House vacation rentals in Lakeside

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Popular amenities for Lakeside house rentals

House rentals with a pool

Guest favorite
A spacious living area features light wood flooring and modern furnishings. A comfortable sofa and a low coffee table are positioned on a decorative rug. A wall-mounted TV is visible, alongside a set of stairs leading to the upper level.
Home in St. Augustine
4.96 out of 5 average rating, 105 reviews

New luxury heated pool home steps from the beach!

GeorgiaRating, 5 stars1 month ago
Our stay was absolutely perfect! The house was beautiful, clean, and had everything we needed for a comfortable stay. The location couldn’t have been better—just steps away from the beach, making it so easy to enjoy the ocean any time of day. Eason was an amazing host, incredibly responsive and helpful throughout our stay. We couldn’t have asked for a better experience and would definitely stay here again! Highly recommend!
Guest favorite
A modern living area is complemented by sleek white furniture and a glass coffee table adorned with flowers. The open kitchen features stainless steel appliances and a spacious island. Ambient lighting enhances the pristine white floors and creates a welcoming atmosphere throughout the space.
Home in Orange Park
4.83 out of 5 average rating, 167 reviews

Stunning Modern Oasis with a Huge Pool

JamesRating, 5 stars2 weeks ago
Fantastic home. I want to stay shading in the future.
Top guest favorite
A private backyard showcases a sparkling pool with a stone patio. Two blue lounge chairs are positioned by the poolside, and a shaded seating area can be seen nearby. The house features large windows, allowing for natural light to fill the space.
Home in Southwest Jacksonville
4.96 out of 5 average rating, 162 reviews

+A Taste of Britain entire house / heated pool+

Ashley Rating, 5 stars4 days ago
Stay was amazing, had no issues and James was easy to reach and excellent with responses, house was clean, nice in a great area and very well equipped with everything we needed! Will use again!
Top guest favorite
The outdoor area features a private pool surrounded by palm trees and greenery. Lounge chairs with blue cushions are arranged by the poolside, complemented by striped umbrellas. Potted plants with vibrant flowers add color to the space, creating a tranquil setting for relaxation.
Home in St. Augustine
5 out of 5 average rating, 124 reviews

Private oasis, private pool, exceeds expectations

StefanieRating, 5 stars1 week ago
We had such a special weekend at this beautiful property. The space was peaceful, fun, and full of charm — perfect for making memories with family. Every part of the house and grounds felt so thoughtfully put together, with little hidden gems to discover everywhere you looked. Collecting eggs each morning turned into a fun little game, with everyone trying to call dibs on who got to do it that day. The man cave was a major hit — packed with personality and details that made it feel like staying at a friend’s place. We also loved spending time by the pool and relaxing in the screened-in patio — the perfect spot to wind down in the evenings. Thank you for sharing this one-of-a-kind home with us. We’re leaving with full hearts and some unforgettable memories.
Top guest favorite
Home in St. Augustine
4.98 out of 5 average rating, 164 reviews

Historic St. Augustine 2/2 Duplex & Pool

DaimierysRating, 5 stars2 weeks ago
What a beautiful place and fantastic location. Walked to downtown St. Augustine. Lili was very friendly and asked us a few times if we needed anything. Very clean and having a pool was an added bonus for us. We took advantage of the porch area and sat outside and just relaxed with the fantastic weather. It honestly was the best, very peaceful and relaxing, just what I was looking for, for my birthday weekend. Highly recommend. I would definitely stay here again and would recommend this rental to family and friends.
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 140 reviews

Southern Charmer w/Pool - Walk to Everything!

TiffanyRating, 5 stars1 week ago
Came for a wedding. The home was exactly as the pics showed and it was pristine inside with all the necessities including beach chairs, umbrellas and towels. Perfect location, walkable quaint little area, lots of great recommendations too. Great space, amazing host, Pauline always responded quickly and went above and beyond to accommodate us. We thoroughly enjoyed our time there, just needed another day or two to enjoy the town. Highly recommend.
Guest favorite
A cozy outdoor seating area features a sectional sofa with blue and cream cushions, accompanied by a glass-top table and four metal chairs. Soft lighting creates a welcoming ambiance, while a ceiling fan offers comfort during warmer days.
Home in Orange Park
4.87 out of 5 average rating, 175 reviews

Cheerful three bedroom home with a pool

AnnsleyRating, 5 stars5 days ago
Beautiful space! Absolutely recommend and will be staying here next time we are back in town!
Guest favorite
Home in Lincolnville
4.96 out of 5 average rating, 187 reviews

Walk downtown, pool beach min to everything pet ok

MikeRating, 5 stars1 month ago
Beautiful house,spacious, clean,lots of amenities, good location, walkable to shopping and restaurants. Very nice!

