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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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Home in Fleming Island

4.94 out of 5 average rating, 140 reviews

Game Room+3 Kings+Fast Wi-Fi+Close to river

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

Home in Fleming Island

5 out of 5 average rating, 120 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 installed.

Farm stay in Middleburg

4.91 out of 5 average rating, 205 reviews

A Private Loft at Grand Landings Equestrian Center

Welcome to "The Loft" at Grand Landings LLC! Enjoy a taste of the country in our over-the-barn apartment, conveniently located on the outskirt of Jacksonville, Florida. Our recently renovated loft offers all the luxuries of home and comfortably sleeps 4 (with the option of a crib upon request). Enjoy a one-of-a-kind experience and go on a ride on our friendly horses, or venture out and enjoy easy access to nearby natural springs, beaches and restaurants. There's something here for everyone!

Home in Orange Park

4.86 out of 5 average rating, 162 reviews

Cheerful three bedroom home with a pool

Relax with the whole family at this peaceful place to stay. Enjoy the pool or just lay out in the pool area with friends. Have a bbq and enjoy family. Spacious backyard with two hammocks and a tree swing. Front porch has a nice sitting area and tree swing. Connect to your favorite streaming platforms on the smart TV's, tv room has karaoke and free WiFi. Board games in hall closet to enjoy with family. 3 miles from Orange Park Mall, AMC movie theatre and many restaurants just minutes away

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 362 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.

Home in Southwest Jacksonville

4.9 out of 5 average rating, 113 reviews

Cozy Home with Heated Private Pool and Patio

Nice and very clean house for your vacation and a comfortable stay. Cozy sitting area with a small pool. A protective screen around the recreation area will keep you from Florida insects))). Parking for 4 cars. Our home is located in a very convenient location: Less than 1 mile to the main road I-295 as well as the Costco store and Walmart Supercenter. At the same time, the house is located in a quiet area where you will not be disturbed by the various noises of city life.

Home in Orange Park

4.84 out of 5 average rating, 160 reviews

Immaculate Home with Private Pool and Patio

Welcome to our beautiful, cozy home in the heart of Orange Park, FL, only blocks away from shopping center, movie theater, variety of groceries, fine dining restaurants and fast food chains. The house fully equipped, pool, swing chair and relaxing patio. It’s a safe and wonderful neighborhood, perfect for beach lovers, 30min drive to St. Augustine historic town, and many long white sand ocean beaches. It’s a perfect choice for the away from home relaxing stay.

Home in Southwest Jacksonville

4.9 out of 5 average rating, 326 reviews

Retreat on the river

Deep water access to anywhere in Jacksonville with dock available. Back yard pavilion with outside kitchen, gazebo and Jamestown smoke pit 50 feet from river connecting to a remodeled home and landscaped pool. Home is not lived in and void of all personal property giving you open space to feel at home as your own. Bring your boat and tie up to the dock, or bring your kayak and take a paddle down the river. Two beds, four guest and plenty of room on couch

Guesthouse in Mandarin

4.98 out of 5 average rating, 103 reviews

Charming, Pet Friendly Retreat in Heart of NE FL

Welcome to Pop's Garage! Nestled in Jacksonville's vibrant Mandarin area, this beautifully renovated property blends modern comforts and rustic charm. As the perfect Northeast Florida retreat, Pop's Garage offers a cozy and convenient stay. The pet-friendly space includes a private and secure fenced-in area, allowing your canine to stretch out and explore. Discover the perfect balance of comfort and convenience at this one-of-a-kind vacation rental.

Home in Orange Park

4.96 out of 5 average rating, 152 reviews

Mr. Rogers Place (Family Friendly , Cozy, Clean)

Mr. Rogers house is conveniently located right off college drive in Orange Park. Making this the perfect spot for anyone visiting family in Fleming Island, Orange Park and even Middleburg. The house is on a quiet culdesac. This home is an extension of our Farm House just a 1.5 down the road. We welcome our guest to visit us during feedings to meet our lovely animals at HayStays Farm.

Guest suite in Saint Johns

4.92 out of 5 average rating, 202 reviews

Adorable studio with river access.

Relax with your friend or with family at this peaceful place with direct Saint John's river access. You can watch the beautiful sunset on the river. Bring your kayaks and fishing accessories. The river at the property is more than two and a half miles wide. You may fish or do a BBQ at the river. Motor home or RV parking is OK.

Cottage in Southwest Jacksonville

4.91 out of 5 average rating, 134 reviews

River Front Cottage

Entire property with covered patio and private dock on the Cedar River which is navigable to the Atlantic Ocean. This special place is close to everything, making it easy to plan your visit. 20 minutes to the Jaguar stadium or go to historical neighborhoods within a few miles or go 45 minutes south to St. Augustine.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Lakeside vacation rentals

Free parking on premises

Air conditioning

Stay near Lakeside's top sights

Whitey's Fish Camp31 locals recommend

Grumpy's Restaurant15 locals recommend

Texas Roadhouse12 locals recommend

OP Fish House and Oyster Bar10 locals recommend

Walmart Supercenter9 locals recommend

Pepper's Cocina Mexicana9 locals recommend

Other great vacation rentals in Lakeside

Townhouse in Orange Park

4.92 out of 5 average rating, 13 reviews

Orange Park Main Level Suite Cable Pet Friendly

Guesthouse in Green Cove Springs

4.86 out of 5 average rating, 29 reviews

Country home

Cabin in Middleburg

4.93 out of 5 average rating, 14 reviews

Rest, relax, revive-lovely 1 bedroom cabin

Guest suite in Saint Johns

5 out of 5 average rating, 41 reviews

Spanish Style Guest Suite-River Oasis Retreat

Villa in Orange Park

4.93 out of 5 average rating, 58 reviews

Blue Jade Villa w/ coffee shop/ private pool

Home in Middleburg

5 out of 5 average rating, 15 reviews

Country living at its Best!

Home in Middleburg

4.96 out of 5 average rating, 54 reviews

Black North Creek House &gardens

Rental unit in Southwest Jacksonville

4.84 out of 5 average rating, 61 reviews

Lake View Escape to The Exchange

Quick stats about vacation rentals in Lakeside

Total rentals
80 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
20 properties have a pool

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 50 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 50 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 60 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.
Are there Lakeside vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 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 40 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 60 homes with wifi, over 60 homes with air conditioning, over 50 homes with free parking, over 50 homes with a kitchen, 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 40 vacation rentals for guests traveling with pets.
Do house rentals in Lakeside have wifi?
Absolutely! We offer over 60 house rentals with wifi in Lakeside. Enjoy a tailored experience with all the comforts you desire.

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