Holiday rentals with a pool in La Mesa

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, 184 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

LocationFamilyCondition

The property features a spacious backyard with a heated pool surrounded by lounge chairs. Palm trees line the perimeter, and soft lighting illuminates the outdoor area during sunset. The two-story house overlooks the pool, creating an inviting atmosphere for relaxation and gatherings.

4.93 out of 5 average rating, 252 reviews

Family Pool Retreat + Gym, Fire Pits, Views (Sleep

Find your family's dream spot in San Diego! Our cozy house sits on a quiet hill, offering privacy and amazing sunset views. Dive into our pool year-round (heating at an additional cost), roast marshmallows by the fire, and cook up fun meals together. With 3 bedrooms and 2 bathrooms, it’s perfect for families, accommodating up to 9 guests. Plus, we're close to all the best attractions. Want a vacation you'll always remember? Send us a message to make it happen! 🌅🏠 We have 3 comfy beds that can

FamilyValueComfort

4.98 out of 5 average rating, 137 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

LocationFamilyHot tub

4.85 out of 5 average rating, 263 reviews

A spacious outdoor area features a clear blue pool surrounded by palm trees. Lounge chairs are positioned nearby, and a shaded table with chairs offers a spot for relaxation. The backyard showcases a privacy fence and ample sunlight.

Home in El Cajon

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

Escape to a fresh 4-bedroom retreat for family and friends (10 ppl max). Updated in January of 2024 with new furniture, and fixtures. Bask in the sun on the deck, take a dip in the pool. Enjoy the private and fenced backyard, BBQ, or the recently renovated and modern Kitchen. This home is perfect for vacations or remote work. Explore San Diego beaches and all the area has to offer, the most popular tourist destinations are all within a 20-30 minute drive. 20 minutes to the beach! Book with us!

LocationFamilyAir conditioning

4.9 out of 5 average rating, 116 reviews

*NO TAX*/Heated Pool/Hot Tub/Pizza Oven/Playground

Escape to our luxury 5bd/4ba retreat with San Diego’s best backyard on a massive 10,000+ sqft lot: ✨SAVE 10.5% TAX!✨ 🏖️ Heated saltwater pool*, hot tub, outdoor shower 🍕 Outdoor lounge w/ TV, fire pit, pizza oven, BBQ 🍊 Abundant free-to-pick blood orange, passionfruit, avocado, macadamia trees 🎥 Giant movie projector + screen 🛝 Kids playground 🐶 Dog-friendly Ideal for groups, this private haven sits by Lake Murray’s beautiful hiking trails for the perfect mix of relaxation & adventure!

LocationValueSleep quality

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.

4.96 out of 5 average rating, 180 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.

ValueFamilyBeach

A dining area is highlighted by a round wooden table surrounded by six wooden chairs. A cozy blue sofa is positioned nearby, with large glass doors opening to a pool area. Natural light enhances the space, complemented by a modern pendant light overhead.

4.92 out of 5 average rating, 102 reviews

San Diego Oasis- A Retro Retreat w/ King Size Bed!

Welcome to San Diego Oasis, a retro retreat--a mid-century modern oasis in sunny San Diego! This stylish home combines classic charm with all the modern upgrades you desire. Unwind by the sparkling pool, enjoy a friendly game of air hockey or corn hole, board games or enjoy s'mores around the gas fire pit . The retro retreat is the perfect blend of comfort, convenience, and timeless design. SD's most popular attractions are all within a 20-30 minute drive. Only 20 minutes to the beach!

LocationFamilyBeach

4.94 out of 5 average rating, 210 reviews

A swimming pool reflects sunlight under a clear blue sky, surrounded by a patio area. A colorful hammock is suspended near the pool, while potted plants add greenery. The adjoining building features large windows and a seating area.

Guest suite in La Mesa

Hacienda de las Campanas (Bell Hacienda)

Stay in classic, historic California Hacienda style! A complete, self-contained apartment--your casita--within our beautiful, historic Monterey Spanish Revival hacienda home, situated on a half acre. The apartment has a separate, private entrance and includes a sunlit living/dining room opening on to a large swimming pool; a small kitchenette; and a private bedroom and bathroom down your own hallway. The suite is tastefully furnished consistently with the historic Spanish architecture.

LocationFamilyCheck-in

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, 205 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.

