Holiday rentals with a pool in Ramona

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.

Retreat:GameRoom/PuttGreen/Volleyball/Pool/HotTub

Located high on the mountain and surrounded by the best trails & wineries, this house offers something for everyone to enjoy their vacations at its best. See SD hot spots - Little Italy, Sea world, Balboa park, Lego land, Beaches, 30-40 mins away, SD safari zoo in 20 mins. Once you enter the house, you might not want to go out. A fully stocked kitchen, all kinds of games you can dream of from indoor to outdoor. When everyone is tired, just relax in the pool & enjoy sunset at the pool side bar.

French Garden Poolside Retreat -Wine & Safari Park

180 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.

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!

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.

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

Welcome to your personal resort! This is your private Guest House with a salt & heated pool + hot tub. Located in a very quiet & safe neighborhood in beautiful San Diego. Drive 15 minutes to the beach, downtown, La Jolla, Zoo, stadiums, Sea World, Convention Center + more. Hike next door at Cowell Mountain or Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo, top quality finishes & furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

Plateau Retreat | Panoramic View | Close Safari Park

This is an estate that rivals its surrounding beauty by its wonderful views, and comforting rooms. This property invites guests to spend their days hanging out at the pool, having a friendly competition playing foosball, and even gazing at the starry night sky at dark at the campfire! Go outside to relax in the comforting hot tub! In the morning, the view is a stunning European country style view, while at night it is a glamorous city view. This is the perfect place to go for family trips!

Ramona Wine Country Cabin Near San Diego

This Tiny Cabin is located on beautiful 8 acres in Ramona Wine Country. Walking distance to Turtle Rock Ridge winery and many more nearby. 600 acre open space preserve next door with miles of trails. Enjoy a pool in the summertime. Forever views to enjoy from your private patio area. Comfy queen size bed in the loft (remote control stairs)Small Refrigerator, freezer, microwave and coffee pot. Only 55 minutes from downtown San Diego and within an hour from all areas of San Diego County.

Jamul Hacienda | Couples Retreat | Pool & Views!

The Casita retreat is a guesthouse situated among a private 20 acre oasis surrounded by majestic mountain views and a citrus grove 30-40 minutes from San Diego. The space is designed for nature enthusiasts to retreat from the daily hustle and bustle and find peace and slowness. Come take a pause, relax poolside, pick citrus (when in season), enjoy nearby trails, and wineries. The sunsets and starry skies are breathtaking. We hope you get to experience their magic for yourself.

Adorable Hawaiian themed Guest House

Enjoy the quaintness of country living just 35 miles from San Diego. Ramona is the heart of San Diego's wine country; home to many boutique winery’s and vineyards. Our guesthouse will provide the perfect space to unwind and relax after sightseeing, beaching, or visiting the world famous San Diego zoo. Guest home has one bedroom with king bed, separate great room/kitchenette w/hide-a bed and a couch. Fire pit, large grassy play area with zip-line and a pool to cool off in.

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.