
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.

Ski-In/Ski-Out Remodeled Property at Snow Summit
Experience the best of Big Bear with this remodeled townhouse, only a two-minute walk from the top snowboarding destination in town! Located adjacent to Snow Summit Ski Resort, you can enjoy skiing/snowboarding in the winter and mountain biking once summer arrives. Fantastic amenities including private parking, air conditioning, a rare gem in Big Bear. Community amenities, such as barbecue area, sauna and a seasonal pool to make your stay more enjoyable. The ultimate ski and ski out experience.

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.

Tranquil Retreat | Private Guest Quarters + Pool
Escape to our tranquil Guest Quarters retreat, nestled in the serene rural surroundings of Jurupa Valley. With its own private entrance and seamless self check-in, this peaceful retreat offers a large, completely private, lush outdoor patio space, with a shared pool/backyard space. The estate is situated on a secluded cul-de-sac 10 minutes from Ontario Int. Airport, UCR, and CBU, with easy freeway access. In-N-Out Burger, Raising Cane's, Chipotle, & Aldi’s Grocery walking distance away! 🏳️🌈

Boulder Bay cabin steps to the lake & hot tub
Upgraded condo just steps from Boulder Bay Park, the lake, hiking trails, fishing & the main boulevard. Kayak & paddle board rentals conveniently located next door. A convenience market is just around the corner to help with any last minute needs. The Village, full of shops & restaurants, is just down the road a bit. You are only a few minutes from all major snow play & skiing on the mountain. Don't feel like driving? Hop on the Mountain Transit Shuttle with a stop located near the parking lot.

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.
Popular amenities for Highland rentals with a pool
House rentals with a pool

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

Pool Home w/ Game Room near NOS Center

Charming 5 bed, 3 bath home with pool

Modernized condo in the Arrowhead Village with spa

Valley of Guadalupe Escape gem

The Maze House—Pool & Theatre Room

Golden Hour Oasis~MovieTheater~Hot Tub

SoCal’s Pet Friendly Luxury Family Pool spa Resort
Apartment rentals with a pool

Charming Condo W/ Pool, Hot Tub & Pet Friendly

Lakefront Walk 2 Village w/ Dock Access & Pets

The Cozy Cottage Condo - Jacuzzi/3mi to slopes

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

Rch Cucamonga Luxury Cozy Modern Style w/Pool

Amazing New Condo (Victoria Garden/Ontario Mills)

Lakeside condo

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

Beautiful 3 Bedroom with Pool and Jacuzzi

Relaxing Poolside Getaway Guest House

Feel the Tropics: Stunning Getway Free Spa Heating

Exquisite Comfort Stay

SoCal Base Camp

Cheerful 5 Room Home w/ Salt Water Pool & Hot Tub

Pine Rose Cottage, Pine Rose

Carlton Serenity |Pool|Hot Tub|Games|Pets Friendly
When is the best time to visit Highland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $115 SGD | $136 SGD | $137 SGD | $153 SGD | $137 SGD | $153 SGD | $145 SGD | $141 SGD | $140 SGD | $115 SGD | $115 SGD | $114 SGD |
| 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 $52 SGD 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
- Bear Mountain Ski Resort
- Knott’S Berry Farm
- Snow Summit
- Pechanga Resort Casino
- Disney California Adventure Park
- Honda Center
- Angel Stadium of Anaheim
- Alpine Slide at Magic Mountain
- Indian Canyons
- Palm Springs Aerial Tramway
- Mesquite Golf & Country Club
- Mountain High
- Tahquitz Creek Golf Resort
- Dos Lagos Golf Course
- Big Bear Alpine Zoo
- Indian Canyons Golf Resort
- Chino Hills State Park
- Big Morongo Canyon Preserve
- Whitewater Preserve
- Snow Valley Mountain Resort
- Mt. Baldy Resort
- Palm Springs Air Museum




