Highlands Holiday Rentals
House
- Jacksonville
- ·
- Northside
- 4.04 mi to center
10.0Exceptional
(97 Reviews)
2 Bedrooms
1 Bath
5 Guests
Oceanfront
Parking
Ocean View
Balcony/Terrace
US $204/Night
7 Nights - US $1,425
House
- Jacksonville
- ·
- Northside
- 0.76 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
6 Guests
13993.08 ft²
- Parking
- Balcony/Terrace
Air Conditioner
Internet
US $177/Night
7 Nights - US $1,238
Hotel
- Jacksonville
- ·
- Northside
- 1.51 mi to center
6.8Good
(223 Reviews)
1 Bath
- Parking
Kitchen- Air Conditioner
- Internet
US $84/Night
7 Nights - US $588
Apartment
- Jacksonville
- ·
- Northside
- 1.13 mi to center
10.0Exceptional
(5 Reviews)
1 Bedroom
1 Bath
2 Guests
700 ft²
- Oceanfront
- Parking
- Ocean View
View
US $177/Night
7 Nights - US $1,239
Apartment
- Jacksonville
- ·
- Northside
- 1.13 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
699.65 ft²
- Parking
Spa- Internet
Pet Friendly
US $140/Night
7 Nights - US $978
Apartment
- Jacksonville
- ·
- Highlands
- 1.54 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
4 Guests
850 ft²
- Parking
Pool- Balcony/Terrace
- Kitchen
US $247/Night
7 Nights - US $1,728
Apartment
- Jacksonville
- ·
- Highlands
- 1.45 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
892 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $266/Night
7 Nights - US $1,864
Apartment
- Jacksonville
- ·
- Hollyford
- 0.57 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,355
Cottage
- Jacksonville
- ·
- Lake Forest
- 0.39 mi to center
9.8Exceptional
(223 Reviews)
2 Bedrooms
2 Baths
6 Guests
1670 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $250/Night
7 Nights - US $1,751
Luxury Holiday Rentals in Highlands
Over 161+ Luxury Holiday Rentals in or Near Highlands
House
- Jacksonville
- ·
- Hollyford
- 1.06 mi to center
4 Bedrooms
2 Baths
8 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $1,362/Night
7 Nights - US $9,537
House
- Jacksonville
- ·
- Hollyford
- 0.87 mi to center
3 Bedrooms
3 Baths
8 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $1,340/Night
7 Nights - US $9,377
New
House
- Jacksonville
- ·
- Northside
- 4.34 mi to center
4 Bedrooms
2 Baths
8 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $981/Night
7 Nights - US $6,866
House
- Jacksonville
- ·
- Northside
- 4.14 mi to center
9.8Exceptional
(7 Reviews)
4 Bedrooms
3 Baths
10 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $578/Night
7 Nights - US $4,048
New
House
- Jacksonville
- ·
- Riverview
- 0.58 mi to center
9.6Exceptional
(20 Reviews)
4 Bedrooms
3 Baths
10 Guests
Private Pool
Hot Tub
Breakfast- Parking
US $539/Night
7 Nights - US $3,773
House
- Jacksonville
- ·
- Riverview
- 0.69 mi to center
7.2Very Good
(5 Reviews)
6 Bedrooms
3 Baths
18 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $487/Night
7 Nights - US $3,412
House
- Jacksonville
- ·
- Riverview
- 0.56 mi to center
9.6Exceptional
(5 Reviews)
6 Bedrooms
5 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $478/Night
7 Nights - US $3,349
House
- Jacksonville
- ·
- Highlands
- 1.26 mi to center
4 Bedrooms
4 Baths
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $452/Night
7 Nights - US $3,164
House
- Jacksonville
- ·
- Biscayne
- 0.34 mi to center
4 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $364/Night
7 Nights - US $2,551
Top-Rated Holiday Rentals with a Pool in Highlands
Over 23+ The Best Private Villas and Holiday Rentals in Highlands with a Pool
Apartment
- Jacksonville
- ·
- Northside
- 1.48 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
1050 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $170/Night
7 Nights - US $1,187
House
- Jacksonville
- ·
- Northside
- 1.38 mi to center
10.0Exceptional
(4 Reviews)
3 Bedrooms
1 Bath
8 Guests
1600 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $294/Night
7 Nights - US $2,056
New
Cottage
- Jacksonville
- ·
- Lake Forest
- 0.29 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $315/Night
7 Nights - US $2,203
