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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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Guesthouse in Rancho Bernardo

4.92 out of 5 average rating, 701 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.

Home in La Mesa

4.99 out of 5 average rating, 147 reviews

Mid-Century Style Family House with Spa

Beautiful Mt. Helix mid-century modern family home with incredible views, designed by architect of original Las Vegas, Desert Inn 3/4 acre.Less than 20 minute drive to beaches/Zoo/Sea World/Downtown, 40 minutes to Legoland. With a swimming pool/hot tub, huge lawn surrounded by California Oak/orange/lemonpomegranate trees and herb garden, this home is the epitome of 1950’s luxury. A perfect family oasis, you won’t even want to leave the property. No loud parties please, this is a quite community.

Guesthouse in Ramona

4.93 out of 5 average rating, 333 reviews

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.

Farm stay in Lakeside

4.96 out of 5 average rating, 326 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.

Home in Lakeside

4.95 out of 5 average rating, 111 reviews

Vibey😎Pool House🏡 ModernFarmhouse 1700sqft + View🌄

Come and relax as this home gives you the open concept, views, and coziness we all desire when you're on vacation. It is the perfect location, right off of San Diego's main freeway with options to drive to the beach, mountains, or desert. The backyard is an oasis that you can enjoy during the day and at night with our splash pool that easily heats into an extra large jetted hot tub with waterfall. Enjoy the view from inside with floor to ceiling windows or outside with plenty of seating.

Yurt in El Cajon

4.97 out of 5 average rating, 315 reviews

Glamping @ Eden East

Looking for the perfect place to chill with your favorite person or just some alone time? Yome with private patio and spacious pool area. Not just a place to stay but an artsy retreat full of color, butterflies, birds and life. Hot shower and flush toilet in plant filled outdoor bathroom. We've been told the shower alone is worth the stay. Come glamping and get cozy with heated blanket, heater and flannel sheets. By reserving, we assume you've read the entire ad and agree to all rules.

Home in Lakeside

4.93 out of 5 average rating, 133 reviews

The Hills Oasis Pool, Jacuzzi & Pickleball

SEND US A MESSAGE FOR SPECIAL OFFER! Imagine booking the most memorable experience with your party! Kick back and relax in a safe stylish, family and friend oriented experience! Check in contactless and enjoy! Cozy, modern and includes an outdoor fire pit, spa, and pickle ball! With the whole house comes parking up to 6 cars, 2 bathrooms (1 is ADA compliant), and an alluring kitchen. The entire house is 30 minutes from the beach, 45 to the snow, and 30 minutes from downtown San Diego.

Guesthouse in Ramona

4.96 out of 5 average rating, 113 reviews

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.

Guest suite in La Mesa

4.89 out of 5 average rating, 158 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.

Guesthouse in La Mesa

4.9 out of 5 average rating, 167 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.

Guesthouse in Allied Gardens

4.95 out of 5 average rating, 369 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. Full kitchen for easy meal preparation. Located in a nice usually quiet neighborhood, close to major freeways. Enjoy the gorgeous San Diego weather in the quaint outdoor patio area.

Guesthouse in La Mesa

4.93 out of 5 average rating, 130 reviews

Pool Side Safari Cabin (On Backside of our Home)

This newly remodeled Safari Cabin is your ticket to a relaxing vacation in the exciting Southern California area. The large master suite and living space with kitchen sleeps 4, with 1 queen bed , 1 queen sofa bed. The Cabin sits on the backside of our house. You will have a private locked entrance and parking for one vehicle in front and another space past our driveway.

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Popular amenities for Lakeside rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Escondido

4.99 out of 5 average rating, 134 reviews

Lake Views, Entire House, Pool & Hot Tub

Home in Scripps Miramar Ranch

4.96 out of 5 average rating, 194 reviews

Kids Paradise San Diego - Funhouse

Home in Valley Center

4.98 out of 5 average rating, 119 reviews

Private View Home w/Salt Water Pool, Spa, 9 acres!

Home in Ramona

5 out of 5 average rating, 104 reviews

The Dell, a relaxing country estate in Ramona.

Home in Pacific Beach

4.94 out of 5 average rating, 347 reviews

PB Dream HOUSE Steps to Beach Bay ❤️Modern Private

Home in South Oceanside

4.88 out of 5 average rating, 120 reviews

Betty's Beach House with Seascape Cozy Cottage

Home in Escondido

4.95 out of 5 average rating, 111 reviews

Stunning 3 bedroom w/Views! Game Room/Pool/Hot Tub

Home in Escondido

4.99 out of 5 average rating, 149 reviews

California living at its finest!

Condo rentals with a pool

Condo in Del Mar

4.87 out of 5 average rating, 386 reviews

Studio Condo and Wave Crest Resort

Condo in Pacific Beach

4.85 out of 5 average rating, 144 reviews

Ocean front one bedroom condominium

Condo in University City

4.95 out of 5 average rating, 222 reviews

Centrally located n UCSD/ utc-laJolla

Condo in Oceanside

4.97 out of 5 average rating, 169 reviews

Breathtaking Views-Steps to Sand, Beach Resort

Condo in San Diego

4.79 out of 5 average rating, 193 reviews

Comfortable & convenient accommodation @ San Diego

Condo in Pacific Beach

4.91 out of 5 average rating, 135 reviews

Enchanted Ocean Sunsets

Condo in Oceanside

4.91 out of 5 average rating, 162 reviews

Couples Retreat Beachside Studio, King Bed

Condo in Pacific Beach

4.94 out of 5 average rating, 455 reviews

Oceanfront Elegant Condo - Remarkable Amenities

Home rentals with a private pool

Rental unit in Oceanside

4.96 out of 5 average rating, 243 reviews

Beach Apartment near Oceanside Pier

Home in Point Loma Peninsula

4.92 out of 5 average rating, 83 reviews

Historic Home with Amazing Views of San Diego Bay

Home in Pacific Beach

4.9 out of 5 average rating, 172 reviews

Eco-Friendly Mount Soledad Pad with Views and Heated Pool

Home in Torrey Hills

4.75 out of 5 average rating, 8 reviews

Luxury San Diego House: Beach, Pool & Pet-Friendly

Home in Ramona

4.9 out of 5 average rating, 29 reviews

Vista Grande

Quick stats about vacation rentals with a pool in Lakeside

Total rentals
30 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Destinations to explore