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Holiday rentals with a pool in Lakeside

Find and book unique homes with a pool on Airbnb

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Popular amenities for Lakeside rentals with a pool

House rentals with a pool

Guest favourite
Home in Jacksonville
4.91 out of 5 average rating, 164 reviews

Cozy ranch near Jax

LaurenRating, 5 stars1 month ago
April’s place was exactly as described. There are thoughtful amenities and plenty of space. The location was very convenient to the airport. After a small miscommunication, April went above and beyond to make sure we felt comfortable.
Top guest favourite
Home in Southeast Jacksonville
4.86 out of 5 average rating, 207 reviews

Private FL Home with Pool, Hot tub & Luxury Master

JoanRating, 5 stars2 weeks ago
Sandra was a terrific host. her place was as described even better. beds were comfortable,lots of bathrooms, lots of outdoor seating, and pool toys and indoor and outdoor toys/games. perfect for us as we had a family wedding in the area. neighborhood was nice, quiet nearby to stores and restaurants.
Guest favourite
Home in Southeast Jacksonville
4.79 out of 5 average rating, 120 reviews

Private Pool Home • Quiet • Near Beaches & Dining

LoriRating, 5 stars2 weeks ago
Pool was lovely. Layout was very open. Such a nice place for us as well as our dogs.
Superhost
Home in Middleburg
4.82 out of 5 average rating, 11 reviews

The Retreat ~ Pool ~ Gameroom

AllenRating, 5 stars2 days ago
It was a nice and comfortable stay felt like I was right at home. Lots to do in the area and couldn’t have asked for a better house. Really enjoyed our stay and made some great memories.
Top guest favourite
Home in Southwest Jacksonville
4.95 out of 5 average rating, 166 reviews

+A Taste of Britain entire house / heated pool+

NeftaliRating, 5 stars1 week ago
Can't say enough about how great a host James was. He was responsive in a timely manner everytime I had a question. The place was immaculate!! A well spent Birthday getaway!!
Top guest favourite
Home in Jacksonville
4.91 out of 5 average rating, 154 reviews

The Pink Cabana

Ma'KaylaRating, 5 stars3 days ago
The house was amazinggg! It was literally like a girly girl house & was super pretty and it was just so relaxing! Definitely loved the aesthetic & the pictures on the walls! Felt like I was out of town even tho I was still in jax! The pool was also veryyy pretty! If I had to stay again I most definitely would!!! 10/10!!
Top guest favourite
Home in St. Augustine
4.98 out of 5 average rating, 106 reviews

Driftmark Cabin - RV friendly, Pool + Beach!

CaraRating, 5 stars3 weeks ago
The house was perfect for us and the dogs! The beach is a hop and skip away loved the pool very spacious place! The downstairs was a plus having two washer and dryers also very spacious upstairs and downstairs! Everyone felt like they had there on little space and not on top of each other. The ice machine downstairs was so convenient for the coolers to go straight to the beach! We will defiantly be back it was the perfect place for us!
Top guest favourite
Home in St. Augustine
4.93 out of 5 average rating, 118 reviews

Peaceful Oasis Pet Friendly heated Pool & Gameroom

KacieRating, 5 stars1 week ago
This place was amazing! Perfect location, only 15 minutes of St. George street. The pool was amazing and very refreshing! My dog absolutely loved the backyard. We even got to see a few deer! Very clean and the host is very responsive. My nephew loved the pool table! I would definitely recommend this location!

Apartment rentals with a pool

Guest favourite
Apartment in St. Augustine
4.94 out of 5 average rating, 126 reviews

My HOUSE is your HOUSE

RodneyRating, 5 stars3 weeks ago
We had a great stay. The condo was lovely, clean and beautifully appointed. Our host was very helpful and communicative. We loved the area and the property overlooking the gorgeous pool. We highly recommend this property and would love to stay again.
Guest favourite
Apartment in St. Augustine
4.88 out of 5 average rating, 155 reviews

Luxury 2/2 condo w/patio, beautiful golf community

LauraRating, 5 stars2 weeks ago
This was our 4th time staying here. Always a blessing! Convenient to everything and we enjoy the amenities.
Top guest favourite
Apartment in St. Augustine
4.93 out of 5 average rating, 111 reviews

Spanish Colonial Design One Bedroom Condominium

HannahRating, 5 stars2 weeks ago
Nicki’s place was a perfect, peaceful and private getaway for my husband and I. We thoroughly enjoyed our stay! Close to a Publix and quick bites. Only a 25 minute drive to historic St. Augustine, and 35 minutes to the beach. We felt safe in the gated community and enjoyed the pool/hot tub.
Guest favourite
Apartment in St. Augustine Beach
4.95 out of 5 average rating, 109 reviews

Steps to Beach, Bikes & Beach Equipment Included!

ElizabethRating, 5 stars4 days ago
Sea winds was a great place to stay for a vacation. It was quiet and relaxing and the beach was really close too. The owners were responsive with any of our questions. I would definitely like to stay here again.
Top guest favourite
Apartment in Beaches
4.97 out of 5 average rating, 198 reviews

Beachcomber Oceanfront 180* panoramic view

ChrisRating, 5 stars1 day ago
This place was amazing. The beach views were stunning. No picture could capture it! The surrounding neighborhood was very nice and safe. Even though you’re in a complex, walls aren’t paper thin which creates more privacy for your family! Tiffany was very responsive and helpful - even informed us of local events. The place is as listed, fully stocked for pretty much every need, and super convenient for the beach. You can watch the sunrise from the balcony or even the bed. We would love to rebook in the future!
Guest favourite
Apartment in Beaches
4.9 out of 5 average rating, 101 reviews

Oceanfront Condo with Views, Pool, Park

SavannahRating, 5 stars1 month ago
My family two babies and a dog stayed here for a long weekend trip. It accommodated all of our needs and was easily located to pool beach. The park right next door was ideally the best part for babies and dog. Would stay here again
Top guest favourite
Apartment in Fernandina Beach
4.99 out of 5 average rating, 136 reviews

Resort~ Amelia Island~ Ocean Front~ Condo

TeriRating, 5 stars2 weeks ago
This place was incredible. The amenities that were provided were greatly appreciated. The unit was extremely clean and included beach chairs that looked like new. The lunch baggies, gallon bags, aluminum foil, laundry pods, and snacks were a blessing for us. The unit is two story with the bedrooms downstairs and the kitchen and living room upstairs. The ocean view was beautiful as well as the daily visit from the bunnies. We enjoyed seeing the turtles; not so much the black snack, but he was harmless. We can’t wait to return. Brook and Jarod were great host. Their recommendation of Baxter’s was better than they explained. One of the best meals my husband and I have ever had. I got trigger fish and he got steak. I made him share and I cut my piece with a butter knife. Thank you again Brook and Jarod for great experience. We did not want to leave.
Guest favourite
Apartment in St. Augustine
4.94 out of 5 average rating, 118 reviews

2 Bedroom Luxury Condo in World Golf Village

StephanieRating, 5 stars3 weeks ago
We had a fantastic stay for our short vacation! Everything was like it was in the picture. Location was perfect for us my kids loved the pool. Everything worked like it should and felt right at home. Beds were comfortable and had plenty of room. Would definitely stay here again when we come back down.

Quick stats about holiday rentals with a pool in Lakeside

  • Total rentals

    20 properties

  • Nightly prices starting at

    ₹4,300 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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Clay County
  5. Lakeside
  6. Rentals with pools