Vacation rentals with a pool in Lakeside

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Lakeside

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in St. Augustine

4.86 out of 5 average rating, 353 reviews

Condo in St. Augustine’s World Golf Village Resort

Escape to St. Augustine and enjoy a one bedroom studio with new brand new renovations and upgrades! Located within the private gates of the World Golf Village in the Laterra resort, home of the King and Bear Golf Course. Explore the resort amenities including access to golf, multiple pools, a full service spa, lighted tennis courts, hot tub, and fitness center. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

Superhost

Home in Orange Park

4.94 out of 5 average rating, 145 reviews

Super Clean (Fantastic Pool) Home Near Everything

Your Home Away From Home Featuring A Fabulous Pool! You will say "Wow" as you walk in to your very private, very exclusive spacious 4 bedroom, 2 bathroom. Set in a quiet neighborhood thats still near everything. Grocery store, Orange Park Mall, 30 minutes from Downtown Jax, 30 miles from the beach. Sit back and enjoy one of 4 Tvs as you relax in the soothing ambiance. Want to cook? Perfect we have everything you need, and we have it twice! Fully equipped kitchen. Very Clean! BetterThan A Hotel.

Guest favorite

Camper/RV in Jacksonville

4.99 out of 5 average rating, 143 reviews

Couples clothing optional escape hot tub nude deck

You'll love this unique and romantic escape. Designed to create an intimate setting to enhance your time together. The RV is quite large and fully equipped . Master bedroom features a cashmere topped California king bed. The property has so many amenities starting with a very large pool, lighted at night. A dock on the river to enjoy the views. Access to kayaks on premises. There’s a private clothing optional area/deck with a massage table , hot tub and loungers. We recently added a fire pit

Guest favorite

Condo in St. Augustine

4.96 out of 5 average rating, 143 reviews

Luxury World Golf Village 1 Bed 1 Bath Condo

Escape to St. Augustine and enjoy a luxury one bedroom condo with new renovations and upgrades! Located within the private gates of the World Golf Village in the Laterra resort, home of the King and Bear Golf Course. Explore the resort amenities including access to golf, multiple pools, a full service spa, lighted tennis courts, hot tub, and fitness center. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

Guest favorite

Tipi in Middleburg

4.95 out of 5 average rating, 134 reviews

2-Relax- Retreat-Revive-boutique camping -A/C-Pool

- If having difficulty booking your preferred date or you have a group, message us for more info on 2 additional tents located on property . -Experience nature with all the comforts of home-A/C keeps you cool! see below for special bundle options - Casper King size bed, deck,fire pit, coffee maker, kayaks - Located on Black Creek - Large above ground pool with deck - Grill - Less than 15 min from grocery stores/local restaurants - 40 min from downtown Jax - 50 min to St. Augustine

Guest favorite

Home in Southwest Jacksonville

4.97 out of 5 average rating, 189 reviews

Sunset near the Lake: up10guests/2baths/4bdrs/pool

This vacation home is remodeled on a safe & quiet street. Inside the home is a beautiful decorated full-size kitchen, and comfy living/dining room etc. In addition you have access to Lake in back for fishing. Our stylish home is located near downtown Jax area, you will have easy access to Walmart, restaurants, 20 mins to the beautiful beaches, Blue Springs, historic sites, NASJax, airport, seaport, & college campus nearby and many other attractions. We look forward to your stay in our home.

Guest favorite

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

Guest favorite

Bungalow in Springfield

4.98 out of 5 average rating, 338 reviews

❤️Private Pool Couples Getaway- Downtown

Our place is perfect for you and your loved one to escape your daily routine, recharge, relax and reconnect. The getaway features: PRIVATE not shared salt water POOL surrounded by relaxing Zen Garden. Spa-like bathroom with soaking tub, 24 inch rain shower head, Smart TV+WIFI in every room including bathroom. Central location with close proximity toTIAA Bank Field, airport, Downtown, Florida Theater, Times Union PAC. Walking distance to local restaurants and breweries. Hope to see you

Guest favorite

Home in Southeast Jacksonville

4.84 out of 5 average rating, 189 reviews

Private FL Home with Pool, Hot tub & Luxury Master

This is a lovely family home in the Mandarin area of Jacksonville which has undergone many renovations and upgrades. The master boasts its own, ensuite, tv, fireplace and sitting area, as well as a private entrance from the pool and hot tub area. The house itself has newer furnishings, flooring, modern decor, a large fenced in backyard, pickle ball court and firepit. Located safe South East Suburb of Jacksonville, not far from shopping, beaches and many other Florida attractions.

Guest favorite

Home in Southwest Jacksonville

4.9 out of 5 average rating, 114 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.

Superhost

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.

Superhost

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