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House vacation rentals in Lakeside

Find and book unique houses on Airbnb

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 paved driveway winds through lush greenery, leading to a charming farmhouse nestled among trees. The surrounding landscape features a variety of shrubs and mountains in the distance, offering a serene natural setting.
Home in Julian
4.96 out of 5 average rating, 131 reviews

"PINE Ridge VIEW" Private Large Deck Dogs ok Gated

"Pine Ridge View" is a charming farmhouse nestled in a private mountain setting, but only about 7 minutes from the town of Julian. Come relax and take in the magnificent mountain views—on a clear day, you can see all the way to the ocean. It's the perfect place to relax and create lasting memories with family and friends. Enjoy peaceful mornings with breathtaking sunrises and unforgettable sunsets. **We are pet-friendly ($65 per dog - per stay). Please note- the property is not fully fenced.

Top guest favorite
Home in Lakeside
4.93 out of 5 average rating, 138 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.

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, 910 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, 198 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.

Top guest favorite
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.
Home in La Mesa
4.99 out of 5 average rating, 195 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.

Top guest favorite
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
4.98 out of 5 average rating, 101 reviews

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.

Top guest favorite
An outdoor seating area is equipped with a sectional couch surrounding a stone fire pit, with flames flickering invitingly. A large dining table offers ample seating. The heated pool glistens in the background, surrounded by lounge chairs and shaded umbrellas.
Home in El Cajon
4.96 out of 5 average rating, 109 reviews

Family Fun Oasis Pool Spa and Game Room

Exceptional home w/heated pool and spa in a quiet neighborhood; kitchen has everything you need and more! Perfect for families with kids of various ages or multiple families. What to Expect: - Heated pool w/safety cover - Hot tub - Game Room - Trampoline - Jungle gym - Baby/toddler supplies (pack N play/High Chair) - Spacious master suite. - 20 mins to the beach, the San Diego Zoo, Balboa Park, Sea World, Little Italy and downtown San Diego and all that it has to offer!

Superhost
Home in La Mesa
4.84 out of 5 average rating, 109 reviews

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. ☀️

Guest favorite
Home in La Mesa
4.94 out of 5 average rating, 140 reviews

Palm Cottage, San Diego

Palm Cottage sits in the heart of La Mesa Village, San Diego. Enjoy the charm of a historic home with a fully remodeled and stylish interior featuring both Dutch & French doors letting in plenty of sunshine. A large private yard w/ covered outdoor living area creates the ultimate indoor/outdoor lifestyle. You're steps from the local grocery store, village shopping, coffee shops, restaurants, bars and the trolley. You could not ask for a better location!

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, 120 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.

Guest favorite
A spacious living area features a large leather sectional sofa positioned around a circular wooden coffee table. A wall-mounted TV is visible above a decorative fireplace, while natural light streams through a large window adorned with sheer curtains. A dining area is seen in the background.
Home in La Mesa
4.89 out of 5 average rating, 125 reviews

Sunny & Spacious 3BR Retreat w/ Parking & A/C

Discover your La Mesa retreat! This newly refurbished home offers a perfect blend of comfort and convenience. Enjoy a gourmet kitchen, stylish dining, three bedrooms, two modern bathrooms, and an expansive yard. Explore nearby attractions like the Grossman Center (10-min walk) with shopping and dining, or venture to San Diego's heart (20-min drive). Perfect for families and groups seeking a relaxing getaway.

Top guest favorite
Home in El Cajon
4.99 out of 5 average rating, 111 reviews

Quiet Country Home

Extremely clean home. Fenced private yard with BBQ & Tables. Outdoor smoking. 25 minutes to beach or downtown. Rural area with animals “talking”. Horses 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 completely separate granny flat.)

Popular amenities for Lakeside house rentals

When is the best time to visit Lakeside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$58,565 GYDG$47,479 GYDG$52,081 GYDG$49,989 GYDG$52,918 GYDG$67,350 GYDG$67,350 GYDG$55,218 GYDG$43,924 GYDG$50,408 GYDG$48,944 GYDG$55,218 GYD
Avg. temp15°C15°C16°C17°C18°C20°C21°C22°C22°C20°C17°C14°C

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 G$20,916 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,030 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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