Holiday rentals with a pool in Lady Lake

4.95 out of 5 average rating, 126 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

4.9 out of 5 average rating, 10 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.

5 out of 5 average rating, 31 reviews

Ranch Retreat~10 beds~New

This ranch retreat home is perfect for large groups with plenty of parking. Perfect for celebrations, family gatherings, and even corporate or church events. Located on a large parcel of land in Lady Lake, FL, this home offers a quiet and secluded location that is centrally situated near the Villages and Chain of Lakes. We are 5 minutes away from Lake Griffin boat ramp, minutes away from Lake Griffin State Park, within 15 minutes of Venetian Gardens/Ski Beach and Lake Harris, and Eatons Beach.

4.96 out of 5 average rating, 313 reviews

Cozy Lady Lake Guest House

Private guesthouse in a quiet, rural area of Lady Lake. 1 bedroom, 1 bath, furnished with pool privileges. Kitchen, dining bar, living room and sunroom. Sunroom opens to the pool deck and sparkling blue pool, which is completely privacy-fenced in a common area shared with the owners. Suitable for 1 or 2 adults. Central heat and air, 40” Smart Television , WiFi, washer and dryer. Bed linens and bath towels provided. Kitchen with full sized refrigerator/freezer ice maker and electric stove.

4.9 out of 5 average rating, 112 reviews

Cottage in Clermont

Hermosa casa de campo

Lleva a toda la familia a este fantástico lugar con muchas zonas para divertirse. contamos con 5 acres de terreno solo para ti, hermosa casa de campo en las únicas colinas del estado de florida, disfrutaras de la tranquilidad, privacidad, conexión con la naturaleza y presenciaras un bello atardecer sin igual, quédate y observa las estrellas, espacios aptos para unas fotos únicas de recuerdo. Area ideal para ciclismo y senderismo. NOTA: si quieres un evento consulte primero por nuestras tarifas

4.99 out of 5 average rating, 142 reviews

Whole House-sleeps 10 The Villages Spanish Springs

Live Music on the Square. Golf, Pools, tennis, etc. Entire house in the Village of Del Mar located within the exclusive gated community of The Villages, Florida! A three-bedroom, two-bathroom spacious home with a living room with a sleeper sofa, dining room, lanai and a patio with a grill. It is located on a corner lot, only an 8-minute walk (2 minutes by car or golf cart) to Spanish Springs Town Square and a short distance to three different executive golf courses and dozens of amenities.

5 out of 5 average rating, 18 reviews

The Mulligan House-The Villages

BRAND NEW Golf-Front Furnished Home for rent- "Million Dollar View" This 3 bedroom 2 bathroom home sits on the 18th fairway of Orange Blossom Hills Championship Golf Course!! Enjoy panoramic GOLF COURSE VIEWS from the Great Room. Kitchen, Screened Lanai and from your Master Suite. Located within WALKING DISTANCE from the Orange Blossom Hills Country Club with its RESORT STYLE POOL. A short golf cart ride over the bridge brings you into Spanish Springs with Shopping, Dining and entertainment.

4.93 out of 5 average rating, 134 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!

4.97 out of 5 average rating, 32 reviews

Del Mar Paradise, The Villages, FL Golf Cart!

Del Mar Paradise in The Villages! Beautifully furnished home with Golf Cart & Bikes! Bring your family & grandchildren; sleeps 6. 2 large bedrooms, Florida Room with twin, & 2 full baths. Fully equipped kitchen, tiled rooms, BBQ. Large front yard! Short walk/drive to Spanish Springs Town Square to enjoy a great meal, see a show, shop, dance to live music nightly! Close to Chula Vista Recreation Center & Golf Course, pool & courts! 2 dogs under 30 lbs each. Dog fees cleaning see Details

4.94 out of 5 average rating, 85 reviews

Magnolia Cottage under the Paradise sun.

Stay in my quiet neighborhood 1 hour and 15 minutes from Disney. Enjoy the country club pools. Just five minutes away listen to free music every night at Spanish Spring Town Square. Restaurants & shopping are also minutes away. For your enjoyment there are recreation centers, golf courses & sports courts. Pickleball anyone! New Roku TVs are located in the living room & bedroom. Take a bike ride on the bicycles. For your convenience there is a new grill, laundry & covered free parking,

5 out of 5 average rating, 36 reviews

Pool Home Great Location 3/2 & 2 Golf Carts

POOL HOME! Excellent location between Lake Sumter and Spanish Springs squares, just around the corner from Tierra Del Sol Country Club. You will enjoy 3 Bdrms/2 full Baths and 2 golf carts. Large Master Bedroom with ensuite bath, a King Guest Bedroom and a Queen Guest Bedroom. All bedrooms are provided with premium bedding and SmartTV's. Six guests can enjoy plenty of seating inside and a 70" SmartTV. The kitchen is fully stocked and your choice of Keurig or drip coffee.