Holiday rentals with a kayak in San Diego Bay

Jan'25 remodel apt. for young family or 3 adults

In S. Mission Beach on Ensenada Ct a cpl blocks South of Belmont Park. We live upstairs and offer a small 1 and 2 bedrm apartments (approx 500 sq. ft each) on the ground floor to vacationers. Please note that the 2nd room is very small with twin bunkbed suitable for children or small adult (3 adults max or 2 adults/2 children max (no exceptions), top bunk 110lbs. max) We enjoy having guests from all over the world come to visit and love watching you enjoy South Mission Beach as much as we do.

Outdoor spaces · Value · Parking

Panoramic Ocean Views at a Mid-Century Modern 2BR

Welcome to The OB Overlook, a stunning modern retreat perched above the heart of Ocean Beach. This coastal escape blends sophisticated architecture, relaxed luxury, and sweeping 180° ocean views. On the second floor, you’ll find two beautifully appointed bedrooms, dedicated workspaces and a spa-like bathroom. Upstairs, the third-floor open-concept living, kitchen, and dining area open to a spectacular balcony — your front-row seat to breathtaking sunsets, surf, and a sparkling coastline.

Outdoor spaces · Location · Walkability

Casa Rosada - Spanish Charm on Mission Bay

Pink Paradise on the Bay. 1930s Spanish home, family-owned and managed since the 1990s. 2 BR, 2 Bath beach house, with pull-out couch in downstairs living room. Private patio deck on ground level with table and chairs for families- just steps to either bay or beach side. Upper balcony off Master bedroom overlooking Sail Bay. Suitable for 4-6 guests and families welcome-- highchair, safety gates and crib provided. PLEASE NOTE: One car parking included for SMALL SUV/CROSSOVER maximum.

Outdoor spaces · Location · View

Beach House one block from Mission Bay w/AC

Just one block from the bay, this quiet and cozy beach house with a fully fenced private patio is ideal for anyone who wants a coastal getaway, while still being close enough to the attractions, restaurants, shopping, and nightlife of San Diego. We have all the amenities you need, a new AC unit, a comfy King-size bed, coffee bar, BBQ, 2 beach cruiser bikes, 2 stand-up paddleboards, beach chairs and floats. Walkable to restaurants, parks, the beach, and the bay. 1 private parking spot.

Location · Value · Checkout

Modern Ocean View Home+Free Parking+Steps to ocean

Beautiful ocean views, a private balcony, and easy access to the sand. Enjoy a morning cup of coffee while listening to the sounds of the waves, or spend your evenings strolling along the shoreline. Take a dip in the waters, or simply soak up the sun on the white sandy beach. Charming decor & all the amenities you need for a comfortable stay, this home is the ideal destination for an unforgettable vacation. The perfect spot for a romantic retreat or a fun-filled family vacation.

Location · Value · Parks

Surf to Skyline | 6BR Luxury Stay w/ Stunning View

Welcome to Surf to Skyline – Where luxury, nature, and city views unite. This newly remodeled 6-bedroom retreat sleeps 16+ and offers stunning views of San Diego and Lake Murray. With 3 full and 2 half baths, it’s perfect for families, couples, or large groups. Enjoy high-end finishes, spacious living, and unforgettable sunsets in a serene setting just minutes from everything. Whether you're relaxing on the deck or exploring the city – comfort and connection await.

Value · Location · Parking

Garden Retreat in North Park.

Nestled behind a vine-covered gate in the North Park area, this serene 1BR/1BA home is the perfect retreat. Enjoy hardwood floors, a spacious eat-in kitchen, and a cozy front porch overlooking a rose-filled garden. Located on a quiet street just minutes from dining, shopping, and Balboa Park. Includes secure off-street parking and EV charging. Ideal for solo travelers or couples seeking charm, privacy, and convenience in the heart of San Diego.

Value · Outdoor spaces · Indoor spaces

Coastal San Diego Family Retreat with Huge Yard

Welcome to The Gathering Place – your home base for connection in San Diego. This spacious, single-level Point Loma home is designed for people who travel together: families, couples, friends, work teams, and everyone in between. Whether you’re here for theme parks and beaches, sunset walks and wine, or simply a quiet place to land between adventures, The Gathering Place makes it easy to slow down, spread out, and enjoy each other’s company.

Location · Outdoor spaces · Walkability

The Crown Jewel Villa with AC!Bikes,Kayak and SUP!

Escape to the peaceful and coveted beach community of Crown Point in San Diego! This highly sought after neighborhood boasts mostly permanent residents, creating a serene and tranquil environment for our guests. Right across the street from the home, you can find Ski Beach and Park, a favorite spot for families and kids. Explore the variety of local eateries and coffee shops, or take a short walk to popular Sail Bay and the ocean.

Value · Outdoor spaces · Pets

Ben's Beach Bungalow 3, Ocean View Mission Beach 1

Just steps to the sand, this property is beachside of Mission Blvd and has recently been completely updated to provide you with the feel of luxury. It has a separate dining area and a full kitchen, so you always have the option of dining in or experiencing the vast array of PB restaurants and bars. But the highlight of this unit is the full ocean view from the bedroom...not many units in Mission Beach can boast this view!

Location · Outdoor spaces · Long stay

Large 4br Hillcrest Home-Big Backyard

This is a newly remodeled craftsman, centrally located 4 bedroom and 2.5 bathroom unit with living room, kitchen, parking, and a large backyard. Perfect setup for large groups who want a stylish yet historic home. It is centrally located in San Diego's uptown district and within walking distance to some of the best places in town. Please inquire about our discounts for essential workers, educators and extended stays.

Outdoor spaces · Location · Parking

Atomic Beach Pad - Incredible Beach Access!

Are you looking for an amazing beach stay with non-stop action sports adventures? We’ve got you covered! We can outfit you with beach bikes for cruising down the boardwalk, stand up paddle boards, boogie boards, wet suits, beach chairs, umbrellas, coolers… you name it! The ocean is directly across the street from this apartment with a private entry having both a bay and an ocean view. Your dream vacation!

Value · Outdoor spaces · Decor