Holiday rentals with a pool in Eastlake

4.99 out of 5 average rating, 143 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

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

4.89 out of 5 average rating, 153 reviews

The outdoor pool glows in the evening light, revealing clear water with a unique shape. Surrounding the pool, lounge chairs and umbrellas create a tranquil space for relaxation. A gas fire pit adds warmth to the area, enhancing the captivating view of the cityscape beyond.

Home in Otay Mesa

Ocean View Private Pool & Spa Home w/Putting Green

Welcome to your Private, resort style, pool and spa home with spectacular views day and night! 4 bedrooms, 3 baths (1 King and bathroom with shower on main/ground level and CA King in primary suite. Tropical setting, a short drive to major attractions like our world famous Beaches, Zoo, Sea World, Balboa Park, Downtown, Coronado, Outlet Shopping, & Sesame Place! Soaring 18 foot ceilings in the Living room and Dining room. Outdoor dining, Putting Green, and lounges for resort-like relaxation!

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.

4.98 out of 5 average rating, 192 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.

4.95 out of 5 average rating, 114 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

Welcome to CityPoint where you'll be staying in a modern 2BR apartment that's perfect couples, medical visits, or business travelers. Located on Paseo del Rio with easy access to major roads, it's convenient for city exploration or crossing the border. We offer private parking for your convenience and a range of upscale amenities, including: rooftop pool with panoramic city views, a well-equipped gym, a common area for relaxing. Walking distance to restaurants and important landmarks.

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, 183 reviews

Mid-Century Style Family House with Spa

Beautiful Mt. Helix mid-century modern family home with incredible views, designed by architect of original Las Vegas, Desert Inn 3/4 acre.Less than 20 minute drive to beaches/Zoo/Sea World/Downtown, . With a swimming pool/hot tub, whole House have AC to. surrounded by California Oak/orange/lemonpomegranate trees and herb garden this home is the epitome of 1950’s luxury. A perfect family oasis, you won’t even want to leave the property. No loud parties please, this is a quite community.

4.88 out of 5 average rating, 375 reviews

A solar-heated pool glimmers in the sunlight, surrounded by inviting lounge chairs and a shaded umbrella. A cozy outdoor dining area with a table is visible in the background, framed by lush greenery and large eucalyptus trees.

Guest suite in Bonita

Resort-Style Living, Pool, Close to All San Diego

Nestled in a quiet, discreet neighborhood, our private air-conditioned studio offers a safe & serene retreat. Attached to a stunning ranch-style executive home, it features an amazing pool for your relaxation. We are conveniently located a short distance away from the Gaylord Convention Center, the Olympic Training Center, downtown San Diego, Comic-Con, major attractions, concert venues, beaches, airport & Mexico. Enjoy a complimentary butler tray that includes coffee, tea & snacks.

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.

4.95 out of 5 average rating, 118 reviews

Casa Bahia Beautiful San Diego Home with Pool

Welcome to Casa Bahia! Our home has been completely upgraded and is ready to host your perfect getaway. Conveniently located close to the Chula Vista Bayfront and 10 minutes to downtown San Diego or the beach. Our home features a kitchen with top of the line appliances, brand new furniture, 4 bedrooms, 2 full bathrooms, a large pool, a yard with a lounge area, BBQ, and a clean peaceful feel. In addition, our stylish and minimalist place to stay is perfect for group or family trips.

Guesthouse in Lake Murray

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, 137 reviews

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

This is your 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 beaches, Downtown, La Jolla, Zoo, Stadiums, Sea World, Convention Center + more. Hike next door at Mission Trails & Lake Murray. Smart TV, wifi, two zone AC, full kitchen, W/D combo and top quality finishes and furniture. Everything you need for memorable vacation! No smoking or vaping on the property.

A spacious living room features a plush sectional sofa with an assortment of decorative pillows. A modern coffee table made from natural wood sits on a patterned area rug. Large sliding doors allow light to enter and provide views of the outdoor pool area.

