Pet-friendly holiday rentals in Lakeside

4.98 out of 5 average rating, 115 reviews

The vibrant sunset sky is filled with hues of pink, orange, and purple, reflecting beautifully in the calm water of the pool. Palm trees stand in silhouette, framing the picturesque view of the surrounding mountains and valleys.

Guesthouse in Jamul

San Diego Mountain Retreat

3 bedroom 1 bathroom loft (2 separate sides) open concept guest house. Very peaceful East San Diego getaway. Enjoy beautiful ocean and Mountain Views during the day then relax in the jacuzzi with breath taking sunsets and the city lights at night. Best views in San Diego! Only 25 minutes from the SD airport and beaches. Minutes away from 2 local wineries and casinos. House sleeps 6 but you can invite guests up for the day for a fee. Event prices will be discussed per event. We live in main home

Outdoor spacesPetsBiking

4.98 out of 5 average rating, 132 reviews

A bright living area is visible, featuring a mix of modern furnishings including a cozy sofa, a smart TV, and a circular dining table with wooden chairs. Large windows allow natural light to fill the space, highlighting the warm wooden flooring and inviting decor.

Guesthouse in La Mesa

East Watch- a private getaway

East Watch is a 740 sq ft, 1 bedroom private retreat that provides the comforts and amenities of home with the style of a high-end hotel. All 5 to 15 min from shopping, downtown, and the beach. It's a short walk from Mt. Helix Park which offers a 360* view, weekday yoga, and stunning sunrises and sunsets. We have EV high speed car charging, a full kitchen with all appliances, workspace with dedicated fast WIFI, a spa shower, and super comfortable beds and pillows. Stay and let us charm you!

Outdoor spacesPetsBarbecue

4.96 out of 5 average rating, 420 reviews

A cozy living area showcases a modern yet rustic design, featuring a large wooden table and comfortable seating. Warm lighting from pendant fixtures complements the natural wood accents on the walls, while a decorative fireplace enhances the inviting atmosphere.

Farm stay in Lakeside

The Outside Inn at The Tipsy Goat Ranch

Nestled near Iron Mountain, a popular hiking destination, and less than 16 miles from San Diego's pristine beaches and local attractions, enjoy all SD has to offer in a one-of-kind farm-to-beach experience. Immerse yourself in a rarely seen side of San Diego you won't find anywhere else. Based on adventure, wrapped in luxury, a deep love for nature and the creatures it inhabits (mini goats, alpacas, babydoll sheep, lop bunnies, and chickens), it'll be a tranquil getaway you'll never forget.

Outdoor spacesWalkabilityCheck-in

4.92 out of 5 average rating, 101 reviews

A dining area is highlighted by a round wooden table surrounded by six wooden chairs. A cozy blue sofa is positioned nearby, with large glass doors opening to a pool area. Natural light enhances the space, complemented by a modern pendant light overhead.

Home in San Diego

San Diego Oasis- A Retro Retreat w/ King Size Bed!

Welcome to San Diego Oasis, a retro retreat--a mid-century modern oasis in sunny San Diego! This stylish home combines classic charm with all the modern upgrades you desire. Unwind by the sparkling pool, enjoy a friendly game of air hockey or corn hole, board games or enjoy s'mores around the gas fire pit . The retro retreat is the perfect blend of comfort, convenience, and timeless design. SD's most popular attractions are all within a 20-30 minute drive. Only 20 minutes to the beach!

Outdoor spacesWalkabilityLocation

A spacious outdoor area features a swimming pool, accompanied by colorful lounge chairs and a large umbrella for shade. A unicorn float is visible in the water, with potted flowers adding a touch of vibrancy. The home's façade offers multiple windows and seating options nearby.

4.99 out of 5 average rating, 205 reviews

Mid-Century Style Family House with Spa

This home is the epitome of 1950’s luxury. A perfect family oasis, you won’t even want to leave the property. Beautiful Mt. Helix mid-century modern family home with incredible views, designed by architect of original Las Vegas Desert Inn situated on nearly an acre. Less than 20 minute drive to beaches/Zoo/Sea World/Downtown. With a swimming pool, jacuzzi, and AC. Surrounded by orange, lemon, pomegranate trees and herb garden. No loud parties please, this is a quiet community.

