
Holiday rentals with a pool in Sumter County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Sumter County
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

2/2 custom pool home with 4 person gas golf cart
Beautiful Monterey style 1600 SQFT home, 2BR/2BA, fully furnished with a heated pool at 85' year round. Great location in Rio Grande; just a short golf cart ride to Spanish Springs & Lake Sumter. Home is on a quiet cul-de-sac; no neighbors behind. Private lanai from the Florida room. Tile and granite countertops throughout; Stainless steel appliances; sleeper sofa in the LR. 4 person gas golf cart also included. Sorry, hot tub not included. Dog friendly! Smart Tvs in both BRs, cable in LR only

Entire Home with an Office in Fenney
My home is furnished for the ultimate in guest comfort & for working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, TV, printer Furnishings are modern & luxurious, making you feel right at home. Fast Internet & YouTube TV Fully stocked kitchen Coffee & tea is complimentary Filtered home water system Please NON-smokers ONLY welcome NO pets Not suited for children Fees reduced for 28+ days, ask for details

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

Pool, golf cart, private backyard. Paradise!
Come and enjoy this relaxing piece of paradise surrounded by lush greenery with your own, small, private pool (not heated). "Serene on the Green" is a beautifully remodeled 3 bedroom, 2 bathroom designer home (1,536 sqft) with a large screened outdoor pool area with lots of privacy. Our location 320 steps from the Santiago Recreation Complex with two golf courses and a short ride to Lake Sumter Landing and Spanish Springs is perfect. A new custom 2021 Yamaha QuieTech golf cart is included!

2 min walk to pool, 4 seat cart, 5 min to Eastport
4-seat golf cart included. Well-located home in The Villages, 5 minute golf car ride to Eastport and Middleton. Literally a 2 minute walk to Shady Brook Adult Pool, 5 minute walk to Saluki Rec Center's Family Pool with pickleball courts, and indoor games like classic video games tables, billiards, pinball machine, darts, table tennis, etc. Multiple golf courses, easy access to Sawgrass Grove or Brownwood town squares' nightly music, dancing, dining choices at many great restaurants.

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.

Incredi-Bill Jo's
Get ready for an incredible stay at our Incredi-Bill Jo's stylish and cozy pool home. You'll be steps away from world class shopping, dining, entertainment, sports, recreation and GOLF. This three bedroom home is close to all of the amenities that make The Villages the number one destination for active adults year after year. And to make your stay even more incredible, you'll have the convenience and use of a beautiful golf cart! Come and see what all the fuss is about!

Spacious 3BR in The Villages | King Bed | Golfcart
Four Seaters Golfcart Available! With an amazing view of the landscape right from the balcony with comfy chairs, this home is a perfect spot for relaxation! With a four seater golf cart, you will be minutes away from golf courses & recreation centres like the Water Edges Postal, Eastport Town Square, Saluki Recreation Center, Brownwood Paddock Square, etc. Please be advised that a $50 charge applies to get the lifestyle ID. There's also a $20 golfcart insurance fee.

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.

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
Popular amenities for Sumter County rentals with a pool
House rentals with a pool

StJohns is a great area for golf, hiking, Kayaking

Pool home on Lake Panasoffkee - Boho Fish Camp

Villages home with unique elevated front porch

Begonia on the Bend – Stylish Home Near Sawgrass

Huge & luxurious home w/view of preserves & fenced

Dreaming of DeLuna

Brownwood Square - Villages Home

New, private pool getaway in The Villages, FL
Other holiday rentals with a pool

Spotless Villa Near Brownwood Sq- Lanai & King Ste

Renovated! Between Two Squares with Golf Cart !

Heart of The Villages-guest pass for pool, golf

Patio Villa - Pet Friendly 2/2 Home (South of 44)

The Villages Oasis

Pool and Spa Luxury Retreat

Robin's Song in Brownwood

The Villages, Citrus Grove home away from home
Destinations to explore
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- Rentals with pools United States
- Universal Studios Florida
- Orange County Convention Center
- Universal Orlando Resort
- Universal's Volcano Bay
- Disney Springs
- SeaWorld Orlando
- Old Town Kissimmee
- Disney's Animal Kingdom Theme Park
- Busch Gardens Tampa Bay
- Magic Kingdom Park
- Epcot
- Weeki Wachee Springs
- ESPN Wide World of Sports
- Walt Disney World Resort Golf
- Amway Center
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Aquatica
- Island H2O Water Park
- Disney's Hollywood Studios
- ICON Park
- Southern Dunes Golf and Country Club
- Rainbow Springs State Park
- Universal's Islands of Adventure




