Holiday rentals with a pool in Rancho San Diego

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.

4.99 out of 5 average rating, 169 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

LocationValueLong stay

4.98 out of 5 average rating, 122 reviews

A well-appointed backyard features a heated pool with a waterfall, surrounded by palm trees and lounge chairs. An outdoor dining area is under a covered gazebo, providing a view of the landscaped space. Soft evening light hints at a serene atmosphere.

Home in Spring Valley

Tropical Oasis: spa, solar heated pool, waterslide

This home is ideal for FAMILY trips and QUIET friend groups Hours of entertainment in the private backyard that includes heated pool, waterslide, grotto, spa, gazebo, half bath, BBQ, and more. Clean and spacious home with over 2,100 sqft of living space. Minutes from everything San Diego has to offer. Distance to main attractions: SDSU- 5 mi Downtown/PetcoPark park-11 mi SD Zoo/balboa park-12 mi SD Airport- 13 mi Old town- 14 mi Coronado-15 mi Belmont park/Mission beach-18mi Sea world- 18mi

ValueFamilyParking

4.98 out of 5 average rating, 107 reviews

The vibrant sunset sky is filled with hues of pink, orange, and purple, reflecting beautifully in the calm water of the pool. Palm trees stand in silhouette, framing the picturesque view of the surrounding mountains and valleys.

Guesthouse in Jamul

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

LocationValueWi-Fi

4.89 out of 5 average rating, 114 reviews

Entertainers Dream Pool Home

The Lemon Ave Pool Home! Ready for your enjoyment, this home has EVERYTHING you need to enjoy a large get-together with beautiful San Diego sunshine! Sparkling pool, relaxing spa, fire pit, kids' playhouse/grass area, decks to view the gorgeous sunsets, and more! The vast open living space has a full-size kitchen for any chef's needs! 3 bedrooms, 1 King/1 Queen/2 full/1 twin mattress with 2 queen pullout couches/1 queen &1 twin portable mattress, 2 1/2 bathrooms (2 full showers with bathtubs).

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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.

4.97 out of 5 average rating, 160 reviews

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.

FamilyValueTV

A spacious outdoor area features a swimming pool, accompanied by colorful lounge chairs and a large umbrella for shade. A unicorn float is visible in the water, with potted flowers adding a touch of vibrancy. The home's façade offers multiple windows and seating options nearby.

4.99 out of 5 average rating, 195 reviews

Mid-Century Style Family House with Spa

This home is the epitome of 1950’s luxury. A perfect family oasis, you won’t even want to leave the property. Beautiful Mt. Helix mid-century modern family home with incredible views, designed by architect of original Las Vegas Desert Inn situated on nearly an acre. Less than 20 minute drive to beaches/Zoo/Sea World/Downtown. With a swimming pool, jacuzzi, and AC. Surrounded by orange, lemon, pomegranate trees and herb garden. No loud parties please, this is a quiet community.

ValueFamilyHiking

4.98 out of 5 average rating, 102 reviews

A serene pool area is framed by vibrant green foliage and terracotta walls, with lounge chairs positioned nearby. Majestic mountains rise in the background under a clear blue sky. A shaded picnic table is visible, inviting relaxation in a tranquil outdoor setting.

Home in Jamul

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.

ValueLocationGetting around

4.96 out of 5 average rating, 210 reviews

A dining space features a round table with four white chairs, complemented by a potted plant. Large glass doors slide open to reveal expansive views of the backyard, pool, and surrounding hills, with soft evening light illuminating the scene.

Home in Spring Valley

Upscale Resort House /Views, Saltwater Pool/Spa !

This home offers Saltwater pool and Spa. Saltwater pools and Spa produce softer-feeling water. breathtaking views from its location high in the hills overlooking Rancho San Diego. In the backyard you can enjoy the sunrise from the private pool or deck or practice your putting on our putting green. The House is a mid-century modern home perched above the City. It's great for groups seeking easy access to San Diego's highlights (15 to 20 minutes to Beaches and Downtown)

ValueFamilyGetting around

4.97 out of 5 average rating, 329 reviews

Home in Ramona

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. 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 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 til Noon!

ValueFamilyCleanliness

A cozy interior features wooden paneling and a comfortable grey sofa with a decorative pillow. A small kitchenette is equipped with cabinets and appliances. A dining table is set for two, and a guitar is displayed on the wall, adding a touch of creativity to the space.

4.92 out of 5 average rating, 218 reviews

La Cabana

Perfect getaway for the wandering individual, couple, or young family. This rustic casita is surrounded by beautiful mountain and ocean views! Enjoy swimming in the pool, stargazing, lounging, or casual day trips around San Diego (All the amenities are shared with the main house) . The casita has one queen bed and a sofa bed, small kitchenette. Plenty of parking in driveway. Please read entire listing for details.

