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Cottage holiday rentals in Wildwood

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Top-rated cottage rentals in Wildwood

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

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Top guest favourite
A charming cottage exterior is showcased, featuring a welcoming porch adorned with potted plants. The lush green lawn surrounds the home, with a large tree providing shade. A fenced area is seen in the background, enhancing the outdoor space.
Cottage in Umatilla
4.95 out of 5 average rating, 147 reviews

Cozy & Quaint! The Little Cottage for Big Hearts.

❤️Near to springs and Manatee watch areas, Ocala Forest, Fishing🎣 equestrian🐎 activities, Mount Dora &🪑Antiques Markets. Just 39 miles to Orlando - Disney & 43 miles to the beach 🏖 🏡You’ll wake up in one of the last true Florida cottages, built in wood with heart and time.❤️A truly quaint cottage for a joyful stay. Entire Place! Pet Friendly! Free Parking! 2 bedrooms + 2 full baths! Original wood floor in master bedroom and Kitchen! No carpet floors! Nice quiet, safe neighborhood!☀️🌳

Top guest favourite
The charming cottage features a yellow exterior with a welcoming porch. Vibrant flowers surround the entrance, while steps lead up to the front door. Rocking chairs are positioned on the porch, inviting relaxation amidst the natural setting.
Cottage in Ocala
4.96 out of 5 average rating, 199 reviews

The Little Yellow House

Cozy cottage with “Old Florida Rustic Charm”. Home has a 3 day min stay w/firm cancel policy. Nestled in wooded setting, close to town & shopping, restaurants & I-75. High speed Star-link internet. Queen bed and bunk(w/full/twin beds), full kitchen, washer&dryer. Accessed by well maintained non-paved driveway (1/10 mi) with night-time reflectors, & motion light on porch. Two pets max (tell host). WEC & FAST 5 mi West. Host pays ALL airbnb fees!! Guest ONLY pays occupancy taxes. NO cleaning fees.

Top guest favourite
A white mailbox with the number 936 is prominently displayed in the foreground. Behind it, a charming cottage features light peach-colored siding and blue accents, including a front door. Neatly landscaped gardens with flowers and shrubbery are visible, creating an inviting entryway.
Cottage in Mount Dora
4.93 out of 5 average rating, 116 reviews

Cozy Cottage 3 blocks from town

Come as guests, leave as friends. This super-clean 1 bed, 1 bath cottage sleeps up to 4 adults. "Cozy Cottage" is pet friendly and laid back with a super-fast internet connection. Historic Mount Dora is only steps away. Enjoy the many quaint shops, restaurants and regional festivals. The rolling hills and lakeside views give this town its New England seaside charm. Orlando theme parks are only 1 hour away. We are the perfect place to retreat after the hustle and bustle of the theme parks.

Guest favourite
Four red Adirondack chairs are positioned on a grassy area, facing a calm body of water lined with lush trees. The sun casts long shadows, creating a serene and inviting outdoor space.
Cottage in Inverness
4.88 out of 5 average rating, 130 reviews

Sweetwater Cottage private dock, canoe & kayaks

Come enjoy our lakeside cottage and its fun relaxing vibe! This private home is fully fenced and features a private dock. We are pet friendly for well behaved four legged friends that enjoy traveling. We have a 14 ft canoe and 2 kayaks for you to enjoy. We do have a small gas motor you can rent for the canoe allowing you to truly explore the lakes. Bring your boat! We have a community boat ramp one street over. Only minutes to downtown Inverness! PET FEE $25 per pet paid directly to host.

Guest favourite
A quaint cottage is nestled among greenery, featuring a wooden deck with a railing. Pink chairs sit invitingly on the porch, while vibrant flowers and manicured plants frame the entrance. A metal roof reflects sunlight, enhancing the cottage's charming exterior.
Cottage in Brooksville
4.88 out of 5 average rating, 154 reviews

Spotted Dance Ranch

Spotted Dance Ranch is a small guest ranch and horse breeding facility that has been hosting guests since 2014. Come stay in our cozy Cowboy Cottage located on the beautiful ranch grounds, and enjoy the peace and quiet of the ranch located adjacent to the Croom Tract of the Withlacoochee State Forest! Bring your horse if you have one; otherwise, many other outdoor activities and attractions are available nearby, or just relax! We are conveniently located outside Brooksville, FL near I-75.

Top guest favourite
A well-appointed sleeping area features a white bed frame with plush bedding in navy and white tones. Two bedside tables with navy blue lamps flank the bed. Decorative pillows, including a map-themed cushion, add interest, while framed botanical prints hang above the headboard.
Cottage in Mount Dora
4.98 out of 5 average rating, 174 reviews

Newly Renovated Cottage, Easy Walk to Downtown!

