Vacation rentals with a pool in Lakeside

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lakeside

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

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Guest favorite

Guesthouse in Escondido

4.92 out of 5 average rating, 638 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.

Nov 30 – Dec 7

G$35,051 GYD per night

Guest favorite

Farm stay in Lakeside

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.

Sep 11 – 18

G$58,121 GYD per night

Superhost

Guest suite in La Mesa

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.

Nov 17 – 24

G$37,151 GYD per night

Guest favorite

Tiny home in Escondido

4.94 out of 5 average rating, 225 reviews

Sunrise View Chateauette

Covid-19 vaccinations required. Located in picturesque San Pasqual Valley. Along with host and her husband, 3 friendly dogs & a dozen hens roam on this fully fenced 2 acre hobby farm & mini orchard. Infinity pool & hot tub w/ panoramic views of surrounding mountains. Minutes to historic Old Escondido, San Diego Safari Park, Stone Brewery, boutique wineries, trails and Lake Hodges. Mins to hwy, 30 minutes to San Diego, beaches and Airport. 25 minutes to Temecula wine country.

Oct 3 – 10

G$22,124 GYD per night

Guest favorite

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 is ASL fluent

May 28 – Jun 4

G$18,495 GYD per night

Guest favorite

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.

Apr 11 – 18

G$34,630 GYD per night

Guest favorite

Apartment in Spring Valley

4.86 out of 5 average rating, 139 reviews

Comfy, Cozy Flat With Pool & Spa!

Our flat has a patio that enjoys great sunsets. We are freeway close to all, easy in and easy out!! You’ll love the place because of the comfy bed, space, patio and access to pool and spa. Also, the yard can be enjoyed for relaxing, eating, bonfires, horseshoes and cornhole. An adjoining space is also an AIRBNB studio suite. Great for traveling friends or as an alternative place to consider for your stay. Look for Foemer man Cave with Pool And Spa.

Sep 5 – 12

G$24,609 GYD per night

Guest favorite

Home in Ramona

4.97 out of 5 average rating, 304 reviews

Wine Country Retreat - Tranquility Hottub/Views

Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Our place is right in the heart of San Diego Wine Country. It's a rather well appointed place situated on 10 private acres that overlooks expansive green space. With only few neighbors in any direction, you can either sleep with the windows open and wake early to roosters crowing, or close the windows and sleep quietly til Noon.

May 18 – 23

G$41,729 GYD per night

Guest favorite

Guest suite in La Mesa

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 4 – 11

G$28,369 GYD per night

Guest favorite

Guest suite in La Mesa

4.89 out of 5 average rating, 141 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 4 – 11

G$36,367 GYD per night

Guest favorite

Guesthouse in La Mesa

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.

Jan 1 – 8

G$32,960 GYD per night

Guest favorite

Guesthouse in San Diego

4.94 out of 5 average rating, 333 reviews

The BEST NEST Clean, peaceful, private, affordable

This lovely private & separate unit is comfortable, clean and convenient. Your completely private suite is accessible via your own entrance. Minutes from major attractions, away from the hustle and bustle. Newly remodeled living room and FULL kitchen. Located in a nice neighborhood just off major freeways. Sip your morning coffee, relax and enjoy the gorgeous San Diego weather in the quaint, outdoor garden.

Nov 1 – 8

G$23,175 GYD per night