Vacation rentals with a pool in San Diego County

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Top-rated rentals with a pool in San Diego County

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

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Top guest favorite
A cozy living area is seen, featuring a fireplace with a simple round decorative piece above it. A flat-screen TV is mounted on the wall opposite a sectional sofa, accompanied by a leather armchair. Large doors open to a green yard, enhancing the natural light.
Guest suite in Encinitas
4.98 out of 5 average rating, 481 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.

Guest favorite
An inviting outdoor space features a swimming pool surrounded by decorative rocks and comfortable seating. A covered dining area is equipped with a large table and multiple chairs, complemented by lush greenery and palm trees in the background, providing a sense of relaxation.
Guesthouse in Rancho Santa Fe
4.94 out of 5 average rating, 176 reviews

Posh Guest House ~ Pool, Spa, Pickleball & Tennis

Stunning Guest House with Pickleball/Tennis and Pool/Spa~ Serene, upscale guest house designed for comfort and fun. Nestled in a prime Rancho Santa Fe location, this retreat offers stunning views, resort style amenities and easy access to the best of Southern CA. Ultra comfortable California King Bed Fully equipped Chefs Kitchen Smart TV with Cable & WiFi Designated work area with garden views Expansive Outdoor Space – perfect for dining, lounging, soaking in the peaceful surroundings and sun

Guest favorite
A scenic view captures lush hillsides and a calm lake under a clear sky, with a rainbow arching gracefully over the landscape. Green vegetation sprawls across the area, adding vibrancy to the tranquil scene.
Guesthouse in Escondido
4.91 out of 5 average rating, 798 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
Two red Adirondack chairs are positioned under a covered patio, facing a serene backyard with a pool. Lush greenery surrounds the area, creating a tranquil atmosphere. A BBQ room and various seating arrangements are visible beyond the pool, enhancing the outdoor retreat experience.
Guesthouse in La Mesa
4.99 out of 5 average rating, 134 reviews

Private 1 BR Paradise retreat

Private, yet central. It is your exclusive paradise retreat to enjoy from your spacious 1 bedroom guest house located on the lower level of our home. Hang out in the expansive and private backyard with pool, different sitting areas and covered BBQ room. Or maybe a workout in the gym. Centrally located in the Village of La mesa. Just a 1/4 mile jaunt into the quaint village with its numerous assortments of dining options, stores and trolley station. Freeway close to beaches, downtown and airport

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, 196 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
A green, manicured lawn is highlighted with a white gazebo and ornamental garden seating. Towering palm trees flank the scene, while a staircase leads up to a spacious home nestled in the background. Shadows create a gentle pattern on the grass from surrounding elements.
Guesthouse in Escondido
5 out of 5 average rating, 168 reviews

Infinity Poolside Apt. In San Diego Wine Country

168 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.

Guest favorite
A living room features a luxury hanging chair suspended from the ceiling. Natural light filters through sheer curtains, illuminating a cozy seating area with a plush sofa and wooden coffee table. A 50” television is mounted above an elegant fireplace, enhancing the room's comfort.
Home in San Diego
4.93 out of 5 average rating, 121 reviews

Designer Luxury Rental With Pool

Welcome to Wander Haven, a luxury central rental. With it’s on trend design, custom built stock tank pool, array of amenities and thoughtful touches throughout, you won’t ever want to leave. But when do you do decide to venture out and explore all that beautiful San Diego has to offer, you will find the central location gets you to anywhere you want to be in minutes. You’re 15 minutes or less from beaches, downtown, balboa park, sea world, the zoo and hundreds of amazing bars and restaurants.

Top guest favorite
A bright living room features large glass doors opening to breathtaking ocean views. A comfortable white sectional sofa is surrounded by two plush armchairs. Wall art and a round coffee table enhance the inviting atmosphere, while a potted plant adds a touch of greenery.
Condo in San Diego
4.98 out of 5 average rating, 181 reviews

Luxury Oceanfront Condo with Unbelievable Views

Welcome to your oasis! Prepare to be awestruck by the breathtaking views at Sunset Pacifica. This fully renovated condo features two ensuite bedrooms with the beachy SoCal vibe you desire. Ideally located on the boardwalk, you're minutes from La Jolla, Downtown, the San Diego Zoo, Embarcadero, and top restaurants, bars, and entertainment spots. Whether you're in the mood for exploration or relaxation, you'll find it here- lounging poolside or on the sandy shores of the stunning Pacific Ocean.

Guest favorite
A cozy living area showcases a modern yet rustic design, featuring a large wooden table and comfortable seating. Warm lighting from pendant fixtures complements the natural wood accents on the walls, while a decorative fireplace enhances the inviting atmosphere.
Farm stay in Lakeside
4.96 out of 5 average rating, 374 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.

Guest favorite
A serene outdoor space features a salt-water pool surrounded by a concrete patio and manicured grass. An umbrella provides shade over the poolside area, with lush greenery and mountains visible in the background under a partly cloudy sky.
Home in San Diego
4.88 out of 5 average rating, 208 reviews

Bright and spacious home with views, pool & spa.

This beautiful and recently remodeled, open-floor plan home is conveniently located directly across from Cowles Mountain, one of San Diego's most visited hiking trails. Each bedroom has its own full bathroom. Perfectly located for the outdoorsy family. Tons of hiking and mountain bike trails are just across the street. Only 15 min. away from beaches, zoo, & Sea World. Gaslamp/Downtown is only 20 min. by car. After a day of exploring, come home to a newly-built, salt-water pool and spa.

Guest favorite
The tropical pool features gentle waterfalls cascading into vibrant blue water. Surrounding palm trees and lush greenery enhance the serene environment. A tiki bar and a hot tub grotto provide inviting leisure options. A second-story balcony overlooks this tranquil outdoor space, illuminated by soft evening lights.
Guesthouse in San Diego
4.97 out of 5 average rating, 191 reviews

Luxury Tropical Private Guesthouse in La Jolla

Beautiful private guesthouse on $5 million property with stunning views and luxury amenities. Take a dip in the tropical pool with waterslide, tiki bar, and hot tub grotto. Enjoy indoor or outdoor dining. Gated property, vaulted ceilings, marble bathroom, private balcony, parking, and trail for guests. Guesthouse has 1 bedroom with a queen bed and can accommodate an extra twin bed on the loft. House has closet, bathroom with beautiful stone shower, modern kitchen, two patios, WiFi, TV.

Top guest favorite
The poolside area features a well-maintained saltwater pool reflecting the colors of the sunset. Comfortable seating arrangements, including lounge chairs and a cozy fire pit, are visible. Large umbrellas provide shade, and lush greenery adds to the serene ambiance.
Guesthouse in San Diego
4.96 out of 5 average rating, 128 reviews

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

This is the perfect Guest House with a salted & heated pool & hot tub. We are located in a super quiet & very safe neighborhood in beautiful San Diego, 15 minutes drive to Downtown, La Jolla, Beaches, Zoo, Sea World & Convention Center. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes await you inside. Everything you need for memorable vacation! No smoking or vaping on the property.

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