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Cottage vacation rentals in Wildwood

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Top-rated cottage rentals in Wildwood

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Guest favorite
A set of wooden steps leads up to a charming cottage nestled among trees. The entrance features large glass doors, inviting natural light into the space. The surrounding area is landscaped, enhancing the tranquil ambiance of the private property.
Cottage in Eustis
4.95 out of 5 average rating, 132 reviews

Redbird cottage and farm. Equestrian lake cottage

Step back into “Old Florida” charm at this updated 1968 lake cottage, on a 7-acre equestrian farm. Secluded from main roads yet just minutes from downtown Mount Dora and Eustis, this peaceful retreat offers the perfect blend of rustic serenity and comfort. Located on a lake that offers direct water access. Campfires are welcomed, and the tranquil setting is made even more magical by the sight of horses. Inside, you'll find cozy touches and comfortable furnishings, including pillow-top mattresses

Guest favorite
A screened porch offers a view of the water and surrounding landscape, with seating options including a red leather chair and a light-colored sofa. Natural light fills the space, enhancing the connection with the outdoors.
Cottage in Inverness
4.95 out of 5 average rating, 121 reviews

Serendipity Lake private dock, canoes & kayaks

What a view, what a really good view, YES IT IS! Watch the sunrise and sunset over the water on a private dock. We have 2 canoes and 2 kayaks to enjoy the water or bring your boat! This is a place you will want to come back to time and time again. Water views from all angles, you will feel like you're on a houseboat there's so much water! Plenty of room for outdoor games and activities. Pet friendly. Just a short drive to downtown Inverness and 30 minutes to Crystal River. Simply perfect!

Top guest favorite
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, 117 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 favorite
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, 155 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 favorite
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
4.97 out of 5 average rating, 185 reviews

Charming Mount Dora Cottage • 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 favorite
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!

Top guest favorite
A cozy living area features a gray sofa adorned with decorative pillows. A red lamp and a vibrant artwork are positioned nearby. Natural light fills the space, highlighting wooden flooring. A wooden screen and a console table with coffee-making supplies add functionality to the room.
Cottage in Dunnellon
4.98 out of 5 average rating, 316 reviews

Cozy Cottage. Surrounded by nature, not neighbors.

Our one-bedroom cottage sits in the middle of over 25 acres of the beautiful Florida Nature Coast. Even though we are secluded, we have all the comforts of home, from indoor plumbing and hot water to AC and Wi-Fi. Our TV has a Firestick, so bring your streaming accounts and relax night away after you retire from roasting Smores on the outdoor firepit. A fold out sleeper couch takes this from a 2 person cottage to 4 in just minutes. Parking is not an issue, even if you have a trailer.

Top guest favorite
A wooden dock extends over calm waters, framed by lush greenery and moss-draped trees. The tranquil scene is complemented by a screened dockhouse nearby, providing a secluded spot for relaxation and enjoying the natural surroundings.
Cottage in Floral City
4.94 out of 5 average rating, 219 reviews

Waterfront Cottage 2BR 1B

This charming house is located on nearly an acre of woodland. Fish from the dock of the screen room on the canal or kayak to the nearby lake. Relax in the private backyard Jacuzzi. Bike on the nearby Withlacoochee Trail. There are 2 bedrooms plus living room sleeper sofa, and a lanai with a day bed. Fully furnished. Orlando theme parks are 1 1/2 hour away, Busch Gardens 1 hour. Close to Weeki Wachee, Homosassa and Crystal River for manatee viewing or scallop season.

Top guest favorite
Cottage in Coleman
4.97 out of 5 average rating, 173 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 favorite
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, 109 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 favorite
The exterior of a two-story detached home is presented, featuring white siding and black shutters. The entrance is adorned with planters, and a small walkway leads to the front door. Lush greenery surrounds the property, and a clear blue sky is visible above.
Cottage in Umatilla
4.98 out of 5 average rating, 122 reviews

Cottage by the Lake

Cute, comfortable 1935 detached home which is 900 SQUARE FEET AND PET FRIENDLY. The other side of the property has our main home. The cottage is newly remodeled and fenced in. Views of Lake Umatilla from all rooms. 8 miles to beautiful Mount Dora and 3 miles to downtown Eustis. 1 hour to attractions, airport and east coast beaches. We are 20-30 minutes from most local Springs. Our Lake Umatilla does have public boat ramp access

Guest favorite
The exterior of a light blue guesthouse is presented, featuring two windows adorned with dark shutters. Flower boxes with colorful blooms enhance the entrance, accompanied by a decorative pot in the center. A clear blue sky and green trees create a serene backdrop.
Cottage in Dunnellon
4.94 out of 5 average rating, 140 reviews

Gracie's Morning Glory Guesthouse

King bed studio with no added cleaning fee. Come and relax in this peaceful, private space with a king memory foam bed, 65 inch Smart TV, and a spacious bathroom with tub and shower. Full size frig, Keurig coffee station and microwave. Located in the historic district, we are within walking distance to quaint downtown Dunnellon, 4 miles to beautiful Rainbow Springs State Park, and a short country drive to Crystal River and Ocala.

Popular amenities for Wildwood cottage rentals

Quick stats about cottage rentals in Wildwood

  • Nightly prices starting at

    Wildwood vacation rentals start at ﺩ.ﺇ294 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!

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  4. Sumter County
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