Guesthouse holiday rentals in Poway

Charming Guest House in Poway - Kid friendly

Welcome to our cozy and private 1 bed/1 bath guest house, nestled in the heart of Poway. Our space offers a queen-sized bed, spacious bathroom with a walk-in shower, a living area and kitchen with large windows providing great natural lights. The kitchenette is well-equipped for you to channel your inner chef and comes with a fully stocked coffee/tea station. Stay connected with high-speed Wi-Fi and unwind with Smart TV entertainment. Enjoy the luxury of a private entrance for added privacy.

Family · Location · Parking

Posh Guest House ~ Pool, Spa, Pickleball & Tennis

Stunning Guest House with Pickleball/Tennis and Pool/Spa~ Serene, upscale guest house designed for comfort and fun. Nestled in a prime Rancho Santa Fe location, this retreat offers stunning views, resort style amenities and easy access to the best of Southern CA. Ultra comfortable California King Bed Fully equipped Chefs Kitchen Smart TV with Cable & WiFi Designated work area with garden views Expansive Outdoor Space – perfect for dining, lounging, soaking in the peaceful surroundings and sun

Family · Location · Indoor spaces

Private GuestHouse with Kitchen,Bath,Dryer, Washer

Our 1b1b guesthouse(485 sqft)features a private entrance, full bathroom, brand-new mini split with both heating and cooling, and an in-unit washer and dryer. The full kitchen is equipped for all your cooking needs, and you’ll find a coffee and tea station ready to help you start your mornings right. Enjoy high-speed WiFi to stay connected and a Smart TV for relaxing evenings. Whether you're here to work or unwind, you'll love the comfort, privacy, and peaceful vibe of our quiet neighborhood.

Value · Family · Walkability

Cozy Spanish Casita w/ Mountain View in Ramona

Perfect getaway for wine lovers and hikers in this serene spanish ranch style casita with beautiful orchard & mountain views! Enjoy visiting Ramona's local wineries, hiking Mt. Woodson or Iron Mountain, swimming in the pool, stargazing, golfing, a day trip to Julian, or San Diego Wild Animal Park. The Casita has one private bedroom with a king bed and a cozy upstairs loft with a full bed located in a second room. Casita sits on top of a hill with the main house. Please read entire listing.

Location · Value · Breakfast

Vacation Paradise-Heated Pool+Hot Tub+FirePit+EV

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Location · Value · Accuracy

Adorable Hawaiian themed Guest House

Enjoy the quaintness of country living just 35 miles from San Diego. Ramona is the heart of San Diego's wine country; home to many boutique winery’s and vineyards. Our guesthouse will provide the perfect space to unwind and relax after sightseeing, beaching, or visiting the world famous San Diego zoo. Guest home has one bedroom with king bed, separate great room/kitchenette w/hide-a bed and a couch. Fire pit, large grassy play area with zip-line and a pool to cool off in.

Family · Value · Breakfast

Private 2 bedroom apt in new craftsman ranch!

This 2 bedroom apartment has two queen beds, a full kitchen and laundry! With beautiful views all around, it is very close to the San Diego Safari Park, wine tasting (walking distance to 4 wineries) and several wedding venues. You’ll love the privacy and spaciousness, the fresh fruit and farm animals, and the tranquility of the place, while being only 4.5 miles off the freeway. This space is excellent for couples, business travelers, small groups, solo adventurers, and families.

Value · Location · Getting around

Hilltop Horizon Haven San Diego

Welcome to our San Diego retreat! Our two-bedroom haven offers a blend of tranquility and convenience. Enjoy stunning sunrise views and cozy comfort. Explore the vibrant neighborhood and major shopping hubs like Walmart, Costco, Target, Aldi, and a Mediterranean store—all nearby. Indulge in relaxation and accessibility, where nature meets city living. 20-25 Min: SD Safari Park Torrey Pines State Beach Old Town BalboaPark 30-40 Min La Jolla Shores Beach LegoLand

Value · Family · Sleep quality

Private Retreat With Amazing View

Escape to our private guesthouse in Poway, “The City in the Country,” where stunning canyon views create the perfect backdrop for your stay. Nestled on a secluded hillside, this cozy retreat is just minutes from scenic hiking trails, Lake Poway, and the famous Potato Chip Rock. Enjoy nearby dining, shopping, and parks, with San Diego’s top attractions only 25–30 miles away. Relax, explore, and experience the best of nature and city life!

Value · Location · Heating

Casita in the Vineyard. Privacy & Beauty combine.

Enjoy our newly updated resort-style Casita with hot tub, propane fire pit, and shaded pagoda. This tranquil and private getaway has a full kitchen, bath and laundry facilities and is only 7 minutes from the San Diego Safari Park. Numerous vineyards in the popular “Highland Valley Wine Country”, some with live music and food, are within a 2 mile radius. Only 4 miles from Highway 15. See the stars, hear nature and relax.

Value · Location · Biking

Family & Pet-Friendly San Diego Guest Suite

Welcome to our cozy Mira Mesa guesthouse in San Diego! This private 600 sq ft suite is perfect for families, friends, and pet-friendly stays. Conveniently located near Freeway 15, you’re just 15–20 minutes from beaches, downtown, and top San Diego attractions. Planning a longer stay or traveling during flexible dates? Feel free to message us—we may be able to offer a special rate depending on availability.

Family · Location · Long stay

Relaxing 2-Bedroom Guest House Immersed in Nature

Peaceful 2-bedroom guesthouse in Poway, near San Diego. Sleeps 4 with 2 queen bedrooms, full kitchen, fast Wi-Fi, dedicated workspace, washer/dryer, Roku TV, free parking, and self check-in. Relax on the deck, enjoy garden and park views, or walk to parks, restaurants, the farmers market, and Old Poway Park. Great for families, couples, visiting relatives, and remote workers.

Value · Location · Check-in