
House vacation rentals in Highland
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Top-rated house rentals in Highland
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House & Barn Historic Beauty •Events & gatherings!
A block from downtown State street. Tall trees line the streets of the historical magic that is Redlands 🍊 ✨I have a sister house! Next door is The Olive Branch. This is perfect for larger parties An inground fire pit is the perfect way to get everyone together & cuddle. Or maybe just night under the stars as the sound from The Redlands Bowl Plays into the yard Spend the day playing poker downstairs in the Carriage house or make your way up the stairs and drift away in to hippie land.

Balsam Bungalow - Lake View 1 min to ski - Hot Tub
Balsam Bungalow is a Mid-century bungalow, nestled on a piney hillside, with state forest and Lake views, in the exclusive & charming Moonridge neighborhood. Walk/drive to Big Bear slopes located .3 miles away. Snow Summit 9 min drive. State Forest Hiking trails 2 blocks away. Snuggle by the masonry fireplace & take in the picturesque view w/ ceiling to floor windows. Enjoy the wooded yard with wrap around deck, fire pit, BBQ, eating area & scenic hot tub- that is serviced after each guest.

Bright Vibes Home|Sleeps 8|1Blk to Univ|Pacman+BBQ
Step into our inviting Redlands home full of bright vibes and fun! Centrally located near the University, this lively gem features an indoor gym, playful outdoor spaces with Tic-Tac-Toe, fire pit + BBQ, and a lively atmosphere. Whip up culinary delights in the fully equipped kitchen, unwind in cozy bedrooms, and enjoy modern amenities. Explore downtown's lively scene, indulge in local attractions, and create unforgettable memories at our spirited Redlands retreat! 30+ day/ insurance stays okay.

Cottage Grove Haus
Kick back and relax in this stylish space, vintage cabin. Luxurious amenities include: 1. Fully prepped kitchen with Le Crueset pots and pan, Kitchenaid appliance and many more. 2. Comfortable and stylish living room with Sonos sound system and television with soundboard & subwoofer. 3. Large and sophisticated dining room to enjoy a gourmet meal or to useas an office space. 4. One third acre of property surrounded by forest and privacy. 5. Large outdoor patio to have a meal with nature.

Ray of sunshine Cottage.
Cozy and centrally-located home to relax, work, go to the casino, attend concerts or events near by. Down the street (1.2 miles) from Yaamava Resort & Casino. 14 min (6.8 miles) from National Orange Show Event center (NOS). 9 min (4.3 miles) from San Bernardino International Airport. 25 min (25 miles) from Ontario International Airport. Conveniently located as it’s at walking distance to restaurants, Starbucks, retail store; as well as food market, fast food places and more!

Bright Modern 2-Bd House in Quiet neighborhood!
This bright modern house was recently remodeled and it's ready for you to enjoy! The home is situated in a very quiet and safe neighborhood at the end of a cul-de-sac in the foothills of the San Bernardino mountains. This house is the perfect place to use as a basecamp when exploring San Bernardino (Yaamava Resort and Casino, NOS, the first McDonald's museum, Big Bear, Lake Arrowhead, Joshua Tree, Palm Springs, Orange County (Disneyland, Knotts), LA and so many more places.

Hot Tub, Fire Pit/Game Room/ Near NOS Center
Welcome to our meticulously clean three-bedroom, two-bath haven in San Bernardino! This gorgeous house is designed for comfort and entertainment. Unwind in the game room with a pool table or gather around the patio's fire pit. Experience the charm of our outdoor space, featuring a second fire pit in the grass area. Create lasting memories surrounded by freshly painted murals near the inviting pool and brand-new Jacuzzi – perfect for starlit evenings with friends and family.

Magical lake house with spectacular views
Gorgeous, tranquil retreat with enriching views of the lake and nature. A storybook bridge with the soothing flow of the stream beside it sets the mood for relaxation, inspiration and/or romance immediately. The home opens to captivating views of the entire lake from the curated, open floor plan. Ideal for cooking, quality dining, working on something creative or simply a peaceful escape from the city. Multiple terraces and balconies to enjoy the crisp air and setting.

Quiet Vineyard View 2-bedroom Home Near Oak Glen
This 1700sqft spacious vineyard-view home is nestled on Yucaipa's North Bench in a peaceful, rural cul-de-sac. Close proximity to Oak Glen and Yucaipa's dedicated open space make this home a perfect landing spot for comfort and safety. Beautiful views of the mountain and vineyards. Centrally located to Oak Glen, Big Bear, Palm Springs. Bedroom 1: CalKing Bed Bedroom 2: Queen Bed Additional Beds: (2) Twins and pack-n-play upon request No parties/events are permitted

Spacious 4 bedroom home in the heart of town!
Your entire group will enjoy easy access to everything from this centrally located home. Only one mile to the University of Redlands, and less than a mile to all the great restaurants, bars, and shopping boutiques on State St. Easy access to both on and off-ramps of the 10 freeway. Almost everything inside the house is new! With over 2 years of ALL 5-star reviews, this is hands down the best place to stay in Redlands! Don't hesitate, we book up fast.