Walking distance to all Downtown Mount Dora has to offer! Our lovely 2 bedroom, 1 bath 1940s cottage has been recently renovated. Features fully outfitted kitchen, deck with gas grill and outdoor firepit. Comfortable and elegant living space with 65 inch smart TV. Primary bedroom features King bed and smart tv. Second bedroom has two cozy twin beds. Bikes available for use. Whether you’re coming to relax, boat, shop or partake in one of Mount Dora's many festivities, consider staying here!

Guest favourite
A wooden dock extends into the calm waters, surrounded by lush greenery and mature trees. Steps lead up from the dock to a cottage nestled among the foliage, offering a serene and natural setting.
Cottage in Leesburg
4.91 out of 5 average rating, 113 reviews

Waterfront Cottage on The Harris Chain in Leesburg

Cozy waterfront cottage on Haynes Creek. Whether its relaxing, fishing from your own dock, boating the Harris chain, paddle boarding, birdwatching, use our kayaks or pedal boat, or exploring the nearby towns and springs... we have it all. Fully equip kitchen, outdoor grilling area, wifi and cable, parking, laundry, gas fire pit on your private deck, boat parking at your dock or book a tour with Monster Bass fishing. Walkable to nearby stores or Gator Bay for a drink, meal, or music!

Guest favourite
A comfortable living room features two light-colored armchairs and a small table, oriented towards large windows. The serene lake view is visible, framed by trees, creating a calm atmosphere. Natural light fills the space, enhancing the connection to the outdoors.
Cottage in Hernando
4.91 out of 5 average rating, 223 reviews

The Hernando Lake House

Relax our Lake House. The water touches the back yard and the lake is loaded with Bass and many other fish. Relax in the living room falling asleep for afternoon naps while gazing at the serenity of the water. The house is quiet and set up for some nice long weekends. The Gulf of Mexico is just 14 miles to Crystal River which has a nice local beach. Scalloping and Manatee watching and much more to do in Citrus county. Orlando and Disney are just a little over an hours drive.

Top guest favourite
Cottage in Coleman
4.96 out of 5 average rating, 169 reviews

Peaceful Farm Cottage Near Villages | Garden, Pets

Escape to this cozy tiny cottage with king-size bed, full bath, kitchenette, and pet-friendly comfort. Relax under starry skies, enjoy farm views, and pick fresh vegetables or fruit from the garden and trees when in season. Just 15 min to The Villages, 20 min to Wildwood, 35 min to Ocala, 1 hr to Orlando, minutes from Brownwood live music, and quick access to the Turnpike & I-75. Perfect for a romantic, stylish getaway close to springs, trails, and local attractions.

Top guest favourite
A charming cottage is showcased, featuring a light-colored exterior with red shutters. The entrance is framed by a covered porch and planters, while a landscaped area with low shrubs and flowers adds a welcoming touch to the pathway.
Cottage in Eustis
4.94 out of 5 average rating, 106 reviews

Anneliese's Cottage

Just a delightful walk from Lake Eustis and its quaint downtown shopping & dining district, a 10 minute drive to Historic downtown Mt. Dora, and less than an hour from Orlando / Daytona Beach, this cottage , decorated with cozy elegance, is the perfect place to relax and truly enjoy all that the area has to offer. Right next door, you'll find an eclectic day spa, where you can set up a relaxing massage, facial, or have your hair & nails done during your stay!

Top guest favourite
Cottage in Clermont
4.91 out of 5 average rating, 122 reviews

Beautiful country house

Take the whole family to this fantastic place with many areas to have fun. We have 5 acres of land just for you, beautiful country house in the only hills of the state of Florida, you will enjoy the tranquility, privacy, connection with nature and you will witness a beautiful sunset unparalleled, stay and watch the stars, spaces suitable for unique souvenir photos. Ideal area for cycling and hiking. NOTE: if you want an event, check first for our rates

Superhost
A comfortable living area is highlighted by a spacious sectional sofa with decorative cushions. A ceiling fan and overhead lights provide ambient lighting. A large television is mounted on the wall opposite, while a patterned rug adds color to the wooden floor.
Cottage in Mount Dora
4.91 out of 5 average rating, 112 reviews

Refreshing 1930s Cottage in Mount Dora

Enjoy this refreshed cottage, originally built in 1931, located in the historic district and within walking distance to downtown Mount Dora. The cottage is equipped with queen and king beds, full kitchen, fire pit, smart TVs, outdoor patio, enclosed porch, washer/dryer, and private driveway. Take in the historic sites and homes nearby, beautiful lakes, boardwalk, lighthouse as well as all the shopping, dining, and entertainment downtown has to offer.

Popular amenities for cottage rentals in Wildwood

Quick stats about cottage rentals in Wildwood

  • Nightly prices starting at

    Wildwood holiday rentals start at $105 SGD per night before taxes and fees

  • Verified guest reviews

    Over 490 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wildwood rentals

  • 4.9 Average rating

    Wildwood stays are highly rated by guests – averaging 4.9 out of 5!

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Sumter County
  5. Wildwood
  6. Cottage rentals