Holiday rentals with a pool in Sumter County

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Top-rated rentals with a pool in Sumter County

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Superhost
A modern living area features a spacious sectional sofa in gray, complemented by a wooden coffee table. The open floor plan connects to a kitchen with stainless steel appliances and seating for four at the bar. Decorative wall elements add interest to the neutral walls.
Home in Lake Panasoffkee
4.87 out of 5 average rating, 104 reviews

Heated Pool & Kayaking House in Lake Panasoffkee

Bring the whole family to this great place with lots of room for fun. Enjoy this stylish house very close to the lake. Create new memories while staying at this beautiful property and all its amenities such as an indoor pool with nature view. Designed play room with pool/hockey air table and so much fun. With lake access from the its yard and 5 minutes from all restaurants and entertainments at Lake Panasoffkee. This fully renovated house will make your trip a unique and unforgettable experience

Top Guest favourite
A private screened-in pool is framed by lush greenery and palm trees, offering a serene view of the lake. The spacious pool features a set of steps leading into the water, with a shaded gazebo visible in the background.
Home in Inverness
4.96 out of 5 average rating, 141 reviews

Nature Coast Lakeside Getaway- Pool Home w/ Dock

Enjoy lakefront living close to everything the Nature Coast has to offer. Entire home is for your use with a private pool and boat dock. Beautifully decorated and comfortable living space to enjoy some family time. The 3 bedroom home has 2 king beds, 1 bunk bed (twin and full size) and 1 twin trundle bed. Sleeps 8. Enjoy using the 3 kayaks on the lake during the day, then challenge each other to a game of 8 ball at night on the billiards table. Swim and enjoy cocktails by the pool on the lanai.

Guest favourite
A collage of outdoor and indoor experiences at the Moto Ranch, featuring a modern living area with recliners and a dining table, vibrant outdoor pool surrounded by greenery, ATV riders exploring trails, mountain bikers on a path, horseback riders enjoying the forest, and kayakers along the water.
Apartment in Brooksville
4.94 out of 5 average rating, 132 reviews

Fuel Your Passion, Epic Moto Ranch Privateer

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 getaway 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

Superhost
A single-story villa is displayed with a light beige exterior and a neatly paved driveway. The two-car garage is situated on the left side, while manicured hedges and green grass create an inviting approach to the front entrance.
Home in The Villages
4.74 out of 5 average rating, 150 reviews

3 bdrm 2 ba fully furnished!

An active Senior Community 55+, in Summerhill Village . Children are welcome guests. This home is beautifully decorated and boasts a bright open floor plan.The kitchen is complete with everything you'll need to prepare meals. The Living room offers plenty of comfortable seating if you're entertaining friends or family or just enjoying your favorite TV shows on the flat screen TV. Both bathrooms are set up with extra towels and linens. PETS NOT ALLOWED!!! Wi-fi AVAILABLE BUT NOT COMPUTER.

Top Guest favourite
An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.
Place to stay in The Villages
5 out of 5 average rating, 115 reviews

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!

Guest favourite
An exterior view of the patio villa showcasing a well-maintained façade. A garage door is located to the left, with a Yamaha gas golf cart parked on the driveway. A white picket fence and colorful flowers enhance the entrance.
Villa in The Villages
4.86 out of 5 average rating, 118 reviews

Location Can’t be Beat! With cart!

Experience The Village's retirement community lifestyle! The patio villa is located near Spanish Springs Town Square and the shopping corridor, where you will find nightly entertainment, dining and shopping. Walk to Savannah Center & Glenview Country Club. Your rental includes the complimentary use of a Yamaha gas golf cart and Guest ID cards that provide you access to our recreation facilities. Monthly guests may purchase Resident ID cards ($50) that include free executive golf.

Top Guest favourite
The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.
Home in The Villages
4.97 out of 5 average rating, 103 reviews

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.

Top Guest favourite
An elegantly appointed dining area is highlighted by a dark table surrounded by gray upholstered chairs. Two candles sit atop the table, with a decorative bowl in the center. Soft lights hang overhead, illuminating the blue walls adorned with framed art and decorative shelves.
Villa in The Villages
4.86 out of 5 average rating, 261 reviews

Perfect "get-away" home for a couple or family!

Great getaway for a single, couple, or a family. Only an hour from the Disney Parks! By golf cart, you are only minutes from pools, rec. centers, golf courses and many dining options as well as the grocery store. The home includes a nice outdoor seating area. The "squares" provide FREE nightly entertainment. I offer a golf cart for getting around in The Villages. This get-away home is perfect for people looking to relax OR never be bored! It's always a great day at The Villages!

Top Guest favourite
An aerial view captures a rustic property surrounded by lush greenery, including oak and hickory trees. A winding path leads from the road to the guest house, which is nestled within the expansive landscape. A serene lake is visible in the background.
Guesthouse in Dade City
4.95 out of 5 average rating, 227 reviews

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.

Guest favourite
The exterior of a charming single-story house features a wide porch supported by columns, creating a welcoming entrance. American flags are displayed, and a well-maintained yard is bordered by flowering plants. The roof is adorned with a light blue hue that complements the house's exterior.
Home in Bushnell
5 out of 5 average rating, 11 reviews

Historical Home away from Home

Discover the perfect blend of comfort, convenience, and entertainment in this charming 3-bedroom house. With desirable amenities, including a saltwater pool, a gas grill, a fire pit, and RV storage, this rental offers the ideal home away from home for unforgettable experiences and lasting memories. Home is 1.5 miles to I-75 and only 20 miles to Florida Turnpike, making an easy 40-45 drive to all Florida amusement parks.

Top Guest favourite
An enclosed patio features a heated saltwater pool, accentuated by stone tile and decorative mosaic. Nearby seating options are visible, including a lounge chair under a shaded canopy. Lush greenery surrounds the area, providing a sense of privacy and tranquility.
Home in The Villages
4.96 out of 5 average rating, 145 reviews

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

Guest favourite
A welcoming entrance features a garden area with vibrant plants, bordered by natural stone and mulch. A black horse statue stands gracefully near a wooden fence, framing a scenic view of open land and distant structures under a large oak tree.
Tiny home in Bushnell
4.84 out of 5 average rating, 57 reviews

Country getaway

You won’t forget the peaceful surroundings of this rustic destination. Former inn-keeper offering this unique space on Wildfire's Ranch. Centrally located from Ocala, Tampa and Orlando. Short drive to the Villages. Set in the country but minutes from shopping and restaurants. Secured gated entry and easy access to interstate 75. If you like the holidays you will love it here.

Popular amenities for Sumter County rentals with a pool