Pet-friendly holiday rentals in Sumter County

Get to the Choppa! One-of-a-kind 2/1 Helicopter!

Experience a truly UNIQUE Stay! “Chinook” is situated on a serene 5-acre compound inside the breathtaking Withlacoochee State Forest and the thrilling Croom Motorcycle Area, outside of Brooksville, FL. This unforgettable vacation experience is sure to take your adventure to new heights! Our one-of-a-kind accommodation, a REAL repurposed Chinook CH-47D helicopter, promises a stay like no other. This iconic “choppa” with the modern amenities of home, can not be found anywhere else in the world!

Serendipity Lake private dock, canoes & kayaks

What a view, what a really good view, YES IT IS! Watch the sunrise and sunset over the water on a private dock. We have 2 canoes and 2 kayaks to enjoy the water or bring your boat! This is a place you will want to come back to time and time again. Water views from all angles, you will feel like you're on a houseboat there's so much water! Plenty of room for outdoor games and activities. Pet friendly. Just a short drive to downtown Inverness and 30 minutes to Crystal River. Simply perfect!

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

Quaint Cottage on an Old Florida Orange Grove

Come stay with us at The Grove! Located on a retired orange grove on the Floral City chain of lakes, you are sure to have a one-of-a-kind Florida experience. Stroll amongst citrus, ancient oaks, and abundant flora on our 66-acre property. We have a walking path right on the water, or get adventurous and explore the wild "north 40" acres! An exceptional piece of land, we neighbor the Flying Eagle Preserve. And only a few miles away from some of Floridas most famous freshwater springs!

Duck Haven - Wildlife Sanctuary - 5 miles to I75

Have you ever wanted the opportunity to feed an egg to a fox? Or feed a lemur? Hand feed a deer or sheep? Dance with a cockatoo? If so you’ll get to have these and many more experiences here during your stay. Our Airbnb is different, and our main focus is on offering rememberal experiences to our guests. We have a small family run 501C-3 wildlife sanctuary here on our 18 acre facility that you will be staying at. We do live on the property, but in a detached house across the driveway

Tranquil guest home with beautiful salt water pool

Our tranquil getaway! Whether on vacation or traveling for work, this is the place to stay! With a beautiful pool and gigantic screened in area with comfortable patio furniture and a place to have your meals outside, you can't beat our guest house for enjoying Florida's weather. Inside, we have just added a stunningly comfortable new Queen sized bed with a "Purple" mattress on an adjustable frame. We have hi speed wi-fi and a large screen TV with Amazon Prime, Netflix, and more.

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.

The Cove Point House

Escape to this beautiful retreat surrounded by picturesque ferns on beautiful Lake Henderson. Relax on a screened in porch in one of the most utilized rentals around! Our piece of paradise offers a private dock with stunning views of the sunset and scenic native plants. Lounge on the back deck and grill your favorite meal. Be wonderstruck by personalized touches, customized light fixtures and knotty pine ceilings. Bring the family as the second bedroom offers two twin sized beds!

Cypress Cottage

Handicap accessible. Relax with the whole family at this peaceful place to stay. On a dead end street on a channel that goes out to some lakes in the area. Have a canoe,peddle boat and four bikes included to use during your stay. Little over an hour from Orlando Airport and about the same from Tampa Airport. 30 minute drive to Homosassa Springs that has many attractions. If you see any alligators please do not feed them. They become a nuisance and it’s also against the law.

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

Log cabin on the river

Experience the charm of the great outdoors in this rustic riverfront log cabin. Surrounded by nature, this cozy retreat offers a blend of comfort and adventure for nature lovers. Unwind by the fireplace, fish off the dock, and explore the tranquil wilderness right outside your door. Ideal for those seeking an escape with a touch of rugged charm.

Peaceful Cottage in the Heart of Wildwood

Peaceful home... -Full kitchen for cooking any meal. -Pet friendly with $25 pet fee per dog. No cats please. -Keurig coffee maker for that morning cup of joe. -WiFi and smart tv. -Washer and dryer available for use. -Large lanai with a fenced in backyard for privacy. -Close to all amenities. -One mile from The Villages!