Holiday rentals with a pool in Downtown Jacksonville

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.

Pool Home with Game Room in Heart of Jax Beach!

Beautiful pool home in Jax Beach! This updated and sparkling clean home is in the perfect spot for the whole family! This home is in the perfect location, minutes to the ocean, restaurants, Mayo Clinic and more! It is equipped with everything you need for your ideal coastal vacation. Your stay includes a fully stocked kitchen, pool table, ping pong table, dart board, Smart TVs, a beautiful pool with set up with lounge chairs, outdoor dining, beach chairs, beach towels, and a charcoal grill.

Oasis in the Hill

Beautiful pool home and private backyard oasis. This walkable neighborhood is quiet and popular with professionals and families. It's a short walk from many restaurants, bars, and entertainment. This home includes a heated* saltwater pool, pool table, huge covered lanai, fire pit, and campground-style grill. Enjoy this oasis, surrounded by tropical landscaping and pond. We are glad to offer a military/first responder discount of 10% per day up to $100 for your stay upon request w/ valid id.

Lake View Escape to The Exchange

Give us your worries and we will give you an escape. Welcome to the Exchange! This Orange Park unit supports your work requirements and your playful desires. Multiple high volume healthcare facilities surround the area and the Naval Air Station is in the backyard. Luxury dinning and outdoor water activities abound. This new unit offers access to a resort style salt water pool, private garages, state of the art fitness center and wellness studio, dog park, clubhouse and lounge, and much more.

San Marco Home • Pool, Hot Tub, Grill

Welcome to your Jacksonville getaway! This stylish 3-bedroom, 2-bath home in the heart of San Marco is just 10 minutes from Jaguars Stadium and close to vibrant cafes, parks, and boutiques. Ideal for families, couples, groups, or long-term stays, this home combines comfort, charm, and resort-style amenities. Pool Heating: $100 per stay for short visits (≤4 nights). For longer stays or winter months: $50 setup + $12/night, or $200 flat. Please request at least 48 hours in advance.

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.

Spacious 2/1 in historic neighborhood- NO parties

Welcome to Happy's Hideaway, a family-friendly carriage house that checks all the boxes! Our bright 2-bedroom carriage house apartment is close to downtown and 12 miles from JIA. Nestled on a quiet street among mature oaks with a saltwater pool, it is just 15 miles to Atlantic Beach (a 22-28 minute drive.) We are just off Main Street, where you can enjoy local beer, ice cream, coffee, pizza & axe-throwing! This unit is on the 2nd floor and accessible only by stairs.

❤️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 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!

Avondale Retreat - Private Home with Heated Pool

Enjoy the best of both worlds in Riverside! Walk or bike to many shops and restaurants in Historic Murray Hill, Avondale and Five Points, then return to your private, peaceful backyard oasis. Relax in your heated salt water pool, grill outdoors or prepare a meal in the fully stocked kitchen and wind down with a nightcap by the fire pit. Right off I-10 and I-95, close to the Jaguar Stadium, JAX, Mayo Clinic and only 25 minutes to Jax Beaches.

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.

*Heated Pool, Hot Tub & Grill Retreat • Free Wi-Fi

Welcome to your private Jacksonville oasis — a relaxing, well-equipped home featuring a heated pool, hot tub, and outdoor grill, perfect for families, couples, or small groups looking to unwind in comfort. Whether you’re here for a getaway, work trip, or visiting loved ones, this home offers the space, amenities, and privacy you need for a great stay. Pool heating available for $100/night with 48h notice. Hot tub heating is complimentary.

Gorgeous Florida Pool and Spa Home

Have fun with the whole family at this stylish pool and spa place. Our home boasts a sparkling pool and rejuvenating spa, perfect for unwinding after a day of exploring the Sunshine State. Surrounded by lush greenery, the pool area offers a private oasis where you can soak up the sun or sip cocktails. Whether you're lounging poolside or enjoying a relaxing soak in the spa, this tranquil retreat promises the ultimate vacation experience.