WalkabilityOutdoor spacesFamily

4.98 out of 5 average rating, 125 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!

The Casita retreat is a guesthouse situated among a private 20 acre oasis surrounded by majestic mountain views and a citrus grove 30-40 minutes from San Diego. The space is designed for nature enthusiasts to retreat from the daily hustle and bustle and find peace and slowness. Come take a pause, relax poolside, pick citrus (when in season), enjoy nearby trails, and wineries. The sunsets and starry skies are breathtaking. We hope you get to experience their magic for yourself.

Outdoor spacesPetsBreakfast

4.97 out of 5 average rating, 133 reviews

A light-filled dining area features a simple white table set for two, complemented by wooden chairs. A comfortable seating area with neutral cushions is positioned against a green wall, while a glimpse of the kitchen is visible in the background, showcasing charming decor and a welcoming ambiance.

Guest suite in El Cajon

Farmhouse Cottage Retreat with Beautiful View’s

Welcome to the Farmhouse Cottage a serene countryside escape set on a former horse & cattle ranch, where wide open skies, rolling pastures, and quiet vintage luxury come together. Tucked away in a peaceful valley, this thoughtfully designed cottage invites you to slow down and reconnect-with nature, with loved ones, and with yourself. Once home to horses and grazing cattle, the land still carries that grounding , pastoral beauty. The Cottage sleeps 2 in a comfortable Queen bed.

PetsOutdoor spacesLayout

4.97 out of 5 average rating, 116 reviews

Villa in Jamul

@ Paradise villa, Top view, 4600sqrt on 10 acres

TOT #COSD-00749 Experience stunning 360-degree views from every corner of this spacious villa, which spans 4,600 square feet on 10-acre lot. This is the perfect place for family gatherings and celebrations. The house features five oversized bedrooms and four bathrooms. There is parking +25 cars. Max 50 guests. Enjoy a massive pool, deck, golf, chess, pool table, foosball, ping pong, Nintendo game, and screen projector. This truly one-of-a-kind property is not to be missed!

WalkabilityOutdoor spacesFamily

4.98 out of 5 average rating, 123 reviews

Home in El Cajon

Quiet Country Home

Extremely clean home. Fenced private yard with Webber Genesis BBQ & Tables. Outdoor smoking. 25 minutes to beach or downtown. Rural area with animals “talking”. Horse visits and carrots included. Seasonal Fruits & Vegetables. 1st bedroom: king/full bath. 2nd bedroom: queen/work desk. 3rd bedroom: full & 2 twin trundle. All dishes/appliances. Crib & Highchair available Host lives in a separate complete 1 bedroom studio with a shared laundry room.

WalkabilityOutdoor spacesWi-Fi

4.97 out of 5 average rating, 102 reviews

A spacious Western-inspired home is presented, featuring a dark green exterior and a sloped roof. The front of the house displays large windows and a two-car garage, flanked by boulders and landscaped areas. A clear blue sky enhances the serene setting.

Home in Alpine

Japatul Haven

Enjoy a serene and relaxing time at this spacious Western inspired home with incredible views. We're sure that you'll love exploring the surrounding 8 acres of private property as well as various nearby hiking trails. A quick drive will take you to Descanso Junction, Viejas Resort, or the quaint town of Alpine for restaurants and entertainment. More spirited adventurers will love the close proximity to Julian and Mount Laguna for outdoor adventures.

WalkabilityOutdoor spacesBarbecue

4.96 out of 5 average rating, 178 reviews

Home in El Cajon

Beautiful 3,000 Sq Ft Tropical Oasis

Beautiful 4 Bedroom, 2 1/2 Bath Family Home Located in Tranquil Fletcher Hills. This 3,000 sq. ft. Home is Perfect for large families who wish to Relax in a Peaceful Setting. 24-hour self check-in keypad after 4pm and check-out at 11AM. Host does not allow parties/events. This is NOT a Party House! This home is located in a quiet residential neighborhood, Guests who do not respect this will be asked to leave.

