Vacation rentals with a pool in Ramona

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ramona

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Top guest favorite

Guest suite in Encinitas

4.98 out of 5 average rating, 475 reviews

Lux Casita with Pickleball & Resort Amenities

White walls and French doors open up each room to create a feeling of calm throughout the home. From the designer furnishing and tasteful decor items to the tennis court and pool outside, this Casita is as spacious as it is stylish. The property is resort like, without the crowds. Play tennis, shoot hoops, lay by the pool, or stroll through the garden. Hiking and mountain bike trails are out the back door. PLEASE NOTE: price indicated is for two guests staying in the one bedroom one bath with full kitchen. Optional second bedroom, bathroom can be added for an additonal $198 per night. Our place is very private, yet close by car to many attractions. 7 miles to the beach, 20 minutes to Legoland. Hiking out the back door, you will find endless trails and great mountain biking. Guests can use the tennis court and relax in their own private yard. Pool is available, although it is not heated. Hot tub is also available, but a $20.00 usage fee is needed to get it hot (It's big, and takes a lot of gas to get hot!) We live on the property, but it is very private. I can be reached easily by phone or text if something is needed. Nestled in a quiet neighborhood that evokes a country vibe, the casita is accessible to all San Diego has to offer. Hiking trails are just outside with the beaches, local restaurants, and boutique shops just a short drive away. Permit Number: RNTL-007165-2017 A car is needed. The City of Encinitas charges an additional 10% TOT tax which I will add to the booking after confirmation. You will receive a request for payment before your arrive and it is separate from your reservation fee. Extra person charge of $25 per night The casita is close to Del Mar race track, Legoland, beaches, hiking, and equestrian centers.

Superhost

A tranquil saltwater pool is framed by landscaped gardens featuring lush greenery and blooming flowers. The surrounding hills create a serene backdrop, and two lounge chairs are positioned near the pool's edge, inviting relaxation.

Guesthouse in Rancho Bernardo

4.91 out of 5 average rating, 768 reviews

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.

Top guest favorite

An outdoor seating area is nestled under a large tree, featuring comfortable wicker sofas with light cushions. A rectangular coffee table is surrounded by small, matching stools. Sunlight filters through the leaves, illuminating the space, and a wooden deck extends in the background.

Cottage in Pauma Valley

5 out of 5 average rating, 182 reviews

La Casita at Quixote Farm

You need a rest. See you soon™️ Since 2022, Quixote Farm has become a beloved getaway for countless guests who have returned time and again to enjoy the farms uniquely restorative effects. Modeled after a European farmstay, guests love walking in the orange groves, visiting with the rescue animals, shopping in the farmshop, enjoying a beautiful breakfast, or taking in our very popular sunset and charcuterie experience. Note:European Farmstays are exactly that: A family farm. Not a 5-star resort.

Top guest favorite

Guesthouse in Escondido

5 out of 5 average rating, 155 reviews

Infinity Poolside Apt. In San Diego Wine Country

150 Perfect 5.0 Reviews-Amazing views, peaceful and beautiful space in a wine country setting. A perfect setting to celebrate a special occasion and create memories. Amazing sweeping views of wine country, lake, golf course and mountains on the 14th green of a golf course with full access to the estate pool, spa, covered parking, EV charger w/private European park. Large luxury suite with a Kitchen, Sitting Room, Bathroom, Steam shower/Sauna and bedroom with luxurious robes, linens and towels.

Superhost

Cabin in Ramona

4.81 out of 5 average rating, 115 reviews

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!

Top guest favorite

A remodeled barn home is set amid a vibrant country landscape, featuring light-colored exterior walls and a welcoming porch. A garden area is visible beyond a rustic fence, complemented by surrounding trees and open skies, suggesting a serene outdoor space.

Farm stay in Ramona

4.95 out of 5 average rating, 379 reviews

Newly re-imagined space. Fresh & bright. Eggs too!

This space, formally a working barn, was remodeled into an amazing, one-bedroom home. Every detail was thoughtfully crafted to create an experience that caters to couples deserving of a destination escape in a country-like setting, yet close enough to all of San Diego's local attractions. We just completed a mini remodel with newly inspired spaces that include the living room with new furniture and a cozy reading nook and all new linens for both the bedroom and bathroom. Come see the changes!

Guest favorite

The casita is viewed from a pool, reflecting its Spanish ranch style architecture and surrounding greenery. Warm evening lights adorn the exterior, enhancing the inviting appearance of the home, while the tranquil water surface captures the serene atmosphere.

Guesthouse in Ramona

4.92 out of 5 average rating, 358 reviews

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.

Guest favorite

A sparkling pool with gently flowing waterfalls is surrounded by lush greenery and lounging chairs. The water’s clear turquoise hue reflects the warm light, creating a serene atmosphere. Natural stones frame the pool, enhancing the rustic elegance of the outdoor retreat.

Farm stay in Lakeside

4.96 out of 5 average rating, 365 reviews

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.

Top guest favorite

A serene outdoor area features comfortable wooden chairs beside a pool, surrounded by landscaped gardens. A pergola provides shade over a small table, inviting relaxation. Clear blue skies enhance the tranquil atmosphere, and the distant view includes lush greenery and distant structures.

Farm stay in Santa Ysabel

5 out of 5 average rating, 125 reviews

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!

Superhost

A charming wooden tiny cabin features multiple windows, allowing natural light to fill the interior. Outside, a covered patio area includes a table and chairs, complemented by a colorful umbrella. The surrounding gravel area is lined with stones and blends with the natural landscape.

Tiny home in Ramona

4.93 out of 5 average rating, 122 reviews

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.

Top guest favorite

A refreshing pool area is surrounded by shaded lounges and several large umbrellas. Lush green grass provides ample space for relaxation, while trees offer natural shade. The background features a gentle landscape, enhancing the outdoor experience.

Guesthouse in Ramona

4.96 out of 5 average rating, 126 reviews

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.

Superhost

A pool area is displayed, featuring a clear blue pool surrounded by lounge chairs and umbrellas. The backdrop includes rolling hills and greenery, providing a serene outdoor setting. The area is well-maintained, offering an inviting space for relaxation under the sun.

Hotel room in Ramona

4.84 out of 5 average rating, 126 reviews

One Bedroom Condo in San Diego Country Estates

San Diego Country Estates is nestled against the foothills near the quaint and historic towns of Ramona and Julian. Resort guests enjoy “The Good Life,” a perfect blend of active play and total relaxation with a variety of indoor and outdoor activities. A resort fee of $27.00/night is included in the total price shown on Airbnb. This fee covers parking, Wi-Fi, and access to on-site amenities. Please read through full House Rules prior to booking.