Apartment
- Jacksonville
- ·
- Highlands
- 1.36 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
- Parking
- Pool
- Air Conditioner
- Internet
US $123/Night
7 Nights - US $859
House
- Jacksonville
- ·
- Biscayne
- 0.33 mi to center
9.8Exceptional
(120 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $263/Night
7 Nights - US $1,840
Apartment
- Jacksonville
- ·
- Highlands
- 1.41 mi to center
9.6Exceptional
(5 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $264/Night
7 Nights - US $1,848
House
- Jacksonville
- ·
- Northside
- 4.35 mi to center
9.4Exceptional
(3 Reviews)
3 Bedrooms
1 Bath
6 Guests
1700 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $314/Night
7 Nights - US $2,200
Apartment
- Jacksonville
- ·
- Highlands
- 1.52 mi to center
9.2Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
892 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $231/Night
7 Nights - US $1,615
Apartment
- Jacksonville
- ·
- Highlands
- 1.33 mi to center
9.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
4 Guests
892 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $241/Night
7 Nights - US $1,685
Pet-Friendly Holiday Rentals in Highlands
Over 61+ Pet-Friendly Holiday Rentals in or Near Highlands
Apartment
- Jacksonville
- ·
- Highlands
- 1.35 mi to center
9.4Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
894 ft²
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $262/Night
7 Nights - US $1,835
Apartment
- Jacksonville
- ·
- Highlands
- 1.32 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
796.53 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $92/Night
7 Nights - US $644
House
- Jacksonville
- ·
- Northside
- 4.62 mi to center
4 Bedrooms
2 Baths
8 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $295/Night
7 Nights - US $2,065
Apartment
- Jacksonville
- ·
- Hollyford
- 0.84 mi to center
8.8Fabulous
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,308
House
- Jacksonville
- ·
- Northside
- 3.85 mi to center
9.0Exceptional
(44 Reviews)
3 Bedrooms
3 Baths
10 Guests
2002.09 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $213/Night
7 Nights - US $1,491
Apartment
- Jacksonville
- ·
- Highlands
- 1.27 mi to center
1 Bedroom
1 Bath
4 Guests
892 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $275/Night
7 Nights - US $1,928
Apartment
- Jacksonville
- ·
- Highlands
- 1.32 mi to center
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $195/Night
7 Nights - US $1,367
Apartment
- Jacksonville
- ·
- Highlands
- 1.29 mi to center
1 Bedroom
1 Bath
4 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $194/Night
7 Nights - US $1,358
Apartment
- Jacksonville
- ·
- Highlands
- 1.59 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $194/Night
7 Nights - US $1,356
Large Holiday Rentals and Private Villas in Highlands
Over 27+ Large Holiday Rentals and Private Villas in or Near Highlands
Cabin
- Jacksonville
- ·
- Northside
- 4.50 mi to center
2.0Average
(1 Review)
2 Bedrooms
2 Baths
13 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $47/Night
7 Nights - US $327
House
- Jacksonville
- ·
- Northside
- 4.46 mi to center
7.3Very Good
(6 Reviews)
3 Bedrooms
3 Baths
10 Guests
1345.49 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $271/Night
7 Nights - US $1,895
House
- Jacksonville
- ·
- Biscayne
- 0.12 mi to center
10.0Exceptional
(8 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $360/Night
7 Nights - US $2,519
House
- Jacksonville
- ·
- Northside
- 3.64 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
3 Baths
10 Guests
- Air Conditioner
- Internet
- Laundry
Bedding/Linens
US $349/Night
7 Nights - US $2,444
House
- Jacksonville
- ·
- Riverview
- 0.75 mi to center
9.2Exceptional
(5 Reviews)
3 Bedrooms
2 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $314/Night
7 Nights - US $2,196
House
- Jacksonville
- ·
- Northside
- 4.46 mi to center
8.6Fabulous
(9 Reviews)
3 Bedrooms
2 Baths
10 Guests
1342 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $313/Night
