Vacation rentals in Lake Jennings

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Top-rated vacation rentals in Lake Jennings

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A welcoming entrance features a textured walkway leading to a front door, framed by a wooden railing. Colorful flowers bloom along the sloped landscape, enhancing the natural appeal of the surroundings. Clear skies and distant homes provide a serene backdrop.
Guesthouse in El Cajon
4.99 out of 5 average rating, 229 reviews

Modern mountain guest house. Incredible views

Neighboring San Diego, quaint country living with incredible views minutes from everything, breathtaking sunsets, 20 mins to beach, close by hiking trails, and only 3 minutes hop on the freeway. Full Kitchen, Laundry, and Living area and with beautiful furnishings, a perfect home away from home. Whether traveling for work or play we have had guests stay for a conference in San Diego or just to visit friends and hit the beach a few days, we look forward to you loving our home as much as we do.

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Superhost
A private deck features a small round table surrounded by two blue chairs, situated under a palm tree. The view includes rolling hills and a clear blue sky with scattered clouds, offering a peaceful outdoor space to enjoy the scenery.
Home in Lakeside
4.88 out of 5 average rating, 41 reviews

Studio In Home with Private Entry

Take a break and unwind in this peaceful setting in a quiet neighborhood. This studio apartment is inside a single family residence, with its own upstairs private entrance from the outside. It has an efficiency kitchen equipped with a refrigerator, microwave, air fryer, electric skillet & Keurig coffee maker. Private bath & trundle style sofa sleeper. TV and cozy fireplace type heater. Pet friendly with a fenced area. Beautiful view to the west from a private deck with spectacular sunsets.

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Top guest favorite
Home in Lakeside
4.99 out of 5 average rating, 95 reviews

Resort Backyard • Pool & Spa • Game Room •Sleeps 8

☀️ Summer Special: FREE Pool Heating Through September 30! 🌴 Escape to The Birdhouse SD, where your family can enjoy a private heated pool, relaxing spa, resort-style backyard, game room, and direct access to beautiful Lindo Lake Park. Just 20–25 minutes from San Diego's beaches, zoo, and downtown, it's the perfect home base for your vacation. Sleeps up to 8 with 5 beds, a fully equipped kitchen, BBQ, fire pit, fast Wi-Fi, and Smart TVs. Everything you need for a PERFECT STAY!

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Top guest favorite
An outdoor seating area is equipped with a sectional couch surrounding a stone fire pit, with flames flickering invitingly. A large dining table offers ample seating. The heated pool glistens in the background, surrounded by lounge chairs and shaded umbrellas.
Home in El Cajon
4.96 out of 5 average rating, 121 reviews

Family Fun Oasis Pool Spa and Game Room

Exceptional home w/heated pool and spa in a quiet neighborhood; kitchen has everything you need and more! Perfect for families with kids of various ages or multiple families. What to Expect: - Heated pool w/safety cover - Hot tub - Game Room - Trampoline - Jungle gym - Baby/toddler supplies (pack N play/High Chair) - Spacious master suite. - 20 mins to the beach, the San Diego Zoo, Balboa Park, Sea World, Little Italy and downtown San Diego and all that it has to offer!

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Guest favorite
Home in Lakeside
5.0 out of 5 average rating, 13 reviews

4 Bedrooms | Pool | Views | Games | Gym |

🏜️ Western Ranch in the Lakeside Hills A renovated home for 10 where everyone ends up out back 🏊 The Backyard: A private pool with incredible views Lawn games all afternoon, the fire pit once it cools off 🎮 Nobody Gets Bored: Pool table and a stand-up arcade off the kitchen Ping-pong by the pool, cornhole on the lawn, a full gym 🛏️ Everyone Sleeps Well: A king suite, a bunk room the kids will love, two king rooms 🌄 Quiet hills, but San Diego is 25 minutes down the 8

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Top guest favorite
A spacious living area features comfortable reclining chairs and a neutral-colored rug. A wooden bookshelf filled with books and decorative items is visible to the right. A kitchen island with modern appliances is located in the background, illuminated by natural light from multiple windows.
Guest suite in Santee
4.95 out of 5 average rating, 102 reviews

