Holiday rentals with a pool in East County, San Diego

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.

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

XTRA 10% OFF until Nov: Pool, outdoor fire pits, c

Find your family's dream spot in San Diego! Our cozy house sits on a quiet hill, offering privacy and amazing sunset views. Dive into our pool year-round (heating at an additional cost), roast marshmallows by the fire, and cook up fun meals together. With 3 bedrooms and 2 bathrooms, it’s perfect for families, accommodating up to 9 guests. Plus, we're close to all the best attractions. Want a vacation you'll always remember? Send us a message to make it happen! 🌅🏠 We have 3 comfy beds that can

Wine Country Retreat - Tranquility Hottub/Views

Our famed Wine Country Retreat is back online! (LTR for the last year) Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. 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 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 til Noon!

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit

VERY PRIVATE, COMPLETELY RENOVATED 4BR 3 Bath mid-century home with heated pool, hot tub and fire pit in totally private backyard retreat. The house was redone top-to-bottom, inside/out with everything new. The beds are top quality with very high quality 100% cotton sheets and bath towels. Conveniently we are centrally located in a safe, friendly neighborhood with beautiful mountain views in the back. We never charge any fees - as we want to provide the experience we hope to get when traveling.

French Garden Poolside Retreat near Wine & Safari

170+ Perfect 5.0 Reviews – Amazing views, peaceful and beautiful space on a French estate in San Diego Wine Country, adjacent to the Wild Animal Park. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of wine country, golf course and mountains on the 14th green with full access to the pool, spa, covered parking, EV chg. and private European garden park. Beautiful luxury ADU suite with a kitchen, sitting room, bathroom, steam shower/sauna and bedroom.

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.

Welcome to Luna Bleu!

Luna Bleu welcomes you to a serene mountain getaway! Located on our 4 acre home property. Off the beaten path yet not too far from surrounding areas, including San Diego. Shared access to our swimming pool, tennis&basketball court, gym/yoga studio, equipped with treadmills/peloton, meditation gardens, walking paths and a sound healing dome. Please note that we are in natural setting. We love nature,respect the plant life and critters. Please share the same sentiment, should you book a stay.

8BR 21 Bed Sprawling Villa! Great For Large Groups

Amazing European style villa sitting on 1.5 acres with over 5000 sq ft of living space in central San Diego County, perched up in highly prestigious Mt Helix with a huge private driveway, tons of privacy and views! Brand new saltwater pool with slide, jacuzzi, waterfall, swim up bar, fire pit, tennis court, vineyard, plus more! Furnished brand new top to bottom with high end furniture, just completed a remodel on all 7 bedrooms and 3 bathrooms. Truly one-of-a-kind property don’t miss out!

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

This is your 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 beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Vista Retreat! Pool, Spa, Game Room, FirePit

Just minutes from town, beaches, and wineries—but it feels like your own private mountain playground! Dive into the heated pool, soak in the hot tub, toast s’mores by the fire pit, or stargaze with a glass of local wine. Set on 10 acres of pure serenity, this stylish hideaway brings luxury and fun together with chic décor, top-notch amenities, and pampering perks like in-home massages and private yoga sessions. Your dream getaway starts here!

Lux Casita with Pickleball & Resort Amenities

Escape to this inviting Casita, where bright white walls and French doors fill each room with light and warmth. Thoughtfully furnished and full of charm, it offers a serene retreat with private resort-style amenities, including a tennis court, pool, and lush gardens. Step outside to hiking and biking trails, then return to cozy comfort. An optional second suite provides extra space for a relaxed, luxurious stay.