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Holiday rentals with a pool in Lakeside

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Lakeside

  • Total holiday rentals

    Explore 30 holiday rentals in Lakeside

  • Nightly prices starting at

    Lakeside holiday rentals start at ₹4,756 per night before taxes and fees

  • Verified guest reviews

    Over 1,470 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 of Lakeside holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Lakeside rentals

  • 4.9 Average rating

    Lakeside stays are highly rated by guests – averaging 4.9 out of 5!

Top-rated rentals with a pool in Lakeside

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

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Guest favourite
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

✨ Luxury Hillside Retreat | Private Entrance | Saltwater Pool & Spa Enjoy this luxuriously furnished 4-bedroom, 2-bath home in Fletcher Hills, CA, perched on a hill with stunning mountain and San Diego city views. Relax in your private saltwater pool and jacuzzi with color-changing LED lights, or unwind indoors with full kitchen access, high-speed Wi-Fi, and smart TVs with Netflix. Perfect for couples, business travelers, and families, this cozy yet elegant retreat makes you feel right at home.

4.94 out of 5 average rating, 155 reviews
Top guest favourite
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.
Guest house 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

4.98 out of 5 average rating, 115 reviews
Superhost
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!

4.85 out of 5 average rating, 260 reviews
Top guest favourite
An aerial view of the estate shows a sprawling layout with a swimming pool and outdoor leisure areas. A basketball court is visible beside the home, surrounded by lush greenery and landscaped gardens. The arrangement of buildings and paths creates an inviting outdoor space.
Home in Ramona

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.

4.98 out of 5 average rating, 121 reviews
Guest favourite
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

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.

4.96 out of 5 average rating, 418 reviews
Top guest favourite
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.
Guest house in La Mesa

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.

4.97 out of 5 average rating, 176 reviews
Guest favourite
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.
Home in San Diego

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!

4.93 out of 5 average rating, 98 reviews
Top guest favourite
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.
Home in La Mesa

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.

4.99 out of 5 average rating, 204 reviews
Top guest favourite
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.

4.98 out of 5 average rating, 120 reviews
Top guest favourite
An outdoor seating area is equipped with a sectional couch surrounding a stone fire pit, with flames flickering invitingly. A large dining table offers ample seating. The heated pool glistens in the background, surrounded by lounge chairs and shaded umbrellas.
Home in El Cajon

Family Fun Oasis Pool Spa and Game Room

Exceptional home w/heated pool and spa in a quiet neighborhood; kitchen has everything you need and more! Perfect for families with kids of various ages or multiple families. What to Expect: - Heated pool w/safety cover - Hot tub - Game Room - Trampoline - Jungle gym - Baby/toddler supplies (pack N play/High Chair) - Spacious master suite. - 20 mins to the beach, the San Diego Zoo, Balboa Park, Sea World, Little Italy and downtown San Diego and all that it has to offer!

4.96 out of 5 average rating, 123 reviews
Guest favourite
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)

4.96 out of 5 average rating, 222 reviews
Top guest favourite
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.
Villa in Rancho San Diego

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

4.9 out of 5 average rating, 295 reviews

Popular amenities for Lakeside rentals with a pool

KitchenWifiPoolFree parking on premisesAir conditioning

House rentals with a pool

Top guest favourite
The image captures a modern saltwater pool illuminated in vibrant blue tones. Surrounding vegetation and trees frame the pool area, enhancing privacy. A gated fence ensures security, while landscaped features and lounge chairs offer inviting relaxation options.
Home in La Mesa

Mt. Helix Resort+ Pool/Spa, Pickleball, Amenities!

4.99 out of 5 average rating, 101 reviews
Superhost
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.

4.87 out of 5 average rating, 239 reviews
Top guest favourite
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

4.98 out of 5 average rating, 115 reviews
Superhost
An outdoor dining area is shown with a table and six chairs adjacent to a sparkling pool. Lush palm trees frame the scene, while a BBQ grill is positioned nearby. The sky is painted with soft hues of purple and pink during sunset.
Home in El Cajon

4BR Pool and Fast WiFi Fifteen Min to SD

4.77 out of 5 average rating, 104 reviews
Superhost
Home in La Mesa

San Diego Oasis: Private Pool & Sunny Escape!

