Holiday houses in Lake Sumter

4.98 out of 5 average rating, 64 reviews

Villa in The Villages

Perfect location Lake Sumpter Villa w/ Golf Cart

Location, Location, beautiful 2 bedroom villa with 2-seater golf cart, is located in the desirable neighborhood of Creekside Landing. This villa is within walking distance of Lake Sumter Landing town square where you will find shopping, restaurants, a movie theater and FREE nightly live entertainment. Edgewater neighborhood Recreation Center with a pool, as well as Canal Street Recreation Center with activities such as shuffleboard courts, bocce courts, card rooms and so much more. This villa is beautifully decorated in a warm and inviting style. The kitchen is fully equipped with everything you’ll need to prepare meals and entertain friends. The living room offers plenty of comfortable seating with a flat screen TV. The master bedroom has a king size bed, flat screen TV, large walk-in closet and a private master bath with a walk-in shower, complete with towels and linens. The guest bedroom and guest bath comes completed with lines and towels for your guest’s comfort. There is a screened lanai with comfortable seating and a privacy wall . This villa comes complete with WiFi. With the purchase of resident ID cards you can use any of the 29 executive golf courses with no greens fees. You pay resident rates in greens fees at the 11 championship courses. You are also entitled to use any of the family- friendly and adult (30 and older) swimming pools, and organized activity swimming pools, There are over 1,000 organized activities each week through the recreation centers. Rates are based on double occupancy. Rates shown do not include taxes and additional fees

4.89 out of 5 average rating, 9 reviews

Charming Villages Retreat

Charming 2B/2B Cottage Villa near Sumter Landing and Spanish Springs Escape to this beautifully updated villa in The Villages. Enjoy a designer kitchen, cozy living room with sectional and 75” TV, and French doors leading to a screened lanai. The private, fenced courtyard is perfect for relaxing under party lights. The master suite includes a walk-in closet and blackout shades. Explore with the included golf cart, access 50 golf courses, 100+ pickleball courts, pools, and nightly entertainment.

4.94 out of 5 average rating, 142 reviews

Remodeled 2/2 Baja style villa w/4 person cart

4 person, yamaha gas golfcart offered at this baja style 1000 sqft 2BR, 2BA courtyard villa! It comes fully furnished with pots, pans, linens, and does have a blow dryer and keurig! located in the De La Vista South area just off Morse, this villa is just a short cart ride to Spanish Springs or Sumter Landing. The villa has new stainless appliances, beautiful plank flooring, and fresh paint. King bed in the master, queen bed in the guest bedroom. All bedrooms have smart TV's, cable in LR only

4.94 out of 5 average rating, 86 reviews

Walk to Sumter w/cart - Beautiful Courtyard Villa

We love this home because the location is FANTASTIC! It's under a mile to Sumter Landing (walking distance for us :)). Also, new floors, paint, etc! The living room furniture is extremely comfortable! The kitchen has everything you need. The beds are comfortable and there is a tv in every room. (The second bedroom but needs your own Roku or Firestick!) There is a cart included which is the best way to see The Villages. We know you will love it here! Let us know if you have any questions.

4.98 out of 5 average rating, 112 reviews

Private 2/2 Villa w/ New 4 Seat Gas Golf Cart

Relaxing home in quiet neighborhood w/ private yard, screened porch - rare in The Villages! Roanoke Retreat is a beautifully remodeled 2 bed/2 bath home - only 15 minute golf cart ride to Spanish Springs, 20 minutes to Sumter Landing . Rental includes 4 seat gas golf cart w/ access to community amenities - pools, tennis, pickleball, 55 golf courses, walking trails, gyms & more. Smart TV's in every room, fully equipped kitchen, new BBQ grill. 55+ community but no age restriction to visit

4.93 out of 5 average rating, 89 reviews

1199 Merryweather - Walk to Lake Sumter Landing Sq

Wow! Gorgeous 2br/2ba courtyard villa; 5-star reviews. Walk to Creekside Landing pool & town square in THE most sought after location in the entire community. Private yard. Granite counters, vaulted ceilings, big birdcage, French doors & vinyl plank floor. No carpet. Newer recliners, patio chairs, and sofa. King in master. Queen in guest br. Cable. WIFI. Rent a golf cart if you like. No pets here any longer. I manage a pet friendly 3br across street (sleeps 6). Jun-Dec 2025=just 2nt min.

4.99 out of 5 average rating, 116 reviews

VIEW-T-FUL! w/Golf cart

Stunning entry with one of a kind picturesque setting and unbeatable location all in one. This lanai was redesigned with no support columns to have this spectacular highly desirable panoramic golf front & water view. Sweeping view of Southern charm, cluster of mature oak trees with Spanish moss. The back of the home facing the morning sunshine lighting up the lanai and screen area for a fine morning of relaxation. Don't hesitate, this home has it all, golf cart too!

4.96 out of 5 average rating, 181 reviews

Home in Ocala

Cozy A-Frame Retreat w/ hot tub!

