Vacation rentals with a pool in Lakeside

4.98 out of 5 average rating, 124 reviews

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.

FamilyValueWifi

4.98 out of 5 average rating, 115 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

FamilyLocationComfort

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!

ValueFamilyNearby

4.84 out of 5 average rating, 221 reviews

A tiny house is nestled in a hillside, surrounded by lush greenery and cacti. The wooden structure features a spacious deck with seating, and large windows that invite natural light. Scenic mountain views are present in the background, enhancing the tranquil setting.

Tiny home in Escondido

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.

ValueFamilyWifi

4.81 out of 5 average rating, 98 reviews

Home in Alpine

Montecito Cottage - Tuscan Farmhouse, Pool, Views

Welcome to The Montecito Cottage in Alpine, Ca. where Tuscan whimsy meets farmhouse charm amidst breathtaking mountain views. Perfect for a serene getaway, this idyllic vintage 2-bedroom, 2.25-bathroom abode sleeps up to 4 guests in the main house, we also have a guest cottage . We welcome your furry friends, ensuring a memorable stay for all. With several gardens, 5 fountains, an outside kitchen, and a sprawling yard, immerse yourself in nature's embrace while enjoying the comfort of the home

FamilyLocationView

4.96 out of 5 average rating, 421 reviews

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.

LocationFamilyParks

4.96 out of 5 average rating, 180 reviews

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 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.

LocationFamilyKitchen

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!

FamilyLocationParking

4.99 out of 5 average rating, 205 reviews

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.

FamilyValueComfort

4.98 out of 5 average rating, 127 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.

FamilyValueAir conditioning

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

Brand New Property! Massive garden of Eden style resort home with sprawling outdoor entertainment area and spacious open concept inside, perfect for large families with kids and responsible adults. Updated top to bottom with all new outdoor and indoor furniture, modern upgrades in all bedrooms and common areas. Centrally located and 20 minutes from the beach and all of SD's top attractions! 8 person hot tub, sparkling saltwater pool and new outdoor kitchen. Don't miss out!

ValueLocationLayout

4.92 out of 5 average rating, 215 reviews

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 !

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)

LocationValuePool

Popular amenities for Lakeside rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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.

4.87 out of 5 average rating, 239 reviews

Bright and spacious home with views, pool & spa.

FamilyValueCondition

4.9 out of 5 average rating, 114 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.

Home in La Mesa

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

FamilyLocationPool

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

ValueFamilyTV

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

FamilyValueGrill

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

FamilyLocationBackyard

4.98 out of 5 average rating, 520 reviews

Home in Encinitas

Lux Casita with Pickleball & Resort Amenities

FamilyValueHiking

4.9 out of 5 average rating, 116 reviews

Home in La Mesa

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

ValueFamilyIndoor spaces

A spacious backyard is showcased with a glistening pool surrounded by a concrete deck. Green grass offers a soft contrast, while lounge chairs and a shaded seating area are positioned for relaxation. String lights illuminate the space, enhancing the outdoor ambiance during twilight.

4.95 out of 5 average rating, 110 reviews

San Diego Pool House with Luxury King/Queen Suites

ValueFamilyIndoor spaces

Condo rentals with a pool

4.92 out of 5 average rating, 200 reviews

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.

Condo in Mission Valley

Cozy home central to beaches & attractions

ValueFamilyLong stay

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.

Condo in Spring Valley

Spacious 2 BR w/ Free Parking & WiFi

FamilyValueParking

4.78 out of 5 average rating, 170 reviews

4.82 out of 5 average rating, 122 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

ValueLocationLong stay

4.94 out of 5 average rating, 336 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.

Condo in Pacific Beach

Beach Front Condo - Capri by the Sea - Remodeled

LocationValueSleep quality

4.97 out of 5 average rating, 143 reviews

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.

Condo in Pacific Beach

Bay View Condo in Pacific Beach

FamilyLocationCheck-in

4.89 out of 5 average rating, 568 reviews

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.

Condo in Del Mar

Studio Condo at Wave Crest Resort

FamilyLocationLaundry

4.92 out of 5 average rating, 145 reviews

A modern kitchen showcases white cabinetry and sleek stainless steel appliances. A quartz countertop features a black sink, complemented by stylish pendant lighting. A bowl of lemons adds a pop of color, while glass-front cabinets display dishware. Natural light illuminates the space, enhancing a clean aesthetic.

Condo in Carlsbad

Resort Life in La Costa

ValueLocationCheck-in

5.0 out of 5 average rating, 142 reviews

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.

Condo in Pacific Beach

The Endless Summer Condo!

FamilyLocationLaundry

Other vacation rentals with a pool

4.96 out of 5 average rating, 139 reviews

A serene pool area features a cascading waterfall illuminated in soft purple hues. The water flows gently into the heated pool, adding a calming effect to the ambiance. Wood paneling surrounds the pool, creating a private and tranquil atmosphere.

Villa in San Diego

Lux Villa: Heated Pool & Sauna

ValueFamilyNearby

4.99 out of 5 average rating, 183 reviews

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

Private 1 BR Paradise Retreat

FamilyLocationNearby

Farm stay in Santa Ysabel

A serene outdoor area features comfortable wooden chairs beside a pool, surrounded by landscaped gardens. A pergola provides shade over a small table, inviting relaxation. Clear blue skies enhance the tranquil atmosphere, and the distant view includes lush greenery and distant structures.

Adobe Acres Ranch House

FamilyValueNearby

5.0 out of 5 average rating, 153 reviews

5.0 out of 5 average rating, 433 reviews

Guesthouse in La Mesa

Private Poolside Cabana

LocationFamilyWifi

4.81 out of 5 average rating, 93 reviews

Guesthouse in Lakeside

Bright cozy guesthouse in the hills

ValueFamilyAir conditioning

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

LocationValueCheck-in

4.88 out of 5 average rating, 48 reviews

4.91 out of 5 average rating, 97 reviews

An outdoor pool features a comfortable lounge area at its edge, surrounded by tall palm trees. Scenic mountain views are visible in the background. The pool design incorporates a stone border and gentle water features, contributing to the serene ambiance.

Home in Alpine

Luxury Escape | Heated Pool/Spa • Views + Events

ValueLocationWalkability