Vacation rentals in Fruitland Park

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

Getaway on the Waterway/ Kayak+SUP Fishing Firepit

Welcome to your peaceful Getaway on the Water. Whether you or your group are visiting the Villages, or just need a peaceful getaway to recharge, this is the place!There's something for everyone! Paddleboard or Kayak (provided) the beautiful canal to either lake. Enjoy your morning coffee or evening cocktail in nature on the dock. Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, they also offer sunset cruises and water taxi to Eaton's Beach restaurant right from our dock!

Whole House-sleeps 10 The Villages Spanish Springs

Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

Luxury home with a pool and 3 bedroom

Spacious water front home that sits on a beautiful freshwater canal with access to the great Lake Griffin. Offers a perfect blend of luxury & comfort, a perfect space for entertaining & relaxation. Escape the pressures of everyday life, enjoy the outdoors in style with the lanai in the rear of the home, perfect for barbecuing or lounging while enjoying the water view. Has access to onsite community boat ramp, campgrounds, nature trails, kayaking, major roads, stores, restaurants, and more.

1199 Merryweather - Walk to Lake Sumter Landing Sq

Wow! Gorgeous 2br/2ba courtyard villa; 5-star reviews. Walk to Creekside Landing pool & town square in THE most sought after location in the community. Private yard. Granite counters, vaulted ceilings, big birdcage, French doors & vinyl plank floor. No carpet. Newer recliners, patio chairs, and sofa. King in master. Queen in guest br. Cable. WIFI. Rent a golf cart (optional). No pets here. I manage a pet friendly 3br across street (sleeps 6). Apr & Dec 2026=5nt min. Other 2026=just 2nt min.

Amazing home in The Villages, FL

Enjoy your stay in one of America's most vibrant communities, The Villages, at this stylish and modern three-bedroom home in Pine Hills. This recently built house is the perfect home-away-from-home, with everything you'll need to relax and unwind after a busy day of adventure in Central Florida! Our home can accommodate up to eight guests. We have four beds and a sleeper sofa, up-to-date appliances, a screened lanai, grill and more! We also have a golf cart guests can use, free of charge!

Adorable Fruitland Park 3/2, King Beds, Great Yard

Adorable, peaceful, fully renovated 3/2 close to every amenity imaginable in The Villages and Hwy 441/27 in Fruitland Park/Lady Lake. Fully remodeled home sits on 1/3 acre with nice fenced in back yard. Sit on porch just outside the kitchen slider & enjoy your morning coffee. Back yard also boasts a fire pit. Relax! Home features 2 king beds, 1 full, master w/his & her sinks, 55 inch tv in living room, office space, kitchen island w/cooking utensils, + 6 seater dining table & chairs.

Safari themed private addition with pool/hot tub.

This special Guest house addition is close to everything in The Villages! Making it easy to plan your visit.! We are in The Village of Osceola Hills at Soaring Eagle Preserve. A short golf cart or car ride to Brownwood Square and Sumter Landing Square for dining, shopping, and dancing! A 5 min jaunt to two plazas for groceries, gas, and eating:-) Access to play over 50 golf courses at a minimal fee. Ask us about our easy 4 seater Golf-cart rental and upon request free Guest passes!

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

Spacious 3/2 Getaway in The Villages

Your friends/family will enjoy easy access to everything from this centrally located home as it is 15 min from Sumter Landing and 15 min to Brownwood. Picture yourself in this Ultra Clean 3 Bedroom/2 Bathroom (One Bedroom has a sofa, coffee table and desk). Every room has a smart tv and we offer Live YouTube Tv. The Open Floor Plan lends itself to entertaining while preparing a home cooked meal in the well appointed kitchen. Make your vacation memories in this beautiful home.

Dirty Dog Cottage

Come stay in our cute Florida cottage located at Dirty Dog Organic Farm. Relax at the Pergola and watch the Koi fish. We have chickens, Roosters, Goats and 2 sweet pigs. I am happy to help you feed the animals a treat. Leesburg Florida has many hiking trails, and water sports. The farm seems worlds away yet is only 10 minutes from downtown Leesburg and many other activities. The villages is also only a short drive away. The cottage is fully fenced in.

Fruitland Lakefront 2brm w/beach & dock

Enjoy the serene lakefront of Lake Griffin with the whole family at this stylish place. Two queen beds and a pull out sofa for extra guests to enjoy this exquisite piece of Old Florida where wildlife, birds, fish and more can be observed in a natural setting. Relax lakeside in the Adirondack chairs by the firepit or on the dock to drop a line in the bass fishers dream freshwater lake Griffin!