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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.

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Home in Jacksonville

4.91 out of 5 average rating, 125 reviews

Quiet and Cozy place with Heated pool year around!

🥰 🏝 Enjoy Brand New house with open concept floor plan, high ceilings and AMAZING paved backyard with HEATED POOL and propane grill for Quiet and Relaxing family time. We just minutes from 🏥 Mayo clinic and beautiful ☀️Jax, 🏝Neptune and 🏖 Atlantic beaches. We are locating close to everything: - 🏖 15 min to Jax, Neptune and Atlantic beaches, - 20 min to Ponte Vedra, - 10 min to Mayo Clinic, - 10 min to University of North Florida, - 15 min to Jaguars Stadium, - 35 min to St. Augustine.

Apartment in Jacksonville

4.94 out of 5 average rating, 186 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.

Bungalow in Jacksonville

4.99 out of 5 average rating, 277 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!

Townhouse in Jacksonville

4.87 out of 5 average rating, 244 reviews

Salty Dolphin Cottage with Pool ❤

Our riverfront townhome sits on the intersection of the St. Johns River and Intercoastal waterway. For off shore fishermen, we are three miles from the Atlantic Ocean. You’ll feel like you're in paradise as you dolphin watch from the decks and dock. We’re 20 minutes from the airport, 20 minutes from downtown Jacksonville and Jaguars stadium, 15 minutes from Amelia Island, beautiful golf courses and kayaking, 10 minutes from the Ribault Club, and a ferry ride away from Mayport Naval Station.

Guesthouse in Jacksonville

4.9 out of 5 average rating, 228 reviews

Private Bungalow with Pool/55 tv

"The Oasis" is an cozy backyard guest room, detached and separate from the main house, in a beautiful outdoor oasis located in an older neighborhood in the center of Jacksonville, close to I-95, with easy access to everything. 5-7 minutes (4-5 miles) from downtown, Convention Center, Veterans Memorial Arena, TIAA Bank Field (Jaguar Stadium) and Times Union Center, 20 min to Mayo Clinic (15 miles), 20 min to the beaches (18 miles). NOTE: No animals/pets or children under 12 allowed.

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.

Guesthouse in Jacksonville

4.95 out of 5 average rating, 149 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 4 (1 king size + 1 full size beds) . Close to beaches (4 miles), restaurants, Mayo clinic, 2.5 miles; TPC/ Sawgrass Golf ,10 miles; Saint JohnsTown Center shopping 10 miles; Jacksonville International Airport, 25 min.

Home in Jacksonville

4.93 out of 5 average rating, 200 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.

Home in Jacksonville

4.9 out of 5 average rating, 302 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

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.

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.

Home in Jacksonville

4.94 out of 5 average rating, 147 reviews

Quiet Vacation Home with Pool - Centrally Located

Enjoy your vacation in this fully renovated pool home. New floors, kitchen and appliances. Includes office and play area with mini pool table. Fully remodeled bathroom spaces. The perfect mix of classic and modern! After sunny Florida activities, feel free to take a dip in the spacious pool to cool off. Rinse off in the heated exterior shower. Your home away from home! Come enjoy your stay.

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Popular amenities for Southside, Jacksonville rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Jacksonville

4.99 out of 5 average rating, 150 reviews

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

Home in Jacksonville Beach

4.98 out of 5 average rating, 137 reviews

Beautiful Beach House, Heated Pool+Backyard Oasis

Home in Jacksonville

4.85 out of 5 average rating, 133 reviews

Sunny Florida home with a pool.

Home in Jacksonville

4.94 out of 5 average rating, 123 reviews

+A Taste of Britain entire house / pool+

Home in Jacksonville

4.97 out of 5 average rating, 183 reviews

The Salty Goose, Waterfront Pool Home, Sleeps 6

Home in Jacksonville

4.84 out of 5 average rating, 131 reviews

Fancy Private Pool Home in Jax beach!

Home in Jacksonville

4.89 out of 5 average rating, 194 reviews

Serenity and Amazing Views - Home on River w/ Pool

Home in Jacksonville Beach

4.99 out of 5 average rating, 144 reviews

Renovated Beach House w/ Pool and Outdoor Oasis

Condo rentals with a pool

Condo in St. Augustine

4.87 out of 5 average rating, 239 reviews

Luxury 1 BR 1 Bath World Golf Village Penthouse

Condo in St. Augustine

4.95 out of 5 average rating, 114 reviews

My HOME is their HOME

Condo in Fernandina Beach

4.98 out of 5 average rating, 142 reviews

Amelia Sandcastles Escape

Condo in St. Augustine

4.99 out of 5 average rating, 103 reviews

Alice's Palace Alice in Wonderland St Augustine FL

Condo in Ponte Vedra Beach

4.99 out of 5 average rating, 129 reviews

Gated Sawgrass Beach Club - Infection Control Rx

Condo in St. Augustine

4.87 out of 5 average rating, 329 reviews

Condo in St. Augustine’s World Golf Village Resort

Condo in Fernandina Beach

4.96 out of 5 average rating, 263 reviews

Idyllic Beach*Suite Sandcastles Oceanfront Luxury

Condo in Jacksonville Beach

4.93 out of 5 average rating, 226 reviews

Sunrise Starts Here! Oceanfront panoramic views!

Quick stats about vacation rentals with a pool in Southside, Jacksonville

Total rentals
520 properties
Rentals with dedicated workspaces
290 properties have a dedicated workspace
Pet-friendly rentals
160 properties allow pets
Family-friendly rentals
250 properties are a good fit for families
Total number of reviews
12K reviews
Nightly prices starting at
R369 ZAR before taxes and fees

Destinations to explore