Holiday rentals with a pool in Eastlake

4.99 out of 5 average rating, 149 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.

Guest house 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

4.99 out of 5 average rating, 119 reviews

A spacious balcony offers a serene sunset view over the ocean. A hammock hangs between two supports, complemented by a small wooden table with a glass. Lush green plants frame the space, enhancing the connection to the tranquil coastal setting.

Apartment in Rosarito

Tulum Takes Rosarito, 2-Bedroom, Beach front.

Enjoy our unique Beach front condo, that is perfectly situated near the San Diego/ Tijuana Border and minutes away from Rosarito Downton. Open floor plan, that expands into a massive balcony over looking the Pacific. You can get tan in one of our 3 pools our 8 jacuzzis, or get a ride on the beach on horseback. Our condo is set on the 9th floor of a 20-floor condominium building. The building has a 24/7 gate security. * Our price vary depending on the number of guests *NO pet allowed NO smoking

Home in University Heights

A colorful living area features a vibrant blue couch adorned with decorative pillows. A round white coffee table sits prominently on a multi-colored rug, while a television is mounted above a red cabinet. Artwork and framed prints decorate the pink walls, enhancing the playful ambiance.

4.94 out of 5 average rating, 105 reviews

Casa De Colores

Need some color in you life? Come stay in our one of a kind home- groovy wall mural, bright decor, rainbow speckled floors. Tucked back in the peaceful neighborhood of University Heights, this home includes a lusciously landscaped yard with a: - Pool -Hottub - BBQ -Outdoor patio furniture Our property also offers the ultimate in convenience: - Acclaimed restaurants and cafes are just minutes away - Close to the Airport, Zoo, Balboa Park, and Downtown - Close to many world-class beaches

4.89 out of 5 average rating, 383 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.

An inviting outdoor space is presented with a private heated pool and a spacious deck. Comfortable lounge chairs face the pool, while a dining table with red umbrellas offers shade. Lush greenery surrounds the area, enhancing the sense of privacy.

4.88 out of 5 average rating, 115 reviews

Dream Vacation! Sunny 3 Bedroom Home!

Beautiful family vacation retreat! Amazing backyard includes your own private heated pool, a spacious deck for relaxing with lounge chairs, dining spaces, and fire table. Fenced for privacy. Inside enjoy the game room and arcade, smart TVs located throughout the house, and air conditioning. Strong Wi-Fi signal, including the outdoor deck area. Amazing location close to all SD has to offer: within 20 minutes of the zoo, beaches, Sea World, downtown, and the airport! Private parking.

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.

4.94 out of 5 average rating, 128 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.

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.

Guest house 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.

4.97 out of 5 average rating, 144 reviews

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

This is your perfect Guest House with a salt & 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.

4.96 out of 5 average rating, 191 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)

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.

4.81 out of 5 average rating, 191 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.

4.89 out of 5 average rating, 256 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.

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.

4.79 out of 5 average rating, 154 reviews

Spacious 2 BR w/ Free Parking & WiFi

This stylish place is perfect for group and family trips. We are centrally located and close to all that San Diego has. Only 10 minutes from San Diego Zoo, Gaslamp, Downtown & more. Target and other grocery stores are a 5 minute drive. Directly across the street is fast-food and local restaurants. The complex is very safe, quiet and nicely maintained. The listing includes a free parking space with plenty of parking on the street.

Popular amenities for Eastlake rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

Double glass doors provide access to the patio, revealing views of a kidney-shaped pool surrounded by a deck. Lush greenery and hills are visible in the background, creating a serene outdoor setting.

4.77 out of 5 average rating, 126 reviews

Views - Quiet Mt. Helix Home - Pool -Sleeps 11

5 out of 5 average rating, 206 reviews

A serene backyard is framed by colorful sunset skies, featuring a cozy hammock in the foreground and a comfortable seating area with grey couches. String lights add warmth to the outdoor space, complemented by lush greenery throughout the neatly landscaped yard.

Home in La Jolla

La Jolla Beach House-Family Focused-3min to Beach

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, 110 reviews

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

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, 197 reviews

The Queen House

4.85 out of 5 average rating, 103 reviews

The private pool area is surrounded by palm trees and cacti, with lounge chairs positioned for relaxation. A shaded dining area is visible in the background, complemented by the warm glow of a sunset sky. The scene creates a serene outdoor retreat.

Home in San Diego

Surf Cottage w/Pool & Firepit 10min from the beach

4.84 out of 5 average rating, 139 reviews

A modern kitchen features a large marble island with seating for four. Pendant lights hang above the island, and stainless steel appliances are positioned along the walls. Two windows allow natural light to fill the space, while light green curtains add a soft touch.

Home in San Ysidro

Beautiful 4bd San Diego home with pool

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.

4.85 out of 5 average rating, 232 reviews

San Diego Pool | Fire Pit | Sunshine | Sleeps 10

4.88 out of 5 average rating, 216 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.

Apartment rentals with a pool

4.9 out of 5 average rating, 174 reviews

A bright living area features large sliding glass doors that open to a terrace with ocean views. A dining table is set for six, with additional seating at a breakfast bar. Neutral tones and modern furnishings create a relaxed ambiance, complemented by natural light.

Apartment in Rosarito

Luxury Ocean Front Modern Condo in Rosarito

4.84 out of 5 average rating, 109 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.

Apartment in Tijuana

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

Apartment in Agua Caliente

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, 208 reviews

Luxury studio on the 22nd floor

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 out of 5 average rating, 106 reviews

The Endless Summer Condo!

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, 197 reviews

Luxury Oceanfront Condo with Unbelievable Views

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, 185 reviews

Beautifully remodeled 10th floor oceanfront condo

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, 515 reviews

Oceanfront Elegant Condo - Remarkable Amenities

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, 324 reviews

Beach Front Condo - Capri by the Sea - Remodeled

Other holiday rentals with a pool

5 out of 5 average rating, 16 reviews

Flat in Otay Mesa

Sun-Kissed Retreat

5 out of 5 average rating, 14 reviews

BIG Modern Mt Helix Home with 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.

Flat in Chula Vista

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

4.98 out of 5 average rating, 81 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!

5 out of 5 average rating, 8 reviews

Flat in Tijuana

El Mejor Condo in Tijuana 2 beds/ 2 baths

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.

4.96 out of 5 average rating, 90 reviews

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

5 out of 5 average rating, 23 reviews

Home in Bonita

3792 Vista Pointe

A vibrant outdoor playground features a wooden play structure with a slide, swings, and colorful accessories. Adjacent, a spacious living area showcases a sectional sofa and decorative wall art, illuminated by natural light. The backyard pool area includes yellow umbrellas and lounge chairs, providing a relaxing spot. A mini-golf setup is visible, complete with flags and a maintenance shed.