Holiday rentals with a pool in St. Johns County

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

Your Home Away From Home

1,800 SF, 2 bedrooms, 2 1/2 bathrooms, on a secluded 5 acre lot just minutes from Historic Downtown and St. Augustine Beach. The home is 100% HANDICAPPED ACCESSIBLE! Convenient shopping and close by restaurants. Full kitchen, spacious living area, large bedrooms (1 with TWINKLE mattress) ceiling fans. Pet friendly! (Some restrictions apply, advance notice required!) Base rate covers up to 4 guests and there's a small upcharge for 5 or more. Motorcycle friendly! We also do live on the property!

Sunset Cove 2 - Pool - Sea Views - Walkable

Stunning new luxury 2br/2.5ba pool home with peeks of Salt Run and Anastasia State Park: * Pool Heat Available for $30 per day - Contact us after booking for details * Private pool + backyard * Parking for 3 cars * 2 king bedrooms w/ en-suite bathrooms & smart TVs w/ Netflix * 2 min drive (or 20 minute walk) to historic downtown St. Augustine * 2 min drive to the beach (Anastasia State Park) * 5 min walk to lighthouse, Alligator farm, restaurants & bars * Fully stocked and equipped kitchen

2 Bedroom Luxury Condo in World Golf Village

Looking to get away?!!! Come enjoy this two bedroom luxury St. Augustine condo located within the private gates of the World Golf Village in the Laterra resort, home of the King and Bear Golf Course. Resort amenities at your fingertips including access to golf, multiple pools, hot tub, a full service spa, and fitness center. Minutes away from restaurants, shopping and the Golf Hall of Fame. Absolutely No Pets allowed!!! My daughter is highly allergic, and it will cause an allergic reaction

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 in a safe South East Suburb of Jacksonville, not far from shopping, beaches and many other Florida attractions.

King bed, Lake View, sleeps 8, 6 TVs, Public Pool

Escape to our cozy retreat! You'll unwind in style with up to 6 beds in our safe neighborhood, close to Publix and restaurants. You'll explore nearby beaches, parks and attractions or day trip to St. Augustine and Orlando. You'll enjoy serene lake views and backyard fishing. You'll love our top-notch amenities, including a recreational pool with slide, lap pool, basketball, fitness center and playground. You'll create unforgettable memories - book now! We look forward to hosting you.

Full Condo in St. Augustine’s World Golf Village

Escape to St. Augustine and enjoy a one bedroom condo! Explore the resort-like amenities including free unlimited access to three pools, 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! Pack n play available for babies.

Luxury Retreat in St. Augustine

Escape to Isla Antiguas in St. Augustine, FL, and indulge in luxury at this stunning 2-bed, 2-bath Airbnb. Perfectly designed for comfort and style, this upscale retreat offers a fully equipped kitchen, elegant living spaces, and plush bedrooms. Enjoy top-tier amenities, including a sparkling pool, fitness center, and scenic surroundings. Just minutes from historic downtown and pristine beaches, this getaway is ideal for relaxation and adventure. Book now for an unforgettable stay!

Posh Pool and Pond Landing

Welcome to your own private oasis! This home is the perfect escape from the hustle of everyday life. Whether you're looking to enjoy quality time with family, or simply relax in paradise, this house embodies comfort and tranquility. With spacious living areas, charming decor, this home is the ultimate vacation destination. Enjoy the beautiful environment, surrounded by lush tropical foliage - Perfect to soak up the sun, breathe clean natural air, and make unforgettable memories.

Charming Rustic Boathouse

Come stay at our rustic boathouse along the serene river. Its weathered, wooden, exterior exudes charm, adorned with unique decor. The sunlight reflects the water, casting shimmering light against the boathouse. Surrounding it, is lush greenery and trees that create a picturesque backdrop. Inside the boathouse is a cozy and inviting, with simple furnishings and the gentle scent of wood. It's a haven where one can escape the bustle of everyday life and embrace the countryside.

New Designer Home +Parking for 3 +Steps to Trolley

Brand-new \~2,092 sq ft designer 3BR home in historic Lincolnville — private parking for 3 cars & steps from the trolley. Open-concept layout with gourmet kitchen, spacious living areas, premium beds, 2.5 luxury baths, high-speed WiFi, smart TVs, wraparound porch, and sunny patio with gas grill. Fitness club & pool passes included. Perfect for guests seeking modern luxury, easy parking, and a walkable base near St. George Street, restaurants, shops, and attractions.

Putt Putt Pool Home - Mini Golf,Grill,Ping Pong

Experience an authentic, relaxing vacation retreat in the heart of Jacksonville. Located just off 295 and in a very central location. 3 bedrooms on one side of the home and two bedrooms on another side of the home with common areas in the middle. During your stay, you will have access to the pool, which is ideal for some fun pool time after spending some time at the nearby mini golf course. This house offers everything for a great family vacation or weekend getaway.