Holiday rentals with a pool in Ramona

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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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Guest favourite

Guesthouse in Escondido, California, US

4.92 out of 5 average rating, 639 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.

27 Dec – 3 Jan

$299 NZD per night

Guest favourite

Guesthouse in Escondido

5.0 out of 5 average rating, 101 reviews

Infinity Poolside Apt. In San Diego Wine Country

Gorgeous and peaceful poolside apartment on stunning French estate Domaine Au Soleil. Amazing sweeping views of wine country on the 14th green of a golf course with full access to the estate pool, spa, covered parking, EV charger w/private European park. Walk through the private entrance French doors and you will find a large fully equipped private luxury suite with a Kitchen, Sitting Room, Bathroom, Steam shower/Sauna and bedroom with luxurious robes, linens and towels. Perfect Guest Reviews

14–21 Oct

$557 NZD per night

Guest favourite

Cottage in Pauma Valley, California, US

5.0 out of 5 average rating, 118 reviews

The Cottage at Quixote Farm

Our farmstay has been described as as a "European getaway" without the jet lag or time commitment. Quixote Cottage is a small private cottage overlooking a 15-acre citrus grove on our very remote 130 acre family ranch on a hillside overlooking Pauma Valley. At 1800 feet above sea level, we enjoy temperate seasons. We share our family farm for agri-tourism as a way to offset water costs for running a farm. It’s our hope that you will feel revived and replenished during your time here . Welcome!

20–27 Feb

$484 NZD per night

Guest favourite

Tiny home in Rainbow

5.0 out of 5 average rating, 374 reviews

The Tiny Cabin - Coral Tree House

*Owners live on site, are available to answer questions and provide assistance, but give guests their privacy. *The sleeping porch is not heated. *Cooking is limited. *There are 3 rentals on the property. All have access to the pool/jacuzzi. *Riley, the world's sweetest dog, lives on the property. *Parents, the pool is unfenced and there are no vertical posts in the stair railings. *To preserve the peaceful atmosphere, only registered guests are allowed on the property. *No pets. *No smoking

23–30 Aug

$338 NZD per night

Guest favourite

Guesthouse in Poway

4.99 out of 5 average rating, 117 reviews

⭐️Garden studio guesthouse, resort living with pool

Come relax in this unique and tranquil pet-friendly garden getaway located in a gated community near the heart of Rancho Bernardo and bordering San Diego’s top-rated Maderas Golf Club. Steps away from some of the best hiking trails in San Diego County Tempur-Pedic Queen, full-size couch and crib. Fully appointed kitchenette. Outdoor cooking area (Weber/Green Egg grills). Pool and spa with child-safe fence. Outdoor sitting areas with wood and gas fireplaces. 550 sqft, 1+ acre fenced yard

$216 NZD per night

Guest favourite

Guest suite in Valley Center

4.99 out of 5 average rating, 221 reviews

Rural San Diego Area

Located in beautiful rural (inland), San Diego County. Minutes away from Harrah’s and several other casinos and San Diego Zoo Safari Park. Less than 1 hour to all San Diego attractions and Temecula wine country. Easy day trips to Hollywood, Disneyland, 6 Flags and Tijuana. Located on several acres with outstanding views - a tranquil environment. The suite is 2 bedrooms, bathroom and living room. You are free to enjoy the spaced shared with the owners that includes pool, patio, hot tub and BBQ

17–24 Sep

$208 NZD per night

Guest favourite

Farm stay in Lakeside

4.96 out of 5 average rating, 287 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.

3–10 Jan

$446 NZD per night

Superhost

Tiny home in Ramona, California, US

4.93 out of 5 average rating, 119 reviews

Ramona Wine Country Cabins 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)Refrigerator, freezer, microwave and coffee pot. Only 45 minutes from downtown San Diego and within an hour from all areas of San Diego County.

2–9 Sep

$208 NZD per night

Guest favourite

Tiny home in Escondido, California, US

4.94 out of 5 average rating, 225 reviews

Sunrise View Chateauette

Covid-19 vaccinations required. Located in picturesque San Pasqual Valley. Along with host and her husband, 3 friendly dogs & a dozen hens roam on this fully fenced 2 acre hobby farm & mini orchard. Infinity pool & hot tub w/ panoramic views of surrounding mountains. Minutes to historic Old Escondido, San Diego Safari Park, Stone Brewery, boutique wineries, trails and Lake Hodges. Mins to hwy, 30 minutes to San Diego, beaches and Airport. 25 minutes to Temecula wine country.

23–30 Sep

$189 NZD per night

Guest favourite

Farm stay in Ramona

4.95 out of 5 average rating, 347 reviews

Cozy, country farmstay w/fresh eggs & animals!

This space, formally a working barn, was remodeled into an amazing, one-bedroom home, meant to be enjoyed by couples and small families looking to make incredible memories. Every detail was thoughtfully crafted to create an experience that caters to those deserving of a destination escape in a country-like setting, yet close enough to all of San Diego's local attractions. There is so much to do nearby this winter..ice skating, shopping, wine/craft beer.

23–30 Dec

$435 NZD per night

Guest favourite

Home in Ramona

4.97 out of 5 average rating, 305 reviews

Wine Country Retreat - Tranquility Hottub/Views

Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Our place is 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 only 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 quietly til Noon.

24–31 Jul

$338 NZD per night

Guest favourite

Guest suite in Valley Center, California, US

4.9 out of 5 average rating, 142 reviews

Hilltop Hideaway. Incredible Mountain Views

This quaint two story guest house comes complete with stunning Mountain View’s. Enjoy the beautiful sunset each night sipping on a glass of wine while lounging by the pool on a summer night. The space is a great couple getaway destination. The entire backyard pool area is designated just for you! I respect your privacy and will be available upon request.

29 Nov – 6 Dec

$205 NZD per night