
Holiday rentals with a pool in Lakeside
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Top-rated rentals with a pool in Lakeside
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Popular amenities for Lakeside rentals with a pool
House rentals with a pool

Newly Renovated - Private Pool, Fire Pit, Walkable
Great spot for a long weekend in St Augustine. We love this neighborhood due to the beautiful surrounds, quiet, and walkability. Ashley’s place was so comfortable, as we spent more time at the actual house this trip - the backyard is great! So many lounge areas in addition to the pool, which was where we spent most of the time! Kitchen is well appointed & beds were super comfy. We’d definitely stay here again!

+A Taste of Britain entire house / heated pool+
Kids loved the pool. Had an awesome stay. James was very responsive. Will definitely be our go to in Jacksonville.

Private oasis, private pool, exceeds expectations
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.

steps to the beach, double mastersuite- pool home
Awesome place! Super clean and cute. We had everything we needed and then some. Loved that it was such a quick walk to the beach. The beach was quiet and not crowded at all. You do have to go up and over a sand dune with your beach gear, so for someone not as stable on their feet, it might be an issue if you have a wagon, etc. We’re already talking about our next trip back!

Historic St. Augustine 2/2 Duplex & Pool
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.

Cheerful three bedroom home with a pool
Beautiful space! Absolutely recommend and will be staying here next time we are back in town!

Relaxing SWEET HOME 9mi Downtown Pool&Hot tub.
Jessicas place was nice and great for family. perfect layout, calm serene environment, clean and thoughtful. The host was very communicative and helpful. we will stay again! place definitely met expectations.

Elegant & Stylish Pool House with Arcade!
Yu was a great host and very responsive! The house was beautiful in a very quiet neighborhood! If we return to Jacksonville, we would book with Yu again for sure!
Apartment rentals with a pool

Heated Pool, Ocean Views, Beach, Playground, BBQ
Can't say enough about Dani and the place. She was extremely responsive and helpful with everything. And the place was great, clean, lots of space, three bedrooms and nice kitchen, plenty of places to sit/lounge, great patio with wonderful view of the outdoor pool and ocean. We had one small issue and Dani was very fast in getting it fixed. Totally recommend. A couple comments on the resort. The outdoor pool is very large and nice, but in late March it's still a bit cool and the water was very cold. So we swam a lot in the indoor pool, which is advertised as heated, but it's not very warm, warmer than the outdoor pool but could have been warmer. Also, the outdoor hot tub broke on our first day there and we were there for multiple days and it never got fixed.

Our Hawaiian Bliss just steps from the Beach!
Great location close to everything very clean and comfortable

Direct Oceanfront ~ Fantastic Views!
Thank you Marty, it was perfect. The view was amazing. The condo was great for us. We visited the Washington Oaks State Park just down the road. We had lunch at Captains BBQ just south of Marineland on A1A. Tony's Pizza is right across the street from the condo. The beach was access and the beach was super. If you are looking for a beach vacation, this is a great pick. My wife and I enjoyed our stay and will be looking to coming back in the future. The swimming pool was perfectly maintained and everyone that was using it looked like they were having great time. Perfect for young and older people, like I said, this was the perfect spot for us. Thank you so much.

Sunrise Special | Steps to Beach | Ocean Front
If you want an ocean view (and a sunrise AND moonrise!) and to be steps away from the beach, this is your place! For me, waking up and seeing the ocean is soothing and sipping coffee on this deck while experiencing the ocean was perfection. Once you are ready to hit the beach, you walk down the stairs and wa-la, there it is! If you forget something, no worries-- your place is only a few minutes away! It was so nice not to have to lug all the beach stuff and then worry about where we'd find a restroom. Nope-- it's all right there at this place! In addition to the beach, there is a pool and many hot tubs. I'm particular about my hot tubs, but this one did not disappoint. They kept it hot enough to relax those sore spots. We did rent a car and the drive to downtown is about 15 minutes and super easy. We Ubered one night and that was easy. I had a few questions for Butch during our stay and he responded immediately. Recycle in town. Butch will send you the link. Grocery is 2 miles away.

Newly renovated! Steps to BEACH & POOL!
We had an amazing time! My best Friend and I came down with my two kids (ages 8,6) for spring break. Place was just as described. Was clean, and cutely decorated with a beach theme. Had some games for the kids as well. There was a list of great recommendations for things to do and restaurants close by. I had a few questions and host was very friendly and quick to respond! Just a short walk to the beach, but located conveniently right across from the pool! Hot tub was nice and relaxing, located in the middle of the building on the first floor. If you’re driving I would recommend brining your own beach chairs, as the ones provided in the unit are not very comfortable. Beach is gorgeous!we loved staying on the beach and just a short drive to this historic downtown area. We highly recommend staying here! Definitely grab breakfast at island donuts!

Sea Place Ocean View
This condo is perfect. It met our needs and is located in beautiful St. Augustine. Great location. Ocean views. Peaceful.

Oceanside complex B35 1 Bed 1 Bath w/Heated Pool
Great apartment, close to one pool and only 5 min walking to the beach. The complex even has 2 pools one being closer to the beach where we have been mostly alone during our stay. The apartment was extremely clean and the kitchen was well equipped. the apartment is on the street side but we did not hear anything inside, but on the balcony which was fine for us. AC and fans in the living and bedroom. All in all we had an amazing time here!

The Flirty Flamingo St Augustine Beach 3 BR Condo
This is a great place. Great value. Clean, spacious, great pools, and great beach access. Pool is heated to 90 degrees and beach is only a 5 min walk. Beach wagon available with all chairs and umbrellas in a storage unit right next to the front door. Elevator access for anyone that needs it.
Quick stats about holiday rentals with a pool in Lakeside
Total rentals
20 properties
Nightly prices starting at
£38 before taxes and fees
Total number of reviews
1.1K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Ponte Vedra Beach
- Old A1A Beach
- Driftwood Beach
- Matanzas Beach
- Pablo Creek Club
- Kathryn Abbey Hanna Park
- Boneyard Beach
- TIAA Bank Field
- Eagle Landing Golf Club
- Guana Reserve Middle Beach
- St. Augustine Alligator Farm Zoological Park
- Lightner Museum
- Florida Museum of Natural History
- Crescent Beach
- Fountain of Youth Archaeological Park
- Bent Creek Golf Course
- Vilano Beach
- Amelia Island Lugar Lindo
- Amelia Island State Park
- St. Marys Aquatic Center
- Depot Park
- Fort Mose Historic State Park
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