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Vacation rentals in Lakeside

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Lakeside

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

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Guest favorite
The exterior of the house features a two-story design with light blue shutters, a grand entrance, and well-maintained landscaping. A lush green lawn surrounds the property, with colorful plantings adding vibrancy to the setting. Ample natural light reflects off the front windows.
Home in Orange Park
4.88 out of 5 average rating, 8 reviews

Rococo Entire Home- 1 king bed 1 bath/ Game room

Rococo offers plenty of room couples to enjoy a relaxing stay. The home features 1 king bed and 2 sleeper sofas accommodating up to 4 guests comfortably. The master bedroom located on the first floor includes a walk in shower perfect for unwinding. You'll appreciate our recently updated kitchen and the open, spacious living room that's ideal for gathering and relaxation. The property includes a private driveway with ample parking space for your convenience. The garage is not available for use.

Superhost
A modern living area features a light-colored sofa adorned with dark cushions and a soft throw blanket. A glass coffee table is positioned on a textured area rug, complemented by a stylish floor lamp and a leafy plant beside it. A large abstract artwork adds a striking focal point.
Apartment in Jacksonville
4.86 out of 5 average rating, 101 reviews

Lake View Escape to The Exchange

Give us your worries and we will give you an escape. Welcome to the Exchange! This Orange Park unit supports your work requirements and your playful desires. Multiple high volume healthcare facilities surround the area and the Naval Air Station is in the backyard. Luxury dinning and outdoor water activities abound. This new unit offers access to a resort style salt water pool, private garages, state of the art fitness center and wellness studio, dog park, clubhouse and lounge, and much more.

Top guest favorite
Farm stay in Middleburg
4.97 out of 5 average rating, 219 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!

Guest favorite
The kitchen area features modern white cabinetry and stainless steel appliances, including a dishwasher and sink. A colorful rug lies on the floor, enhancing the space. Bright natural light enters through the window, while a dining area with red chairs is visible in the background.
Home in Middleburg
4.95 out of 5 average rating, 113 reviews

Modern E. Orange Park Home 6 bed Fence Beach 45Mn

New Stylishly renovated home just West of Fleming Island in Middleburg, South of Orange Park, West of Jacksonville Florida. Christmas 365! Farmhouse style, TV’s in all bedrooms, with a touch of Christmas theme. 6 beds, Fenced yard, 75" LED TV, front/back porches available up to 10 people. Beaches approx. 40 minutes The home is close to restaurants, grocery stores, banks, gas stations, main hospital(2+miles). There are lakes and rivers locally to fish/boat, parks, shopping, and trails:)

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, 241 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, 156 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.

Top 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, 171 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.

Top 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
4.94 out of 5 average rating, 149 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.

Top guest favorite
Apartment in Middleburg
5 out of 5 average rating, 5 reviews

Escape to the Hidden Gem - a quiet country retreat

Start your adventure in a place where old-world charm meets quiet country luxury. Nestled in a serene gated community is your 1 bed/2 bath retreat, perfect for the seasoned traveler. Spend your days writing, reading, or listening to the sounds of nature. Explore the nearby trails, fish the local creeks or simply sip coffee on the porch. There’s a full kitchen for the culinary minded as well as the convenience of multiple restaurants and shops nearby.

Top guest favorite
Apartment in Jacksonville
5 out of 5 average rating, 31 reviews

Nice studio in Jacksonville

Charming Remodeled Studio with Patio Access & Free Parking Welcome to your cozy home away from home! This recently remodeled studio features a private bathroom and a convenient kitchenette, perfect for short or extended stays. Step outside to enjoy a peaceful patio space—ideal for your morning coffee or evening unwind. Located in a quiet neighborhood with free parking included, you'll have everything you need for a comfortable and relaxing stay.

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, 136 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.

Top guest favorite
A serene view of the North Prong of Black Creek is depicted, showcasing calm water reflecting lush greenery. Trees frame the scene, creating a peaceful atmosphere. Wooden docks are visible in the background, inviting moments of exploration and relaxation.
Guest suite in Middleburg
4.99 out of 5 average rating, 92 reviews

Secluded, Cozy Guest Suite on Black Creek

Come down the driveway and escape the world. Situated on the North Prong of Black Creek, this cute studio suite offers rural with benefits. There's something for all outdoor lovers- birdwatching, kayaking, fishing, paddle boarding, wildlife, and more. If you want to just listen to the birds and cicadas, that's ok, too. The apt has a microwave, Keurig, toaster, and small fridge. Wifi is fast for remote working.

Popular amenities for Lakeside vacation rentals

When is the best time to visit Lakeside?

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Frequently Asked Questions

  • 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 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.

  • Do house rentals in Lakeside have free parking?

    Absolutely! We offer over 40 house rentals with free parking in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • 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 40 house rentals with a kitchen in Lakeside. Enjoy a tailored experience with all the comforts you desire.

  • Are there Lakeside vacation rentals on Airbnb with pools?

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

  • Are there family-friendly vacation rentals in Lakeside?

    Lakeside has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Enhance your stay in our House Rentals with the most popular amenities: over 40 homes with free parking, over 40 homes with a kitchen, over 50 homes with wifi, over 50 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there pet-friendly vacation rentals in Lakeside?

    Four-legged friends are welcome in Lakeside. Choose from more than 20 vacation rentals for guests traveling with pets.

  • 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.

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 € 26 per night before taxes and fees

  • Verified guest reviews

    Over 3,250 verified reviews to help you choose

  • Family-friendly vacation rentals

    30 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 20 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!

  1. Airbnb
  2. United States
  3. Florida
  4. Clay County
  5. Lakeside