Vacation rentals with a kayak in Sail Bay

4.98 out of 5 average rating, 123 reviews

The exterior of a beach cottage features a charming façade with gray shingles, adorned by vibrant potted plants along the fence. A teal umbrella stands open beside the entrance, inviting guests to enjoy outdoor space. Decorative touches enhance the cottage's welcoming presence.

Cottage in San Diego

Pet friendly with AC, parking & steps to beach

Beach cottage restored into the best vacation retreat in Mission beach w/ dedicated parking, AC, & pet friendly. Fantastic location -Walking distance to favorite local restaurants- Mission Cafe, Intaza's, Single Fin, Olive's & Miss B's. And 1 block to ocean beach & steps to bayside beach! Experience all the luxuries of home w/ 55 " 4K TV, remodeled kitchen, private patio with outdoor TV, & 4 beach cruisers/beach chairs, boogie boards & kayak. Short term rental license - 03687L TOT #-518908

An aerial view captures the beach house's proximity to both the coastline and Mission Bay. Gentle waves lap against the sandy shore, while a vibrant sunset casts warm hues across the landscape, highlighting the serene surroundings of San Diego's coastline.

4.92 out of 5 average rating, 305 reviews

Beach House one block from Mission Bay w/AC

Just one block from the bay, this quiet and cozy beach house with private parking and 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, large private patio w/ BBQ, 2 beach cruiser bikes, 2 stand-up paddleboards, and a kayak too. Walkable to restaurants, parks, the beach, and the bay. Just a click away!

The exterior of a modern building is illuminated by the evening light, showcasing large windows and a spacious balcony. Palm trees frame the scene, while the sunset casts warm hues over the surroundings, hinting at the ocean nearby.

4.83 out of 5 average rating, 138 reviews

Modern Oceanview Penthouse

Enjoy panoramic views of the ocean, bay, & beach from nearly every area of this incredibly clean, newer home. Entire top floor is yours. Cook up a storm in the amazing kitchen w/ large breakfast bar or step out onto the oceanview deck featuring a tall table & chairs, lounger, & shady umbrella. Outdoor living is found on the downstairs patio! The 2-car garage comes stocked w/ all the beach toys! 10/10 walkability & quick access to trendy coffee shops, restaurants, bars, & beach activities!

Guest favorite

The charming pink exterior of a 1930s Spanish home is highlighted, featuring an inviting patio area with a table and chairs beneath a large umbrella. Lush greenery adds to the relaxed atmosphere, while the upper balcony provides additional outdoor space.

4.89 out of 5 average rating, 122 reviews

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.

An aerial view captures the vibrant San Diego coastline at sunset, showcasing calm waters and a colorful sky. Residential neighborhoods and palm trees are visible below, highlighting the community atmosphere. The layout of streets and homes suggests a welcoming environment near Mission Bay.

5 out of 5 average rating, 3 reviews

One block to Bay | Firepit, AC & Putting Green

Welcome to your coastal escape—just one block from the calm shores of Mission Bay and a short stroll to the waves of Mission Beach! This fully renovated, thoughtfully designed 4-bedroom, 3-bathroom home features a private putting green, firepit, BBQ, A/C, and free parking—perfect for families, friend groups, and travelers seeking a luxurious yet laid-back San Diego getaway. Whether you're here to unwind, explore, or entertain, this sunny retreat places you right in the heart of it all.

A bright living area featuring a snug couch with striped cushions and a wooden coffee table. The adjacent kitchen is seen through a wide entry, with blue cabinetry and a dining set. Natural light enters through a set of glass doors, enhancing the openness.

4.96 out of 5 average rating, 142 reviews

Newly remodeled! Home away from home

We are located in South Mission Beach on Ensenada Ct a couple blocks South of Belmont Park. Bob and I live upstairs and offer a small 1 bedroom and 2 bedroom apartment (approximately 500 sq. feet each) on the ground floor to vacationers. Please note that the 2nd room is a very small with twin bunkbed suitable for children or small adults. We enjoy having guests from all over the world come to visit and love watching everyone enjoy South Mission Beach as much as we do.

4.84 out of 5 average rating, 114 reviews

A bright living area features a black sofa with colorful cushions, complemented by two yellow armchairs. A wooden coffee table with decorative items is at the center. The open layout leads to a modern kitchen and dining area, illuminated by natural light through large windows.

Townhouse in San Diego

Brighton Ct. Exterior remodel just finished

Exterior remodel completed July of 2025 including all new windows. Will update photos asap. You’ll love this place because of the location adjacent to the widest and least crowded portion of South Mission Beach, its proximity to the bay (5 houses) and the ocean (11 houses), the unshared yard contiguous with main living area for seamless dining and lounging inside and out, numerous windows, cooling cross breeze and soothing sounds of breaking waves.

Guest favorite

The property displays a charming two-story building with arched balconies and a red-tiled roof. A spacious patio features vibrant outdoor furniture, including a large umbrella, providing shaded seating. The modern garage blends seamlessly with the structure, further enhancing the property's appeal.

Villa in San Diego

4.93 out of 5 average rating, 144 reviews

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.

A bright and inviting living area features a blue sofa paired with a yellow accent chair. Colorful artwork adorns the walls, complementing the warm tones of the space. Large windows allow natural light to fill the room, with a view of the outdoor area visible through the open door.

4.8 out of 5 average rating, 188 reviews

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, tandem kayaks, 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!

4.98 out of 5 average rating, 143 reviews

An open living area displays a mix of warm wood cabinetry and vibrant decor. A retro red refrigerator contrasts with the neutral tones of the walls and furnishings. Plants and artwork add color, while a comfortable seating area features a patterned chair and a cozy sofa.

Guesthouse in San Diego

2 BR/ 2 BA San Diego Getaway

This 2 bed/2 bath home in San Diego is located in the Bay Park neighborhood, 1/2 mile from Mission Bay. It has an open and inviting living area, kitchen and dining space, and a relaxing/private outdoor patio with a BBQ and fountain...very So Cal! Also, there is a new "white sandy beach" steps from the rental. It is not the "real" beach but very private and nice. Check out the new beach photos..super cool.

A contemporary living space is visible, featuring a light wood dining table set for four. The kitchen area showcases wood cabinetry and modern appliances, including a stove and microwave. Natural light enters through large windows, illuminating the open layout that connects to a cozy seating area.

4.96 out of 5 average rating, 243 reviews

2 Blocks to ocean, walk to Sunset Cliffs 2Bd, 1 Ba

2 bedroom house located in the exclusive Southern Ocean Beach neighborhood of Sunset Cliffs. Hear the waves crashing just two blocks away. Enjoy a private lounging deck with fire pit and an outdoor dining patio. Ocean Kayaks, Boogie Boards, Beach chairs, and all the gear for your enjoyment. Close to many beaches and San Diego attractions. 3.5 miles to Sea World, 7 miles to The San Diego Zoo/Balboa Park.

Guest favorite

A spacious living area features two dark sofas and a wooden coffee table. A ceiling fan hangs above, and colorful cushions add a touch of brightness. The open layout connects to a kitchen area, illuminated by natural light, with a neutral color palette throughout.