Vacation rentals with a pool in Southside, Jacksonville

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Southside, Jacksonville

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 favourite

Apartment in Jacksonville

4.87 out of 5 average rating, 61 reviews

Lux King Bed Stunning View Pool Mayo Clinic Beach

Start your Jacksonville stay with comfort and style! This modern 1-bedroom apartment in a prime location puts you just 10 minutes from Mayo Clinic and 15 minutes from the beach. You’ll enjoy a fully equipped kitchen, a cozy bedroom, and a stunning view that will elevate your experience. Whether you’re here for treatment, work, or a beach escape, you’ll find everything you need for a relaxing, stress-free stay. Enjoy the comfort, convenience this apartment offers for a seamless long or short stay

Guest favourite

Bungalow in Springfield

4.98 out of 5 average rating, 404 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 - Valentine's Day is coming! The getaway features: PRIVATE salt water POOL and Garden Spa-like bathroom with soaking tub, refreshing 24 inch rain shower. Smart TV+WIFI in every room including bathroom. Central location with close proximity to TIAA Bank Field, airport, Downtown, Florida Theater, Times Union PAC. Walking distance to local restaurants and breweries. Hope to see you soon!

Top guest favourite

Townhouse in Ponte Vedra

4.99 out of 5 average rating, 106 reviews

Waterfront Villa in TPC Sawgrass (2 Bedroom)

Coastal Vibes Villa is newly renovated, spacious, and has a view! Your vacation Oasis awaits! Located in beautiful TPC Sawgrass. Community pool is right across the street and you are walking distance to Sawgrass Village- home of some of Ponte Vedra’s finest restaurants and shopping. You will also enjoy the close proximity to various spas, beautiful beaches and the iconic TPC golf course. Coastal Vibes Villa is perfect for your next event, golf outing, wedding, or just a relaxing getaway.

Superhost

Apartment in Jacksonville

5 out of 5 average rating, 3 reviews

Serenity Retreat| 1BD Lux King in Southeast Jax

Welcome to your own personal retreat! Let go of the weight of daily life and step into a world of tranquility, where stress fades and serenity takes over. Experience the calming ambiance of a spa like retreat, relaxing music, and soft lighting, all designed to create profound peace. This is more than a stay—it’s a curated experience designed to recharge your spirit, awaken your clarity, and inspire your dreams. Let go, unwind, and manifest your best self. Your escape begins here!

Top guest favourite

Home in Jacksonville

4.86 out of 5 average rating, 209 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 favourite

Apartment in Jacksonville

4.9 out of 5 average rating, 20 reviews

Blue Skies 1 Bedroom 1 Bath Apt

Stylish, centrally-located w/resort-like amenities. Just off of the main highwway minutes from the Mayo Clinic, UNF, & St. Johns Town Center. • pool & loungers • grills • club room /TVs & billiards • private offices & conf room • vehicle E charging stations • covered parking/elevator & wheelchair accessible ** upon confirmation, you will be required to complete a short form and to submit a copy of your ID. The complex requires this to secure the safety of residents and guests.

Guest favourite

Apartment in Jacksonville

4.95 out of 5 average rating, 227 reviews

Top floor modern getaway w/resort amenities!

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.

Guest favourite

Guesthouse in Jacksonville

4.89 out of 5 average rating, 322 reviews

Private Bungalow with Pool/55” tv

"The Oasis" is an cozy backyard guest room, detached and completely separate from the main house, in a beautiful outdoor oasis located in an older neighborhood in the center of Jacksonville, 1 block from I-95, with easy access to everything. 5-7 min (4-5 miles) from downtown, Convention Center, Veterans Memorial Arena, TIAA Bank Field (Jaguar Stadium), Times Union Center, Mayo Clinic (15 miles), Beaches (18 miles), Airport (18 miles). NOTE: No animals/pets/children under 12.

Guest favourite

Apartment in Jacksonville

4.97 out of 5 average rating, 63 reviews

SuperHost Special! 1BR/1BA Luxe Stay in Jax

Our stunning 1BR/1BA apt, is centrally located; whether you're seeking medical expertise at the Mayo Clinic, sun-drenched days on beautiful beaches, or the vibrant retail, dining or nightlife of St. Johns Town Center, our luxe unit is at the center of it all. We've curated our home with your comfort and lifestyle in mind, enjoy a private/quiet atmosphere with modern amenities, luxe furnishing and bedding, fully equipped kitchen, dining Area and dedicated workspace with wifi.

Guest favourite

Home in Avondale

4.93 out of 5 average rating, 317 reviews

Historic Hollywood House w/Pool

Located in Avondale, this well kept 98 year old house features original hardwood floors throughout, updated kitchen. There are 2 main bedrooms, and a third with a twin bed + trundle but no door. The back yard is private with a beautiful pool (that is not heated) and cabana. Be sure to read the house rules and neighborhood description so that there are no surprises after your reservation is confirmed. Ring cameras monitor all the entrances and are motion activated.

Guest favourite

Cottage in Fort George Island

4.88 out of 5 average rating, 290 reviews

Salty Dolphin Cottage with Pool ❤

Welcome to the Salty Dolphin—where the St. Johns River meets the Intracoastal. This peaceful riverfront townhome offers stunning views, dolphin sightings from the decks and dock, and is just 3 miles from the Atlantic—perfect for fishing. You’re minutes from JAX Airport, downtown, Amelia Island, Ribault Club, and a ferry ride from Mayport. Relax, explore, or cast a line—this hidden gem puts the best of Florida’s First Coast at your doorstep.

Top guest favourite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 289 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.