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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Condo in St. Augustine

4.98 out of 5 average rating, 139 reviews

50 Shades of Grey KING Bed Suite St Augustine, WGV

Passionately in love or just passionate about great design; you'll love this Grey Modern King Bed Suite w/living space & kitchenette. Located in the gated community of World Golf Village and home to two world class golf courses: The King and Bear and Slammer & Squire. Enjoy the Clubhouse for brunch, lunch, dinner & drinks. Relax onsite in the amazing pool, hot tub and the Circles of Wellness day spa. 10 mins to St. Aug Outlets. Historic Downtown St. Augustine & Beaches are 20-25 minutes away.

Jul 1 – 8

R2,073 ZAR per night

Guest favorite

Condo in St. Augustine

4.87 out of 5 average rating, 327 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!

Feb 1 – 8

R2,119 ZAR per night

Guest favorite

Home in Orange Park

4.96 out of 5 average rating, 121 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 3 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.

Jul 24 – 31

R4,922 ZAR per night

Guest favorite

Tent in Middleburg

4.97 out of 5 average rating, 115 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

Jul 30 – Aug 6

R1,795 ZAR per night

Guest favorite

Home in Orange Park

4.85 out of 5 average rating, 132 reviews

Cheerful three bedroom home with a pool

Relax with the whole family at this peaceful place to stay. Have a pool party 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.

Apr 12 – 19

R3,319 ZAR per night

Guest favorite

Apartment in Jacksonville

4.94 out of 5 average rating, 185 reviews

Top floor modern getaway w/resort amenities!

New build! Entire modern, luxurious, and spacious apartment. Stunning lake-front view with gorgeous sunsets. Large king bed and queen sleeper sofa provide a comfortable stay for 4. Whether your stay includes a day of shopping, a trip to golf, going to work, or to unwind at the beautiful Jacksonville beaches, you are never far from your destination. Less than 5 miles to the St. Johns Town Center, 7 miles to the nearest hospital, 11 miles to the beaches, and 6 miles to the nearest golf course.

Jun 16 – 23

R2,792 ZAR per night

Guest favorite

Condo in St. Augustine

4.97 out of 5 average rating, 119 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!

Nov 19 – 26

R2,184 ZAR per night

Guest favorite

Bungalow in Jacksonville

4.99 out of 5 average rating, 276 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 soon!

Sep 18 – 25

R2,385 ZAR per night

Guest favorite

Home in Jacksonville

4.9 out of 5 average rating, 300 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

Sep 2 – 9

R2,635 ZAR per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 254 reviews

Blue Bird Paradise

Welcome to “Bluebird Paradise”. Come visit our bright, beautiful, 400 sq. ft “Guest House”, detached from our home with a porch overlooking our beautiful Florida backyard with pool. The commute is very good; it is located less than 30 minutes from the city, 30 minutes from the beach and 30 minutes from the famous historical St Augustine. Peace and quiet await you. A guesthouse is a detached building that shares the property with the host.

Aug 2 – 9

R1,531 ZAR per night

Guest favorite

Guesthouse in Saint Johns

4.97 out of 5 average rating, 209 reviews

Entire Cottage in St Johns, FL with a Water View

We are an easy 35-minute drive to downtown Jacksonville and 45 minutes to historic St. Augustine. Our property is nestled in a serene, tree-lined neighborhood on a canal that flows into the St. Johns River. The cottage is thoroughly cleaned and sanitized before your arrival with a minimum of 24 hours between bookings. The nightly rate INCLUDES St Johns County's bed tax, but Florida sales tax will be added to your booking fees by Airbnb.

Jul 9 – 16

R2,249 ZAR per night

Guest favorite

Home in Jacksonville

4.94 out of 5 average rating, 123 reviews

+A Taste of Britain entire house / pool+

Relax by the private pool & enjoy the spacious 4 bedroom house with family friends or even just a loved one. I’ve decorated the place to pay homage to my birthplace, Britain. The house is equipped with everything you would need for a short or extended long stay. A gas grill is ready for your poolside BBQ while you relax in the hammock or enjoy a cold drink under the patio.

Oct 29 – Nov 5

R3,562 ZAR per night