Holiday rentals with outdoor seating in Sumter County

4.94 out of 5 average rating, 126 reviews

Holiday home in Bushnell

Withlacoochee River House on the main channel

Located on the main channel of the Withlacoochee River across from the State Forest, this home offers relaxation and recreation. The home is equipped with canoes & kayaks to launch from the backyard, and bikes to enjoy the 40+ miles of paved and mountain bike trails. Come home to relax by the fireplace and enjoy the river view, hang out and fish from the river bank, lie out back in a couple hammocks, or fire up the grill. This home is a great vacation getaway for couples, families, & friends!

4.96 out of 5 average rating, 166 reviews

Latitude 28 a little Patch of Paradise!

"Latitude 28" in Floral City is a spacious 2 BR/2BA Mobile Home. Once inside you'll find semi-open living concept with split bedrooms; Ciozy bedding wi/Queen Pillowtop & ensuite bath in MBR, GBR offers Full gel-foam topper. Living area has unique design elements from a local artisan. Amenities include 40" Smart TV, Wi-Fi, fully equipped eat-in Kitchen w/Keurig. Large Sun Room overlooking the expansive lawn great for Birdwatching and located just .07 miles from Trail for Cycling Enthusiasts!

4.93 out of 5 average rating, 327 reviews

Farm stay in Dade City

Florida Breeze -Wildlife Sanctuary- 5 miles to I75

Have you ever wanted the opportunity to feed an egg to a fox? Or feed a grape to 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 rescue 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.

4.99 out of 5 average rating, 145 reviews

Private, remodeled 3/2, Golf Cart - 4, Pizza Oven!

3-bedroom (sleeps 6), 2-bath home in The Villages! Screened & covered patio includes grill, pizza oven, fire table, outdoor seating, table and privacy - rare in The Villages! Access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Use 2023 4-seat gas golf cart or 3 bikes to get to it all! Smart TV's in family room, all bedrooms & patio, fully equipped kitchen, gaming table & more! 10 minutes to Spanish Springs & Sumter Landing Town Squares.

4.95 out of 5 average rating, 100 reviews

Cottage in Inverness

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!

4.97 out of 5 average rating, 109 reviews

Home in Brooksville

Fuel Your Passion, Epic Moto Ranch Factory Ride

Embark on your escape to the Moto Ranch at Croom; an unforgettable off-road & outdoor adventure in the heart of nature. Situated on a serene 5-acre compound inside Croom Motorcycle Area & Withlacoochee State Forest, this is your exclusive gateway to almost endless thrilling motorcycle/ATV trails, outdoor experiences like mountain biking, horseback riding, kayaking, etc. and best of all… endless natural beauty! ☑ Many modern amenities of home ☑ Private access to Croom’s trails ☑ Pets welcomed

4.97 out of 5 average rating, 132 reviews

Cabin in Floral City

Private Waterfront Cabin Retreat with Kayaking

Your private retreat on an acre nestled on a canal to the Withlacoochee River, wrapping around 2 sides of the property. Relax on your porch overlooking the water as you watch the birds and deer play. Kids will love the tire swing, toys such as Lego, Lincoln logs, pool table and ski ball. Kayaks available to our guests awaiting adventure. Bond around the fire pit, walk the trails, lounge in the hammocks, and fish on the dock. Setup the big screen to watch a movie. Welcome to your get-a-way!

4.88 out of 5 average rating, 150 reviews

Cottage in Brooksville

Spotted Dance Ranch

Spotted Dance Ranch is a small guest ranch and horse breeding facility that has been hosting guests since 2014. Come stay in our cozy Cowboy Cottage located on the beautiful ranch grounds, and enjoy the peace and quiet of the ranch located adjacent to the Croom Tract of the Withlacoochee State Forest! Bring your horse if you have one; otherwise, many other outdoor activities and attractions are available nearby, or just relax! We are conveniently located outside Brooksville, FL near I-75.

4.95 out of 5 average rating, 220 reviews

Home in Inverness

Inverness Home with a View

Relax in a clean, welcoming, home that has been updated. There are 2 fishing poles available for your use. We make sure they are in working condition and well maintained. Shopping, restaurants, and entertainment is close by. Want a beach....35 minute ride to Fort Island Trail Beach and boat ramp. We do allow hypoallergenic small dogs (2 max), non-shedding, 25 lbs. or less, each w/ proof of shot records, please bring a kennel with you. There is a non refundable $25.00 per dog fee.

4.88 out of 5 average rating, 113 reviews

Guesthouse in Inverness

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.