Weekly house rentals

Top guest favorite
A wooden storage box with the phrase 'Life is a Beach' holds neatly rolled beach towels in vibrant colors. A round area rug spreads across the wooden floor, while a tall, metal bar stool stands nearby, complementing the cozy corner of the living space.
Home in Beaches
4.99 out of 5 average rating, 154 reviews

Renovated Beach House w/ Pool and Outdoor Oasis

LisaRating, 5 stars6 months ago
Leslie and Joe were so welcoming and friendly and helpful. Their home was perfect for us. The house is a true beach house just a quick drive across the street from the ocean. The back yard is beautiful and the pool and jacuzzi were a nice way to help ease the stress of the storm. We actually came during Milton the Hurricane. We were seeking a safe place from the Tampa Bay Area. They were both able to ease massive anxiety by being so accommodating and we greatly appreciate everything. Can’t wait to visit again for a true vacation.
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, 230 reviews

Luxury Home w/ Glass Room & Patios

AlissaRating, 5 stars2 weeks ago
This was a great stay and home base while we were at my daughter’s dance competition. The home was very clean and located in a charming neighborhood. Lori was very responsive and had great communications. We would definitely stay here again!
Top guest favorite
A spacious sleeping area features a cozy king-size bed adorned with soft linens and pillows. A large screen TV displays a serene waterfall scene, while a shimmering gold accent wall adds a touch of elegance. Mood lighting creates an inviting atmosphere.
Home in Jacksonville
4.99 out of 5 average rating, 195 reviews

The Hothouse-Couples Escape: Play-Relax-Reconnect

NajiahRating, 5 stars1 week ago
I decided to book this place to celebrate my boyfriends 25th birthday. It looks like a page from magazine. This was a spectacular sensual mini staycation. It’s exactly what we both needed. Directions for utilization were precise & clear. I adored all of the sexy decor, sleek appliances and supplied amenities. The bed felt as if we were sleeping in the clouds. The space is absolutely spotless and smells wonderful. The time went by too quick ! We will definitely be back! Thank you Juliana & Mike.
Superhost
A comfortable living area features a gray sectional sofa adorned with blue throw pillows and a wooden coffee table. A large mirror reflects the room, and a stone fireplace adds a modern touch. Natural light is welcomed through a nearby glass door.
Home in Southeast Jacksonville
4.81 out of 5 average rating, 100 reviews

Cozy 3BR Home near San Marco - Sleeps 6

KatyRating, 5 stars2 weeks ago
Lisa's place will hold a special place with my family. we had a wonderful time and loved every minute spent at "home"
Guest favorite
A welcoming living area is presented with two comfortable sofas, one adorned with light blue cushions. A wooden coffee table sits at the center, topped with decorative items. Soft lighting from multiple fixtures illuminates the space, revealing an open layout connecting to the kitchen and dining area.
Home in Beaches
4.94 out of 5 average rating, 18 reviews

Coastal Chic Chalet

BrittneyRating, 5 stars1 week ago
I really enjoyed my stay at Jacksonville beach. The property is walking distance from the beach. There were beach towels and chairs already provided for us at the property. The house was located in a nice quiet neighborhood with plenty of privacy. The backyard was my favorite part, it was well manicured. I would rate my over all experience a a 10/10.
Top guest favorite
A spacious living area features soft blue and neutral furnishings, including a sectional sofa and a circular coffee table. Light streams in through large windows, illuminating natural accents and a contemporary artwork piece on the wall. The open layout connects to a dining area in the background.
Home in St. Augustine
5 out of 5 average rating, 32 reviews

5BR, Pool,HotTub, Putput, Walk to Beach,Game RM!

AshtonRating, 5 stars1 month ago
We had a wonderful time staying at this house. Jessica was super sweet and super friendly and make sure we had everything we needed. 10 out of 10 would recommend and we will absolutely stay there again when we come back in town!
Superhost
A two-story home is presented with a light-colored exterior and large front windows. A concrete driveway leads to a two-car garage. The front yard is landscaped with grass and shrubs, complemented by a small tree on the right.
Home in Jacksonville
4.9 out of 5 average rating, 29 reviews

30+day Rental, minutes from Beach, Mayo, Downtown

LidiaRating, 5 stars2 weeks ago
Comfortable home, clean and easy access to to hwy and parks nearby.
Superhost
Home in Beaches
4.87 out of 5 average rating, 111 reviews

Luxury Pool House Perfect for Family Getaway

StephanieRating, 5 stars3 weeks ago
The house was great for what we needed it for. The pool was awesome for our two kids. The master bathroom/bedroom was my husband and my favorite part of the house. We also loved how close it was to the beach just a two minute golf cart ride. The host was very responsive and when we had a couple issues they got them fixed quickly. My family would definitely stay there again.