Outdoor spacesPetsSleep quality

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, 219 reviews

The Queen House

Welcome to Endless Summer, your ideal family retreat! This beautiful 4-bedroom, 2.5-bath home is just 15 minutes from Downtown San Diego, near attractions like Petco Park, the San Diego Zoo, and local beaches. Located in Mount Helix, La Mesa, enjoy stunning canyon views and a refreshing swimming pool with a waterfall. Experience a unique stay at a home that has it all!

PetsOutdoor spacesGetting around

Popular amenities for Lakeside pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A contemporary casita is featured with a neatly landscaped front yard and stone pathway leading to the entrance. A garage is visible to the left, and large windows allow natural light to illuminate the welcoming exterior, which is surrounded by lush greenery.

4.9 out of 5 average rating, 141 reviews

Sunnyside Resort Spa, Beach, Zoo, Arcade

PetsWalkabilityTV

4.91 out of 5 average rating, 145 reviews

A multi-sport court is featured in the backyard, designed for basketball, pickleball, and badminton. The bright blue court is surrounded by wood fencing and includes seating for relaxation. Lush trees provide a natural backdrop, enhancing the outdoor space.

Home in El Cajon

*Family Haven: Sports court/ Game Room/ King Beds

Outdoor spacesPetsKitchen

A welcoming living area features a spacious beige sectional sofa adorned with patterned throw pillows. Natural light filters through a large window, complemented by soft, flowing curtains. A dark ottoman with decorative details adds a contrasting element to the cozy space.

4.96 out of 5 average rating, 142 reviews

Zen Retreat: 3-Bedroom Oasis near La Mesa Village

PetsOutdoor spacesIndoor spaces

4.97 out of 5 average rating, 155 reviews

A custom cedar soaking tub is positioned on a stone patio, offering sweeping views of the surrounding hills and valleys. Two wooden chairs are situated nearby, providing a serene spot to relax. The clear blue sky enhances the natural beauty of the landscape.

Home in Julian

Luxury Julian Home w/ Cedar Tub, View, Horse Stall

PetsOutdoor spacesLocation

4.83 out of 5 average rating, 130 reviews

Large Home Heated Pool Spa | Game Room (Sleeps 30)

WalkabilityOutdoor spacesAir conditioning

The image captures a modern saltwater pool illuminated in vibrant blue tones. Surrounding vegetation and trees frame the pool area, enhancing privacy. A gated fence ensures security, while landscaped features and lounge chairs offer inviting relaxation options.

4.99 out of 5 average rating, 102 reviews

Mt. Helix Resort+ Pool/Spa, Pickleball, Amenities!

Outdoor spacesPetsParking

An inviting game room is highlighted by a polished pool table, surrounded by warm wooden beams overhead. A modern kitchen area is visible, featuring sleek appliances. Nearby, a laundry area is equipped with stacked machines, creating a functional and comfortable space for relaxation and entertainment.

4.96 out of 5 average rating, 101 reviews

San Diego Retreat ·Jacuzzi + Billiards +Sleeps 12!

Outdoor spacesHikingNearby

4.96 out of 5 average rating, 159 reviews

A well-lit bedroom featuring a spacious bed adorned with decorative pillows and a soft bedspread. Two stylish lamps flank the bed, providing additional lighting. Natural light enters through a window, which is dressed with light curtains, emphasizing a serene and relaxing atmosphere.

Home in Spring Valley

Paradise View Staycation Q Bed, Sofa-bed *420 *

PetsOutdoor spacesCleanliness

Pet-friendly home rentals with a pool

Villa in Rancho San Diego

An inviting outdoor entertainment area features a heated saltwater pool surrounded by elegant lighting and stylish lounge furniture. Inflatable swan floats rest in the water, while vibrant umbrellas provide shade over seating. Lush landscaping enhances the serene environment, making it ideal for relaxation.

4.92 out of 5 average rating, 215 reviews

Enchanted Paradise! Pool+Spa+Outdoor Kitchen

PetsOutdoor spacesFamily

4.99 out of 5 average rating, 102 reviews

An outdoor space presents a well-maintained pool surrounded by lounge chairs and tropical plants. A fire pit is set with a bottle of champagne on an oval table. Deck umbrellas offer shade, creating a relaxing atmosphere near the pool’s edge.

