Vacation rentals in Lakeside

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Top-rated vacation rentals in Lakeside

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

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Top guest favorite
The back patio features a cozy seating arrangement with a modern sofa and a small table. Twinkling string lights illuminate the area as evening approaches, providing a warm ambiance. A dining table for four is visible on the patterned outdoor rug, amidst a spacious fenced yard with trees.
Home in Fleming Island
4.96 out of 5 average rating, 188 reviews

The Flemingo- Game Room 3 Kings

Welcome to the Flemingo where can relax on the back patio with a glass of wine and twinkling string lights above. You'll watch the dogs and kids play in the large fenced yard while throwing a frisbee (provided). You'll love cooking a delicious meal in the spacious kitchen. You’ll have a blast in the garage game room! Battle it out on the air hockey table, foosball, darts or boxing bag. At night, the kids will hang out in the garage game room, in the living room playing board games or on

Top guest favorite
An outdoor patio area features a wooden table and chairs, providing a relaxing space to enjoy views of the water. A flag flies in the distance, while a covered structure offers shade. Lush green grass surrounds the area, enhancing the natural setting.
Place to stay in Orange Park
4.93 out of 5 average rating, 120 reviews

Beautiful 3 bedroom 2 bathroom waterfront home

Welcome to Cedar house, located on Drs. lake in orange park Fl. Conveniently located to 295 and just 15 mins from N.A.S. Jax ,30 mins from down town Jax, and 30 mins from the shopping at St johns town center, our home has been recently remodeled in 2022 and is a cosy and relaxing escape. With brand new kitchen, bathrooms, and open floor plan and the new dock/ boat house its perfect for getting the boat on the water or relaxing with friends/family and enjoying the fishing under the Florida sun.

Guest favorite
A modern kitchen is showcased, featuring white cabinetry and a spacious countertop. Stainless steel appliances, including a refrigerator and oven, are visible. The tiled floor provides a practical surface, while a doorway leads to a dining area adorned with a decorative light fixture.
Home in Middleburg
4.95 out of 5 average rating, 133 reviews

Modern Orange Park Home w/6+Beds&Wash/Dryer Fence

Stylishly renovated home North of Middleburg and South of Orange Park Florida. 6+beds TV’s IN ALL ROOMS, available for use to accommodate up to 9 people. One King bed, 2 twin beds, double bed, a pull out queen sofa bed, and air mattress. Peace and quiet just minutes away from the city yet still comfortable. The home is close to many restaurants, grocery stores, banks, gas stations, and main hospital (1/2-2+miles). There are creeks and lakes locally to fish, parks. Beaches approx. 45 mins.

Guest favorite
A two-story house is set back on a spacious driveway, surrounded by lush trees and vegetation. A manicured lawn features well-maintained plant beds near the entrance, while the garage is visible on the left side of the structure under a clear blue sky.
Vacation home in Orange Park
4.91 out of 5 average rating, 110 reviews

Casandra House - Peaceful / Salt Pool and Hot Tub

Welcome to Casandra House. A peaceful getaway in Orange Park, FL. Located in the vicinity of Doctor's Lake, this house sits on 3/4 of an acre surrounded with trees and vegetation. It provides just enough privacy to make you feel away from everything while minutes from shops and restaurants. Home includes a large backyard, patio screen enclosure, salt pool and hot tub. About 2 1/2 miles from the Orange Park Thrasher-Horne Center and 10 miles from NAS Jacksonville. Note: No direct lake access.

Guest favorite
Farm stay in Middleburg
4.97 out of 5 average rating, 230 reviews

Haystays Farm-Cozy, Charming, Country, Modern Home

Welcome to our special farm house! The home sits on 1.5 acres that is perfectly located on the Orange Park and Fleming Island line. Our location is ideal to everyone! We have plenty of space that makes our farmhouse so AMAZING! You will experience the feel of country living with all the perks of great restaurants, shopping and convenience of being near everything Jacksonville has to offer. Our home is super clean with many amenities to make you feel at home. We love it here and so will you!

Top guest favorite
The kitchen features white cabinetry with ample storage and a spacious countertop. Stainless steel appliances, including a double oven and dishwasher, are visible. A window allows natural light to illuminate the workspace, and a small area rug adds a touch of warmth.
Guesthouse in Jacksonville
4.98 out of 5 average rating, 394 reviews

Private Apartment

Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen. Property access for our guests only. Complimentary beer, sodas, water and coffee! Adults only.

Guest favorite
The entryway is highlighted by double doors that open to a welcoming view of the front yard. Natural light floods the space through a large transom window above the doors, framing a picturesque scene of manicured grass and distant trees.
Home in Orange Park
4.9 out of 5 average rating, 249 reviews

Luxury Home w/ Glass Room & Patios

Spectacular Inside and Out This magnificent 2940 sq foot home is in a prestigious lakeside neighborhood. It offers a large open concept living area with an adjoining 400 sq foot climate controlled sun room with a pocketing glass interior wall; to bring the outside in and the inside out. The exterior of the sun room is constructed of glass doors which can also be opened and stacked to facilitate an open air porch. Owner lives in the neighborhood and is quick to respond to your needs.

