Vacation rentals with a pool in Santee

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Top-rated rentals with a pool in Santee

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favourite

Guesthouse in Escondido

4.92 out of 5 average rating, 639 reviews

Hilltop cabin retreat with lake & mountain views

Rustic hilltop cabin overlooking Lake Hodges. Surrounded by open canyons & mountains, you will feel like you're a million miles away from everything as you take in the views from the cabin, deck or the outside shower, swim in the saltwater pool, or relax by the fire bowl. A short walk to lake with boating, fishing & miles of hiking/mountain biking trails. Property offers swimming pool, fire bowl, and shaded arbor. SD Zoo Safari Park, wineries, breweries, & ocean beaches all within easy reach.

Jan. 31 – Feb. 7

$244 CAD per night

Guest favourite

Guest suite in San Diego

4.84 out of 5 average rating, 277 reviews

Amazing View, Pool, 1BR w/ full kitchen & sofa bed

Recent major renovations include a full-kitchen. Separate apartment within a house (the 1st floor of a 3-story house; this is not a space for partying as we live upstairs and you will hear footsteps). Quiet hours at 10pm. Private entrance. 1 bedroom w/queen, 1 queen sleeper-sofa, full bath, full kitchen, wonderful view of hot air balloons at sunset. Hot tub is not available for guests. LGBT-friendly. Multicultural Ally. 24-hour check-in. 7 m. to the beach, 20 m to downtown. No smoking, no pets.

Oct. 11 – 18

$190 CAD per night

Guest favourite

Guesthouse in Poway

4.99 out of 5 average rating, 117 reviews

⭐️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

Guest favourite

Farm stay in Lakeside, California, US

4.96 out of 5 average rating, 287 reviews

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.

Oct. 11 – 18

$365 CAD per night

Guest favourite

Guesthouse in San Diego

4.93 out of 5 average rating, 122 reviews

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.

Sep. 5 – 12

$195 CAD per night

Superhost

Guest suite in La Mesa, California, US

4.94 out of 5 average rating, 162 reviews

Hacienda de Las Campanas

Stay in classic, historic California Hacienda style! A complete, self-contained apartment--your casita--within our beautiful, historic Monterey Spanish Revival hacienda home, situated on a half acre. The apartment has a separate, private entrance and includes a sunlit living/dining room opening on to a large swimming pool; a small kitchenette; and a private bedroom and bathroom down your own hallway. The suite is tastefully furnished consistently with the historic Spanish architecture.

Mar. 8 – 15

$271 CAD per night

Guest favourite

Camper/RV in La Mesa

4.97 out of 5 average rating, 180 reviews

“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.

May 16 – 23

$135 CAD per night

Guest favourite

Guesthouse in El Cajon

4.93 out of 5 average rating, 165 reviews

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.

Oct. 16 – 23

$254 CAD per night

Guest favourite

Farm stay in Ramona

4.95 out of 5 average rating, 347 reviews

Cozy, country farmstay w/fresh eggs & animals!

This space, formally a working barn, was remodeled into an amazing, one-bedroom home, meant to be enjoyed by couples and small families looking to make incredible memories. Every detail was thoughtfully crafted to create an experience that caters to those deserving of a destination escape in a country-like setting, yet close enough to all of San Diego's local attractions. There is so much to do nearby this winter..ice skating, shopping, wine/craft beer.

May 15 – 22

$240 CAD per night

Guest favourite

Guest suite in La Mesa, California, US

4.9 out of 5 average rating, 172 reviews

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.

Oct. 10 – 17

$203 CAD per night

Guest favourite

Guest suite in La Mesa

4.89 out of 5 average rating, 142 reviews

Mountain Retreat Ocean View-Great for Staycation

Located on the historic Mount Helix. High above the valley below, with an exquisite view of the ocean evening sunsets through the beautiful valley. Beautiful Mountain Retreat with ocean view. Private entrance. Full kitchen (toaster oven only). Access to shared pool. Beautiful sunsets. Newly remodeled. (NO SMOKING) Your Co-host lives upstairs and is available for you if needed! The backyard is a shared area.

Sep. 6 – 13

$283 CAD per night

Guest favourite

Guesthouse in La Mesa, California, US

4.9 out of 5 average rating, 142 reviews

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.

Jun. 1 – 8

$205 CAD per night