Bungalow in Escondido

Bella Vita,Majestic Resort w/ Bungalow Pool House

WalkabilityOutdoor spacesQuiet

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, 136 reviews

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

PetsOutdoor spacesParking

4.91 out of 5 average rating, 401 reviews

The casita is illuminated under a night sky, with the warm glow of string lights reflecting off the tranquil pool. The charming architecture features a second-floor window, while the inviting outdoor area showcases a blend of nature and modern design.

Guesthouse in Ramona

Cozy Spanish Casita w/ Mountain View in Ramona

Outdoor spacesPetsLayout

4.97 out of 5 average rating, 317 reviews

An aerial view highlights a spacious backyard featuring a solar heated pool, hot tub, and tropical landscaping. Lounge chairs are arranged around the pool, and a palapa style cabana with seating is visible, offering an inviting outdoor space for relaxation and entertainment.

Home in Bay Park

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

PetsWalkabilityCondition

4.98 out of 5 average rating, 517 reviews

Home in Encinitas

Lux Casita with Pickleball & Resort Amenities

WalkabilityPetsCondition

Holiday home in San Diego

A covered patio area is highlighted with a round table and two black chairs. Red cushions add a pop of color to the seating. The inviting hot tub is located adjacent to a turquoise pool, surrounded by landscaped greenery.

4.85 out of 5 average rating, 117 reviews

Cozy Home by SDSU - 8ft deep heated pool+hot tub

PetsOutdoor spacesGetting around

4.94 out of 5 average rating, 210 reviews

A swimming pool reflects sunlight under a clear blue sky, surrounded by a patio area. A colorful hammock is suspended near the pool, while potted plants add greenery. The adjoining building features large windows and a seating area.

Guest suite in La Mesa

Hacienda de Las Campanas

WalkabilityOutdoor spacesAir conditioning

Private, pet-friendly home rentals

4.93 out of 5 average rating, 717 reviews

The interior of the dome showcases unique angular wooden walls, creating a modern architectural feature. A spacious open area includes a small dining table with a chair, a comfortable sofa, and a television. Large windows provide natural light and views of the outside greenery.

Dome in La Mesa

Dome Life

PetsWalkabilityHospitality

Guest suite in Spring Valley

A comfortable armchair with an ornate design is positioned near a glass door, allowing natural light to illuminate the space. An arched wall leads to the sleeping area featuring a spacious bed and decorative elements. Soft curtains frame the door, enhancing the serene atmosphere.

4.81 out of 5 average rating, 345 reviews

Comfy Mountain Top Casita

Outdoor spacesWalkabilityCheckout

4.98 out of 5 average rating, 278 reviews

A bright and inviting living area features a mustard-yellow sofa complemented by patterned cushions. Two armchairs in light grey are positioned around a wooden coffee table, while an acoustic guitar is mounted on the wall. A television is mounted beside large windows that allow natural light to stream in.

Bungalow in La Mesa

Casa de Pueblo - Hot Tub, Fire Pit La Mesa Village

PetsWalkabilityLayout

4.99 out of 5 average rating, 369 reviews

An aerial view captures the A-frame cabin surrounded by lush greenery. Warm light spills from large windows, illuminating the interior. The expansive deck is equipped with loungers, inviting seating areas, and a built-in BBQ, showcasing a welcoming outdoor space for relaxation.

Cabin in Julian

Mid-Century Modern A-Frame Secluded with Hot Tub

WalkabilityPetsCleanliness

4.95 out of 5 average rating, 240 reviews

A modern loft space features warm wood flooring and a plush area rug. A gray sofa faces a sleek entertainment center. A desk and stool are situated by a window, offering views of the surrounding landscape. Natural light fills the room through large windows.

Guesthouse in La Mesa

Mountain top view getaway loft

Outdoor spacesWalkabilityHiking

5.0 out of 5 average rating, 50 reviews

Home in Lakeside

Villa Del Sole

Outdoor spacesViewLayout

4.81 out of 5 average rating, 27 reviews

A spacious deck is illuminated by string lights, creating a serene atmosphere during twilight. The light-colored home features large glass doors that lead to the interior, while cozy seating arrangements are positioned for relaxation against the backdrop of nature.

Home in Lakeside

Stunning Mountains view

ParkingAccuracyBackyard