Holiday rentals with a pool in Southside, Jacksonville

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Top-rated rentals with a pool in Southside, Jacksonville

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

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Guest favourite

Flat in Southeast 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

Home in Jacksonville

4.9 out of 5 average rating, 270 reviews

Serenity and Amazing Views - Home on River w/ Pool

Beautiful House: Quiet with all amenities on deep water with pool. 12 minutes from Jax Airport, 5 min from Zoo and 10 min from Cruise Ports. Jax Beaches are just a short beautiful drive. Downtown, Stadium, Arena etc. 10 min Lounge on the deck or sit pool side while watching the sunrise/ sunset. Bring your kayaks and paddle across the river to the zoo, or find sharks teeth on the river islands. Fish off the dock and catch some of Florida's best: Reds, Trout, Flounder, Snapper, Blue Crabs.

Guest favourite

Guest house in Southeast Jacksonville

4.94 out of 5 average rating, 191 reviews

Il Rifugio waterfront retreat on the ICW by Mayo!

This peaceful, quiet location on the intercoastal waterway is a perfect place to get away or stay close to Mayo clinic and relax among the bald eagles, owls, dolphins, manatees, etc. Completely private building with raised patio area for you to enjoy. Sleeps up to 5 (1 king size + 1 full size bed+ rollaway cot) . Close to beaches (4 miles), restaurants, Mayo clinic, 2.5 miles; TPC/ Sawgrass Golf ,10 miles; Saint Johns Town Center shopping 10 miles; Jacksonville International Airport, 25 min.

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

Home in Southeast Jacksonville

4.86 out of 5 average rating, 208 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

Flat in Southeast 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

Flat in Southeast 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

Guest house in Southeast Jacksonville

4.89 out of 5 average rating, 321 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

Home in Riverside

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

Home in Ponte Vedra Beach

4.92 out of 5 average rating, 133 reviews

Paradise Palms Estate

Located off the popular, scenic Roscoe Boulevard this home sits directly on Cabbage Creek connecting to the Intracoastal water way. Enjoy a private dock, heated pool, spa, fire pit, hammock and oasis. This contemporary home is nestled on a private street with 300 foot long driveway on an acre and is less than a mile from the world renowned TPC golf course as well as exquisite dining, luxury shopping and the historic city of St. Augustine. Plan your escape today!

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

Guest house in Southeast 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.