Holiday rentals with a pool in East County, San Diego

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

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!

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

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!

Stylish Relaxation-Panoramic Views-Private OASIS!

~BRAND NEW DRIVEWAY~Perched high on granite hills, our comfy, stylish bungalow is perfect for a quiet getaway in San Diego. Brew your morning coffee and stroll to the pool to let the expansive views of the city fuel your daily adventures. Host a barbeque in the spacious, private backyard after your day at the beach. Cozy up in the recliner loveseat and enjoy the big screen 4k smart TV (with cable). 420 Friendly! “Enjoy the hillside pool—just coordinate with Johnny for your own private swim.”

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.

Hilltop cabin retreat with lake & mountain views

Rustic hilltop cabin overlooking Lake Hodges. Surrounded by open canyons & mountains, you'll feel a million miles away as you take in the stunning views, enjoy morning coffee on the deck, refresh in the saltwater pool, indulge in a moonlit outdoor shower, relax & recharge with a poolside massage, or sip wine by the fire bowl. A short walk to lake w/boating, fishing & miles of hiking & biking trails. Great restaurants, SD Zoo Safari Park, wineries, breweries, & ocean beaches all nearby.

Adobe Acres Ranch House

Behind the gates of our modern adobe ranch house is your private oasis while still being steps away from the vibrant but quaint little town of Wynola. Just minutes from Main Street Julian + walking distance to Julian Station with food, Julian Hard Cider, and antique shops. Skip the pie lines in Julian-- walk out your front door to get your goodies at our across-the-street neighbor, Mom's Pie! Combine it with our private Adobe Acres Ranch Casita for the ultimate private mountain retreat!

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

This is your perfect Guest House with a salt & 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.

Upscale Resort House /Views, Saltwater Pool/Spa !

This home offers Saltwater pool and Spa. Saltwater pools and Spa produce softer-feeling water. breathtaking views from its location high in the hills overlooking Rancho San Diego. In the backyard you can enjoy the sunrise from the private pool or deck or practice your putting on our putting green. The House is a mid-century modern home perched above the City. It's great for groups seeking easy access to San Diego's highlights (15 to 20 minutes to Beaches and Downtown)

The Dell, a relaxing country estate in Ramona.

The Dell in Ramona offers a 4 bedroom 2 1/2 bath single story house with a deck with two fire pits, a swim spa/jacuzzi and the most peaceful, serene place to enjoy a sunset. We are set up to handle your next event what ever it may be, We also offer the Pacific Room that's connected to the house and can sleep up to 6. Perfect for a girls weekend or couples that want to gather for wine tasting, hiking or visiting Antiques stores.

San Diego family bungalow!

The bungalow is close to all of the famous San Diego iconic activities. Most are within 20 minutes of the bungalow. Mountains and fishing are less than 1 hour away, desert is 2 hours away and Disneyland is 1 1/2 hours away. You will love our bungalow. It is the perfect place for a family vacation. The pool, trampoline, play structure are wonderful and you don't need to drive anywhere. It is impossible to heat the pool.