
Holiday rentals with a pool in Sail Bay
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sail Bay
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

The Endless Summer Condo!
Let your worries drift away at this 6th floor corner condo with panoramic ocean views! With floor to ceiling windows throughout, you'll feel like you're floating above the sea! Leave your toes in the sand or walk to PB's best restaurants and attractions in minutes! When you're done exploring, put on a Beach Boys record while having dinner with the family amid a golden sunset..ah the good life! Create cherished memories that will linger long after the sun sets, here, at The Endless Summer Condo!

Oceanfront Luxury - Voted #1 SD Rental + AC!
Private parking, a relaxing pool & jacuzzi, and direct beachfront living—all in one stunning retreat. Wake up to waves and breathtaking ocean views. Enjoy coffee with a sunrise over Crystal Pier, then walk to the sand in seconds. Lounge by the pool, grill outdoors, or unwind on the rooftop terrace with a golden sunset. Newly renovated kitchen & bathrooms. No cleaning fees—just a stress-free, luxury stay. Fall asleep to the sound of waves and wake up in paradise. Your beachfront escape awaits.

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.

Ocean front condo heart of pacific beach
Gorgeous ocean-front condo with amenities galore. In the heart of bustling Pacific Beach, this 1 BR condo has it all: a magnificent, unobstructed ocean view on the 10th floor; steps from the beach, restaurants, shops, and bars; a roomy, delightful living space with floor-to-ceiling windows; a modern, fully equipped kitchen, and parking spot! Leave your worries behind, soak up the sun, check out San Diego’s many attractions — or just kick back and relax in this peaceful, beach-front oasis.

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.

Crown Point Gem with Salt Water Pool
This Cottage home is a beautiful Oasis in San Diego's Crown Point neighborhood. Our home is 2 blocks from Mission Bay with access to bike paths, water sports, and playgrounds for the kids. Easily walk to great restaurants, coffee shops, night life and shopping. With our cool saltwater pool, hot tub, grill and relaxing patio space you wont even need to leave the house to get that vacation feeling. Please let us know if you would like the pool heated, we charge $75/night for this service.

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.

Luxe Point Loma Oasis w/ Pool, Spa & Fire Pit
The vacation of your dreams awaits at the luxury 3BR Point Loma oasis. Each of the posh bedrooms has an en-suite bathroom and access to the exquisite backyard oasis-which is complete with a pool, spa, outdoor kitchen, and fire pit area. Enjoy outdoor dining by the pool or the lovely succulent gardens throughout the property. Sleeps 8. Washer/dryer, complimentary Wi-Fi, Netflix and parking are included. Hotel quality sheets and fresh duvets are also included with your stay. No parties.

Mountain View• Solar-heated Pool •HotTub •GameRoom
☀️Welcome to our fun, newly updated home in a quiet, secure neighborhood in La Mesa ☀️ 🌊Swim in our beautiful blue, solar-heated pool while enjoying an elevated mountain view, perfect for relaxation and fun. Unwind in our fantastic game room, equipped with a pool table, arcade machines and pop-a-hoop, offering endless entertainment for guest at all age. End the day in our in-home movie theater, where you can enjoy your favorite films in ultimate comfort. ☀️

La Jolla Beach House-Family Focused-3min to Beach
Escape to our boho-inspired Bird Rock/La Jolla beach house, perfect for families! This serene La Jolla retreat features a private pool, large hot tub, and cozy fire pit. Enjoy a private oasis with hammocks and a BBQ. Recently upgraded with modern decor and new appliances, this home comfortably accommodates your group for the ultimate relaxing getaway just minutes from La Jolla Cove and famous beaches.

Bay View Condo in Pacific Beach
Close to the beach and even closer to the shops! Set on the top floor in a beautiful condo complex with legitimate charm. Enjoy a cup of coffee on the balcony while enjoying the gorgeous views of palm trees, mountains, & Mission Bay. All guests, young or experienced, are welcome here. Bright and airy one-bedroom with a queen-size bed and brand-new kitchen and furnishings.