Private house rentals

Guest favorite
The exterior of a two-story home is presented, showcasing a blend of light and dark siding. Large windows provide a view of the front entryway, flanked by greenery. A separate structure is visible to the left, adding to the overall spaciousness of the property.
Home in St. Augustine
4.93 out of 5 average rating, 164 reviews

5*Pool Oversized Home*Beach*Walk to all

TomRating, 5 stars4 months ago
We loved staying here. Beautiful home, extremely comfortable and very convenient to the old town. A nice surprise that Nancy decorated for Christmas with a tree, lights, etc. and set the mood for our Thanksgiving week with the town’s lights.
Guest favorite
A cozy bedroom is illuminated by natural light through two windows adorned with white blinds. A spacious bed is dressed in a gray quilt, complemented by decorative pillows. A small bedside table holds a lamp, creating a calm and restful ambiance.
Home in St. Augustine
4.93 out of 5 average rating, 15 reviews

Whole House Not Shared, Private in St Augustine FL

KaterynaRating, 5 stars5 months ago
Staying at Matt and Tashas was great. Its a serene home with all the basic amenities you need. Its very clean and centrally located to crescent beach and st augustine downtown. Matt was very communicative and proactive if I needed anything. It was greatly appreciated as I ended up having to do the trip alone instead of with my friend like I originally planned. The sitting area in the backyard was also very private and made for peaceful mornings enjoying the sunshine and birds chirping with a cup of tea. Overall a great stay in a quaint location with a lot of tranquility & convenience.
Superhost
An inviting entryway is displayed with a light-colored wooden console featuring storage drawers. A decorative wall tapestry adds a touch of warmth, while a cozy seating area with patterned cushions is visible. Natural light floods the space, leading towards the adjoining living area.
Home in St. Augustine
5 out of 5 average rating, 3 reviews

Sand and Waves: side by side Beachfront Bliss

MarkRating, 5 stars2 months ago
We stayed at Paola's place for a company retreat. We were able to book both houses and they very comfortably accommodated our group of 14, with room to spare. The houses were very comfortable. The property is amazing, with direct beach access and plenty of room. Paola was a great host. Very responsive and very helpful. I would definitely stay again.
Superhost
A covered porch is featured at the front of the home, supported by a wooden structure. Two blue chairs are positioned on the porch, providing a spot to relax. Surrounding the porch, low landscaping consists of small shrubs and patches of grass.
Home in Springfield
4.79 out of 5 average rating, 24 reviews

Blue Haven

TomRating, 5 stars1 week ago
Host was able to meet my groups unique needs, included some last minute changes!
Guest favorite
A bright dining area is highlighted by a large mirror framed in gold, reflecting the space's light tones. A wooden table is set with a vase of fresh flowers, while a stylish coat rack stands beside a hanging black jacket, enhancing the inviting design.
Home in St. Augustine
4.98 out of 5 average rating, 115 reviews

Country Cottage 3-bedroom home with free parking

CynthiaRating, 5 stars3 weeks ago
Love the entire home . Just a few folks driving through the neighborhood loudly a night or two. It’s super close to the beach and fun local restaurants ! So much to see and do . Everyone in our family had comfy beds !!! Def agent coming back
Superhost
A welcoming living room features a comfortable gray sectional sofa adorned with decorative pillows. A white coffee table sits at the center, surrounded by two contemporary chairs. Natural light enters through the windows, and a small lamp adds a soft glow to the space.
Home in St. Augustine
4.74 out of 5 average rating, 124 reviews

Uptown "Hide-Out" Stylish Home in Prime Location

NicoleRating, 5 stars1 week ago
Thank you for sharing your home with us! It is such a great location & super comfy! The parking pass was a nice bonus too! We love St Augustine & will definitely keep it in mind when we return!
Guest favorite
A bright turquoise door welcomes guests, set against a neutral-colored exterior wall. A small potted plant adds a touch of greenery near the entrance. The concrete area is spacious, providing easy access to the home, which is framed by lush foliage in the background.
Home in Beaches
4.93 out of 5 average rating, 27 reviews

Private Beautiful Beach House - steps to the beach

MistyRating, 5 stars1 week ago
This little house was so adorable and the beach was right across the street. Loved the location and that there was parking. The little backyard was fully fenced and perfect. It felt private and was great for dogs and included and outdoor shower and foot rinse. Kitchen was stocked with everything we needed to prepare meals. There was also beach chairs and umbrella that made going to the beach a breeze, didn't have to bring much with us! The place was clean and well maintained. Would love to visit again!
Top guest favorite
A screened outdoor area features a spacious deck with a central table. Palm trees add greenery, while playful decorations hang above. Soft lighting enhances the relaxing atmosphere, with glimpses of a lawn and recreational items visible in the background.
Home in Southwest Jacksonville
4.97 out of 5 average rating, 254 reviews

Single House: 12guests/4beds/2baths/huge backyard

LaurieRating, 5 stars2 weeks ago
Wonderful stay! We only needed to stay for one night but would have been extremely comfortable if we had needed to stay longer. We had five in our party. The house is very spacious and is exactly as described. Host was helpful with questions and helpful with other accommodations that were needed. Quiet area and absolutely perfect for a family. I highly recommend this house. We will be returning. Thank you for a perfect place.

Quick stats about house rentals in Lakeside

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    1.9K reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

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