LocationFamilyView

A well-maintained putting green is surrounded by lush greenery, featuring multiple flags indicating different holes. A sand trap is positioned nearby, and a winding path made of stone leads through the garden space, enhancing the serene outdoor environment.

4.94 out of 5 average rating, 152 reviews

Pool Side Safari Cabin-On the backend of our Home

This newly remodeled Safari Cabin is your ticket to a relaxing vacation in the exciting Southern California area. The large master suite and living space with kitchen sleeps 4, with 1 queen bed , 1 queen sofa bed. The Cabin sits on the backside of our house. You will have a private locked entrance and parking for one vehicle in front and another space past our driveway.

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A view of the inviting swimming pool surrounded by a spacious patio. Natural rock elements and vibrant landscaping enhance the outdoor area. The multi-level deck is visible, offering seating options and picturesque canyon surroundings under a clear blue sky.

4.89 out of 5 average rating, 205 reviews

The Queen House

Welcome to Endless Summer, your ideal family retreat! This beautiful 4-bedroom, 2.5-bath home is just 15 minutes from Downtown San Diego, near attractions like Petco Park, the San Diego Zoo, and local beaches. Located in Mount Helix, La Mesa, enjoy stunning canyon views and a refreshing swimming pool with a waterfall. Experience a unique stay at a home that has it all!

FamilyValuePool

Popular amenities for Rancho San Diego rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

An open-concept living space features a modern kitchen with a large island and bar seating for four. A light-colored sofa is positioned nearby, with a stone fireplace adding warmth to the room. Natural light streams through the skylight and windows, enhancing the airy feel.

4.89 out of 5 average rating, 115 reviews

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

ValueLocationDecor

4.94 out of 5 average rating, 141 reviews

A modern living room features a light wooden floor and white walls, complemented by a pink accent wall. A flat-screen TV is mounted above a stylish cabinet, with two potted plants on top. A comfortable seating area includes a rattan chair and a coffee table.

Home in Chula Vista

Casa Bahia Beautiful San Diego Home with Pool

FamilyLocationPool

4.88 out of 5 average rating, 225 reviews

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

Bright and spacious home with views, pool & spa.

FamilyValueCheck-in

5 out of 5 average rating, 102 reviews

A landscaped backyard features a pathway of concrete pavers lined with gravel, leading to a seating area with modern outdoor furniture. To one side, a wooden deck provides elevated space with views of the surrounding area and palm trees, complemented by open sky.

Home in Del Cerro

Modern Hilltop Home: Roomy, Views, Family-Friendly

ValueFamilyParks

4.99 out of 5 average rating, 103 reviews

A serene outdoor space showcases a sparkling pool adjacent to a jetted hot tub, with canyon views stretching in the background. A glass fence enhances the vista, and the surrounding landscape features palm trees and gentle hills under a clear blue sky.

Home in San Diego

ModernCoastal I View I Pool ITub

FamilyLocationBackyard

4.97 out of 5 average rating, 136 reviews

A serene backyard oasis features a small spa surrounded by lush greenery and decorative plants. The space is framed by an open wooden structure with a sloped roof, providing a cozy seating area with soft cushions. Unique pendant lights hang above, adding a touch of elegance.

Home in Normal Heights

Luxe Home w. Serene Backyard Spa

ValueFamilyParking

4.99 out of 5 average rating, 284 reviews

The kitchen view highlights a smooth white countertop with a double sink and modern faucets. In the background, large glass doors provide a view of the pool and backyard, while a comfortable seating area is visible. Decorative accents are placed on the countertop.

Home in Escondido

Luxury Four Bedroom Home with pool and game room!

LocationFamilyBackyard

4.78 out of 5 average rating, 207 reviews

A spacious outdoor area is set beside a shimmering pool, featuring a comfortable sectional sofa with soft cushions and a glass-topped coffee table. An oversized umbrella provides shade, while the surrounding patio is designed for relaxation and enjoyment in a family-friendly environment.

Home in Chula Vista

Family Home w/Pool, Hot Jacuzzi and Park Access

ValueFamilyAccess

Condo rentals with a pool

4.98 out of 5 average rating, 273 reviews

A spacious bedroom area features a large window with city views, allowing natural light to illuminate the room. A comfortable bed is placed beside the window, while a cozy seating area with a sofa is positioned nearby, offering a relaxing space to enjoy the scenery.