Luxe Home w. Serene Backyard Spa
Escape to the heart of San Diego in our chic and luxurious 3-bed oasis, where upscale meets laid-back California cool. Steps from vibrant eateries, buzzing bars, and unique boutiques, this retreat offers a serene backyard with a soothing spa. Experience local attractions, beaches, and the San Diego Zoo, all a short drive away. Your ultimate San Diego adventure awaits!
Popular amenities for Sail Bay rentals with a pool
House rentals with a pool

Heated Pool, XXL Spa, Mini-Golf & Chef’s Kitchen!

Bright Contemporary 5-Bedroom Oasis, Pool and Yard

The Queen House

Casa Del Oceano, Solana Beach

Lionhead - Private Boutique Home

Luxury Family Home Near Dining, Shops + Zoo

1 bedroom, 1 bath /Hillcrest/San Diego Zoo/Balboa

Designer Luxury Rental With Pool
Condo rentals with a pool

Studio Condo at Wave Crest Resort

Centrally located n UCSD/ utc-laJolla

Del Mar Beach Club-AC, pool,jacuzzi,tennis, views!

One Bedroom Ocean Front Condo!

Del Mar Ocean View! Walk to the Beach!

REJUVENATE @Ocean123 *Available Now,Just Send Msg*

Spacious 2 BR w/ Free Parking & WiFi

Cozy clean 1 bedroom centrally located by beaches
Other holiday rentals with a pool

NEW! Hot Tub/Pool/Fire Pit/10 Mins to Beach

Luxury Resort: Pool, Spa, Swim-Up Bar & Bay Views

Paradise just south of the border.

Pacific Beach Gem | Heated Pool | Free Parking

Mid-century Modern with Water Views & new Jacuzzi

Breathtaking Ocean, Bay, City & Petco Park Views

Sunset house

San Diego Oasis- A Retro Retreat w/ King Size Bed!
Destinations to explore
- Southern California Holiday rentals
- Los Angeles Holiday rentals
- Stanton Holiday rentals
- Channel Islands of California Holiday rentals
- Las Vegas Holiday rentals
- San Diego Holiday rentals
- Palm Springs Holiday rentals
- San Fernando Valley Holiday rentals
- Henderson Holiday rentals
- Las Vegas Strip Holiday rentals
- Santa Monica Holiday rentals
- Joshua Tree Holiday rentals
- Apartment rentals Sail Bay
- Rentals with a washing machine and dryer Sail Bay
- Fitness-friendly rentals Sail Bay
- Rentals with beach access Sail Bay
- Waterfront rentals Sail Bay
- Condo rentals Sail Bay
- Rentals with a kayak Sail Bay
- Cottage rentals Sail Bay
- Rentals with a hot tub Sail Bay
- Beachfront rentals Sail Bay
- Pet-friendly rentals Sail Bay
- Townhouse rentals Sail Bay
- Rentals with a patio Sail Bay
- Rentals with lake access Sail Bay
- Hotel rooms Sail Bay
- Family-friendly rentals Sail Bay
- Rentals with a fire pit Sail Bay
- House rentals Sail Bay
- Rentals with an EV charger Sail Bay
- Rentals with a fireplace Sail Bay
- Rentals with outdoor seating Sail Bay
- Smoking-friendly rentals Sail Bay
- Rentals with pools San Diego
- Rentals with pools San Diego County
- Rentals with pools California
- Rentals with pools United States
- Rosarito Beach
- San Diego Convention Center E Ent
- SeaWorld San Diego
- Oceanside City Beach
- San Diego Zoo Safari Park
- Ocean Front Walk
- Pacific Beach
- Coronado Beach
- Tijuana Beach
- Torrey Pines State Beach
- Balboa Park
- San Diego Zoo
- Pechanga Resort Casino
- San Clemente State Beach
- San Diego State University
- Moonlight State Beach
- Mission Beach
- San Onofre Beach
- Oceanside Harbor
- Liberty Station
- LEGOLAND California
- Belmont Park
- Sesame Place San Diego
- Black's Beach





