Holiday rentals in Fruitland Park

5.0 out of 5 average rating, 33 reviews

An open living space features a cozy sleeping area and a small dining arrangement. Wooden beams highlight the ceiling above. Natural light enters through the door and windows, while a television and kitchenette with appliances are visible against the walls.

Flat in Lady Lake

Desperado 2 - Cozy Peaceful Apt. Lady Lake FL.

Escape to your unique and private 2nd story apartment nestled on 2 acres of serene land and just a short 7-minute drive to The Villages. Enjoy the tranquility of nature while still being close to vibrant entertainment, shopping and dining options. Your cozy and well appointed space offers the perfect blend of seclusion and convenience making it an ideal getaway for relaxation and rejuvenation. *perfect for vacation *perfect for traveling workers *perfect for visiting family in the The Villages

4.96 out of 5 average rating, 352 reviews

A sun-drenched pool area features a sparkling blue pool surrounded by comfortable seating. A table with an umbrella and colorful chairs offer space for relaxation. The sunroom with large windows provides views of the inviting outdoor space, enhancing the overall tranquil setting.

Home in Lady Lake

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.

4.99 out of 5 average rating, 145 reviews

A scenic view of a tranquil canal is presented, bordered by lush greenery. A wooden dock extends into the water, accommodating a boat. Nearby, comfortable outdoor seating is available, surrounded by natural landscaping, offering a peaceful outdoor space.

Home in Summerfield

Getaway on the Waterway- Dock+Kayaks+SUP board

Welcome to your peaceful Getaway on the Water. Whether you or your group are visiting the Villages, or just need a peaceful getaway to recharge, this is the place!There's something for everyone! Paddleboard or Kayak (provided) the beautiful canal to either lake. Enjoy your morning coffee or evening cocktail in nature on the dock. Bring your boat/ jet ski or rent one from Eaton's Beach Aquatic sports, they also offer sunset cruises and water taxi to Eaton's Beach restaurant right from our dock!

4.91 out of 5 average rating, 90 reviews

A spacious hallway leads to a living area featuring a large window with natural light filtering through. A neutral color scheme is complemented by a decorative lamp and fresh flowers on a sideboard. Comfortable seating arrangements are seen in the inviting living space.

Villa in The Villages

3BR at 1198 Merryweather Way; just 4nt min; pet ok

Large 3BR/2BA courtyard villa. Affordable luxury & 5-star reviews. PRIME LOCATION in CENTER of it all. Upscale furnishings. Walk to Lake Sumter Landing town square w/shops & restaurants. King & queen (new mattresses) & a full bed will sleep 6 comfortably. Fast WIFI; 2 Samsung Smart TVs (65" living room); 2 desks for laptop/at-home work. Private yard w/patio chairs. Vinyl plank floor. No carpet. I also manage 2br home across street. Rent both & sleep 10; Rest of 2026=2nt min. Pet ok $40 fee.

5.0 out of 5 average rating, 13 reviews

Luxury Villages Stay • Golf Cart • Near Brownwood

Welcome to your Villages retreat! Step into comfort and style in this beautifully decorated, designer home fully furnished with everything you need for a relaxing stay. From cozy bedding to modern furniture. Located in the sought-after Village of Osceola Hills, end of Moyer Blvd just south of Route 44, this spacious 3-bedroom, 3-bathroom home (2021 sq. ft.) features a 2-car garage and comes with a golf cart. You're just minutes away from Brownwood (3 miles) and Sawgrass Grove (2 miles).

Place to stay in The Villages

An inviting outdoor space features a spacious in-ground pool with a sunken hot tub nearby. The pool area is enclosed by a screened lanai, allowing for privacy. Light reflections dance on the water's surface, creating a peaceful ambiance.

5.0 out of 5 average rating, 127 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!

A heated saltwater pool is highlighted under a screened enclosure, with ambient lighting creating a calming atmosphere. Patio seating is arranged around the pool, and views of the adjacent living area are visible through expansive windows, enhancing the inviting indoor-outdoor connection.

5.0 out of 5 average rating, 58 reviews

Pirates & Parrots - The Villages - Golf Cart &Pool

GREAT LOCATION!! A beautiful 2 bedroom 2 bath home with a saltwater pool and a hot tub. 77 inch TV with sound system, and 2 car garage/golf cart . Outdoor bar with big screen TV with seating area and a second seating area outside the bird cage. TV’s in both bedrooms. Great out door living! Minutes to everything via golf car: Brownwood 12 Sumter 16 Sawgrass 19. 4 champ golf and 7 exec golf courses 5-10. Publix, Walmart 5 minutes Golf Car 2022 Yamaha included! No smoking!!

Farm stay in Fruitland Park

5.0 out of 5 average rating, 5 reviews

Madre Tierra

Reconnect with nature and create unforgettable memories at Madre Tierra, your perfect destination for any occasion. Whether you're celebrating with family and friends, hosting a family reunion, tying the knot, or planning a milestone birthday like a quinceañera or sweet sixteen, our beautiful home offers the ideal backdrop. Embrace the tranquility and let Mother Nature be the canvas for your next celebration. Book your stay with us and make your special moments even more memorable!

The exterior of the villa is seen, featuring well-maintained landscaping with palm trees and neatly trimmed shrubs. A spacious driveway leads to the entrance, while a two-car garage is visible on the left. The sunlit facade showcases a welcoming atmosphere.

4.97 out of 5 average rating, 105 reviews

Fabulous Courtyard Villa close to Sumter Landing

This home is the perfect vacation. When we saw this beautifully decorated villa, we felt like we were home. The exquisite landscaping was exactly what we have been looking for! The location is a mile from Sumter Landing and a stone's throw from the two pools, billiards, shuffleboard, pickleball, bocce ball. The best way to see it all is by the golf cart!!! The Villages has its own GPS for the Cart Paths. Schedule your stay and start packing your bags for an amazing experience.

4.96 out of 5 average rating, 47 reviews

A spacious living area is displayed, featuring a large flat-screen television on a decorative stand. Two comfortable sofas face a glass coffee table, surrounded by natural light from multiple windows. A dining table with chairs is visible in the background, adjacent to the kitchen.

Home in Fruitland Park

Spacious 3/2 Getaway in The Villages

Your friends/family will enjoy easy access to everything from this centrally located home as it is 15 min from Sumter Landing and 15 min to Brownwood. Picture yourself in this Ultra Clean 3 Bedroom/2 Bathroom (One Bedroom has a sofa, coffee table and desk). Every room has a smart tv and we offer Live YouTube Tv. The Open Floor Plan lends itself to entertaining while preparing a home cooked meal in the well appointed kitchen. Make your vacation memories in this beautiful home.

4.9 out of 5 average rating, 29 reviews

Endless Love, Pool, and a Water View! Pool & Cart

Oh my! This 3 BR 2 BA home is your ticket to paradise in The Village of Osceola Hills! This home boasts everything that you could possibly want for your vacation in The Villages! If you want a perfect home away from home, you just succeeded. Great location, great view, endless pool, and a golf cart to cruise down to the squares that have live music nightly, restaurants, pickleball courts, golf restaurants, shopping and nature trails. Water view, endless pool, endless love!!