Vacation 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

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.”

Bamboo Lake House-Tropical paradise & LOTS OF FUN

LEGOLAND and best BEACHES nearby. Pool, spa, tennis court, pickle ball, basketball, game room, ping pong, fishing, canoeing on 1/2 acre pond with fish and ducks and birds, bbq, firepit all for your EXCLUSIVE private use. Unique TROPICAL PARADISE comfortable to RELAX and have FUN in beautiful SAN DIEGO north county. Many attractions and CRAFT breweries and cuisine. ***There are 3 private residences on the 2.5 acre property. Your residence is your own house, everything is for your private use.

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.

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.

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.

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.

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.

Beautiful 3,000 Sq Ft Tropical Oasis

Beautiful 4 Bedroom, 2 1/2 Bath Family Home Located in Tranquil Fletcher Hills. This 3,000 sq. ft. Home is Perfect for large families who wish to Relax in a Peaceful Setting. 24-hour self check-in keypad after 4pm and check-out at 11AM. Host does not allow parties/events. This is NOT a Party House! This home is located in a quiet residential neighborhood, Guests who do not respect this will be asked to leave.

Surf Cottage w/Pool & Firepit 10min from the beach

Welcome to the Wavvy Surf Shack, a charming surf cottage, with a private pool oasis and modern amenities. This surf-inspired home is located in a quiet and central neighborhood, only a short 10 minute drive to La Jolla Shores Beach, Pacific Beach, UCSD, and downtown. Lounge by the pool or enjoy the surf at a nearby beach - you won’t want to leave this beautiful coastal getaway.