7 Nights - US $2,188
House
- Jacksonville
- ·
- Northside
- 4.82 mi to center
6.0Good
(2 Reviews)
4 Bedrooms
2 Baths
12 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Laundry
US $330/Night
7 Nights - US $2,307
Villa
- Jacksonville
- ·
- Northside
- 4.57 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $57/Night
7 Nights - US $396
House
- Jacksonville
- ·
- Northside
- 3.90 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
10 Guests
1600 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $180/Night
7 Nights - US $1,260
Wheelchair Accessible Holiday Homes in Highlands
Over 7+ Wheelchair Accessible Holiday Homes in or Near Highlands
Apartment
- Jacksonville
- ·
- Highlands
- 1.36 mi to center
1 Bedroom
1 Bath
2 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $208/Night
7 Nights - US $1,456
Hotel
- Jacksonville
- ·
- Hollyford
- 1.07 mi to center
4.3Average
(54 Reviews)
2 Baths
333.68 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $97/Night
7 Nights - US $679
Hotel
- Jacksonville
- ·
- Hollyford
- 1.07 mi to center
5.6Average
(519 Reviews)
1 Bath
- Parking
- Pool
- Kitchen
- Air Conditioner
US $65/Night
7 Nights - US $453
House
- Jacksonville
- ·
- Northside
- 3.08 mi to center
3 Bedrooms
2 Baths
8 Guests
1438 ft²
- Kitchen
- Air Conditioner
- Internet
- Pet Friendly
US $200/Night
7 Nights - US $1,400
Hotel
- Jacksonville
- ·
- Northside
- 1.47 mi to center
3.9Average
(143 Reviews)
1 Bath
376.74 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $65/Night
7 Nights - US $453
House
- Jacksonville
- ·
- Northside
- 4.18 mi to center
4 Bedrooms
2 Baths
12 Guests
1865 ft²
- Oceanfront
- Ocean View
- View
- Kitchen
US $106/Night
7 Nights - US $742
US $65/Night
7 Nights - US $455
Highlands Private Villas and Holiday Homes Under $200
Over 68+ Highlands Private Villas and Holiday Homes Under $200
Cabin
- Jacksonville
- ·
- Northside
- 4.35 mi to center
2.0Average
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $125/Night
7 Nights - US $876
House
- Jacksonville
- ·
- Highlands
- 0.38 mi to center
5.0Average
(1 Review)
1 Bedroom
1 Bath
4 Guests
602.78 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $196/Night
7 Nights - US $1,372
Apartment
- Jacksonville
- ·
- Northside
- 0.81 mi to center
1 Bedroom
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $153/Night
7 Nights - US $1,068
Apartment
- Jacksonville
- ·
- Hollyford
- 0.56 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $190/Night
7 Nights - US $1,332
Apartment
- Jacksonville
- ·
- Highlands
- 1.36 mi to center
1 Bedroom
1 Bath
2 Guests
893.4 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $135/Night
7 Nights - US $946
Cottage
- Jacksonville
- ·
- Highlands
- 0.61 mi to center
1 Bedroom
1 Bath
4 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $188/Night
7 Nights - US $1,315
Cabin
- Jacksonville
- ·
- Highlands
- 0.46 mi to center
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Laundry
- Bedding/Linens
US $178/Night
7 Nights - US $1,249
Apartment
- Jacksonville
- ·
- Northside
- 1.24 mi to center
2 Bedrooms
2 Baths
4 Guests
1184 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $171/Night
7 Nights - US $1,200
Apartment
- Jacksonville
- ·
- Northside
- 1.24 mi to center
2 Bedrooms
2 Baths
4 Guests
1184 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $170/Night
7 Nights - US $1,190
Instantly Bookable Holiday Homes in Highlands
Over 79+ Instantly Bookable Holiday Homes in or Near Highlands
New
House
- Jacksonville
- ·
- Riverview
- 0.43 mi to center
2.0Average
(1 Review)
2 Bedrooms
1 Bath
4 Guests
676 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $268/Night
7 Nights - US $1,875
New
House
- Jacksonville
- ·
- Highlands
- 0.19 mi to center
2 Bedrooms
1 Bath
4 Guests
720 ft²
- Parking
- Kitchen
- Air Conditioner
- Internet
US $341/Night
7 Nights - US $2,388
Apartment
- Jacksonville
- ·
- Highlands
- 1.36 mi to center
1 Bedroom
1 Bath
2 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $207/Night
