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

4.98 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

G$22,738 GYD 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 20 – 27

G$52,643 GYD 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

Jan 20 – 27

G$20,752 GYD 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.

Dec 24 – 31

G$41,527 GYD 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 2 – 9

G$23,975 GYD 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!

Nov 3 – 10

G$22,529 GYD per night

Guest favorite

Home in Jacksonville

4.99 out of 5 average rating, 150 reviews

Sunset near the lake up to 10guests/4bds/2baths

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.

Feb 14 – 21

G$48,434 GYD per night

Guest favorite

Home in Jacksonville

4.84 out of 5 average rating, 170 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.

Apr 19 – 26

G$40,024 GYD 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

Aug 4 – 11

G$28,943 GYD 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

G$16,826 GYD 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 14 – 21

G$24,734 GYD 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.

Aug 9 – 16

G$31,373 GYD per night