
Vacation rentals with a pool in Ramona
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Ramona

Total vacation rentals
Explore 30 vacation rentals in Ramona

Nightly prices starting at
Ramona vacation rentals start at G$12,560 GYD per night before taxes and fees

Verified guest reviews
Over 2,490 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Ramona vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Ramona rentals

4.8 Average rating
Ramona stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Ramona
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

“El Granero” Lower Barn 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 enjoying the very popular Sunset and Charcuterie experience. Note:European Farmstays are exactly that: A family farm. Not a 5-star resort.

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.

Luxury Four Bedroom Home with pool and game room!
Perfectly located renovated home! Features include: -Fully stocked kitchen -Grill, fire pit, & outdoor dining -Large yard with pool (NOT HEATED) -Ping pong, foosball, & air hockey -Washer & dryer -Approx. 12 mins to Safari park -Approx. 30 mins to Legoland, Seaworld, Zoo, & beaches! -5 to 10 mins to grocery stores, restaurants, parks, & hiking trails -2 mins from highway Perfect place for you and your family to enjoy! NO PARTIES ALLOWED Please read the house rules before booking. Thank you!

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.

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.
Popular amenities for Ramona rentals with a pool
House rentals with a pool

♥ Of Wine Country | Privacy+, Gazebo, BBQ, Jacuzzi

Luxurious Midcentury Home, Private Pool at DeAnza

Vineyard Vista | Modern • Renovated • Private

Mountain Top Getaway w/ Pool & Hot tub

Borrego Surf Club (@borregosurfclub)

Casa de Adobe - Large home, pool/spa & yard!

Stunning 3 bedroom w/Views! Game Room/Pool/Hot Tub

6BR Vineyard Estate | Pool, Spa & Views
Condo rentals with a pool

Studio Condo and Wave Crest Resort

Del Mar Beach Club-AC, pool,jacuzzi,tennis, views!

The Endless Summer Condo!

Luxury Oceanfront Condo with Unbelievable Views

Beautifully remodeled 10th floor oceanfront condo

🌴La Costa Resort Château🌴 Luxury Suite for 2

Beach Front Condo - Capri by the Sea - Remodeled

The Coast Getaway
Other vacation rentals with a pool

el Castillo - spanish-inspired getaway in SD mtns

Lux Villa: Heated Pool, Sauna, & Gym

Bella Casita Guest House

Leafland West Country Casita | Pool + Private Yard

Private Mountaintop Retreat

Moonrise Cottage at Buena Terra Lavender Farm

Adobe Acres Ranch House

Rams Hill Golf Retreat - Hot Tub, Stargazing
When is the best time to visit Ramona?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$31,190 GYD | G$31,190 GYD | G$31,400 GYD | G$32,028 GYD | G$31,609 GYD | G$28,678 GYD | G$32,865 GYD | G$33,074 GYD | G$32,237 GYD | G$31,190 GYD | G$33,702 GYD | G$32,237 GYD |
| Avg. temp | 15°C | 15°C | 16°C | 17°C | 18°C | 20°C | 21°C | 22°C | 22°C | 20°C | 17°C | 14°C |
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