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House vacation rentals in Lakeside

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Top-rated house rentals in Lakeside

Guests agree: these houses are highly rated for location, cleanliness, and more.

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Top guest favorite
A spacious backyard is illuminated by string lights, creating a warm ambiance. Lush greenery, including tall palm trees and banana plants, frames the area. A wooden deck provides an outdoor seating space, while comfortable patio furniture is visible nearby. The sky displays soft pastel colors at twilight.
Home in Del Cerro
4.97 out of 5 average rating, 374 reviews

SDSU Beach Cottage

Welcome to our stunning SDSU Beach Cottage. Our home is 10 minutes away from everything amazing in San Diego! Our home is Centrally located in San Diego and in a desirable neighborhood. We are steps away from a Local favorite Eatery, Wine Bar, Beer Pub, Natural-Holistic Market, Pizza shop, Liquor Store, Nail shop, and Einstein's Bagels. Play in San Diego or stay and relax in our tropical yard that is set up to entertain you and your family with outside games and Ping Pong. 25 Yr's of age req'd

Top guest favorite
Home in Ramona
4.97 out of 5 average rating, 317 reviews

Wine Country Retreat - Tranquility Hottub/Views

Our famed Wine Country Retreat is back online! (LTR for the last year) Take the back roads scenic drive 50mins up the hill from San Diego and enjoy some much needed quiet and comfy tranquility. Right in the heart of San Diego Wine Country, it’s a rather well appointed place situated on 10 private acres that overlooks expansive green space. With few neighbors in any direction, you can either sleep with the windows open and wake early to roosters crowing, or close the windows and sleep til Noon!

Top guest favorite
An open-concept living space features a spacious bed draped with a light gray blanket, a comfortable sofa with bright red accents, and a dining area with a table. Light flows through large windows, illuminating the cozy atmosphere.
Home in Felicita
4.94 out of 5 average rating, 231 reviews

Spacious Gated Home: Spa & Mountain View

This house is located in a peaceful neighborhood with mountain views, close to I-15, Escondido Mall, & Felicita Park. The guesthouse is attached to the MAIN home, but it has a private entrance with a private driveway and your own auto gate. It has an outdoor private spa, 1 closed and 1 open floor plan bedroom, patio, kitchen, walk-in closet with 1 bath. The facilities include fast WiFi, 75” 4KTV, cooktop, oven, microwave, refrigerator etc. 15 mins SD Safari & 30 mins to sea world or LEGOLAND

Guest favorite
A spacious kitchen and dining area feature wooden cabinets and stainless-steel appliances. A round dining table with chairs is positioned near large windows, allowing natural light to fill the space. A cozy living area is visible, decorated with plants and comfortable seating.
Home in La Mesa
4.85 out of 5 average rating, 396 reviews

4bd 3ba, Family Home Close To All SD Attractions!

Great SD location for families vacations & business trips! Centrally located with easy freeway access & grocery stores etc. Sunny 4bd. home on private cul de sac in Mt Helix area. Comfortably furnished, fully equipped kitchen. Great for work trips and family vacation! We have beach toys & pac-n-play for the kids! Fast WFI, smart TV’s. Quiet, private fenced back yard with trees, & room for kids to play, covered patios & BBQ! We don’t allow any parties, or events. Primary Guest must be 30.

Guest favorite
A contemporary casita is set against a vibrant sunset, showcasing large windows that reflect the warm colors of the sky. The entrance features a clear path leading to a well-lit doorway, surrounded by natural landscaping and scenic hillside views.
Home in Eucalyptus Hills
4.93 out of 5 average rating, 123 reviews

San Diego Casita for 6 Morey de Prieto Surf Ranch

The Morey de Prieto Surf Ranch is truly awesome! Reserve your stay in this 2 Bed/1 Bath 650 sq. ft. casita for six. Home includes a kitchen with a GE electric cooktop, refrigerator, microwave/air fryer, rice cooker, mixer for drinks, sink with prep trays, Moen faucet fixtures, gorgeous shower, Krups coffee maker, 50" smart TV equipped with WiFi and NetFlix, mountain views, workspace and a sofa bed. Relax on the large 240 sq. ft. private deck featuring a fire pit, adirondack chairs and BBQ.

