Holiday rentals in Pine Ridge

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Top-rated holiday rentals in Pine Ridge

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite

Flat in Lady Lake

5 out of 5 average rating, 12 reviews

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

Guest favourite

Home in The Villages

4.93 out of 5 average rating, 88 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. Zero carpet. Newer recliners & patio chairs & new sofa in 2024. 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). May-Dec 2025=5nt min.

Guest favourite

Home in Homosassa

4.93 out of 5 average rating, 99 reviews

#2 Cozy 2 Bdrms* Boat Parking* Convenient Location

Sit back & relax in our charming, coastal-themed oasis. On your adventure, take a short drive to the beach, swim with manatees, fish, catch scallops, & more! Perfect for business, small families, or friends looking to enjoy a relaxing getaway, this vacation home has a private back patio as well as a front porch. PLUS onsite Boat Parking. Hammocks, fire-pit, & BBQ grill are located in the courtyard, shared between our four vacation homes. Contact us for info on group stays (up to 17 people).

Guest favourite

Home in Ocklawaha

5 out of 5 average rating, 6 reviews

As good as it gets! Lakefront - with a pool!

This 2/1 house sits directly on a large private beach with a massive enclosed pool area including an outdoor kitchen, smart TV and lots of space to relax. This is our family vacation home, so everything is there to ensure an amazing stay. A new two story dock offers spots to moor a boat or jet skis, and lots of sun and fun space: paddle boards, fire pit, picnic table, etc. A separate cottage is just behind it. Find it listed under my profile. Rent both together for a big family gathering!

Superhost

Villa in The Villages

4.9 out of 5 average rating, 20 reviews

Beautiful villa near Sumter Landing w/ Golf Cart

Perfect central location between Lake Sumter Landing and Brownwood Paddock! 4 seat electric golf cart provided to enjoy exploring all that The Villages has to offer. Totally remodeled, new appliances, new flooring, new furnishings, large screen TV's in every room. Luxurious king bed in master and queen bed in guest bedroom. Fully equipped kitchen with everything you would need to prepare a delicious meal. Decorated with comfort in mind including 4 power recliners & extra comfy bedding.

Guest favourite

Home in The Villages

4.93 out of 5 average rating, 15 reviews

The Sandpiper Villa

Located in the Village of Monarch Grove, this beautiful patio villa has everything you need to get away and have a relaxing vacation. Located minutes from shopping centers, golf courses, recreational centers with resort style pools, and so much more! Close by are Sawgrass Grove and Brownwood square, which host live music and entertainment every night! With a spacious layout, that is meticulously cleaned and well kept, and ample amenities, this villa has so much to offer!

Guest favourite

Home in The Villages

4.88 out of 5 average rating, 26 reviews

Entire Home in The Villages Absolutely Beautiful!!

Neighborhood Pool, WIFI, Free Parking, Backyard View Excellent location, 2 bed 2 bath open floor plan home that borders a nature preserve looking out the lanai in the Village of Palo Alto. Walking distance to Spanish Springs and close to Lake Sumter Landing. Enjoy area amenities including pools, golf courses, tennis, pickle ball, shuffleboard and live entertainment every night of the week in three different locations. I do not live there. Prices include golf cart!

Guest favourite

Home in Crystal River

4.94 out of 5 average rating, 146 reviews

WaterFront Beauty (St. Martin’s Riverfront)

Direct Gulf access with no bridges - Sunsets like no other! Deep water with Floating Dock. Unique Waterfront home sleeps up to 14 people with breathtaking views of the St. Martins River and Preserve! Sunsets like no other from the wrap around porches and upper decks. Fish from the dock or watch the dolphins and manatees swim by. Take the kayaks out for a spectacular backwater adventure into the preserves. New furniture updated 9-15-23 (pics soon)

Top guest favourite

Home in Crystal River

5 out of 5 average rating, 119 reviews

Stones Throw Riverhouse and Private Dock

ON CRYSTAL RIVER, WATERFRONT HOME. Private floating 20' x 8' dock with seating,kayaks included, trailer parking, natural easy kayak launch, large backyard with shade and Two Bedrooms, Two full bathrooms newly refurbished, sleeper sofa for your extra guests. *Use of kayaks, dock, firepit and all recreational activities are at users' own risk as this is a natural landscape as are all river homes and use of door code to enter property is acknowledgement of such.

Guest favourite

Home in Ocala

5 out of 5 average rating, 19 reviews

Family Vacation house with Pool

Welcome to our stunning Airbnb property, the ultimate family oasis! This spacious and inviting home features 4 bedrooms, 2 bathrooms, and a private pool for endless hours of fun in the sun. Enjoy the BBQ, Located just 30 minutes away from WEC, this is the perfect getaway for family and friends to create unforgettable memories together. Don't miss out on this perfect blend of comfort, convenience, and entertainment - book your stay with us today!

Guest favourite

Home in The Villages

4.95 out of 5 average rating, 84 reviews

Custom luxury Ranch in Sunset Point

Beautiful luxury rental in The Villages. Close to Lake Sumter Landing. All Marble, Granite, Flat screen TV's in Every Room, Bathrooms with amenities like rain forest showers, steam room, Bidet toilet in master, and Jacuzzi tub. Built in Sound system, upgraded Kitchen and Lanai with TV and AC. No Smoking, parties, or Pets. Primary renter Has to be 35 yo or older.

Guest favourite

Home in The Villages

4.82 out of 5 average rating, 17 reviews

Location, Location! Hot Tub!

Best location in The Villages. Abutting Bonifay Country Club; close to shopping, Sarasota golf practice facility, multiple pools, pickleball courts, and other recreational amenities. Equal distance to Brownwood and Sumter landing. Golf Cart included in rental. Modern, clean, and bright. Check out reviews on Vrbo. Property listing number 2007250. New to airbnb