4.91 out of 5 average rating, 138 reviews

An Oasis,Heated Pool, JQZ,Grill,Ocean&MTN View

Welcome home to this gorgeous remodeled and upgraded single story 3-bedroom, 2 bath panoramic view property in the heart of Chula Vista. This home is absolutely perfect to soak up the sun, relax or stay pool side and work remotely. As you walk up to the home you will notice a stunning manicured palm tree and a beautiful landscaping. Warmth and light welcome you into the spacious Living Room which offers a wall-to-wall sliding door that overlooks the back yard and the pool.

Apartment in Spring Valley

A serene sunset view is captured with soft hues of purple, pink, and orange streaking the sky. Silhouetted hills create a calming backdrop, while the dimming light gently transitions the scenery into evening.

4.88 out of 5 average rating, 169 reviews

Comfy, Cozy Flat With Pool & Spa!

Our flat has a patio that enjoys great sunsets. We are freeway close to all, easy in and easy out!! You’ll love the place because of the comfy bed, space, patio and access to pool and spa. Also, the yard can be enjoyed for relaxing, eating, bonfires, horseshoes and cornhole. An adjoining space is also an AIRBNB studio suite. Great for traveling friends or as an alternative place to consider for your stay. Look for Foemer man Cave with Pool And Spa.

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.

4.79 out of 5 average rating, 179 reviews

Family Home w/Pool, Hot Jacuzzi and Park Access

Spacious, pet-friendly home perfect for families or groups up to 10. Located in a quiet, residential neighborhood with direct access to a large park featuring 2 playgrounds, basketball court, fitness stations, and picnic areas. Enjoy 3–4 car parking, a full kitchen, fast Wi-Fi, and plenty of room to gather. This clean, well-loved home offers comfort, value, and a central location — ideal for those who appreciate space, convenience, and a responsive host.

4.88 out of 5 average rating, 250 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 La Mesa

Tranquil Poolside Studio

Quiet Poolside Studio Suite! Perfect for visiting family in La Mesa or enjoying everything San Diego has to offer! Please note: this is not a party house. Private side entrance to a relaxing poolside studio. Very quiet with TV, and full kitchen. Comfortable queen size bed and sofa that can sleep one more person comfortably. We are 20 min to the beach, or relax and enjoy the pool! Close to SDSU and easy freeway access to anywhere in San Diego.

Popular amenities for Eastlake rentals with a pool

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 192 reviews

The Queen House

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.

4.9 out of 5 average rating, 106 reviews

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

Home in Greater North Park

An outdoor living space is showcased, featuring a circular pool surrounded by wooden decking. Comfortable lounge seating with dark cushions and a fire pit is positioned under string lights. Umbrellas provide shade while a gas grill is visible nearby, creating an inviting atmosphere.

4.96 out of 5 average rating, 181 reviews

Luxury North Park Home I Near Dining, Shops + Zoo

4.93 out of 5 average rating, 268 reviews

A vibrant heated pool is surrounded by minimalistic landscaping, featuring tall cacti and a clean white fence. Soft lounge chairs are positioned nearby for relaxation. The clear water reflects the blue sky, creating a refreshing setting for leisure and enjoyment.

Home in Mission Hills

Lionhead - Private Boutique Home

4.88 out of 5 average rating, 211 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 Lake Murray

Bright and spacious home with views, pool & spa.

Home in University Heights

A tranquil pool area is surrounded by lush landscaping, featuring palm trees and various plants. Two lounge chairs with an umbrella are positioned beside the pool, reflecting a serene evening sky with hues of pink and purple.

4.97 out of 5 average rating, 153 reviews

University Heights Oasis Getaway

4.82 out of 5 average rating, 126 reviews

The outdoor area showcases a clear pool surrounded by a spacious patio. Lounge chairs, a poolside table, and an umbrella are positioned for relaxation. The backdrop features low landscaping with cacti and a glimpse of the house, enhancing the tranquil setting.

Home in Lake Murray

Mid-Century Modern and Contemporary House

A scenic hillside is displayed, featuring a variety of homes nestled among lush greenery. The landscape showcases a blend of residential architecture within a mountainous region, with expansive views of the surrounding area under a clear blue sky.

