
Holiday rentals with a pool in Highland
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Highland
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

DMO 1 Bdr+ Suite. Private Pool, Spa, Luxury & Fun
Located in canyon country near the Cajon Pass, where rural serenity meets comfort, charm & luxury, all enhanced by the DMO's famous top-tier privacy, views and quiet surroundings. The Suite's Double French Door entry is accessed within a guest only area where a scenic, 5-star resort type setting, that includes a private patio, Deck, Gazebo, Pool & Spa. Inside is a Queen Bed, Queen sofa, kitchen, dining table, games, 75" TV, and a Luxurious 5-star bath. The separate Bedroom includes a King bed.

Hilltop Retreat | Heated Pool + Spectacular Views
Welcome to The Vibe Estate 🌴✨ A hilltop retreat designed for meaningful moments with family and friends. Enjoy breathtaking views 🌄, a heated cocktail pool 💧, and a spacious home perfect for meals, games 🎲, and connection. A peaceful escape to unwind, recharge, and create unforgettable memories together 💛. 🆓 Enjoy the Heated Pool and Propane BBQ Grill free of charge. Everything is set up to help families and friends spend quality time together. Please message host with special requests.
Modern Farmhouse Condo steps from Lake | Jacuzzi
This modern farmhouse style condo is perfectly located just steps from the lake. The front deck offers gorgeous sunset views of the mountains. A short path from the private back deck leads straight to the heated pool and jacuzzi. Thoughtfully designed interior has eye-catching details including floating wood shelves, cedar beams, a river-rock fireplace, and historical Big Bear photos. Adjustable wall lighting creates a perfect relaxing atmosphere. Kayak and paddleboard rental is next door.

Quaint Farmhouse Getaway - Entire Place (Condo)
Enjoy your stay at this farmhouse style 2 bed 2 bath condo! Extremely clean and well maintained, this space is conveniently located a few minutes from the downtown area, Central Plaza, and walking distance from Riverside's well known Mt. Rubidoux Hike; a 1-mile trek that gives a stunning view of the entire city. There is a park across the street that kids love which also has a nice walking path. The neighborhood is very quiet and peaceful. Access to Wifi, washer/dryer, 2 car garage, and more!

SOUTH REDLANDS CHARMING COTTAGE WITH POOL!
Located in beautiful South Redlands near Prospect Park, this detached cottage has its own private and inviting fenced backyard, nicely landscaped with comfortable patio furniture. Inside you will find separate living and bedroom spaces, charming decor, Heating/A/C, Cable TV, WIFI, kitchenette with microwave, Keurig coffee maker and compact refrigerator, fine linens, comfortable queen sized bed, and newer bathroom. Conveniently located near Downtown Redlands, University of Redlands and ESRI!

Peaceful Private Retreat In The Heart Of Town
Meticulously designer-renovated modern home “The Nest “is surrounded by mature tree and nestled beneath the mountains in South Redlands. Whether you’re looking to spend time with loved ones, vacationing or work remotely in a peaceful environment, this is the place to do it all. Relax by the fireplace while light pours in from the wall of windows, with pleasant sparkling pool, grill and chill on the backyard, and explore nature right outside your front door. Conveniently located in Redlands!

The Blue Cabin
Relax at this unique, tranquil, and comfortable mini home in our backyard. Surrounded by a beautiful garden with a wide variety of succulents and a relaxing pool. With a space to enjoy reading or listening to music. Equipped with microwave, Keurig coffee machine, mini refrigerator, toaster, blender, washer/dryer, and tableware. The mini home has air conditioning and heating system for comfort and a smart TV. No parties allowed.(SPACE EQUIPPED ONLY FOR 2-3 PEOPLE *no more than 3 fit*)

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.