7 Nights - US $1,448
Apartment
- Jacksonville
- ·
- Northside
- 1.24 mi to center
2 Bedrooms
2 Baths
4 Guests
1184 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,085
Apartment
- Jacksonville
- ·
- Northside
- 1.24 mi to center
2 Bedrooms
2 Baths
4 Guests
1184 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $155/Night
7 Nights - US $1,085
Apartment
- Jacksonville
- ·
- Northside
- 1.24 mi to center
2 Bedrooms
2 Baths
4 Guests
1184 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $154/Night
7 Nights - US $1,079
Apartment
- Jacksonville
- ·
- Highlands
- 1.38 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $148/Night
7 Nights - US $1,038
Apartment
- Jacksonville
- ·
- Northside
- 4.54 mi to center
1 Bedroom
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $148/Night
7 Nights - US $1,034
Apartment
- Jacksonville
- ·
- Northside
- 1.24 mi to center
1 Bedroom
1 Bath
2 Guests
764 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $142/Night
7 Nights - US $994
Book a Last Minute Place to Stay in Highlands
About Casai's Private Villas and Holiday Rentals in Highlands
Discover more than 170 vacation rentals available in Highlands. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Highlands.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Highlands, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Highlands. On average, places to stay near Highlands offer 1077.44 ft², with nightly prices averaging US $238.
With Casai, finding and comparing holiday rentals in Highlands is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Show more
Show less
Top Accommodation Types in Highlands
| Type | Count |
|---|---|
| Vacation Homes | 100 |
| Holiday Apartments | 52 |
| Cottages | 5 |
| Villas | 1 |
Use these Quick Filters to Find a Holiday Rental in Highlands
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Highlands.
Weather in Highlands, FL
View the weather forecast for Highlands before booking your Highlands 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 Highlands?
What are the top holiday rentals in Highlands?
With numerous options available in Highlands, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Highlands:
- Cozy house on the river, enjoy the view or fish right off the river bank
- Riverfront House With Breathtaking Views, Grill, King Bed, Near Jaguars Stadium!
- Emely's place 5 minutes from Jacksonville international airport
- Corporate Luxe 2BR/2BA Apartment with Serene Water View- 5 min from JAX Airport.
- 4 Mi to JAX! Quiet, Pet-Friendly Northside Studio
- The Sanctuary-8 minutes from Jax airport and 5 miles from the Jacksonville Zoo!
- Peaceful Retreat Near St Johns River and the Airport
- Entire 3BR/2.5BA Townhouse Near JAX Zoo & Airport | Sleeps 6
- Cozy pool house minutes to the Zoo!
- Luxury Stay Minutes from JAX AIRPORT + StJohns River
How many holiday rentals have private pools in Highlands?
Discover a selection of holiday rentals with private pools near Highlands with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- Luxury Mansion w/Putting Green and Lavish Pool
- 4000 SqFt Luxury Fun House/Fishing/Dock/Hammocks/Jacuzzi/Relax/75TV/Pool Table
Which holiday homes in Highlands are best for families?
If you're searching for a family-friendly holiday home in Highlands, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Highlands:
- Peaceful Riverfront Cottage with a dock on 1.5 Acres.
- Pool home sleeps 6 with large fenced yard
- Stayable Jacksonville North
How many Casai.com holiday rentals are available in Highlands?
As of 2026, Casai boasts over 170 properties listed in the Highlands area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Highlands.
Nearby Neighborhood (4)
| Neighborhood | Property Count |
|---|---|
| Northside Vacation Rentals in Jacksonville, Florida | 248 |
| Riverview Vacation Rentals in Jacksonville, Florida | 180 |
| Hollyford Vacation Rentals in Jacksonville, Florida | 143 |
| Biscayne Vacation Rentals in Jacksonville, Florida | 143 |
Map
