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Holiday houses in Oak Park

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Top-rated holiday rentals in Oak Park

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A spacious living area features a large beige sofa, complemented by a cozy armchair and a stylish coffee table. A stone fireplace is centered against a textured wall, with a mounted television above. Natural light floods in through tall windows, enhancing the inviting atmosphere.
Home in Thousand Oaks
4.98 out of 5 average rating, 172 reviews

Modern Family Farmhouse pool&spa, treehouse, bocce

Bright, beautiful home full of activities including; kids tree house, bocce ball court, golf putting green and fruit trees in season. Featuring, pool, jacuzzi, two king bed master bedroom suites, kids room, patio furniture, fire pit, BBQ, and farm table for outdoor dining. Close to great hiking trails and Malibu Beach is only 25 minutes away. Come enjoy fruit and the fun at The Orchard House. Have fun with the whole family at this stylish home. Note: Heated pool accommodation is $100-$75 a day.

Top Guest favourite
A spacious living area is bathed in natural light, featuring large windows that frame scenic views of the surrounding hills. A comfortable sectional sofa centers the space, complemented by a dining table nearby. Soft drapes add a touch of warmth to the modern decor.
Home in Thousand Oaks
4.97 out of 5 average rating, 106 reviews

808 Retreat:Casa De Luna, Shops, Pano View, Hiking

Breathtaking Sunsets: Stunning views nightly from the upstairs patio. Total Comfort: High-quality beds + 600TC cotton sheets, jacuzzi soaking tub Nature Lover's: Ideal for hiking & mountain biking in surrounding hills or just relax! Fully equipped to cook! Coffee corner w/ K-cup, Drip, French press. BBQ with views! Great for kids also! High chair, crib, games avail Privacy & Convenience: Secluded, yet 5 mins from shops & restaurants. Tranquil: Perfect for meditation, creativity, & finding peace

Top Guest favourite
The modern retreat showcases a long, low-slung structure with large windows reflecting warm light. Surrounded by lush greenery, the exterior features a spacious lawn and elegant outdoor seating arrangements, set against the backdrop of rolling hills and a dusky sky.
Home in Malibu
5.0 out of 5 average rating, 143 reviews

Encinal Mountain Malibu - Gated Retreat EV charger

Located in Malibu, and unaffected by fires. Encinal Mountain is a private gated retreat featuring two King bedrooms, central A/C, spa bathrooms, and luxurious soaking tub. Fully fenced yard is safe for pets and children. Located 2 minutes up from the Pacific Coast Hwy and El Matador State Beach sits an architectural gem on 5 acres, designed by architects Buff & Hensman. Fully renovated down to the studs it has been restored to retain the midcentury history, yet upgraded with modern luxuries.

Top Guest favourite
A bedroom is shown with a spacious bed featuring decorative pillows and a textured white coverlet. Complementary accents are present, including a patterned rug, a side table, and wall sconces. Natural light filters through patterned curtains, illuminating the inviting decor.
Home in Thousand Oaks
4.99 out of 5 average rating, 117 reviews

New Remodel Vintage Curated Canyon House w/Views

Nestled at the base of the Santa Monica Mountains, this home has all the creature comforts you’ll need for your short or long stay. Artfully curated furnishings and decor. On the compact side at 1365 square feet you’ll find plenty of space to cook in the beautiful new kitchen, dine & cozy up in the family room or get some work done in the office with the hillside views. The beautiful deck off the two bedrooms is a perfect spot to wind down at the end of the day. Available for extended stays.

Top Guest favourite
A serene bedroom features a spacious bed with a blue-striped duvet, positioned in front of a vibrant wall art piece. Natural light filters in through a window, complemented by light-colored walls and a wooden dresser. An air conditioning unit is discreetly mounted above.
Guest suite in Thousand Oaks
4.98 out of 5 average rating, 405 reviews

Malibu Room-Remodeled Entire Place-Quiet&Private

Entire place! not attached to the house except for a wall that is filled with insulation & sound proof drywall. Very quiet & a 1/2 mile from freeway or to CLU. Private entry, a patio, remodeled bedroom & bath. Cal King bed, desk for laptop, Kcup coffee, mini fridge, microwave and HD TV w/ RoKu 650mb WifI perfect for a business traveler or couple on vacation. (w/ a baby or toddler,) A toddler mattress is available on request. Free (40 amp 240volts) for your electric car 9pm-4pm off peak house

Top Guest favourite
The kitchen features dark cabinetry and modern appliances, including a stainless-steel refrigerator, oven, and dishwasher. A dual sink is positioned beside a window, while a dining table with light-colored chairs is visible in the foreground, offering a welcoming space for meals.
Apartment in Thousand Oaks
5.0 out of 5 average rating, 16 reviews

Centrally located, 2 King Bds, Gated community

Designed for rest & recovery, but also ideal for family visits, training for athletes, or business stays. Find comfort & peace in this quiet gated 2BD/1BA just 1.8 mi to FSAC, 4.6 mi to CLU & 5 mi to Proactive Sports. Features a plush bed + sofa couch, full kitchen w/ cooking essentials, fast WiFi & Smart TV. Guests really appreciate the private setting, easy access to health clinics, CLU campus & sports training facilities, and the feeling of a true home away from home during their stay.