Condo in Tijuana

ICON Vista Skyline · Mejor opción · Alberca & Gym

ValueLocationLong stay

4.83 out of 5 average rating, 133 reviews

Wooden benches are arranged along a railing, offering views of the ocean. A palm tree and planters filled with flowers enhance the serene outdoor space. The clear blue sky contrasts with the calm ocean waters, creating a peaceful setting for relaxation.

Condo in Solana Beach

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

LocationFamilySleep quality

Condo in Playas de Tijuana

An outdoor area features a shared heated swimming pool and a jacuzzi, both with ocean views. The surrounding space is complemented by lounge chairs and potted plants. The calm waves and clear blue sky create a serene atmosphere for relaxation.

4.9 out of 5 average rating, 117 reviews

Cozy depto. vista al mar•Playas TIJ•Parking priv

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Condo in Hipódromo Aguacaliente

The exterior of a modern high-rise building is displayed against a sunset sky, showcasing multiple glass balconies. Surrounding streets are lined with vehicles, and urban development is visible in the background, highlighting the vibrant atmosphere of the area.

4.84 out of 5 average rating, 217 reviews

Estudio de Lujo en piso 22

LocationValueComfort

Condo in Playas de Tijuana

A round jacuzzi is seen with bubbling water, surrounded by a paved area. The ocean is visible in the background, enhancing the serene ambiance. Lush greenery and a distant building are also present, contributing to the overall setting.

4.84 out of 5 average rating, 123 reviews

Karol’s apartment with 3 pools & jacuzzi Seaview

ValueFamilyBathroom

Condo in Playas de Tijuana

Two bright red chairs are positioned in front of a calm swimming pool, offering views of the ocean. A vibrant sunset paints the sky in shades of pink and orange, while palm trees frame the scene, enhancing the tranquil coastal atmosphere.

4.95 out of 5 average rating, 167 reviews

REJUVENATE @Ocean123 *Available Now,Just Send Msg*

LocationValueKitchen

4.95 out of 5 average rating, 129 reviews

A balcony view reveals a modern apartment complex with multiple balconies and large windows. An open courtyard with landscaped greenery is visible below, featuring stone pathways and seating areas. The clear sky highlights the sleek architecture and contemporary design of the surrounding buildings.

Condo in Tijuana

Modern 2BR Apt w/ Rooftop Pool

ValueLocationCondition

4.82 out of 5 average rating, 114 reviews

A light-filled living area features a comfortable white sofa adorned with various pillows. A small marble table sits in front of the sofa, complemented by fresh tulips in a vase. A side chair and decorative elements add to the inviting ambiance.

Condo in La Mesa

Sweet Little La Mesa Condo(pool+hot tub) NEAR SDSU

LocationFamilyCondition

Other holiday rentals with a pool

5 out of 5 average rating, 23 reviews

Home in Rancho San Diego

Peaceful Family Retreat|Wading pool|Firepit

ValueLocationCondition

4.9 out of 5 average rating, 51 reviews

An inviting outdoor scene showcases a heated pool illuminated with soft purple lights against a backdrop of mountains. Palm trees frame the area, adding a tropical touch. The warmth of the landscape is accented by nearby subtle lighting, enhancing the evening ambiance.

Home in El Cajon

Scenic Getaway w/ Pool, Hot Tub & PS5 GT7 Racing

FamilyValueAccess

4.97 out of 5 average rating, 77 reviews

An elevated view of a spacious backyard reveals a refreshing pool surrounded by lush greenery and palm trees. The home's exterior features solar panels on the roof and ample outdoor seating around the pool, creating a serene oasis for relaxation.

Home in Jamul

Hilltop 2200sqft Oasis: Pool, Views, BBQ

FamilyLocationIndoor spaces

4.74 out of 5 average rating, 73 reviews

A spacious pool area is framed by a smooth, curved edge with clear turquoise water. Lush palm trees and colorful potted plants surround the pool, providing a vibrant outdoor setting, enhanced by natural sunlight filtering through the clouds.

Home in Rancho San Diego

Palmeras House: Pool + outdoor BBQ

LocationValueAccess

4.97 out of 5 average rating, 90 reviews

Home in El Cajon

Listing updated-click host profile for new listing

FamilyLocationQuiet

5 out of 5 average rating, 25 reviews

Home in Descanso

Infinity Pool & Spa-Private-Endless Views-Luxury

FamilyLocationBathroom

4.95 out of 5 average rating, 20 reviews

A serene courtyard features smooth stones and desert landscaping, accented by palm trees and a vibrant green plant. The rustic entryway, marked by wooden doors, invites guests into the home while sunlight filters through the foliage above.

Home in El Cajon

Weekend at Berny's

ValueLocationIndoor spaces