Fitness-friendly holiday rentals in Leesburg

Tiny Hamptons | No Pet Fees | Main Floor Bed

A Masterclass in Luxury Tiny Living Welcome to the "Bridgehampton"— model by Tiny Hamptons LLC. As professional luxury tiny home builders, we designed this space to prove that downsizing doesn't mean compromising. Unlike standard DIY rentals, this home features master-grade craftsmanship, from custom cabinetry to premium quartz finishes. Whether you're here for a 'test drive' before building your own or just a high-end Clermont getaway, you’re staying in a professionally engineered work of art.

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.

Lovely Meadow Farm Cottage

This lovely farm cottage can be found in a secluded meadowland under various oaks and pines along a natural cypress dome. Spectacular star lit night skies accompanied by hooting owls, whippoorwills, and fire flies make for an unforgettable camp fire atmosphere. Amenities include an outdoor shower, washer, dryer, barbecue, fire pit, fishing and outdoor wrap around patio. Ponds, canals, and Florida wetland host a variety of birds, mammals, fish and reptiles including the Florida gator.

Newest Hotspot in The Villages Eastport/Middleton”

Welcome to Eastport! The Villages’ most exciting new lifestyle destination — Eastport! Whether you're visiting for a weekend getaway or an extended stay, this beautifully furnished 2-bedroom, 2-bath Patio Villa w/golf cart puts you in the heart of everything The Villages has to offer — golf, pickleball, shopping, dining, entertainment, recreation, and serene nature. From the moment you arrive, you’ll see why Eastport is the new standard for luxury, leisure, and active adult living.

Crabby Cottage 3 w. Golf Cart, near Brownwood!

Recently remodeled patio villa in the V. of Fernandina, which is centrally located close to Brownwood Town Center and Lake Sumter Landing 2 seater gas golf cart, complete w/ 24/7 roadside assistance 2BR/2Ba, no carpet in main areas, carpets in Bedrooms, with plenty of amenities to enjoy your stay. 55inch Ultra High Def TV with cable in the main area, and a smart TV w/ cable in the main bedroom. Community pools & rec centers close by! Some Pets OK w/ fee and approval, check 1st.

Orlando Private Tiny Guest House

*Quiet, safe neighborhood Premium location *20 minutes to Orlando Airport *20 minutes to Disney parks & Disney Springs *25 minutes to Universal Studios & CityWalk *7 minutes to shopping plaza with top outlets and diverse dining *5 minutes to super Walmart *Local minimarkets. Inside your tiny home: *Queen-size bed *Coffee, fridge & microwave *Private entrance + patio *Modern shower *Air conditioning, Wi-Fi & Smart TV *Need transportation or special arrangements? Let us know

Spacious 2BR Apt in Resort 10 min from Disney

Featuring comfortable, family-friendly amenities, this property provides relaxation in a peaceful, wooded setting while being close to all the major area theme parks. Enjoy the outdoor swimming pool or stay active at the fitness center and tennis courts. Families will appreciate the playground and children's pool. Additional conveniences such as a bar, free Wi-Fi, and free parking ensure this property is your home away from home near Orlando's famous theme parks.

New, private pool getaway in The Villages, FL

The whole group will enjoy easy access to everything from this centrally located 3B/3BA home in the village of St Catherine. Just steps away from Sawgrass marketplace where you can enjoy dinner, nightly entertainment, pickle ball, and golf at the brand new Southern Oaks 18 hole championship golf If staying in is your idea of relaxation, enjoy the oversized lanai and private heated pool while watching your favorite shows or sports on the 65" smart TV.

Lake Sumter 2/2 Villa FREE gas cart/Pet friendly

Super clean 2-bed/2-bath property in Buttonwood with free use of gas cart. Nicely furnished, with washer/dryer, smart tv and vaulted ceilings. This patio villa is in a highly desirable area within walking distance to the Fishhawk pool, rec center and many golf courses. Equal distance between Lake Sumter Landing & Brownwood squares. $89 pet fee. 4 person cart available at $50/day. 2 person cart is free. Return cart full please.

Villages-Private Heated Pool-Central Location

Enjoy a stylish experience at this centrally located 3-bedroom home. 5-7 minutes golf cart ride from Sumter Landing, 15 minutes from Spanish Springs Square, 20 minutes from Brownsville Square. 200 Community pools some for adults only and some for families. 13 Recreation Centers with Pickle Ball, Shuffleboard, Billiards, Study groups, etc. 3 Old Fashion Town Squares with nightly Live entertainment. 44 Golf Courses

Briar Meadow Villa - Dogs are welcome!

Dogs are welcome in this nicely furnished Courtyard Villa, with a fenced in backyard. Near Nancy Lopez Legacy Golf & Country Club, Mulberry Grove Rec Center, dog park, Publix, Walgreens, & The Club Health & Rehab Clinic. Easy access to pools, golf courses, dining, shopping & the squares at Spanish Springs & Sumter Landing. Includes gas Golf Cart, Comcast cable TV, high speed WIFI, & Villages Daily Sun.

Begonia on the Bend – Stylish Home Near Sawgrass

🌴 Modern 3BR/2BA Begonia-style home in The Villages’ new Cason Hammock neighborhood. Built in 2021, this spacious 2,083 sq ft retreat features an open layout, oversized garage + golf cart garage, and stylish comfort throughout. Walk to Sawgrass Town Square, McGrady’s Pub, pool, rec center, and Fresh Market. Enjoy The Villages lifestyle with everything you need for a relaxing stay!