Family-friendly vacation rentals in Lakeside

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Popular amenities for Lakeside family-friendly rentals

Family-friendly home rentals with a hot tub

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, 165 reviews

5*Pool Oversized Home*Beach*Walk to all

TomRating, 5 stars6 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
An aerial view captures the oceanfront outdoor pool, surrounded by lounge chairs, palm trees, and pathways leading to the beach. The expansive sandy shore and ocean waves are visible in the background, emphasizing the relaxed coastal atmosphere.
Villa in St. Augustine
4.88 out of 5 average rating, 94 reviews

St Augustine Villa | Pools, Hot Tub & Beach Access

MonicaRating, 5 stars2 weeks ago
This place was perfect for our anniversary weekend! The location is perfect- you can walk to the pool or beach in minutes, but it is also a close drive to downtown St. Augustine. The beach felt like your own private beach- not crowded at all! I loved that the condo was away from the main building so it was very quiet. They had snacks and coffee available for us as well! We will definitely be back!
Top guest favorite
A screened lanai features a tranquil Koi pond, surrounded by lush greenery and rock accents. Seating is available with several white Adirondack chairs arranged nearby. A paved pathway leads to a well-maintained lawn and a putting green, enhancing the outdoor space.
Home in Southeast Jacksonville
4.95 out of 5 average rating, 189 reviews

The confetti house - 1 mile from the Mayo clinic!

TracyRating, 5 stars3 weeks ago
This house had everything! W e watched the Koi fish, fine tuned our putting game, and enjoyed the wonderful screen porch while watching TV at night. Very clean and lots of extra amenities for the family+
Top guest favorite
A distant view showcases the ocean with gentle waves rolling onto the sandy shore. A wooden walkway leads to the beach, framed by lush greenery and palm trees. The sky is bright with a few scattered clouds, creating a serene coastal atmosphere.
Condo in St. Augustine Beach
4.9 out of 5 average rating, 333 reviews

Beach side condo

DiannRating, 5 stars4 days ago
Doug and Lori's place was great! Enough room for our family of 4. Having 2 beds in the second bedroom is nice, the beds were very comfortable. It was easy to walk to the beach, and this beach is wide and not crowded- a big plus. Kitchen had everything you needed. Supplied beach towels which is nice so you don't have to pack them. Only down side, we didn't stay long enough! It's a great area!
Guest favorite
A scenic view from the balcony shows a large pool surrounded by lounge chairs, with the ocean and sandy beach visible in the background. Lush green landscaping enhances the outdoor area, offering a serene atmosphere for relaxation under a clear blue sky.
Apartment in St. Augustine
4.93 out of 5 average rating, 170 reviews

Ocean View 3br Condo! Indoor pool, steps to beach

AngelaRating, 5 stars2 weeks ago
This is THE PLACE for families. Tons of families with kids we're staying at this condo association, so our children easily found playmates. There's food trucks that come on site during the day and a large field between the pool and the condo buildings where kids congregate after dinner to play games, watch movies, and play music. The pool, field, and playground are all viewable from the balcony. Easy boardwalk to the beach. The condo was perfect for a beach stay- large covered balcony, and master bed was very comfortable.
Guest favorite
A spacious outdoor area is enclosed within a screened area, featuring a heated saltwater pool and a spa. Comfortable lounge chairs are positioned around the pool, while a dining table is visible in the shaded seating area, providing an inviting space for relaxation and gatherings.
Home in Beaches
4.88 out of 5 average rating, 170 reviews

Renovated Beach Escape HTD Pool, Spa, Putt Putt

RobinRating, 5 stars1 month ago
We enjoyed the home and pool! The house was exactly like the photos. It was extremely clean and the kitchen was well equipped! There were plenty of linens, including pool towels. The host was always quick to reply and always polite. We would stay here again!
Guest favorite
The backyard is illuminated by soft lighting, showcasing a private heated pool surrounded by a screened enclosure. Lush palm trees and well-maintained landscaping enhance the tranquil atmosphere. The two-story home is visible in the background, adding to the serene nighttime setting.
Home in St. Augustine
4.93 out of 5 average rating, 134 reviews

