Holiday rentals with outdoor seating in Dana Point

Summit Cabin on the Rocks

Perched atop a miniature mountain with expansive views extending from the Pacific Ocean to the peak of San Gorgonio (highest mountain in SoCal), this concept cabin is like a disintegrated house spread across about a 1 acre area. The interior consists of a lofted queen size bed with a large skylight for stargazing, as well as a lounge space with an oversized leather sofa. The highlight of the cabin is the outdoor space. It features a cabana with a day-bed, bean bag, swing chairs, a kitchen, etc

Outdoor spaces · Value · Quiet

Casa Grotto, Romantic Stone Cottage w/ Ocean Views

Perched 800ft above sea level with panoramic ocean views from La Jolla to Catalina Island, Casa Grotto is a unique stone studio carved into the ocean view hillside of Lake San Marcos . Built in the 80's using stone from the mountain, the space was updated in 2025 with modern touches—featuring a rock shower, full kitchen, AC, and gym. Just 20 minutes from the beach, it’s a dreamy escape for surfers, hikers, and couples looking for a romantic getaway. No pets—our two friendly boxers live on-site

Outdoor spaces · Value · Kitchen

Historic Cottage - Casa Mia

Exceptionally charming cottage by donation: Receptions, Honeymooners, Anniversaries, Birthdays, and Bridal/Baby showers and more! May combine with adjacent cottage and each onsite gathering requires a pre-signed written agreement. Make Casa Mia your destination to celebrate with loved ones in the oldest neighborhood of California, yards from the Mission, River Street Marketplace, the Playhouse, Petting Zoo, train depot, and many fine restaurants and shopping experiences in the heart of town!

Outdoor spaces · Value · Hospitality

Coastal Condo w/Great Amenities, Walkable to Beach

Relax in coastal OC in this bright and modern condo with ample stylish upgrades! Many condos are jam packed with as many beds as possible; this condo is different and is perfectly appointed for 2 couples (2 king bedrooms) or a family. Whether your goal is to walk to the beach (through the prestigious Waldorf Astoria Resort), relax in the pool or 1 of hot tub(s), or visit Dana Point Harbor, Laguna Beach (10min), San Clemente (15min) or Newport Beach (25min), you can do it all here! STR23-0045

Location · Outdoor spaces · Condition

Cottage by the Harbor

This cottage is located in the heart of Dana Point, a beautiful and uncongested beach community! A 5 minute walk finds you at the nearby town center and new downtown area where you can find restaurants, nightclubs and shopping. Down the street is Dana Point Harbor/marina and the famous Doheny Beach surfing and park or get-away to Catalina Island or whale watching! The Cottage is a great pet friendly with enclosed front and rear yards, a great alternative to the over priced resorts.

Location · Outdoor spaces · Amenities

Coastal Studio Apartment, 1.5 miles from beach!

This coastal-getaway is centrally located and perfect for families! It is a 2 mile drive to Doheny beach where you can go whale watching, rent jet skis and kayaks, or learn how to surf. Or head over to the historic town of San Juan Capistrano. Only an 8 minute drive to the Mission San Juan Capistrano. Keep heading south about 5 miles and be sure to spend some time in San Clemente, where the view of the pier never gets old! There are so many family friendy activities for all ages!

Outdoor spaces · Value · Indoor spaces

Castle By The Sea - Dana Point - Permit #16-0537

Castle By The Sea is a highly rated vacation home rental in beautiful Dana Point, CA at the southern terminus of Pacific Coast Hwy. between Los Angeles and San Diego. A mile South of Laguna Beach and close to Mission San Juan Capistrano. It’s close to the beach has great views, dining, parks, arts and festivals, the harbor, resorts and many wedding venues. My place is good for couples, business travel, and families. Many stay for weddings held at the many close wedding venues.

Outdoor spaces · Location · Cleanliness

Betty's Beach Bungalow-Pet Friendly! STR16-0438

Enjoy our cute & cozy 1 bedroom beach cottage a short walk to the Beach. Relax in your fenced front yard with gas grill, 2 Adirondack chairs & glider and basketball hoop. Small dogs welcome. 2 blocks to Pines Park. 5 min to San Clemente, Dana Pt & San Juan Capistrano. IF BOOKED OR NEED MORE ROOM - SEE OUR SECOND COTTAGE UPSTAIRS, THIS COTTAGE IS COMPLETELY SEPARATE FROM ANY OTHER LIVING QUARTERS AND CAN BE FOUND UNDER "BETTY'S BEACH VILLA" - . Dana Point Permit #STR16-0438

Outdoor spaces · Location · Long stay

Modern New Home •Quiet Escape with Panoramic Views

Discover a modern retreat set on Bonsall’s rolling hills, offering sweeping views, glowing city lights, and vivid fall/winter sunsets. This newly built open-concept home features floor-to-ceiling windows and a spacious deck ideal for taking in the breeze, sunbathing, or stargazing. Private, peaceful, and thoughtfully designed for families and friends. Secluded in feel yet minutes from freeways, Oceanside beaches, dining, shops, wineries, wedding venues, and Frontwave Arena.

Value · Location · Family

Whale Rock House (1st FL) - 10 MAX

STR Permit #02-7170 | Minimum Age: 25 🌊 Beachfront Retro Escape | Sleeps Groups 2 -10| Capistrano Beach Dana Point Step into a true Southern California beachfront experience—where vintage charm meets unbeatable oceanfront access. This one-of-a-kind retreat sits directly on the sand in Capistrano Beach, delivering the kind of stay guests remember for years. Designed with a nostalgic 1970s beach vibe, the home blends retro character, comfort, and wide-open ocean views.

Outdoor spaces · Location · Getting around

Starfish | SC Pier, Ocean Views, Parking & AC

Welcome to your perfect coastal getaway! This top-floor retreat offers unbeatable pier & ocean views with breathtaking sunsets from your sofa, dining area or lounging deck. The airy open floor plan creates a relaxed coastal vibe, while the spacious deck is perfect for a morning cup of coffee or an evening glass of wine. Designed for coastal living, this beach retreat is the perfect place to relax & soak in the best of San Clemente. Ask about our other units.

Location · Value · Parks

Modern & Contemporary LARGE 2 bed, 2 bath bungalow

Great 2 bedroom 2 bath, beach cottage with a modern contemporary flare. Open concept to allow a spacious feel with all the amenities to feel at home. This unit was completely gutted and redone, so any reviews prior to May 2022 were about the older unit prior to the major remodel. The City of Newport Beach has strict noise regulations and parties and large gatherings are not allowed at this property. City of Newport Beach Short Term Rental Permit #SLP13923

Value · Location · Hiking