
Vacation rentals with a pool in Crestline
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Crestline

Total vacation rentals
Explore 20 vacation rentals in Crestline

Nightly prices starting at
Crestline vacation rentals start at $40 per night before taxes and fees

Verified guest reviews
Over 330 verified reviews to help you choose

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Wi-Fi availability
20 of Crestline vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Crestline rentals
Top-rated rentals with a pool in Crestline
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Adorable Cozy Cottage, base of Beautiful Mountains
This adorable cottage is located at the base of the San Bernardino mountains where you have views of the snow-capped mountains in the colder seasons & views of the beautiful sunsets all year! Close to freeways, malls & hiking trails. Relax poolside as the cottage doors open to the pool & outdoor BBQ & fire pit. It's a great get-away location with all newly remodeled amenities for a comfortable stay. Plenty of parking. NEW onsite DAY SPA services! THIS SPACE IS NOT SUITABLE FOR SMALL CHILDREN

Lakeside Condo with Pool, Hot Tub and Lake View!
You just found the sweetest Lakeside vacation destination!This condo near Boulder Bay has a Lake view spa & lush greenbelts right out your door. Pleasure point Marina is a super easy 5 minute walk where you can rent boats or kayaks. Your family & friends will love gathering on the comfy couches or the big well lit dining room table(perfect for competitive board gamers).Bar seating around kitchen so cooking is fun for everyone! Only a 5 minute drive to the village & 10 minutes to the ski resorts.

Lakeside Condo 2B/2B - Jacuzzi, 3mi to slopes
Enjoy a Santa Fe vibe with hand painted murals and other unique interior details. Play with dimmable lights to create the perfect mood. Gather by the spacious kitchen countertop. Sit by the wood burning fireplace or relax on the balcony facing the pool. Enjoy the heated spa or walk 100 yards to the picturesque Boulder Bay to fish, swim, rent a kayak or a paddle board. The popular Castle Rock trail is a walking distance away. Big Bear Village is only 2miles away and it is 4 miles to the slopes.

Feet Away From Slopes Modern Snow Summit Cabin
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.

Mountain Paradise: Rare Pool, Spa, Fire Pit & BBQ!
Big Bear's BEST dream getaway! Completely private & unheard-of YEAR-ROUND 365 heated pool in a massive backyard, as well as an in-ground trampoline, fire pit, & dual gas/charcoal grills! 3-bed, 2.5-bath home on a 19,000 sq. ft. lot. Tons of entertainment options indoors, as well as a spacious, well-equipped kitchen. This is the height of space and luxury amenities in Big Bear. Relax, indulge, and enjoy outdoor adventures all year. BEAR MTN/SNOW SUMMIT: 5mi. BIG BEAR LAKE: 2mi. DOWNTOWN: 3-5mi.

Log Cab-Inn | Authentic w/ Modern Luxuries & Spa!
Step into this true Log Cabin and feel like you have escaped back to time when life was more simple. Enter the open concept living space with soaring beam ceiling, custom rock fireplace with natural crystal cluster accents, modern, cozy furnishings, including an over-sized down-filled sofa, WiFi, smart TVs, an expansive outdoor deck, soothing hot tub, relaxing hammocks and a game room to keep all entertained. Close to lake and ski recreation, this is the perfect, picturesque relaxation spot.

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.

Casita Condo | Jacuzzi | 3mi to slopes
Completely renovated with a unique style and trendy touches, the Casita Condo features Spanish accents throughout the home, with arches and terra-cotta details. Enjoy the brand new kitchen, with all upgraded appliances, including a wine fridge. Gather around the fireplace and Smart TV where you can access all your favorite streaming services. The two bed/two bath layout is ideal for small families or two couples looking to enjoy a mountain getaway.

Pool, jacuzzi, marina, on the lake! Close to town!
Relax with the whole family at this peaceful Boulder Bay Condo! Steps from the lake, and a short walk to Pleasure Point Marina to jump on a boat or jet ski. The rear deck looks over the lake and a big wilderness area, that is quiet and peaceful. There are TV’s in every room to keep everyone entertained. An open kitchen and living/dining area makes room for the whole crew.Located near the village, ski resorts, hiking trails and off road adventures!

Snow Summit Townhouse Unit 41
LIC VRR-2025-0380. 2 bed, 2 1/2 ba at Snow Summit. 500 ft to the Resort. 2nd floor: Kitchen, living, dining, and 1/2 bath. 1st floor bedrooms, two baths, and laundry. Relax in private spa. Full kitchen. Drip and Keurig coffee. Keurig pods and cone filters included. Gas fireplace, Living rm has 70 in TV with Cable, 200 channels & Apple TV. Master has 55 in TV with cable tv. Community pool is open May through Labor Day.

The Cozy Cottage Condo - Jacuzzi/3mi to slopes
This newly decorated home is the perfect mix of modern, boho, and mountain! Wood and greenery accents remind you that you're on a mountain retreat, while all new furnishings ensure your stay will be cozy and comfortable. Take advantage of the 2 minute walk to the lake! Our home is equipped with high speed internet, a Smart TV, wood-burning fireplace, and a Keurig coffee maker with complementary coffee, tea, and hot cocoa.

Boulder Bay Fun Retreat, Steps to the Lake & SPA
Welcome to your upgraded lake escape—guests love the unbeatable walkable location and easy access to outdoor fun year-round. Perfect for couples or small families. Sleeps 4 | 2 bedrooms | 3 beds | 2 baths Steps to Boulder Bay, lake & park Near hiking, fishing & rentals Short drive to Village shops & dining Minutes to ski resorts & snow play Private deck for relaxing outdoors Close to shuttle stop for easy exploring.
Popular amenities for Crestline rentals with a pool
House rentals with a pool

Hilltop Escape | Heated Pool & Epic Views

Modernized condo in the Arrowhead Village with spa

Scenic views pool/spa/bbq/karaoke/games No Parties

ClosetoSkiing, Lake&Village! Community Pool/Spa!

Mountaintop Pool Paradise | Mins to NOS Center

Valle de Guadalupe Escape gem

Perfect home for large groups! Newly remodeled

Luxury Estate: Pool, Spa, Lake Views & Game Room
Condo rentals with a pool

1BedrmCondo-Kitchen-WiFi-2Bathrms-King+Sofabed GSL

Steps to Lake. Close to Village and Spa. Pool/Spa

Golden Hour | Jacuzzi, Sauna, Pool, Tennis, Gated!

Steps to Boulder Bay & 4.3 miles to Snow Summit

The best memories are made here.

Big Bear 2BR Condo on Beautiful Resort

Lakeside condo

Pines Haven- Close to Marinas and Shopping
Other vacation rentals with a pool

Serene Escape Tiny House Living/pool /near Yaamava

Snow Summit Cabin in Big Bear- 25ft to Resort!

The Cubist Haüs - Modern Mountain Luxury+ Hot Tub

Spacious Family Retreat, Private Pool, Hot Tub

Stylish Cabin Hideaway•EVCharger•Igloo Lounge•Spa

Escape the heat. Pool and hot tub. Pets ok.

Cozy Lakefront Retreat, Views & Fireplace

Wild Bill's @ Pine Rose
When is the best time to visit Crestline?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $94 | $95 | $85 | $97 | $105 | $119 | $96 | $93 | $97 | $110 | $93 | $107 |
| Avg. temp | 46°F | 49°F | 54°F | 59°F | 67°F | 75°F | 82°F | 82°F | 75°F | 64°F | 53°F | 45°F |
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