Norco country private entrance
~Dog friendly - No cats ~Gated acre of property with secure parking. ~Extra large bedroom w/private entrance & full Bathroom. Mini fridge/microwave, for reheating. No kitchen or sink ; no cooking in bedroom. ~No smoking anywhere on property. ~outdoor shared space ~ porch, back yard covered patios, pool, spa, large grass area. ~registered guest only. No visitors. 1941 farmhouse complete remodel. A lot of dirt & animals. If you want a city experience this is not for you

Serene Escape Tiny House Living/pool/near Yaamava
We are located close to dining , hiking, shopping, movie theaters, National Orange Show Event Center (NOS Events), Yaamava Resort and Casino, some nightlife, Redlands University and Loma Linda University. You’ll love my place because of the location, the people, the ambiance, the outdoors space, and the neighborhood. Our place is good for couples, solo adventurers, and business travelers. Perfect little getaway! I have another listing-click on my photo to view.

Claremont Guesthouse 5 Min to Colleges|Non-Smokers
Enjoy the Mediterranean patio for a morning coffee or a sunset evening glass of wine. Explore Claremont and its surroundings. You'll be 5-7 minutes from the Claremont Village and the Claremont Colleges, close to hiking trails and the mountains. Claremont Short Term Rental Permit Number: STR-001 (Claremont STR permit requires collection of 10% transient occupancy tax, which is already included in the total you see)

Casa de Agua Retreat
Modern Hacienda themed house in a quiet neighborhood with low traffic. Cozy and with a pool so families and friends can have fun, connect, and create life-long memories. Conveniently located near some hot spots like; downtown Riverside 2.5 miles, freeway 1 mile, and UCR is 3 miles, Ontario airport is 17 miles, and if you like tennis, there are free open courts at a 5-minute walk.
Popular amenities for Highland rentals with a pool
House rentals with a pool

Shalimar Serenity|Pool|Hot Tub|Fun Games|Ping Pong

Mountaintop Pool Paradise | Mins to NOS Center

Perfect home for large groups! Newly remodeled

Valle de Guadalupe Escape gem

Modernized condo in the Arrowhead Village with spa

Golden Hour Oasis~MovieTheater~Hot Tub

The Maze House—Pool & Theatre Room

Scenic views pool/spa/bbq/karaoke/games No Parties
Apartment rentals with a pool

Charming Condo W/ Pool, Hot Tub & Pet Friendly

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

Lakefront Walk 2 Village w/ Dock Access & Pets

Next to Lake. Close to Village and Slopes. BBQ.

Rch Cucamonga Luxury Cozy Modern Style w/Pool

Amazing New Condo (Victoria Garden/Ontario Mills)

The Adler's Nest - Lakefront with Pool, Spa, and S

The best memories are made here.
Other holiday rentals with a pool

Relaxing Poolside Getaway Guest House

All-in-One Pool Guest House w Private Backyard!

Pool Home w/ Game Room near NOS Center

Summit Solace, Steps to Snow Summit w/ Hot tub

Golden - 1bd Condo

SoCal Base Camp

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

Honey Bee Hideaway
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £66 | £78 | £79 | £88 | £79 | £88 | £83 | £81 | £80 | £66 | £66 | £65 |
| 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 holiday rentals with a pool in Highland

Total holiday rentals
Explore 20 holiday rentals in Highland

Nightly prices starting at
Highland holiday rentals start at £30 per night before taxes and fees

Verified guest reviews
Over 1,230 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wifi availability
20 of Highland holiday rentals include wifi access

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

4.9 Average rating
Highland stays are highly rated by guests – averaging 4.9 out of 5!
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- Disneyland Park
- Big Bear Mountain Resort
- Knott’S Berry Farm
- Bear Mountain Ski Resort
- Snow Summit
- Disney California Adventure Park
- Pechanga Resort Casino
- Honda Center
- Angel Stadium of Anaheim
- Mountain High
- Alpine Slide at Magic Mountain
- Palm Springs Aerial Tramway
- Mesquite Golf & Country Club
- Indian Canyons
- Tahquitz Creek Golf Resort
- Dos Lagos Golf Course
- Big Bear Alpine Zoo
- Chino Hills State Park
- Big Morongo Canyon Preserve
- Mt. Baldy Resort
- Snow Valley Mountain Resort
- Whitewater Preserve
- Palm Springs Air Museum
- Knott's Soak City U.S.A.