4.93 out of 5 average rating, 204 reviews

Cottage in Floral City

Waterfront Cottage 2BR 1B

This charming house is located on nearly an acre of woodland. Fish from the dock of the screen room on the canal or kayak to the nearby lake. Relax in the private backyard Jacuzzi. Bike on the nearby Withlacoochee Trail. There are 2 bedrooms plus living room sleeper sofa, and a lanai with a day bed. Fully furnished. Orlando theme parks are 1 1/2 hour away, Busch Gardens 1 hour. Close to Weeki Wachee, Homosassa and Crystal River for manatee viewing or scallop season.

4.94 out of 5 average rating, 199 reviews

Guesthouse in Dade City

Hickory Breeze Guest House

We invite you to come and enjoy our little piece of country in north Pasco County, Florida! Not fancy, but comfortable is our objective for our guests! We are not a business (nor are we owned by a business) therefore we do not conduct our hospitality like a business, but rather as hosts looking to meet and make new friends! We do all our own cleaning and set-up in the guesthouse so that we know it is done the way we would do it for our own family.

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Holiday House Rentals with Outdoor Seating

5 out of 5 average rating, 36 reviews

Waterfront Hideaway

Cori McGooden Rating, 5 stars1 week ago

What a great place. As an airbnb host myself, I’m picky about my stays. Laurie communicated well from the moment we inquired about pets and made sure we had everything we needed for our stay. Even made sure we had access to bikes and kayaks. Beds were comfortable, kitchen was well appointed and the screened back porch was a great place to enjoy a cup of coffee or an afternoon cocktail. At times it was so quiet we could hear the bees buzzing outside the screen. We even enjoyed daily visits from a hummingbird. Huge laundry/storage space gave extra room to store coolers and other bulky travel items. Plenty of towels too. An all around great location. It’s our second time staying in Floral City and there are two places we always stop- Sleepy Hollow (only 1/2 mile away with great shrimp from the food truck- beer, wine and seltzers only) and the Side Bar (downtown Inverness- short drive, full bar, great staff and delicious pizza.) We’ll be back!

5 out of 5 average rating, 34 reviews

The Eagle's Nest

TammyRating, 5 stars2 weeks ago

Barbara was an amazing host! The place was so comfortable and peaceful. We had everything we needed for an amazing stay.

4.98 out of 5 average rating, 49 reviews

Home in Webster

Unique Country home in Sumter County, Florida.

TiffanyRating, 5 stars1 month ago

This was one of our very favorite rentals ever! The pictures do not do the home justice. It’s very nicely equipped and decorated. We felt very at home and didn’t want to leave. I could sit on the porch there for hours. And we enjoyed the snacks provided also! Thanks again for a wonderful stay!

4.94 out of 5 average rating, 18 reviews

The Sandpiper Villa

AprilRating, 5 stars1 week ago

Sandpiper is a beautiful home away from home. We visited the Villages to attend my father’s 85th Birthday celebration and party. The Sandpiper is beautifully decorated and the coffee station was so convenient and needed for all the family activities leading up to the party. This two bedroom property was spacious for the 6 of us and very convenient to get to the squares like Saltgrass and Brownwood and grocery stores like Publix. And once Eastport opens you’ll be right there in minutes. The manager owners were extremely helpful and responsive to any questions we had. Would highly recommend Sandpiper to anyone visiting the Villages.

5 out of 5 average rating, 23 reviews

Country Getaway

TraceyRating, 5 stars1 month ago

From the moment we walked in to the house to see how immaculate it was, we felt right at home. It was very comfortable. A lot of our time was spent sitting in a large screened in patio looking out at the birds and listening to the wildlife. It was very peaceful and relaxing. The inside was new and professionally done. The coffee bar was equipped with all the fixings. Greta was wonderful to deal with. She answered our questions promptly and made our stay very pleasant. We visit the area frequently during the year and will definitely want to stay here again. Thank you.

5 out of 5 average rating, 17 reviews

Home in Wildwood

Brownwood Square - Villages Home

SherriRating, 5 stars3 weeks ago

Everything about our stay was great. The pool towels were a great touch. The golf cart made experiencing the area much more fun. We felt right at home and would definitely stay here again. Thanks Brandon!!

4.97 out of 5 average rating, 66 reviews

Central location near shopping-Golf cart included

LeaRating, 5 stars3 weeks ago

This home comes equipped with everything you need and is very spacious. Very, very clean and comfortable. Was very happy with everything including Cheryl’s communication and responsive messages. Having the golf cart is a huge plus. It’s very easy to get around anywhere and a great location to Brownwood and Lake Sumter. The home is pristine. Neighborhood is beautiful. Very quiet and peaceful. Perfect stay