Vacation rentals with a pool in Sumter County

4.96 out of 5 average rating, 123 reviews

Home in Inverness

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.

5 out of 5 average rating, 15 reviews

Entire Home with an Office in Fenney

My home is furnished for the ultimate in guest comfort and working online. Accommodates maximum of 2 guests who plan to sleep in the same bed. Only 1 bed provided. Bright office with large desk, printer, TV 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

5 out of 5 average rating, 17 reviews

Home in Wildwood

Brownwood Square - Villages Home

Indulge in a stylish retreat at this centrally located home, just minutes from the vibrant Brownwood Square in the sought-after Village of DeLuna. Immerse yourself in the full Villages experience with a community pool, recreation center, and included golf cart—perfect for exploring. Enjoy nearby shopping, dining, live music, nightlife, sports, and more. Explore Central Florida or take a short drive to the Gulf Coast, Atlantic Ocean, Disney, or Orlando’s vibrant attractions—all within an hour!

4.97 out of 5 average rating, 109 reviews

Home in Brooksville

Fuel Your Passion, Epic Moto Ranch Factory Ride

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 gateway 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

4.88 out of 5 average rating, 114 reviews

Guesthouse in Inverness

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.

5 out of 5 average rating, 15 reviews

A patio villa in Deluna, The Villages w/ Golf Cart

Enjoy this beautiful 2/2 home in De Luna. With quick access to the turnpike and I-75 to enjoy everything in and around the Villages. This Ruby model villa is close to Brownwood and Ednas’ on the Green & soon to be East Port. It comfortably fit 4 people in two queen beds. The living room can fit two on the pull out sectional. The front screen porch is a wonderful place to wave to your neighbors while you have your morning coffee or just the place to relax before going to bed.

4.91 out of 5 average rating, 70 reviews

Villa la Bella

Stay in one of the most desirable locations in The Villages in the village of Sable Chase. Our beautifully remodeled and newly updated villa is just minutes from Sumter Landing in the heart of The Villages. Bright and airy feeling, tastefully designed and decorated, it features hardwood floors throughout. The 2BD, 2BA house with cozy lanai and new stainless gas grill also includes a Yamaha gas golf cart for your use. Your Villages vacation is ready for you at Villa la Bella!

4.96 out of 5 average rating, 28 reviews

Home in Brooksville

Brooksville Oasis! 3 Bedroom, Heated Pool Home

Have fun with the whole family and escape to your Private Oasis in Brooksville! Relax and unwind in this stunning 3-bedroom pool home, perfect for your next family getaway or friends' retreat! Take a dip in the refreshing pool to escape the Florida heat, then soak up the sun on wooden rocker chairs. In the evenings, fire up the grill and enjoy delicious meals outdoors on the patio seating and bar area, perfect for creating lasting memories with friends and family!

4.95 out of 5 average rating, 200 reviews

Guesthouse in Dade City

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.

4.97 out of 5 average rating, 73 reviews

Home in Wildwood

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.

4.95 out of 5 average rating, 126 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

Superhost

5 out of 5 average rating, 4 reviews

The Villages, Heated Pool Walk to Sawgrass

Enjoy a heated pool, huge outdoor space with dining/lounge areas, and a covered lanai with TV. Just minutes to Sawgrass Grove—golf cart included! This open-concept home features 2 king bedrooms with TVs, one with an ensuite, the other with a massage chair and attached bath. Fully stocked kitchen. Close to golf, pickleball, pitch & putt, and more. Relax and enjoy the best of The Villages!

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Popular amenities for Sumter County rentals with a pool

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Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 9 reviews

Designer Home in The Villages, FL.

JeannineRating, 5 stars2 months ago

Beautiful, beautiful place. Felt right at home....even better than my home as convenient first floor living. Quite neighborhood, many amenities in the house. Safe and clean environment conveniently located in The Villages.

4.97 out of 5 average rating, 32 reviews

Haven Escape at the Village of Richmond

LaurenRating, 5 stars1 week ago

Our stay was absolutely amazing. The house is very comfy and close to many shops and restaurants. The location was perfect for where we wanted to be in reference to family. Besides the host being the nicest person ever; the communication regarding any questions I had was super quick and easy. I would recommend this place 1000x over and I will be staying here again next time I am in town!!

5 out of 5 average rating, 16 reviews

Heated Pool, Dog Friendly, Golf Cart Included

MichelRating, 5 stars2 months ago

Cosy setting, the bar feature is a nice add on. Pool and hot tub setting really nice especially at night with the hung lighting. Hosts very responsive and helpful.

4.95 out of 5 average rating, 126 reviews

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

LauraRating, 5 stars3 days ago

The home is beautiful and has everything you need. The pool is amazing. Check in and out was easy and Dena gave me great advice for where to play pickleball. The neighbors were super friendly too!

5 out of 5 average rating, 15 reviews

Vacation home in The Villages

RyanRating, 5 stars1 month ago

Marty was very responsive and accommodating! My entire family enjoyed our stay and the house was perfect for everyone's needs! Would definitely recommend for anyone looking to visit The Villages!

4.89 out of 5 average rating, 45 reviews

Home in Lady Lake

The Villages, De La Vista West 1762

BradleyRating, 5 stars3 weeks ago

The house was clean and very nice. The location was perfect and the house had all the amenities for my stay. Great communication by Lee!! Would stay again for sure!!!

5 out of 5 average rating, 16 reviews

Perfect home-families/friends in The Villages, FL!

JohnRating, 5 stars6 months ago

Jeff and Aggie were excellent hosts and this is an outstanding house. My wife and I and our three adult children really enjoyed this house. The bedrooms and bathrooms are excellent, the kitchen and living area is large and outstanding and the pool/outdoor kitchen was impressive. This was a great experience, there were no issues or concerns at all. In addition, the communication was outstanding. Everything went very well.

Superhost