4.91 out of 5 average rating, 119 reviews
Top guest favourite
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

4.98 out of 5 average rating, 135 reviews
Superhost
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.
Home in La Mesa

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

4.93 out of 5 average rating, 250 reviews
Top guest favourite
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

5.0 out of 5 average rating, 299 reviews

Apartment rentals with a pool

Superhost
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.
Apartment in Spring Valley

Spacious 2 BR w/ Free Parking & WiFi

4.79 out of 5 average rating, 167 reviews
Guest favourite
A circular pool is surrounded by lounge chairs and vibrant green umbrellas, offering shade and comfort. In the background, the Pacific Ocean is visible, with a clear blue sky above and a few birds flying. Lush landscaping enhances the outdoor space.
Apartment in Del Mar

Studio Condo at Wave Crest Resort

4.89 out of 5 average rating, 563 reviews
Guest favourite
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

4.82 out of 5 average rating, 121 reviews
Guest favourite
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.
Apartment in Mission Valley

Cozy home central to beaches & attractions

4.91 out of 5 average rating, 198 reviews
Guest favourite
A spacious living area features large windows offering panoramic ocean views and allowing natural light to fill the room. A comfortable blue couch is positioned near a glass coffee table, with a television mounted above a dark wooden entertainment unit.
Apartment in Pacific Beach

Enchanted Ocean Sunsets

4.91 out of 5 average rating, 202 reviews
Guest favourite
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.
Apartment in Pacific Beach

Windows to the Ocean

4.92 out of 5 average rating, 215 reviews
Top guest favourite
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.
Apartment in Pacific Beach

Luxury Oceanfront Condo with Unbelievable Views

4.99 out of 5 average rating, 220 reviews
Top guest favourite
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.
Apartment in Pacific Beach

The Endless Summer Condo!

5.0 out of 5 average rating, 140 reviews

Other holiday rentals with a pool

Guest favourite
Villa in El Cajon

@Fantastic villa, giant pool, guest house, golf !

4.96 out of 5 average rating, 170 reviews
Top guest favourite
An outdoor space presents a well-maintained pool surrounded by lounge chairs and tropical plants. A fire pit is set with a bottle of champagne on an oval table. Deck umbrellas offer shade, creating a relaxing atmosphere near the pool’s edge.
Bungalow in Escondido

Bella Vita,Majestic Resort w/ Bungalow Pool House

4.99 out of 5 average rating, 102 reviews
Guest favourite
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.
Villa in Rancho San Diego

Enchanted Paradise! Pool+Spa+Outdoor Kitchen

4.92 out of 5 average rating, 214 reviews
Top guest favourite
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.
Guest house in La Mesa

Private 1 BR Paradise Retreat

4.99 out of 5 average rating, 181 reviews
Guest favourite
Guest house in Lakeside

Bright cozy guesthouse in the hills

4.85 out of 5 average rating, 84 reviews
Superhost
The living area is accented with wooden beams and features a cozy sofa, an armchair, and a round wooden coffee table. Natural light fills the room through a window, with a piece of abstract artwork displayed on the wall, enhancing the inviting space.
Home in Lakeside

Lakeside Haven | Mountain Views, Private Pool

4.87 out of 5 average rating, 45 reviews
Guest favourite
A spacious deck is illuminated by string lights, creating a serene atmosphere during twilight. The light-colored home features large glass doors that lead to the interior, while cozy seating arrangements are positioned for relaxation against the backdrop of nature.
Home in Lakeside

Stunning Mountains view

4.81 out of 5 average rating, 26 reviews
Top guest favourite
An outdoor area showcases a inviting pool surrounded by lounge chairs and sun umbrellas. A fire pit, bordered by stone, sits nearby. Lush greenery and colorful flowers enhance the serene landscape, with distant hills visible against a clear blue sky.
Home in Lakeside

Lakeside Hilltop Retreat w/Amazing Pool & Spa

5.0 out of 5 average rating, 69 reviews

When is the best time to visit Lakeside?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price₹37,760₹28,439₹36,714₹30,912₹37,570₹42,706₹35,192₹49,364₹31,768₹36,904₹35,572₹34,050
Avg. temp15°C15°C16°C17°C18°C20°C21°C22°C22°C20°C17°C14°C

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