Vacation rentals with a pool in Old Town, San Diego

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Top-rated rentals with a pool in Old Town, San Diego

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

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Guest favorite

Guesthouse in Coronado

4.86 out of 5 average rating, 297 reviews

Coronado Island Pool Cottage

2 blocks from the Beach, the Cottage offers a peaceful, clean & private stay with exclusive use of the pool, jacuzzi, bikes, beach items, surfboards, deck chairs, Cable TV & Wifi. 3 rooms: QUEEN BEDROOM has AC, heater, ironing, hangers & 8 foot mirrors. LOUNGE ROOM has AC, heater, QUEEN sofa-bed, Cable TV, microwave, fridge/freezer, toaster, cutlery, coffee/tea, & bottled water. BATHROOM has walk-in shower, all toiletries & towels. BEFORE BOOKING, please click/read the “SHOW MORE" details here:

Guest favorite

Home in Hillcrest

5 out of 5 average rating, 115 reviews

Custom Guesthouse, Balboa Park/Zoo/Hillcrest& pool

2021 CUSTOM guest home with pool in the heart of Hillcrest/San Diego/Zoo/Balboa Park area. Full kitchen, a queen bed in the bedroom & a queen sleeper sofa in the living room. Full bath, indoor & outdoor dining, WiFi, smart TV, pool, AC/heating, BBQ& free parking. Short walk to restaurants, shops & stores (TraderJoe's, Ralph's & Whole Foods). Minutes drive to San Diego beaches & bay. It accommodates 1-4 guests. No rent for children under 3, but $75/stay. High chair and Pack&Play are available.

Superhost

Guesthouse in City Heights

4.9 out of 5 average rating, 273 reviews

Green Door Cottage

Enjoy our new, fully renovated (2021) tiny Cottage which holds a timeless charm and is also filled with a modern touch. Close to all the wonderful things San Diego has to offer - beaches, downtown, the zoo, Padres games, SeaWorld, SAN airport, Old Town, SDSU, you name it! Nice sized turf yard with total privacy and an amazing back deck! Outside table and fire pit are perfect for the cool nights of San Diego. If you need more space, check out our other listing, Pink Door Craftsman (sleeps 7)!

Guest favorite

Condo in Pacific Beach

4.98 out of 5 average rating, 125 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.

Guest favorite

Condo in Pacific Beach

4.94 out of 5 average rating, 447 reviews

Oceanfront Elegant Condo - Remarkable Amenities

Spectacular Oceanfront, 8th Floor. Hear the surf as you slide open the floor-to-ceiling glass door. The Boardwalk and beautiful safe swimming beach are at the foot of your building. Join the surfers using our wet suits and our beach cruiser bikes for an easy ride along the Ocean and Mission Bay or stroll along for vibrant people watching. Return to your elegantly appointed, romantic condo provisioned to meet your every need. Everything you need is in 10 blocks along beautiful California coast!

Guest favorite

Home in Mission Hills

4.93 out of 5 average rating, 216 reviews

Lionhead - Private Boutique Home

Heated pool, spa, cabana and views. Boutique hotel vibes in San Diego. Palm Springs meets South Beach with a splash of groovy. Location is perfect for Downtown, conventions, shows in town. Highway friendly. Private backyard for bbq, food, drinks and relaxing. Pool is heated with cozy spa to relax and watch the planes take off. Hi speed Wifi, smart TV's, HBO, NFL Package, record player with albums. 19 speakers in the ceilings with connected to your phone for optimal happiness. Plug and play!

Guest favorite

Guesthouse in Mission Hills

4.94 out of 5 average rating, 135 reviews

Casita w/ Private Pool, Full Kitchen >1mi Airport

Perfect poolside retreat suitable for small families and couples! This suite boasts a fully-equipped kitchen, a private pool, front patio and sunbathing deck! You'll enjoy a luxurious king-size bed and a convenient full-size fold-out option, accompanied by many amenities necessary for a memorable stay. Located in one of San Diego's most central neighborhoods of Mission Hills, you're just a stroll away from restaurants, cocktail bars, the light rail, and easy access to the I-5 highway.

Guest favorite

Guesthouse in La Jolla

4.98 out of 5 average rating, 165 reviews

Luxury Tropical Private Guesthouse in La Jolla

Beautiful private guesthouse on $5 million property with stunning views and luxury amenities. Take a dip in the tropical pool with waterslide, tiki bar, and hot tub grotto. Enjoy indoor or outdoor dining. Gated property, vaulted ceilings, marble bathroom, private balcony, parking, and trail for guests. Guesthouse has 1 bedroom with a queen bed and can accommodate an extra twin bed on the loft. House has closet, bathroom with beautiful stone shower, modern kitchen, two patios, WiFi, TV.

Guest favorite

Condo in Pacific Beach

4.93 out of 5 average rating, 124 reviews

Enchanted Ocean Sunsets

Ocean front condo In Pacific Beach with spectacular sunsets and stunning views of Mission Beach and La Jolla. Beach front location just steps away from the sand and waves. Enjoy surfing, paddle boarding, long walks on the boardwalk, bike rentals, boat rentals, volleyball, fabulous restaurants and a vibrant night life! Delightful location close to amazing attractions including Sea World, San Diego Zoo and Balboa park. Come spoil yourself in this newly remodeled luxurious space!

Guest favorite

Home in Bay Park

4.98 out of 5 average rating, 253 reviews

Resort Style Living with Pool, Spa, and Bay Views!

Resort style home with a solar heated pool, hot tub, outdoor entertaining space, bay and ocean views, multiple patios, modern amenities, comfortable beds, and more. Convenient location to freeways, Seaworld, Mission Bay, Beaches, Downtown, Balboa Park, Airport, La Jolla and other attractions. Perfect for families and groups. Two car garage parking included. 2300 square feet of indoor living and much more outdoors. Your ideal home base for enjoying all that San Diego has to offer.

Superhost

Rental unit in North Ocean Beach

4.82 out of 5 average rating, 163 reviews

Dog Beach Simple Suite

NEW OCEAN BEACH LISTING FROM ALEX & JEREMY - OB'S BEST SUPERHOSTS!!! No frills, no thrills - The Dog Beach Simple Suite has everything you need, and nothing you don't...starting with it's incredible location just steps from the sands of the world famous Ocean Beach Dog Beach. It's a well equipped 1 bedroom, bottom floor apartment with 2 beds, a kitchenette, TVs, great WiFi, reserved off-street parking, and totally pet friendly WITH NO RESTRICTIONS OR PET FEES :)

Guest favorite

Guesthouse in Mission Hills

4.91 out of 5 average rating, 427 reviews

Mission Hills Charming suite, walkable to all.

Heart of Mission Hills, upscale area, this private guest suite, separate from the house, is perched above the pool (separate building from main house), own entrance; sure to provide privacy. We are minutes from airport, walking distance to coffee & restaurants and central to all of SD. Please note this property is wiped down after each visit with Clorox as well as all linens washed. We also don’t rent back to back giving time for thorough cleaning.