Holiday rentals with a pool in Southeast Jacksonville

Clear-Roof Heated Pool • Luxury All-Season Swim

Imagine swimming under the stars or during a cozy rainy evening, year-round, in your heated saltwater pool beneath a glass roof. This is more than just a stay—it's an exclusive escape. A luxury oasis awaits in Jacksonville: serene comfort, a perfectly warm swim in any season, and a unique all-weather experience. Just minutes from Mayo Clinic and the beaches, you’ll enjoy a perfect balance of privacy, convenience, and year-round relaxation. Nearby Restaurants & shop - 2 min Beach & Mayo - 10 min

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.

Mother-in-law suh-WEET

Take a break and unwind at this peaceful guest house behind 4140 Peach Drive. Cradled at the end of a friendly and established Southside Neighborhood of Beach and Peach Drive (Behind the Orange Dinosaur on Beach Blvd). We are equidistant from Downtown and the Beaches; 10-12 min drive to either. If you’re coming from the North or South end you can take Southside Blvd or 295/95 and or Butler or Beach Blvd going East/Westbound. There’s also the Beach and Peach Urban park in walking distance.

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.

Elegant 2 King Bed Southside Pool Mayo Clinic UNF

Enjoy the comfort of a spacious, luxury apartment designed just for you. With two large master suites, King beds, and private bathrooms, you’ll have all the space you need to relax and recharge. You can lounge by the resort-style pool, stay active in the state-of-the-art gym, or explore nearby shops and dining at the Town Center. You’re just 15 min from the beach and close to Mayo Clinic. With easy access to I-295, you’ll love how convenient everything is around you in this prime location

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.

Sunset Retreat | 1BR | 1.5BA | Pool | Gym | Garage

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 Special! 1BR/1BA Luxe Stay in Jax

Our stunning 1BR/1BA apt, is centrally located; whether you're seeking medical expertise at the Mayo Clinic, sun-drenched days on beautiful beaches, or the vibrant retail, dining or nightlife of St. Johns Town Center, our luxe unit is at the center of it all. We've curated our home with your comfort and lifestyle in mind, enjoy a private/quiet atmosphere with modern amenities, luxe furnishing and bedding, fully equipped kitchen, dining Area and dedicated workspace with wifi.

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.

❤️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!

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!