Vacation 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 favorite

Guesthouse in Southeast Jacksonville

4.94 out of 5 average rating, 188 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 favorite

Bungalow in Springfield

4.98 out of 5 average rating, 393 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!

Guest favorite

Apartment in Southeast Jacksonville

4.95 out of 5 average rating, 223 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.

Superhost

Home in Jacksonville

4.85 out of 5 average rating, 213 reviews

Sunny Florida home with a pool.

Enjoy a stylish experience at this beautiful home that is 16 minutes from the beach, 15 mins from Mayo Clinic and downtown. This home has two bedrooms, two bathrooms, living room, porch, and swimming pool. The living room has a couch that unfolds to a bed. The pool has a screen room around it to keep all the bugs out. There is a smart tv in each bedroom and living room. The house also includes high speed internet and a fence around the backyard. You can enjoy a nice cookout in the backyard.

Guest favorite

Condo in St. Augustine

4.87 out of 5 average rating, 388 reviews

Condo in St. Augustine’s World Golf Village Resort

Escape to St. Augustine and enjoy a one bedroom studio with new brand new renovations and upgrades! Explore the resort amenities including free unlimited access to three pools, a hot tub, lighted tennis and pickleball courts, playground, and fitness center. Located within the private gates of the World Golf Village, home of the King and Bear Golf Course. Minutes away from restaurants, shopping and the Golf Hall of Fame. Travel to Historic St. Augustine and beaches in less than 30 minutes!

Superhost

Home in Southeast Jacksonville

4.9 out of 5 average rating, 153 reviews

Quiet and Serene House with Heated pool near beach

WE ONLY ONE who have clear roof over the HEATED POOL and backyard with screens around so you can ENJOY AMAZING TIME with your family even in harsh weather without rain and bugs! We have gravel road so you can ensure that you will have QUIETEST and SAFEST place to stay! And we just minutes from beautiful beaches and Mayo clinic! We are locating close to everything: - 2 minutes from shopping - 15 min to beaches - 10 min to Mayo Clinic - 15 min to Jaguars Stadium - 35 min to St. Augustine

Guest favorite

Guesthouse in Southeast Jacksonville

4.89 out of 5 average rating, 309 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.

Superhost

Apartment in Southeast Jacksonville

4.73 out of 5 average rating, 132 reviews

King Beds Big Pool Near Mayo Clinic Southisde Jax

***Long Stays Welcome*** This is our new Apartment located inside a Resort type Complex in the Southside area. This is a big apartment with 2 Master Bedrooms, both with King Beds, and big closets. Very comfortable space with a beautiful Balcony view. The place is a block away from I295 Highway and close to Mayo Clinic, Beaches. Short distance to Gas, Publix, Restaurants, Financials, Top Golf, Downtown, Stadiums, and more. Everything is 25 min or less. ¡Hablamos Español!

Superhost

Home in Southwest Jacksonville

4.89 out of 5 average rating, 345 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

Superhost

Home in Jacksonville

4.85 out of 5 average rating, 136 reviews

Lux Oasis: *Heated Pool, Spa/Hot Tub&Grill Retreat

Discover your private oasis in the heart of Jacksonville’s charming San Marco neighborhood. This stylish 1950s home blends vintage charm with modern comforts—featuring a heated pool, hot tub, grill, and space for up to 8 guests. Whether you’re planning a family vacation, a weekend escape, or a long-term stay, everything you need for a relaxing getaway is right here. Pool heating available for $100/night with 48h notice. Hot tub heating is complimentary.

Guest favorite

Guesthouse in Avondale

4.89 out of 5 average rating, 200 reviews

Cute Pool Cottage in the Historic District

Poolside guesthouse in a lush tropical garden yard-this studio with 1 bedroom/1 bath is in Jacksonville’s Avondale Historic District, and just steps away from the popular Shoppes of Avondale with its restaurants and quaint shops. Its perfect for business travelers, singles, or couples. The space features a super cozy queen size bed with luxury linens. There is also a mini-kitchen with microwave, toaster oven and compact refrigerator. There is no stove.

Top guest favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 285 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.