
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.

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

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.

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

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.

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!

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.

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.

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!

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.

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.

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

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
House rentals with a pool

On The Links-4bd w/pool in Spanish Springs!

Begonia on the Bend – Stylish Home Near Sawgrass

2/2 custom pool home with 4 person gas golf cart

Peaceful Home Retreat

Brownwood Square - Villages Home

Pet Friendly in the Villages!

Charming Villages Retreat

Pool and Spa Luxury Retreat
Other holiday rentals with a pool

Designer Home in The Villages, FL.

5-Star Luxury | Prime Location & Top Amenities

2 min walk to pool, 4 seat cart, 5 min to Eastport

Heated Pool Golf Cart Dog Friendly in The Villages

King Bed, Small Dogs OK, and 4-Seater Golf Cart!

Home with private pool, Tierra grande villas

The Villages, Heated Pool Walk to Sawgrass

Crabby Cottage 3 w. Golf Cart, near Brownwood!
Destinations to explore
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- Rentals with pools Florida
- Rentals with pools United States
- Walt Disney World Resort
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Busch Gardens Tampa Bay
- Discovery Cove
- Orlando / Kissimmee KOA
- ESPN Wide World of Sports
- Epcot
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Weeki Wachee Springs
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!




