Vacation 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.

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Guest favorite

Guesthouse in Inverness

4.85 out of 5 average rating, 68 reviews

Tranquil, private pool house!

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 TVwith Apple and prime tv, Netflix, Disney+, and more.

Guest favorite

Home in Inverness

4.97 out of 5 average rating, 108 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 favorite

Home in The Villages

4.93 out of 5 average rating, 54 reviews

King Bed, Golf Cart, Cruising Bikes, & Fast Wi-fi!

Your NEW home includes a very comfortable KING BED, a complimentary GOLF CART with golf clubs, and two cruising BIKES. With its SUPER CLEAN coastal decor, fully equipped kitchen for meal prep, and a whole house water filtration system, you’ll have everything you need for a relaxing and enjoyable stay in The Villages. Find out why The Villages is the fastest growing and largest 55+ community in the WORLD, where visitors of all ages are welcome to play. The fun and sun is only the beginning!!

Guest favorite

Rental unit in Brooksville

4.97 out of 5 average rating, 78 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

Guest favorite

Home in The Villages

4.95 out of 5 average rating, 120 reviews

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

Beautiful Monterey style home, 2/2, 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 for extra folks. 4 person gas golf cart. 2 bikes available but not maintained by owner. Sorry, hot tub not included. Pet friendly!

Guest favorite

Home in The Villages

4.94 out of 5 average rating, 126 reviews

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!

Guest favorite

Place to stay in The Villages

5 out of 5 average rating, 61 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 favorite

Home in The Villages

4.94 out of 5 average rating, 18 reviews

The Sunshine Retreat with Golf Car

Come and enjoy this beautiful 2 Bed/2 Bath Patio Villa Home. We have made it very relaxing and welcoming for your stay. You will enjoy just a 3 minute golf car ride to Sawgrass, 15 minute car ride to new Eastport and a 25 min ride to Brownwood. It’s only a 5 minute walk to the pool and Aviary rec center is about 5 minute golf car ride away. Golf Car included with home. Renter assumes all liability and will be responsible for any damage or injury caused by the use of the golf car.

Guest favorite

Home in The Villages

4.94 out of 5 average rating, 111 reviews

Entire 3 Bedroom House (Sleeps 8) in The Villages

Spacious 3 bedroom house in The Villages. The house is newly renovated and features both a new 70 inch Samsung TV in the living room and a new 50 inch Samsung TV in the master bedroom with Hulu Live and Comcast Business high speed internet. The house is located near the Spanish Springs Town Center, Tierra del Sol and Glenview Country Clubs. We have a jacuzzi for your enjoyment, as well as a grill. The home sleeps 8 with privacy using a sofa bed located in the rec room.

Guest favorite

Guesthouse in Dade City

4.94 out of 5 average rating, 179 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 favorite

Home in The Villages

4.94 out of 5 average rating, 106 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 favorite

Home in Inverness

4.97 out of 5 average rating, 148 reviews

Private 40 Acre Waterfront Retreat on Nature Coast

Welcome to your private oasis; a truly outstanding 40-acre waterfront estate. Experience the exceptional beauty and diverse wildlife that is characteristic of the Nature Coast. Our4400 square foot private vacation retreat invites you to relax by the pool, fish on the river, explore, and take advantage of all the local sites to see. Create special memories reconnecting with nature and each other.