Guest favourite
Townhouse in Oak Park
5.0 out of 5 average rating, 12 reviews

Serene Modern Farmhouse: Fire Pit & Fast Wi-Fi

Escape to this serene, upgraded 3-bed sanctuary in quiet Oak Park. Features solid wood flooring, stylish furniture, and a custom stone fireplace with a 150-year-old wood mantle. The Primary Suite offers a luxury hotel-grade mattress for ultimate rest and recovery. NEW: Private patio with a fire pit, tiered fountain, and ambient lighting. Includes 100+ Mbps Wi-Fi, in-unit W/D, community pool/jacuzzi, and 2 Smart TVs. Steps from elite hiking trails and dining. A peaceful, high-end home base.

Top Guest favourite
Home in Oak Park
5.0 out of 5 average rating, 35 reviews

Mountain View Home in Oak Park

Welcome to this fully remodeled bright home with mountain view! Located in a very quiet and peaceful neighborhood, this family-friendly home boasts three bedrooms with one king bed, one queen bed, one twin over full bunk bed and one single twin bed, each fitted with comfortable new mattresses and beddings. Fun-filling backyard with mini golf course and fabulous mountain view. Close to hiking trails. Short distance drive to Universal Studios Hollywood, UCLA, Los Angeles and Malibu beach.

Guest favourite
The living room features a large leather couch accompanied by two cozy armchairs. A round wooden coffee table sits in the center. Natural light enters through a window adorned with woven shades, while a potted plant adds a touch of greenery.
Guesthouse in Thousand Oaks
4.95 out of 5 average rating, 133 reviews

Private Stay•2/1•King Bed•Central•WD•30 mins to LA

Discover a designer 2 bed/1 bath, 750 sqft getaway where style meets sustainability. Every corner is intentionally curated with polished concrete floors, artisan stoneware, warm salt lamps, and green living essentials. The space feels light, open, and elevated—stocked with everything to make your stay effortless. A perfect hub for traveling professionals or families who want to explore Malibu’s beaches and Los Angeles highlights, while enjoying more space and value outside the city.

Guest favourite
An inviting living area is showcased, featuring a light gray sectional couch and a round wooden coffee table. A textured blue rug anchors the space, while a tall plant adds greenery. A fireplace and built-in shelves are visible in the background, enhancing the bright ambiance.
Home in Thousand Oaks
4.96 out of 5 average rating, 119 reviews

Rose Garden Home, Thousand Oaks

The Rose Garden House, situated in Thousand Oaks on the border of Los Angeles and Ventura counties, is conveniently located near the 101 and PCH. It's an ideal stop for a group road trip through beautiful Southern California. It also provides proximity to serene hiking trails, golf courses, and horse riding clubs, ensuring a balanced blend of convenience and tranquility for your stay. There are Tesla superchargers and EV charging stations 5-7 min driving distances.

Top Guest favourite
Double French doors open to an inviting interior, revealing a spacious living area complemented by wooden ceiling beams and modern decor. Natural light fills the room, enhancing the cozy atmosphere with a plush rug, stylized furniture, and a vibrant artwork accenting the wall.
Guest suite in Thousand Oaks
4.98 out of 5 average rating, 203 reviews

Casa Rancho El Segundo - No Cleaning Fees

No Cleaning Fees – Pets Welcome (Just Ask First!) Escape to our peaceful guest house in Thousand Oaks—your cozy ranch getaway with private entrance, parking, and a fenced side yard perfect for BBQs and evenings by the fire pit. Meet Larry the llama, Bob the alpaca, and their furry friends! Take the bikes for a neighborhood spin or bring along cut-up carrots and apples—they’ll love the treat. Book now and enjoy comfort, charm, and a sprinkle of countryside magic!

Guest favourite
The exterior of the mid-century modern home is showcased at dusk, highlighting a pool in the foreground. A dining set sits beside the pool, with large windows revealing the interior space. Architectural elements include a stone chimney and surrounding greenery.
Home in Thousand Oaks
4.98 out of 5 average rating, 220 reviews

Eichler -Private- Oasis: Pool & Spa Escape

Welcome to the Eichler House in Thousand Oaks! This mid-century modern home features a pool, jacuzzi, fireplace, and built-in BBQ—perfect for entertaining or relaxing. Fully remodeled with modern amenities, it boasts an atrium, open floor plan, and floor-to-ceiling windows for seamless indoor-outdoor living. Nestled on a private lot backing to open space, it offers tranquility while being minutes from hiking trails, shopping, and 30 minutes from the beach.

Popular amenities for Oak Park holiday rentals