Top guest favorite
An open-concept living area is highlighted by high ceilings and large windows, offering natural light. A modern kitchen features wood cabinets and a white island, while a dining table with turquoise chairs accommodates several guests. A cozy seating area is visible in the background.
Home in Ramona
4.97 out of 5 average rating, 893 reviews

The Glass House - A Nature Retreat

Enjoy a unique retreat; 180 degrees of views from inside the home. Nestled at the end of a private road, our place is nearby great hiking and countryside wineries. The Glass House provides a magical space and nature retreat where individuals, couples, families and friends can gather together to re-connect with nature, each other, and themselves. The breathtaking mountain top views, the huge deck, hot tub, fireplace, and the open concept living space is unbeatable for the perfect getaway.

Top guest favorite
A cozy living area features a sleek sofa adorned with decorative pillows. A stylish coffee table is positioned in front of the seating. A light yellow wall provides a warm backdrop, with a shelf displaying decorative plates and art, illuminated by subtle lighting.
Home in La Mesa
4.9 out of 5 average rating, 194 reviews

Classic Mid-Century Mount Helix Home with Views

Located in the exclusive Mount Helix neighborhood of La Mesa, this property is conveniently located near the 8 and 94 freeways for easy access to explore the greater San Diego area. Attractions like the historic Balboa Park with the San Diego Zoo or Sea World are a 15-25 minute drive away. With spacious interior and exterior spaces at the property, though, you may not want to leave. The property includes 4 bedrooms and 2.5 bathrooms with furnished living room, family room and kitchen.

Guest favorite
A dining space features a round table with four white chairs, complemented by a potted plant. Large glass doors slide open to reveal expansive views of the backyard, pool, and surrounding hills, with soft evening light illuminating the scene.
Home in Spring Valley
4.96 out of 5 average rating, 192 reviews

Upscale Resort House /Views, Saltwater Pool/Spa !

This home offers Saltwater pool and Spa. Saltwater pools and Spa produce softer-feeling water. breathtaking views from its location high in the hills overlooking Rancho San Diego. In the backyard you can enjoy the sunrise from the private pool or deck or practice your putting on our putting green. The House is a mid-century modern home perched above the City. It's great for groups seeking easy access to San Diego's highlights (15 to 20 minutes to Beaches and Downtown)

Top guest favorite
Home in Olivenhain
4.98 out of 5 average rating, 488 reviews

Lux Casita with Pickleball & Resort Amenities

Escape to this inviting Casita, where bright white walls and French doors fill each room with light and warmth. Thoughtfully furnished and full of charm, it offers a serene retreat with private resort-style amenities, including a tennis court, pool, and lush gardens. Step outside to hiking and biking trails, then return to cozy comfort. An optional second suite provides extra space for a relaxed, luxurious stay.

Top guest favorite
A serene saltwater pool is featured, surrounded by a stone patio and secured with a safety fence. A spa is integrated at one end of the pool, with two blue lounge chairs positioned nearby. Lush greenery is visible in planters along the patio.
Home in El Cajon
4.97 out of 5 average rating, 164 reviews

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.

Top guest favorite
An open-concept living area is highlighted by vaulted ceilings and natural light from large windows. A spacious L-shaped sofa is positioned around a coffee table, facing a wall-mounted TV above a modern fireplace. Nearby, a dining area can be seen through an archway.
Home in El Cajon
4.99 out of 5 average rating, 114 reviews

Spacious & Fun | 5br, 4.5ba | Hot Tub | Views

Experience sunny San Diego from this 5 bedroom, 4.5 bathroom foothill home. Wake up to panoramic views of the surrounding hillsides and gather in the spacious living and dining rooms. The home is conveniently located just 15-20 minutes from San Diego's famous beaches and top attractions. After a day of exploration, unwind in the backyard area featuring a hot tub, fire pit, pool table, and life-sized chessboard.

Top guest favorite
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.
Home in La Mesa
4.89 out of 5 average rating, 197 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!

Popular amenities for Lakeside house rentals

When is the best time to visit Lakeside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ749ﺩ.ﺇ845ﺩ.ﺇ951ﺩ.ﺇ878ﺩ.ﺇ929ﺩ.ﺇ1,183ﺩ.ﺇ1,183ﺩ.ﺇ970ﺩ.ﺇ771ﺩ.ﺇ885ﺩ.ﺇ859ﺩ.ﺇ970
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Quick stats about house rentals in Lakeside

  • Total vacation rentals

    Explore 30 vacation rentals in Lakeside

  • Nightly prices starting at

    Lakeside vacation rentals start at ﺩ.ﺇ367 per night before taxes and fees

  • Verified guest reviews

    Over 950 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    30 of Lakeside vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lakeside rentals

  • 4.9 Average rating

    Lakeside stays are highly rated by guests—averaging 4.9 out of 5!

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