Unique mountain lake pink bedroom private cabin
Welcome to Hillside House Boutique themed couples retreat in the mountains Here you will find everything you need for the perfect luxury getaway for two or the ideal writers/artist/solo peaceful vacation Every element has been carefully curated to create an unforgettable experience Featuring victorian inspired living room, huge bedroom with claw foot bath and secluded back yard with private hot tub Take a look at our insta page @hillsidehouseca

Charming 3 BR Home - Near NOS Center/Mountains
Welcome to this beautifully renovated 900 sq. ft. home, carefully designed to be your home away from home. Inside you will find a full kitchen, washer/dryer, and three bedrooms (full beds, TVs, desks). Only 10–15 mins to NOS Event Center, plus easy drives to Big Bear, Palm Springs, and beaches. For your peace of mind, the property has 3 exterior cameras which actively record audio/video and are monitored 24/7 for security.
Popular amenities for Highland house rentals
House rentals with a pool

One In A Trillion • 32+ Private Acres!

Casa de Agua Retreat

Charming 5 bed, 3 bath home with pool

Vineyard Retreat, Pool & Amazing Views!

Riverside Serenity Spring Oasis|Spa/Pool/Mini Golf

CHARMING POOL HOME BY DOWNTOWN *FAMILY GETAWAYS*

BOHEMIAN AND MODERN SERENE HOME WITH POOL

North Upland House with a Pool
Weekly house rentals

Mountaintop Pool Paradise | Mins to NOS Center

Cozy, Romantic Cabin for Two | The Squirrel House

Perfect home for large groups! Newly remodeled

Mountain Lake A-Frame | Forest, AC, Auto-Generator

Entire house near Redlands

Backyard Paradise – Pool, Firepit & Outdoor Dining

Luxury A-Frame Retreat w/ Lake Rights

So. Cal. Living near Redlands-Beautiful 3,000+Home
Private house rentals

Chic Guesthouse with Secluded Garden near Downtown

Cozy Home in Loma Linda

Crestline Hideaway

A Pet Friendly, Quiet Space, Imperfectly Country

Home at Grace

Pet Friendly! Modern Decor!Gameroom!Amazing Views!

SoCal’s Pet Friendly Luxury Family Pool spa Resort

Contemporary Cabin, flat entry for 3 cars!
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$25,487 GYD | G$26,531 GYD | G$31,127 GYD | G$25,696 GYD | G$26,531 GYD | G$27,367 GYD | G$28,411 GYD | G$30,918 GYD | G$26,740 GYD | G$27,367 GYD | G$24,233 GYD | G$24,442 GYD |
| Avg. temp | 14°C | 14°C | 15°C | 16°C | 18°C | 20°C | 23°C | 24°C | 24°C | 21°C | 17°C | 14°C |
Quick stats about house rentals in Highland

Total vacation rentals
Explore 70 vacation rentals in Highland

Nightly prices starting at
Highland vacation rentals start at G$8,356 GYD per night before taxes and fees

Verified guest reviews
Over 2,620 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Vacation rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of Highland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Highland rentals

4.8 Average rating
Highland stays are highly rated by guests—averaging 4.8 out of 5!
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- Family-friendly rentals Highland
- Rentals with a patio Highland
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- Rentals with a fire pit Highland
- Rentals with pools Highland
- Rentals with a washer and dryer Highland
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- Pet-friendly rentals Highland
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- Disneyland Park
- Knott’S Berry Farm
- Bear Mountain Ski Resort
- Disney California Adventure Park
- Big Bear Mountain Resort
- Anaheim Convention Center
- Palm Springs Convention Center
- Pechanga Resort Casino
- Snow Summit
- Mountain High
- Honda Center
- National Orange Show Events Center
- Palm Springs Aerial Tramway
- Angel Stadium of Anaheim
- Disneyland Resort
- Indian Canyons
- Glen Ivy Hot Springs Spa
- Tahquitz Creek Golf Resort
- University of California Irvine
- Irvine Spectrum Center
- Chino Hills State Park
- Yaamava' Resort & Casino
- Snow Valley Mountain Resort
- Mt. Baldy Resort