Hawaiian Island Escape ~ Heated Pool/Spa/Beach

GilbertRating, 5 stars2 weeks ago
I can’t say enough about this place! From the beautiful house with all the needed amenities to the gorgeous private pool and hot tub area. The decor was absolutely beautiful and the beds were so comfortable! The location is quiet and private but still close to all the history and beauty of St. Augustine. Abrina was very helpful in recommending a close beach access which is very easy to get to and walkable or just a 2 minute ride if you prefer. She was very responsive to any questions and made things so smooth! I would definitely stay here again without a second thought!
Superhost
The living area features a light blue wall, a large flat-screen television mounted above a dark wooden console, and a comfortable seating arrangement. One brown leather armchair complements a dark sofa, with natural light filtering through a doorway leading to another space.
Home in St. Augustine
4.86 out of 5 average rating, 235 reviews

1st street, Cedar Beach House Retreat

JohnRating, 5 stars1 month ago
An excellent place where I'd happily stay again. It is a just a block from the main road that runs along the beach. The neighborhood was quiet and very conveniently located. We were pleasantly surprised at the near miraculous cleanliness of the location when we arrived. The small items makes this host an A+ choice. MANY towels available for beach and house use. A great blender available in the kitchen.l and more than enough plates and silverware so you didn't have to worry about running out. If you are vacationing do not miss the alligator farm (where the roosting birds may have been more fascinating then the alligators), going on a kayak eco tour, and Mojo Tacos.

Family- and pet-friendly home rentals

Guest favorite
A spacious bedroom showcases a king-size bed with decorative pillows and a tufted headboard. Natural light streams in from adjacent doorways, highlighting wooden flooring. Two bedside lamps provide soft illumination, while a ceiling fan with leaf-shaped blades adds a touch of charm.
Apartment in St. Augustine
4.92 out of 5 average rating, 211 reviews

Elegant, FREE BIKES dog-friendly downtown apart.

SandyRating, 5 starstoday
Location was in a quiet neighborhood. Historic building with so much charm. Enjoyed riding the provided bikes and grilling out back. Being close to downtown was very convenient. Thank you for a lovely stay and the last minute requested change.
Guest favorite
A two-story villa with a light blue exterior features multiple balconies and arched entryways. The front is adorned with white railings and a stone pathway, complemented by landscaped areas with greenery. A mix of cloudy and clear skies enhances the welcoming appearance of the home.
Townhouse in St. Augustine
4.9 out of 5 average rating, 128 reviews

Avery s Ocean Breeze - Family and Pet Friendly !

KyleRating, 5 stars1 week ago
Great place to stay with family. Easy access to the ocean and beaches. Location is spot on, only 20 mins to almost anything you may need.
Guest favorite
A spacious living area features comfortable leather seating and a glass coffee table. Large sliding doors open to a balcony with ocean views, allowing natural light to brighten the room. A flat-screen TV is mounted on the wall, enhancing entertainment options.
Condo in Beaches
4.92 out of 5 average rating, 102 reviews

Beachfront Luxurious Charming 2BR Condo

CathyRating, 5 stars2 weeks ago
Our entire week was perfect! Shastri was kind to us as our schedule changed and I had to move my date staying at his place. The instructions that were sent are clear and they give you everything that you need to know! The view from his place was amazing! Needed a peaceful getaway with family and this was the right spot! I would not hesitate going back again. Great host, great spot and beautiful location!
Top guest favorite
A private entrance is situated at the front of the property, featuring a white door surrounded by large windows with green shutters. The exterior is complemented by a stone patio area with outdoor seating, enhancing usability for relaxing outside.
Vacation home in St. Augustine
4.98 out of 5 average rating, 128 reviews