FamilyValueNearby

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.

4.93 out of 5 average rating, 234 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 king size bed and a memory foam sofa bed, with a well equipped kitchenette. Plenty of parking in driveway (max 2 cars). Please read entire listing for details.

LocationFamilyAccess

Villa in Rancho San Diego

A serene outdoor area features a hot tub surrounded by stone elements and a waterfall feature. Sunlight filters through the overhead pergola, creating a play of light and shadow. Lush greenery and a glimpse of a spacious pool can be seen in the background.

Private Villa: Pool, Slide & Hot Tub

Summary: * Spacious: 5,000 SF indoor living space & 10,000+ SF outdoor living space * Fantastic Pool: Complete with waterslide, cave /grotto & multiple fountains / waterfalls * Relaxing Hot Tub: 5 hours of free heating daily from 5pm-10pm * Event Policy: No weddings, events, or parties with 16 or more guests * Accommodates: This home can accommodate up to 16 guests /see “more things to note" for more info on beds/air mattresses

ValueFamilyHiking

4.9 out of 5 average rating, 297 reviews

A private pool is surrounded by a spacious patio, featuring a built-in spa and floating pool accessories. Lounge chairs are arranged by the poolside, while the nearby house is complemented by green shrubbery and playful palm trees. Bright sunlight highlights the inviting blue water.

4.9 out of 5 average rating, 115 reviews

QUIET HOME -3 Bedroom & Den, + POOL, sleep 8 plus

Welcome to the La Mesa Pool House! Our cozy house in La Mesa is the perfect place to relax and recharge with the family. This house is walking distance to many great La Mesa eateries such as Terra Restaurant and Surf and Soul. We are also located just 10 minutes away from San Diego State University and we are less than 20 minutes from all major attractions in San Diego: downtown, Little Italy, Zoo, Sea World, beaches and more!

ValueFamilyLong stay

Popular amenities for La Mesa rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.87 out of 5 average rating, 239 reviews

Bright and spacious home with views, pool & spa.

LocationFamilyPool

4.91 out of 5 average rating, 120 reviews

San Diego Oasis: Private Pool & Sunny Escape!

ValueLocationAccuracy

A serene outdoor pool area features a refreshing blue pool surrounded by terracotta tiles. Two lounge chairs are positioned nearby, inviting relaxation. A wooden fence offers privacy while views of the landscape and sky are visible in the background, creating a tranquil atmosphere.

4.81 out of 5 average rating, 104 reviews

The Agave House | Mountain Views & Pool

FamilyLocationComfort

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.

4.98 out of 5 average rating, 116 reviews

ModernCoastal I View I Pool ITub

LocationFamilyQuiet

4.96 out of 5 average rating, 227 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 !

ValueLocationCheck-in

4.86 out of 5 average rating, 123 reviews

Entertainers Dream Pool Home

ValueFamilyCheckout

4.94 out of 5 average rating, 156 reviews

An outdoor area features a clear saltwater pool surrounded by elegant lounge chairs. A shaded umbrella stands nearby, and the landscape includes rolling hills and a distant view of the mountains, providing a serene backdrop for relaxation.

Home in El Cajon

Fletcher Hills luxury, Sunset View, 4 BR, Pool/Spa

FamilyLocationDecor

4.92 out of 5 average rating, 103 reviews

Home in El Cajon

San Diego Pool Retreat | Game Room • Sleeps 14

LocationFamilyHospitality

Apartment rentals with a pool

4.82 out of 5 average rating, 124 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.

Apartment in La Mesa

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

LocationValueAmenities

Apartment in Spring Valley

A comfortable living area features a light-toned sofa adorned with colorful cushions and a wooden coffee table. A green chair complements the space, while a decorative wall art piece and potted plant add interest. A dining area is visible in the background.

Spacious 2 BR w/ Free Parking & WiFi

FamilyLocationCheck-in

4.78 out of 5 average rating, 170 reviews

Apartment in Mission Valley

A cozy living room features a comfortable gray couch adorned with a woven throw, complemented by a small circular table and a patterned area rug. Natural light floods the space through glass sliding doors that lead to a balcony with seating, framed by soft curtains.

