Holiday rentals with a pool in Lakeside

Lakeview Tiny House w/hillside pool

Tucked into the hillside by Lake Hodges, the tiny house is a romantic retreat or a place to unwind surrounded by nature, w/plenty of amenities so you don't have to sacrifice comfort. Lake & mountain views from inside & out-- private, large covered deck, dining patio, outdoor shower (& indoor), beautiful saltwater pool, & fire bowl. Though it feels like you're in a secluded retreat, urban amenities are just a few miles away. SD Zoo Safari Park, wineries, breweries & beaches all w/in easy reach.

Tropical Oasis: spa, solar heated pool, waterslide

This home is ideal for FAMILY trips and QUIET friend groups Hours of entertainment in the private backyard that includes heated pool, waterslide, grotto, spa, gazebo, half bath, BBQ, and more. Clean and spacious home with over 2,100 sqft of living space. Minutes from everything San Diego has to offer. Distance to main attractions: SDSU- 5 mi Downtown/PetcoPark park-11 mi SD Zoo/balboa park-12 mi SD Airport- 13 mi Old town- 14 mi Coronado-15 mi Belmont park/Mission beach-18mi Sea world- 18mi

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

French Garden Poolside Retreat -Wine & Safari Park

176 Perfect 5.0 Reviews – Amazing views, peaceful and beautiful guest suite on a French estate in San Diego Wine Country close to the Wild Animal Park. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of the vinyards/mountains situated on the golf course with full access to the pool, spa, covered parking, EV chg. and private European garden park. Beautiful luxury guest apartment with a kitchen, sitting room, bathroom, steam shower/sauna and bedroom.

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.

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.

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!

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)

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.

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.