Holiday rentals with a pool in El Cajon

Guest house in Poway

⭐️Garden studio guesthouse, resort living with pool

Come relax in this unique and tranquil pet-friendly garden getaway located in a gated community near the heart of Rancho Bernardo and bordering San Diego’s top-rated Maderas Golf Club. Steps away from some of the best hiking trails in San Diego County Tempur-Pedic Queen, full-size couch and crib. Fully appointed kitchenette. Outdoor cooking area (Weber/Green Egg grills). Pool and spa with child-safe fence. Outdoor sitting areas with wood and gas fireplaces. 550 sqft, 1+ acre fenced yard

Farm stay in Lakeside, California, US

The Outside Inn at The Tipsy Goat Ranch

Nestled near Iron Mountain, a popular hiking destination, and less than 16 miles from San Diego's pristine beaches and local attractions, enjoy all SD has to offer in a one-of-kind farm-to-beach experience. Immerse yourself in a rarely seen side of San Diego you won't find anywhere else. Based on adventure, wrapped in luxury, a deep love for nature and the creatures it inhabits (mini goats, alpacas, babydoll sheep, lop bunnies, and chickens), it'll be a tranquil getaway you'll never forget.

3–10 Jan

Guest house in San Diego, California, US

Modern Guest House with pool, steps to SDSU

Casita within easy walking distance to SDSU, Viejas Arena, Cal Coast Credit Union Open Air Theatre, shops, and transit. Casita includes Tempur-Pedic Queen bed and a love seat which converts to twin bed. Enjoy the peaceful canyon side garden, firetpit and pool, or relax in the hammock. Panoramic door opens completely to let in our wonderful weather and the view. Note: Pool is heated with a solar cover, comfy for swimming APR-OCT. Max 3 guests, no children/infants due to unfenced pool.

8–15 Sep

Villa in El Cajon

Enchanted Paradise! ♨ Pool+Spa+Outdoor Kitchen ☀

Brand New Property! Massive garden of Eden style resort home with sprawling outdoor entertainment area and spacious open concept inside, perfect for large families with kids and responsible adults. Updated top to bottom with all new outdoor and indoor furniture, modern upgrades in all bedrooms and common areas. Centrally located and 20 minutes from the beach and all of SD's top attractions! 8 person hot tub, sparkling gas heated saltwater pool and new outdoor kitchen. Don't miss out!

4–11 Sep

Campervan/Motorhome in La Mesa

“Pineapple Express”

Aloha! If your looking for a relaxing & mellow vibe, We invite you to stay the night in our cozy 1948 16ft Travelo travel trailer, “The Pineapple Express” Enjoy your private pool and hot tub, behold a beautiful San Diego sunset from the hillside deck or pull up a stool at the Tiki Bar for your morning coffee. We now have an outdoor gas grill, hot water pitcher, microwave, mini fridge and utility sink for food prep! Hablamos español Deaf friendly 🏳️‍🌈. Alycen ASL fluent.

24 Jun – 1 Jul

Guest house in El Cajon

San Diego Bohemian Poolside Lounge @ Eden East

Retreat to a private 1 bedroom poolside apartment. Not just a place to stay, but a retreat to recharge mind, body & spirit and forget everything currently happening on the "outside". Perfect escape for locals and tourists alike...ideal for spending some time with friends and loved ones soaking up the chill vibes of our little hidden gem in the East County of San Diego. Strong WIFI. Shared pool. By reserving, we assume you've read entire ad and agree to all house rules.

16–23 Apr

Guest suite in La Mesa, California, US

Charming Suite in Historic Home

Stay in your own apartment on the second level of our 1907 Landmark Historic home in the Village of La Mesa. Escape to the backyard retreat with a private swimming pool and spa, barbecue grill, and outside dining. Walk to shops and restaurants, and ride the trolley to downtown San Diego or Tijuana. There is convenient free parking on the street and easy drive to mountain, desert, and ocean adventures and major tourist attractions.

11–18 Oct

Guest house in La Mesa, California, US

La Cabana

Perfect getaway for the wandering individual, couple, or young family. This rustic casita is surrounded by beautiful mountain and ocean views! Enjoy swimming in the pool, stargazing, lounging, or casual day trips around San Diego (All the amenities are shared with the main house) . The casita has one queen bed and a sofa bed, small kitchenette. Plenty of parking in driveway. Please read entire listing for details.

10–17 May

Home in El Cajon

Beautiful 3,000 Sq Ft Tropical Oasis

Beautiful 4 Bedroom, 2 1/2 Bath Family Home Located in Tranquil Fletcher Hills. This 3,000 sq. ft. Home is Perfect for large families who wish to Relax in a Peaceful Setting. 24-hour self check-in keypad after 4pm and check-out at 11AM. Host does not allow parties/events. This is NOT a Party House! This home is located in a quiet residential neighborhood, Guests who do not respect this will be asked to leave.

27 Sep – 4 Oct