Vacation rentals with a pool in Lakeside

4.91 out of 5 average rating, 793 reviews

A tranquil saltwater pool is framed by landscaped gardens featuring lush greenery and blooming flowers. The surrounding hills create a serene backdrop, and two lounge chairs are positioned near the pool's edge, inviting relaxation.

Guesthouse in Escondido

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.

The private backyard features an inviting pool, surrounded by various seating areas and lush greenery. A shaded BBQ room is visible, along with an umbrella atop a dining table. The expansive landscape offers a mix of stone pathways and flourishing plants beneath a clear blue sky.

4.99 out of 5 average rating, 133 reviews

Private 1 BR Paradise retreat

Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

5 out of 5 average rating, 167 reviews

Guesthouse in Kit Carson

Infinity Poolside Apt. In San Diego Wine Country

162 Perfect 5.0 Reviews-Amazing views, peaceful and beautiful space in a wine country setting. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of wine country, lake, golf course and mountains on the 14th green of a golf course with full access to the estate pool, spa, covered parking, EV charger w/private European park. Large luxury suite with a Kitchen, Sitting Room, Bathroom, Steam shower/Sauna and bedroom with luxurious robes, linens and towels.

4.78 out of 5 average rating, 127 reviews

Cabin in Ramona

Wine Country Cabin Near San Diego - Private

Kick back and relax in this private cabin on 9 acre ranch. It’s a true get away. Come enjoy all the amenities including: Queen bed, full kitchen/bath, spa shower, 9 acres of private trails, intentional spaces, majestic views and a huge deck with a soaking tub to cool you in the summer (June - October). New A/C and heating. Enjoy a 5 minute walk to Milagro Winery and return to Littlepage for the amazing sunset. Or venture 15 minutes to the towns of Ramona, Julian or San Ysabel. Book Now!

4.96 out of 5 average rating, 373 reviews

A sparkling pool with gently flowing waterfalls is surrounded by lush greenery and lounging chairs. The water’s clear turquoise hue reflects the warm light, creating a serene atmosphere. Natural stones frame the pool, enhancing the rustic elegance of the outdoor retreat.

Farm stay in Lakeside

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.

4.97 out of 5 average rating, 190 reviews

A scenic view of a private pool surrounded by a wooden deck and lounge chairs is presented. A vintage travel trailer is positioned nearby, with lush greenery and trees framing the scene. The clear blue sky and distant hills create a serene backdrop.

Camper/RV 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.

This open concept studio features a light-filled seating area with a plush sectional sofa adorned with decorative pillows. A well-equipped kitchenette and a dining area with bar stools are present. The spacious bed is positioned in the background, complemented by soft lighting and neutral decor.

4.99 out of 5 average rating, 102 reviews

Private Balcony! Sunset & SunriseVIEWS!

~PANORAMIC VIEWS~ ~PEACEFUL & PRIVATE~ ~CENTRAL LOCATION~ ~XL BALCONY~ ~POOL/SPA ADD ON PACKAGE~ OCEAN, Mountain, Harbor, & Valley views~to Pt Loma & Coronado! Historic Mt Helix neighborhood. Balcony with panoramic views~ an outdoor living space! Private entrance, 1 Driveway parking space Ask about our POOL/SPA/LOUNGE-available as an ADD ON fee package only~Scroll down for details on EXTRA deposits/fees & approval terms that apply NON SMOKING/VAPING property indoor & out

Guesthouse in Lake Murray

The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.

4.96 out of 5 average rating, 123 reviews

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

This is the perfect Guest House with a salted & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to Downtown, La Jolla, Beaches, Zoo, Sea World & Convention Center. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes await you inside. Everything you need for memorable vacation! No smoking or vaping on the property.

4.88 out of 5 average rating, 243 reviews

Guest suite in La Mesa

Tranquil Poolside Studio

Quiet Poolside Studio Suite! Perfect for visiting family in La Mesa or enjoying everything San Diego has to offer! Please note: this is not a party house. Private side entrance to a relaxing poolside studio. Very quiet with TV, and full kitchen. Comfortable queen size bed and sofa that can sleep one more person comfortably. We are 20 min to the beach, or relax and enjoy the pool! Close to SDSU and easy freeway access to anywhere in San Diego.

Guesthouse in Tierrasanta

A private swimming pool is set amidst natural landscaping, surrounded by stone pathways and decorative plants. The vibrant blue water reflects the sunlight, creating a serene ambiance. A rock formation is visible near the shallow end, adding to the pool's inviting design.

4.87 out of 5 average rating, 169 reviews

Fig Tree Cottage

The private upstairs addition to our home was built new Spring of 2017. Sitting over our garage, it is a cozy 500 sqft & offers guests a quaint & quiet place to relax. With well appointed furnishings & thoughtful decor, Fig Tree Cottage offers everything you need to enjoy all the comforts of home. Just 15 min away enjoy the beautiful beaches of La Jolla along with some of the best restaurants and boutique shopping San Diego has to offer!

The outdoor area features a refreshing pool surrounded by a spacious deck, lounge chairs, and vibrant landscaping. A gazebo stands nearby, offering shaded seating. In the background, the serene mountains create a picturesque view under a partly cloudy sky.

4.91 out of 5 average rating, 199 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.

A serene outdoor space features a sparkling pool surrounded by lush greenery. Comfortable lounge chairs are positioned nearby, offering relaxation options. A shaded seating area under an umbrella provides a cozy spot for enjoying the tranquil environment.