⭐ Lakefront 3BR Private Dock Stunning Sebring Escape, Golf & Races
- Elegant Villa Retreat
- Lake House
How many vacation rentals have private pools in Highland?
Uncover 1 vacation rentals boasting private pools near Highland. Explore top-rated RBO homes offering access to a swimming pool:
Which vacation homes or resorts in Highland are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Highland. Enjoy great views, locations and save money with SunSki Resorts.™
- Lakehouse on Lake Francis with Huge Game Room next to Boat Ramp
- 5 Mi to Sebring Int'l Raceway: Canal-View Retreat!
- Lakefront Recreation & Relaxation in Lake Placid
How many SunSkiResorts vacation rentals or resorts are available in Highland?
Discover the ideal vacation rental in Highland with SunSki Resorts™. We provide an extensive selection of over 115 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Highland.
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