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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Guest favorite

Condo in St. Augustine

4.99 out of 5 average rating, 100 reviews

Alice's Palace Alice in Wonderland St Augustine FL

Welcome to Alice's Palace; a sophisticated twist on Alice in Wonderland. This unique Madhatter tea party styled 1 bedroom private condominium is like no other. It has a large fully equipped kitchen, spectacular forest King bedroom, onsite spa, stunning pool and hot tub. Located in the King & Bear golf community of World Golf Village and boasts 2 World Class Golf Courses-King & Bear/Slammer & Squire and just minutes from Historic Downtown St Augustine, Outlet Shopping and many amazing beaches

Apr 19 – 26

ﺩ.ﺇ464 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.

Aug 25 – Sep 1

ﺩ.ﺇ611 per night

Guest favorite

Condo in St. Augustine

4.97 out of 5 average rating, 118 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!

Aug 11 – 18

ﺩ.ﺇ385 per night

Guest favorite

Bungalow in Jacksonville

4.99 out of 5 average rating, 273 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 26 – Oct 3

ﺩ.ﺇ473 per night

Guest favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 350 reviews

Private Apartment With Pool Access

Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen, laundry, porch, and pool access for our guests only. Complimentary beer, sodas, water and coffee!

Jan 21 – 28

ﺩ.ﺇ469 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.

Oct 23 – 30

ﺩ.ﺇ645 per night

Guest favorite

Guesthouse in Jacksonville

4.9 out of 5 average rating, 225 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.

Jul 21 – 28

ﺩ.ﺇ273 per night

Guest favorite

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.

Jun 27 – Jul 4

ﺩ.ﺇ538 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 16 – 23

ﺩ.ﺇ510 per night

Guest favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 253 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.

May 8 – 15

ﺩ.ﺇ296 per night

Guest favorite

Guesthouse in Saint Johns

4.97 out of 5 average rating, 208 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.

Jun 6 – 13

ﺩ.ﺇ436 per night

Guest favorite

Home in Southeast Jacksonville

4.94 out of 5 average rating, 144 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.

Sep 9 – 16

ﺩ.ﺇ820 per night