4.93 out of 5 average rating, 124 reviews

Updated TownHome, Great Location, Fantastic Views

Condo rentals with a pool

4.98 out of 5 average rating, 249 reviews

A modern seating area is highlighted by a comfortable gray sofa adorned with textured orange and cream pillows. A plush throw blanket drapes over one arm of the sofa. A marble-top coffee table complements the space, featuring a decorative item.

Condo in Madero Sur

Skyline Views | Luxury Studio with Swimming Pool

An aerial view captures the oceanfront condo alongside the sandy beach, with an expansive coastline stretching below. The surrounding neighborhood features a mix of residential and commercial structures, interconnected by roads and pathways, creating a vibrant coastal community.

4.85 out of 5 average rating, 179 reviews

Ocean front condo heart of pacific beach

4.96 out of 5 average rating, 251 reviews

The kitchen features modern appliances, including a stainless steel refrigerator, microwave, and range. A spacious granite countertop offers ample workspace, while cabinets provide organized storage. The area is brightly lit with recessed lighting, enhancing the clean and functional design.

Condo in University City

Centrally located n UCSD/ utc-laJolla

4.95 out of 5 average rating, 214 reviews

A cozy living area is visible, featuring a spacious gray sofa adorned with patterned pillows. A wooden dining table is placed in the foreground. Large glass windows frame stunning city views, allowing natural light to illuminate the space.

Condo in Agua Caliente

✨newCONDO @ LuxuryTOWER❤ close2⚽ XOLOS✈ airport & BORDER

4.84 out of 5 average rating, 107 reviews

A shared pool area is visible, featuring clear blue water and several lounge chairs lined along the edge. The pool is surrounded by a well-maintained grassy area. In the background, a casual seating area and dining space are partially visible, providing a setting for relaxation.

Condo in Tijuana

CASA MB 2BR 2BR POOL, GYM, CO-WORK AREA

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.

4.92 out of 5 average rating, 176 reviews

Enchanted Ocean Sunsets

4.78 out of 5 average rating, 146 reviews

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

A person stands beside floor-to-ceiling windows that offer a view of the ocean during sunset. The seating area is furnished with a leather recliner, and a vibrant artwork adorns the wall. Soft lighting from two lamps enhances the warm ambiance.

4.94 out of 5 average rating, 510 reviews

Oceanfront Elegant Condo - Remarkable Amenities

Other holiday rentals with a pool

5 out of 5 average rating, 49 reviews

A clear blue swimming pool reflects sunlight, showcasing gentle ripples on the water's surface. A sandy area is visible at the pool's edge, featuring a small starfish positioned on the light-colored surface.

Apartment in Chula Vista

Serene & Spacious Suite in SoCal/1 Queen bed/Pool

4.96 out of 5 average rating, 54 reviews

The entrance is framed by a white door, leading into a well-lit room featuring a spacious bed and a cozy kitchenette with wooden cabinetry. A welcome mat with a floral design sits at the threshold, inviting guests inside.

Tiny home in Encanto

Suburban poolside cozy casita, with a beachy vibe

5 out of 5 average rating, 15 reviews

Airbnb Luxe: Designer Pool, Fitness and Office

4.91 out of 5 average rating, 34 reviews

A serene swimming pool is positioned in front of a single-story home with large windows. Lush greenery and palm trees surround the space, creating a private oasis. Outdoor seating is available on the patio, providing a tranquil area to relax.

Guesthouse in Bonita

Casita Bonita

4.97 out of 5 average rating, 69 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!

A serene outdoor space is showcased at twilight, featuring a modern pool surrounded by green grass. Cozy seating areas, including hanging chairs, are visible. The adjacent bar area is illuminated, enhancing the inviting atmosphere of the private backyard.

4.95 out of 5 average rating, 80 reviews

Traveler's Dream:Outdoor Bar, Cabana, Arcade, Pool

5 out of 5 average rating, 66 reviews

A modern kitchen features green cabinetry and a spacious island with seating. Stainless steel appliances and a window above the sink provide natural light. Open shelving displays kitchen essentials, while a door leads to the outside, enhancing accessibility.

Home in San Diego

San Diego's Finest Retreat