Hidden Gem 2 bedroom sleeps 8 family friendly

Enjoy our centrally-located place. 1700 sq ft 2 story, 2 bed 2.5-ba, gated, Secluded, Less than a mile walk/drive to the trolley station 25 min to Beaches. Living/dining area with 48”TV, Fully equipped kitchen, laundry/bathroom, luxurious master bedroom suite, has private entrance, large on-suite bath with extra-large soaking tub. Upstairs spacious room; has a full bath - dual purpose- Entertainment sleeping area includes 75" TV, 2 queen bed, single bunk, & work space

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Top guest favorite
Home in Descanso
5.0 out of 5 average rating, 34 reviews

Infinity Pool & Spa-Private-Endless Views-Luxury

Discover private luxury mountain living with complete privacy on 40 acres in at aLuna 🔸Infinity edge pool & spa with amazing views of San Diego and Viejas Valley 🔸Unmatched sunsets and stargazing 🔸Perfect escape for couples and families looking for revitalization 🔸Spacious viewing decks and patios throughout the property 🔸Just 15-20 minutes from freeway and Viejas Casino amenities 🔸Year-round comfort with whole house AC/heat 🔸Complete remodel completed in 2025

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Top guest favorite
Home in El Cajon
5.0 out of 5 average rating, 21 reviews

Nature/Zen retreat - 30 Min to SD/near Casino

Escape to Crest, a private 10.5-acre canyon retreat just 30 minutes from San Diego. This spacious 4-bedroom, 2.5-bath home sleeps up to 9 guests and features bluffside views, a chef’s kitchen, fenced yard, arcade system, projector theater, fitness and yoga area, books, games, and musical instruments. Enjoy nearby hiking trails, nature reserves, and Sycuan Casino’s golf course, spa, concerts, dining, and lazy river. Ideal for families, groups, and long-term stays.

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Guest favorite
A modern outdoor pool area features sleek loungers positioned in water, accompanied by gentle water jets creating a relaxing atmosphere. The spacious patio, framed by a stylish roof, offers seating options and unobstructed views of the surrounding landscape.
Home in Alpine
4.9 out of 5 average rating, 93 reviews

Luxury Escape | Heated Pool/Spa • Views + Events

Escape to El Rancho in Alpine – Your Private Mountain Oasis+ Tucked in the scenic foothills near San Diego and Julian, this secluded luxury estate offers panoramic views, total privacy, and serene comfort. Enjoy a year-round heated pool (kept at 85°F), a premium Cantabria hot tub, and sun-filled interiors designed for relaxation. Just minutes from top dining and shopping. Perfect for unforgettable getaways—and approved intimate events. Book your stay today!

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Top guest favorite
Home in Lakeside
4.93 out of 5 average rating, 30 reviews

Luxury Retreat w/ Panoramic Views & Private Yard

Unwind in this private 2-bedroom home with panoramic mountain views, a fully fenced backyard, and a newly remodeled luxury bathroom with floor-to-ceiling stone and glass shower. Thoughtfully designed for comfort and relaxation, it features a private gated entrance, fully private living space, a fenced backyard with patio, private laundry, and designated parking. The driveway is shared, and quiet hours begin at 9 PM to maintain a calm, relaxing environment.

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Top guest favorite
Home in El Cajon
4.98 out of 5 average rating, 120 reviews

Quiet Country Home

Extremely clean home. Fenced private yard with Webber Genesis BBQ & Tables. Outdoor smoking. 25 minutes to beach or downtown. Rural area with animals “talking”. Horse visits and carrots included. Seasonal Fruits & Vegetables. 1st bedroom: king/full bath. 2nd bedroom: queen/work desk. 3rd bedroom: full & 2 twin trundle. All dishes/appliances. Crib & Highchair available Host lives in a separate complete 1 bedroom studio with a shared laundry room.

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Guest favorite
A refreshing pool area is surrounded by lush tropical foliage and rock formations. Waterfalls cascade from a natural stone archway into the turquoise water, creating a serene atmosphere. Smooth stone pathways lead around the pool, enhancing the space's inviting nature.
Home in La Mesa
4.98 out of 5 average rating, 144 reviews

Paradise Lagoon Resort Style Pool Getaway

A unique one-of-a-kind poolside oasis with a tiki bar and spacious 4-bedroom house Welcome to Paradise Lagoon! This stunning home is the perfect place to relax and unwind with your family and friends. With its private pool (*best in San Diego), tiki bar, game room, and roomy 4-bedroom layout fit for multiple families, you'll never want to leave. Come make some magical memories with family and friends in your own resort style vacation home.

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Popular amenities for Lake Jennings vacation rentals