1st Street Retreat, Dog Friendly Updated Apartment

LeslieRating, 5 stars6 days ago
I cannot say enough good things about our stay at Lisa’s in St. Augustine! The location was unbeatable - barely a five minute walk to the beach, with a taco stand and brewery at each corner and lots of amazing walkable places nearby (Kookaburra Coffee and Island Donuts to name a few)! It was barely fifteen minutes to downtown St. Augustine as well. The Airbnb itself was easy to find and had a parking spot. The space was clean, cozy, and comfortable, with an outdoor shower and dog run - it took all the stress out of traveling with dogs! We truly had the best time; my only regret is that I wish we had gotten enough time off work to stay longer! Lisa even allowed us a complimentary late checkout to enjoy more time at the beach. If you are traveling with dogs and looking for a simple, cozy, convenient place to escape to the ocean and historic St. Augustine, this is the place! We can’t wait to come back!
Guest favorite
A spacious living area features light wood flooring and a comfortable couch with decorative pillows. A coffee table with a glass top is centered in the room, accompanied by a relaxing chair. A TV is positioned on a media console, with a dining area visible in the background.
Townhouse in St. Augustine
4.9 out of 5 average rating, 136 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

MarRating, 5 stars1 month ago
Given the need for an immediate relocation, Inga was very helpful and her home was just what we needed to enjoy the rest of our vacation. You could tell her home was cleaned very well and we felt right at home.
Guest favorite
The cottage features a welcoming exterior with a covered porch and two bright blue adirondack chairs. Soft blue walls are complemented by decorative trim, while lush greenery and pebbled landscaping enhance the inviting atmosphere. A privacy fence and palm trees are visible in the background.
Bungalow in Butler Beach
4.94 out of 5 average rating, 184 reviews

Crescent Moon: soft sand beach, pets welcome

SallyRating, 5 stars3 weeks ago
What a gem! Perfectly positioned one block from the beach, this bungalow is just adorable. Fun decor, comfortable bed, more than enough room for my two teens and I to spread out. Shopping and dining are mere minutes away. The beach is a VERY short walk and beach itself is clean and beautiful. Martie was very accommodating and easy to work with. Five stars all the way! We’d love to come back!
Superhost
Home in St. Augustine
4.88 out of 5 average rating, 187 reviews

Crescent Beach House

DianeRating, 5 stars3 weeks ago
I am so very thankful for my stay at this beautiful home. Everything we needed and then some! Absolutely, gorgeous. Made a nice meal in the kitchen as well. The deck is super nice. Chris and Evelyn are excellent host. I loved the bible verse in the sun room too! Felt very comforted by that. Thank you again very much. You made this an amazing weekend for graduation. Thank you ☺️
Guest favorite
The living area features a spacious couch adorned with decorative pillows, situated across from a flat-screen TV on a white media console. A round glass coffee table rests on an area rug with intricate patterns, while light filters through sheer curtains enhancing the room's bright ambiance.
Apartment in St. Augustine
4.92 out of 5 average rating, 137 reviews

5 walking minutes to the beach

SarahRating, 5 stars1 week ago
had a wonderful stay at Sonja's place for my birthday weekend!! exactly as pictured, very quiet and peaceful, super easy and walkable to the beach. not too far from downtown st augustine either :)

Family-friendly home rentals with a pool

Top guest favorite
A private pool area is surrounded by a wooden fence and tropical landscaping. A ladder leads into the clear blue water, inviting relaxation. Sunlight filters through the trees, creating a serene atmosphere. A sign indicating 'Beach Access' is prominently displayed.
Home in St. Augustine
4.94 out of 5 average rating, 133 reviews

The Lazy Anchor-Pool-Walk to Beach-Dog Friendly

SandraRating, 5 stars2 weeks ago
We ended up booking Dalerie’s place at the last minute due to a rental that did not meet our needs due to a recent surgery. Dalerie was quick to respond to our request and the place was perfect for our family. We had an 11 month old along so the availability of a highchair and the large space for us to move around was a huge win. Her house was stocked appropriately for things for the beach as well as the kitchen. The pool was a must as we have a four year-old granddaughter who loves to swim. It was the perfect opportunity in the afternoon to burn off some more energy after the beach before we went to one of many yummy places nearby for dinner. The screen porch is lovely! And her location in Vilano Beach is terrific. If you want to walk to the beach it is easily accessible down the street. We prefer Porpoise Point beach in order to drive with all our stuff and it is 5 minutes down the road. I highly recommend this rental!
Guest favorite
A sandy beach scene features gentle dunes with beach grass swaying in the breeze. A wooden post and rope line mark the pathway, guiding visitors to the shore. The ocean extends towards the horizon, reflecting the soft sunlight under a sky filled with clouds.
Condo in St. Augustine
4.93 out of 5 average rating, 104 reviews