Escape to our cozy A-frame cabin, nestled amidst the serene beauty of nature. Just 10 mins from Santos Trailhead and 35 from Rainbow Springs! After a day of exploration, unwind in the private hot tub, gather around the bonfire pit for s'mores, or snuggle by the fireplace and stream your favorite movie. Whether you seek a romantic retreat or an extended family getaway, our A-frame cabin promises the perfect blend of nature's tranquility and modern comfort!

Superhost

4.86 out of 5 average rating, 122 reviews

Patio Villa, 5 mins from Sumter, FREE Gas Cart!

Adorable Patio Villa in a Prime Location. FREE GAS GOLF CART! Located in the heart of The Villages, in the village of Caroline. 5 minutes from Lake Sumter Landing, with bountiful options for golf, food, and entertainment just a short golf cart ride away. This isn’t your average, ‘bare bones’ investment rental. This is where our family stays when they come to visit. It is furnished with quality linens, furniture, kitchen equipment, Xfinity, & Roku.

4.9 out of 5 average rating, 42 reviews

Beautiful Designer Home -Golf Cart- Walk to Sumter

This stunning designer home comes with a golf cart and is within walking distance to Lake Sumter Market Square. It sleeps 4 adults in 2 bedrooms. 5G Wi-Fi. Kitchen is loaded with amenities & spices, lots of comfy lounging spaces, an inside laundry room, 2-car garage, landscaped yard and easy access to Hwy 466. 3-day min. May-Sep, 7-night min. Oct, Monthly stays only Nov-Apr. You will love staying in this stylish home away from home.

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

4.96 out of 5 average rating, 103 reviews

Villa in The Villages

Villa 2 Master Suites/2 Golf Carts Great Location

Beautifully Remodeled Private Courtyard Villa with two King Master Suites. Both bedrooms come with King Posturepedic Pillow Top Mattresses and Premium bedding, each with their own private bathroom & 32" HDTV's. LOCATED PERFECTLY in the De La Vista North neighborhood between Spanish Springs & Sumter Landing both offering dinning and shopping. The property comes with 2 Golf Carts making getting around SUPER easy & FUN!

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Other great holiday rentals in Lake Sumter

4.97 out of 5 average rating, 37 reviews

Home in Lady Lake

Oasis in Heart of The Villages

GenieRating, 5 stars1 month ago

Great location close to the town square, restaurants and amenities. Super clean house in a quiet neighborhood. Will definitely stay again when I'm in town.

4.95 out of 5 average rating, 20 reviews

Cheerful King Bed Home in the Villages

BobbyRating, 5 stars1 month ago

Amazing host, amazing location, amazing property and amazing value!

4.96 out of 5 average rating, 76 reviews

Home in Lady Lake

Villages, FL. Designer Home 2 blocks from town SQ!

JulieRating, 5 stars2 days ago

We had a wonderful stay! The home was spotless, easy to find, and exactly as described. The directions were clear, and everything we needed was thoughtfully provided. The location was fantastic—tucked in a quiet neighborhood, yet just a quick golf cart ride to Spanish Springs Square and about 15 minutes to Lake Sumter Landing. Having the golf cart included was a huge bonus and made getting around so easy. Truly couldn’t have asked for a better place to stay—we’d absolutely come back!

4.92 out of 5 average rating, 64 reviews

KingBed w/Cart

KimRating, 5 stars1 month ago

Wonderful stay, conveniently located between Spanish Springs and Lake Sumter Town Centers. Loved having the golf cart for easy transportation throughout Villages. Dan was very quick to respond to all questions and concerns - great host!

5 out of 5 average rating, 11 reviews

TikiTiki walk/ride 2 Lake Sumter *Pool & Hot Tub*

MellisaRating, 5 stars5 days ago

By far the most well stocked Airbnb we’ve stayed in! Location was prime to everything, the hosts were very gracious and communicative as well. Adults and kids will have a blast in this house with so many games, activities and fabulous pool and hot tub area. Seriously could not ask for more in a great vacation rental!!

4.95 out of 5 average rating, 22 reviews

Villa in The Villages

Better Than A 5 Star HOTEL IN The Villages

AnthonyRating, 5 stars3 weeks ago

Steven was a wonderful host. The property was as advertised and filled all of our needs. Everything was very clean. Nice location if you’re planning on visiting The Villages.

5 out of 5 average rating, 23 reviews

Close to Two Squares!

AndrewRating, 5 stars2 weeks ago

We stayed at this lovely home in a quiet neighborhood in The Villages, Florida, and had a great experience. The house was clean when we arrived, and everything worked perfectly — washer/dryer, dishwasher, internet, and TVs. The furniture and beds were comfortable, and aside from the occasional yard work noise, it was a very peaceful area. Make sure to get the Lifestyle ID passes if you plan to swim at the pool. The listing was accurate, and the place matched our expectations. The host was prompt and courteous in all communications, and even reimbursed us when we had to pick up extra trash bags — a thoughtful gesture. The location was super convenient to shopping, dining, and entertainment around The Villages. All in all, we’d definitely stay here again!