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.

0 of 0 items showing

1 of 3 pages

Top guest favorite

Home in The Villages

4.96 out of 5 average rating, 134 reviews

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

Top guest favorite

Home in Inverness

4.96 out of 5 average rating, 129 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.

Top guest favorite

Apartment in Brooksville

4.97 out of 5 average rating, 112 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

4.94 out of 5 average rating, 16 reviews

The Villages, Citrus Grove home away from home

Create great memories at this centrally-located home, with an open floor plan with vaulted ceilings. The kitchen is well equipped and the living room has a queen size sleeper sofa and a smart TV (internet/WIFI). The master bedroom has a king size bed, walk in closet, smart TV, master bathroom and a work area with a desk and printer. The guest bedroom has a queen size bed, large closet and smart TV. Both bedrooms have black out curtains and hair dryers, and linens. Grill/2 bikes incl.

Top guest favorite

Home in The Villages

4.96 out of 5 average rating, 53 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 golf car ride to new Eastport and a 20 min ride to Brownwood. It’s only a 5 minute walk to the pool and Aviary rec center is about a 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.

Top guest favorite

Place to stay in The Villages

5 out of 5 average rating, 95 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

Villa in The Villages

4.84 out of 5 average rating, 101 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.

Guest favorite

Guesthouse in Inverness

4.89 out of 5 average rating, 127 reviews

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.

Top guest favorite

Guesthouse in Dade City

4.95 out of 5 average rating, 207 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.

Top guest favorite

Home in Wildwood

4.96 out of 5 average rating, 78 reviews

New home in the new part of the villages.

Beautiful new home in the villages. All new appliances with all brand new furniture, beds and decor. You have quick access to Sawgrass grove Entertainment facility, Ezell recreation center and McGradys pub. This open floor plan with the kitchen opening to living room keeps everyone together. The huge island is a great hanging out spot. You will have access to many close by, pools, shuffle board, parks and golf courses during your stay.

Top guest favorite

Home in The Villages

4.96 out of 5 average rating, 134 reviews

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.

Superhost

Home in Sumterville

5 out of 5 average rating, 3 reviews

Spacious 3BR in The Villages | King Bed, Golf Cart

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