Cozy home central to beaches & attractions

LocationValueQuiet

4.92 out of 5 average rating, 200 reviews

A spacious living area features large glass sliding doors that reveal an expansive ocean view with a sunset. Comfortable seating includes a modern gray sectional and two accent chairs, inviting relaxation. The room is illuminated with warm, natural light, enhancing the serene coastal atmosphere.

4.94 out of 5 average rating, 336 reviews

Beach Front Condo - Capri by the Sea - Remodeled

ValueLocationCleanliness

An arched window frames a serene view of palm trees and distant hills at dusk. The soft hues of a fading sunset create a calming atmosphere. Neighborhood rooftops are visible below, with twinkling lights in the distance hinting at urban life.

4.97 out of 5 average rating, 143 reviews

Bay View Condo in Pacific Beach

LocationFamilyAmenities

A spacious living area is showcased with a comfortable leather sofa and a decorative rug. A dining table with four chairs is positioned near floor-to-ceiling windows, offering natural light. Art pieces adorn the walls, complementing the inviting atmosphere.

4.92 out of 5 average rating, 217 reviews

Windows to the Ocean

ValueFamilySleep quality

A bright and airy living room features large floor-to-ceiling windows showcasing expansive ocean views. Comfortable seating arrangements consist of a plush sofa and armchairs, accented by light decor. A coffee table sits at the center, complemented by side tables with lamps, fostering a relaxing atmosphere.

5.0 out of 5 average rating, 143 reviews

The Endless Summer Condo!

FamilyLocationBeach

A bright living area features a large window with ocean views and light blue skies. A wooden coffee table rests on a patterned rug, surrounded by comfortable seating. A flat-screen TV is located on a white media console, enhancing the room's modern look.

4.97 out of 5 average rating, 208 reviews

Beautifully remodeled 10th floor oceanfront condo

LocationValueAir conditioning

Other holiday rentals with a pool

4.89 out of 5 average rating, 280 reviews

A serene pool area features crystal-clear water, with striped lounge floats anchored in the center. Surrounding palm trees offer shade, while natural stone accents decorate the pool's edge. The sound of a waterfall can be faintly heard, contributing to a calming atmosphere.

Guest suite in El Cajon

Tranquil Poolside Studio

FamilyValueOutdoor spaces

4.93 out of 5 average rating, 100 reviews

The outdoor area features a private pool and hot tub, surrounded by lounge floats. A patio with shaded seating is present, alongside a grill. Indoors, an arcade game stands ready for entertainment, and the living room showcases a comfortable sofa and accent chairs with natural light streaming through the windows.

Guest suite in La Mesa

Hot Tub, Pool, Arcade Game, Patio, Family Friendly

LocationFamilyDecor

4.95 out of 5 average rating, 157 reviews

The outdoor pool area features a clear, inviting pool surrounded by a stone deck. Tall palm trees sway gently in the background, which is complemented by lush greenery. A shade sail is stretched overhead, providing comfort on sunny days.

Guest suite in La Mesa

Birdsong Suite | Family-friendly getaway

FamilyValueWalkability

Villa in Rancho San Diego

An inviting outdoor entertainment area features a heated saltwater pool surrounded by elegant lighting and stylish lounge furniture. Inflatable swan floats rest in the water, while vibrant umbrellas provide shade over seating. Lush landscaping enhances the serene environment, making it ideal for relaxation.

Enchanted Paradise! Pool+Spa+Outdoor Kitchen

LocationFamilyGrill

4.92 out of 5 average rating, 215 reviews

A spacious living area is furnished with a large sectional sofa and an armchair, complemented by a coffee table. A flatscreen TV is mounted on a media console, with natural light streaming in from a nearby window. An open layout leads to the dining area and kitchen.

4.93 out of 5 average rating, 240 reviews

Stunning San Diego Home w/Pool,Spa,Outdoor Oasis

FamilyLocationGetting around

5.0 out of 5 average rating, 302 reviews

A private outdoor area features a heated pool surrounded by lush green grass and modern loungers. An inviting fire pit is centrally located, with two stylish chairs positioned nearby. The backdrop includes well-maintained shrubbery and tall trees, enhancing the tranquil ambiance.

Home in Serra Mesa

Midcentury Lux 4BR home w Pool/Spa/Cabana/Firepit

LocationValueKitchen

4.99 out of 5 average rating, 112 reviews

AmazingVIEWS! Hilltop Guest House with XL Balcony~

ValueLocationCleanliness