Vacation 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.

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Guest favorite

Home in The villages Florida

4.97 out of 5 average rating, 207 reviews

The Village’s Coffee or cocktails on the course !

EXCELLENT ROBUST WI FI FOR THE ENTIRE PROPERTY . CHECK OUT TIME IS 10AM Wake up with Coffee or afternoon cocktails on the fifth hole of the Tierra Del Sol Country Club close to Spanish Springs and Lake Sumter Landing town squares. In the Village of Santiago. Free live music 365 days at each of three town squares. CLose to shopping, golf and pools. Enjoy day of golf, swimming, a country club dinner and dancing on the square NO smoking environment. NO children Also, no pets allowed.

Dec 9 – 16

R2,763 ZAR per night

Guest favorite

Apartment in Brooksville

4.96 out of 5 average rating, 56 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

Jan 16 – 23

R2,276 ZAR per night

Guest favorite

Home in The Villages

4.94 out of 5 average rating, 106 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!

Aug 10 – 17

R3,604 ZAR per night

Guest favorite

Home in The Villages

4.94 out of 5 average rating, 108 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!

Apr 12 – 19

R6,623 ZAR per night

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 19 reviews

Haven Escape at the Village of Richmond

Keep it simple at this brand new, peaceful and centrally-located villa in the new Village of Richmond. We are located less than 5 mintues from Brownwood Paddock Square, which offers nightly entertainment, restaurants and shopping. Our home is close to Clarendon Recreation, which offers a family pool, pickleball, tennis, shuffleboard, bocce, corn toss, outdoor exercise equiment and platform tennis. Lake Okahumpka and Richmond Pitch & Putt are minutes away. Come see what TV has to offer.

Jul 3 – 10

R2,396 ZAR per night

Guest favorite

Home in Wildwood

4.95 out of 5 average rating, 19 reviews

Villa in The Villages Great Location

Kick back and relax in this calm, stylish villa in The Villages. It is in the village of McClure (Fenney area). It is a super clean villa with newer furnishings. The villa comes with a golf cart as a courtesy to enjoy. It is close to Everglades Recreation Center Magnolia Shopping Center, family pools, sports pools, executive golf courses and many other activities. The neighborhood pool is within walking distance to this home! The home is fully furnished and has a fully equipped kitchen.

Jul 13 – 20

R2,086 ZAR per night

Guest favorite

Home in The Villages

5.0 out of 5 average rating, 7 reviews

Central Villages w/ Golf Cart

Centrally located in The Villages. Use the included golf cart for a short golf cart ride away from 2 Town Squares (Brownwood and Lake Sumter Landing), where there is free nightly entertainment 365 nights/ year. The patio villa is well appointed, including a split-king adjustable bed in the main bedroom, queen bed in the guest bedroom. Tucked away at the end of the street, with a side patio w/ retractable awning and grill. Also screened in lanai w/ blinds. LVP throughout-no carpet.

Nov 29 – Dec 6

R2,601 ZAR per night

Guest favorite

Home in Wildwood

4.93 out of 5 average rating, 28 reviews

*May Rates Reduced 2/2 in Village of Citrus Grove

*Newly Redone* - Brand new furniture throughout - Freshly painted - Screened in Lanai 2 Bedroom, 2 Bath located in Citrus Grove in The Villages, FL Great Location! - Very close to Citrus Grove adult pool - Homestead recreation center with family pool 0.7mi - Ezell Recreation Center 1.1mi - Sawgrass Complex 1.3mi There are several amenities for you to enjoy in The Villages - restaurants, bars, nightly live entertainment, shopping, golf, pickleball, shuffleboard, and so much more!

Jun 16 – 23

R1,832 ZAR per night

Guest favorite

Home in Inverness

4.89 out of 5 average rating, 112 reviews

Spacious Family Friendly Pool Home

Our traditional, Spanish-style family home is two full homes in one, completely separated by the laundry room with two doors. We offer the larger side: three bedrooms, three full baths, eat-in kitchen, living room, dining room, den, laundry, and large lanai with big screen TV, games, ping pong, and large swimming pool with diving board. None of this side including the lanai, pool, and the rest of that side of the house, is shared with anyone including my husband and myself.

Oct 8 – 15

R2,919 ZAR per night

Guest favorite

Home in The Villages

4.84 out of 5 average rating, 37 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!

Aug 16 – 23

R1,402 ZAR per night

Superhost

Cabin in Lake Panasoffkee

4.88 out of 5 average rating, 138 reviews

Lake Pan Cabin #1

This quaint one room cabin provides a tranquil lake view with a front porch swing for your ultimate relaxation. Restroom located within a few feet and a larger bath house (with shower) located less than 300 feet from cabin. Charcoal grills and a fire pit located near the cabin for your use. Complimentary use of our single kayaks or canoe. The boats are available after 9am (office opens) and must be returned by 3:30pm. They are not available when the office is closed.

Aug 25 – Sep 1

R1,610 ZAR per night

Guest favorite

Guesthouse in Dade City

4.95 out of 5 average rating, 159 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.

Jan 13 – 20

R1,266 ZAR per night