Top guest favorite
An outdoor space features a stone patio with a circular arrangement of four black chairs surrounding a fire pit on gravel. Verdant landscaping and trees provide a natural backdrop, enhancing the tranquility of the area.
Home in Fleming Island
4.99 out of 5 average rating, 168 reviews

Rustic Owl in Fleming Island with 2 Kings

From our family to yours. Located in the heart of Fleming Island, Rustic Owl was designed and appointed with extended family in mind. We wanted a space for families to visit, relax and enjoy each other.... while being comfortable. This gem offers comfy beds, smart TVs, an open floor plan, laundry facilities, upgrades throughout and with inviting outdoor spaces that overlook a rustic nature preserve. Super clean, Super Fast Wifi and well appointed amenities. Level 2 EV Charger.

Guest favorite
A well-lit bedroom features a spacious bed with soft linens, complemented by stylish lighting and neutral wall tones. The bathroom showcases a walk-in shower with clear glass doors, coupled with modern fixtures. The kitchenette is equipped with essential appliances and a small dining table, enhancing functionality.
Guesthouse in Jacksonville
4.96 out of 5 average rating, 201 reviews

Private, Modern And Cozy Guesthouse

Kick back and relax in this calm, stylish space. Enjoy the privacy of this recently renovated unit which includes a queen-sized bed, and a small living room with a sleeper sofa, so the place can comfortably accommodate up to three. Also included, a 50-inch smart TV, kitchenette, bathroom/shower, closet, and keypad lock for easy access in and out. Please note that we have an exterior security camera on the front to enhance your safety. Conveniently situated 1 mile off Highway 295.

Guest favorite
A spacious bedroom features a king-size bed with white bedding and decorative pillows. A bright yellow throw blanket adds a pop of color. Two modern artworks are displayed above the bed, while a large mirror reflects the room's design, enhancing the sense of space.
Guest suite in Jacksonville
4.93 out of 5 average rating, 168 reviews

Cozy Private Guest Room - Entire Studio Suite

This gorgeous and elegant Suite style room with a great Westside location. Very private, warm and Comfortable large Bedroom where you can have some privacy to work or just relax after a long day. Most of our guests are coming from all over the country for special events, or simply for a getaway as a couple. Brand new furniture’s, smart TV, WIFI, and Netflix. Electronic lock door and security measures, safety and friendly neighborhood You'll love this unique and romantic escape.

Guest favorite
The houseboat is anchored in a serene marina, featuring a modern design with large windows that provide ample natural light. Surrounding boats are docked neatly under solar panel canopies, reflecting a commitment to sustainability. The calm water enhances the tranquil atmosphere of the setting.
Houseboat in Fleming Island
4.9 out of 5 average rating, 107 reviews

New Floating Luxury: Unique Houseboat Retreat

Hit the "♡ Save" button to bookmark our unique property 》 Welcome to Home A Wave, a unique, fully furnished houseboat on the tranquil waterfront, promising an unforgettable stay. ★ Unbeatable Waterscape: Experience tranquility and adventure. ★ Top Deck Bedroom: Enjoy panoramic views and starry nights. ★ Water Activities: Swim, paddle, or fish directly off the deck. ★ Modern Amenities: Benefit from a well-equipped galley and in-house laundry.

Guest favorite
A spacious sleeping area features a large bed adorned with a colorful coral-patterned quilt. Natural light floods the room through a window, highlighted by vibrant curtains. A small dining area with high chairs is visible, along with decorative accents like fresh flowers.
Guest suite in Orange Park
4.88 out of 5 average rating, 150 reviews

Guest Suite

Enjoy your stay at this vivid private space! This suite is a colorful paradise that is surrounded by nature on a 2 acre property. Guests will be surrounded by color and outdoorsy scenery. The designated parking area is to right at a colored bee post. As you walk up the steps that lead you to the patio, you will see the door that will lead you to your lively suite. Our Suite is attached to the main house, with everything private.

Popular amenities for Lakeside vacation rentals

When is the best time to visit Lakeside?

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Avg. priceﺩ.ﺇ477ﺩ.ﺇ485ﺩ.ﺇ510ﺩ.ﺇ529ﺩ.ﺇ488ﺩ.ﺇ510ﺩ.ﺇ521ﺩ.ﺇ510ﺩ.ﺇ474ﺩ.ﺇ485ﺩ.ﺇ496ﺩ.ﺇ496
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Lakeside?

    Lakeside has more than 40 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Lakeside?

    Experience the best of Lakeside with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Lakeside?

    Four-legged friends are welcome in Lakeside. Choose from more than 30 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Lakeside?

    Yes! Work meets play with ease at over 40 vacation rentals in Lakeside featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there Lakeside house rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 10 house rentals with pools in Lakeside, available on Airbnb. Make a splash and soak up the sun in style!

  • Do house rentals in Lakeside have air conditioning?

    Absolutely! We offer over 50 house rentals with air conditioning in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lakeside have a kitchen?

    Absolutely! We offer over 50 house rentals with a kitchen in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lakeside have wifi?

    Absolutely! We offer over 50 house rentals with wifi in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Lakeside have free parking?

    Absolutely! We offer over 50 house rentals with free parking in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Lakeside?

    Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 50 homes with a kitchen, over 50 homes with air conditioning, over 50 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Lakeside

  • Total vacation rentals

    Explore 60 vacation rentals in Lakeside

  • Nightly prices starting at

    Lakeside vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

  • Verified guest reviews

    Over 3,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    60 of Lakeside vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Lakeside rentals

  • 4.8 Average rating

    Lakeside stays are highly rated by guests—averaging 4.8 out of 5!

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  5. Lakeside