Lovely 2BR/2BA Oceanview Condo, St Augustine Beach

LindaRating, 5 stars3 weeks ago
Jeremy’s place was everything we wanted! Incredibly clean, had everything we needed (even had snacks and a bottle of wine waiting for us after our 10 hour road trip). Incredibly easy access to a peaceful beach and tons of cards games and board games for downtime at the condo. He was responsive and very friendly to any and all questions we had. Definitely recommend and would stay again!
Top guest favorite
A community pool is framed by lush palm trees and features lounge chairs arranged along the edges. The pool area is enclosed by a black fence, with a green gazebo visible in the background, creating a relaxed outdoor atmosphere.
Condo in St. Augustine Beach
4.94 out of 5 average rating, 193 reviews

The Beach Retreat!

SheridanRating, 5 stars3 weeks ago
We had a great time! Being so close to the beach, pier and restaurants was perfect.
Guest favorite
An inviting heated pool is surrounded by a stone-paved area, featuring six lounge chairs positioned nearby. Lush greenery and a privacy fence provide a tranquil backdrop, enhancing the outdoor relaxation space.
Home in St. Augustine
4.87 out of 5 average rating, 334 reviews

Pure Relaxation: heated pool, beach, cabana & more

KarenRating, 5 stars4 weeks ago
This is the second time we stayed at this amazing property. It’s quiet and close to so many things. Pet friendly in most areas. Our puppy was super happy to be so close to the beach. The hosts responded almost immediately every time and honestly are so sweet. This is now our go to place for a quick weekend trip! Thank you so much!!!!
Guest favorite
A private balcony features two light-colored chairs and a round table, providing views of the ocean and a nearby pool. The scenery includes lush greenery and a clear sky, while birds can be seen flying in the distance.
Condo in St. Augustine
4.85 out of 5 average rating, 272 reviews

Direct Oceanfront ~ Fantastic Views!

MeganRating, 5 stars2 weeks ago
Beautiful view of the beach and right next to the pool. We had a short stay but so glad we chose to stay here. Also highly recommend Commanders Outpost restaurant (3 minute drive down the street) for a great dinner
Guest favorite
A spacious outdoor pool area is surrounded by well-maintained lounge chairs, with vibrant umbrellas providing shade. The condominium building features multiple levels and has a warm color scheme, highlighted by palm trees. Clear blue skies add to the inviting atmosphere.
Apartment in St. Augustine Beach
4.94 out of 5 average rating, 185 reviews

Modern & Comfy Beach Gem: Pool ~ Ocean Views ~ Pkg

BarbaraRating, 5 stars1 day ago
The location on the beach of Saint Augustine was heavenly. Angela Melanie responded to all of our questions promptly. The pictures do not do it justice. You are on the beach, walking in sand almost immediately after you exit your condo. Weekly price was great and well worth it with everything included in the condo and on the grounds. Love this place and the host and will definitely visit again.
Guest favorite
A heated pool is surrounded by a spacious patio with loungers and vibrant red umbrellas. Lush greenery enhances the area, complemented by a bright yellow building in the background. The serene setting is ideal for relaxation and enjoyment.
Apartment in Lincolnville
4.95 out of 5 average rating, 111 reviews

F2 Downtown, POOL, beaches, free parking!

AlaneRating, 5 stars1 month ago
Kirsten is a great host, very friendly and helpful. The home is in a quiet neighborhood, walkable to restaurants, historical sites and the bay front. Definitely a place I would stay at in the future.
Top guest favorite
Home in St. Augustine
5 out of 5 average rating, 141 reviews

Southern Charmer w/Pool - Walk to Everything!

TiffanyRating, 5 stars2 months 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.

Quick stats about vacation rentals that are family-friendly in Lakeside

  • Total rentals

    30 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    2K reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

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