Holiday rentals with a fireplace in Winter Park

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Top-rated rentals with a fireplace in Winter Park

Guests agree: these rentals with a fireplace are highly rated for location, cleanliness and more.

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Top guest favourite
A modern kitchen with white cabinetry and gold hardware is visible, featuring stainless steel appliances, including a microwave and dishwasher. Natural light floods the space through a large window. An adjacent area displays a dedicated work desk and chair against a light-colored wall.
Home in Winter Park
4.97 out of 5 average rating, 198 reviews

Stylish newly updated home in Winter Park

Sleeps 8 people comfortably but can fit 10. This home has VERY CONVENIENT ACCESS TO I-4 making it easy to get to Orlando's most sought after attractions, including Park Avenue, Downtown Orlando, Rollins College, Leu Gardens, Mills Ave, Baldwin Park, College Park, Camping World Stadium, Amway Arena, SunRail, and many hospitals. SHORT WALK to 3 notable restaurants Also nearby: Universal Studios (20 min) Outlet Mall (20 min) International Drive (25 min) Orlando Airport (30 min) Disney (~30-40 min)

Superhost
Home in Orlando
4.81 out of 5 average rating, 166 reviews

Private Cinematic Zen Loft w/ Spa Tub (6PM–10AM)

Check-in 6 PM • Check-out 10 AM Early check-in (1 PM) or late checkout (5 PM) from $59 Romantic designer loft with fireplace wall, cinematic lighting, and deep soaking tub couples love. Private stylish escape near the airport, downtown Orlando, and major theme parks. Close to top restaurants yet designed for total relaxation with no shared spaces. Features adjustable queen bed, spa-style bath, and second parking spot ($19 extra). Superhost • 4.8 stars from 165+ guests. No smoking, no pets

Top guest favourite
The backyard features a large pool with a hot tub and a patio area shaded by wooden structures. Comfortable outdoor seating is positioned under the patio, providing a relaxing space. A playful inflatable float can be seen in the shimmering water.
Home in Orlando
4.97 out of 5 average rating, 104 reviews

Unique Spacious Home w/ Pool near Downtown Orlando

Nestled on a quiet street, 15 mins from Downtown Orlando. This home has a massive pool, hot tub, water fountain, real outdoor and indoor fire place, outdoor patio area w/seating. The Kitchen is equipped with everything you need to make delicious meals, and there are two living areas to provide ample space for relaxation. There is also a designated office area to take work calls. ☀ College Park – 10 mins ☀ Downtown Orlando – 15 mins ☀ Universal Studios – 28 mins ☀ Walt Disney World – 34 mins

Top guest favourite
A charming bungalow features a welcoming front porch with two sitting areas and a vibrant yellow door. Lush greenery surrounds the front yard, complemented by neatly landscaped flower beds and a well-maintained lawn. The structure showcases classic architecture with a light blue exterior.
Bungalow in Orlando
4.97 out of 5 average rating, 273 reviews

King/Queen Bungalow w/ porch | central vibey area

Our 1920's historic home is nestled in a quiet neighborhood just a few blocks from everything. The ColonialTown North district of Orlando (also called Mills/50) is a vibrant, central area with exceptional walkability to grocery stores, a trendy bar scene, LOTS of coffee and boba options, foodie restaurants and casual late night eats. When you're ready, retreat to our porch swing and watch the sunset reflect off the trees. We lived in this space for four years and left it just as we crafted it.

Guest favourite
A modern lakeside resort is showcased, featuring a stone exterior and a sweeping pool that curves gently around the patio. Lush palm trees and vibrant landscaping frame the water view, offering a tranquil setting for relaxation.
Villa in Orlando
4.95 out of 5 average rating, 124 reviews

The Lakeview Oasis - XL Pool & Jacuzzi - Orlando

Welcome to our stunning lakefront resort, where luxury meets tranquility! Dive into our expansive 100,000-gallon pool, enjoying a refreshing swim surrounded by breathtaking views. Inside, our tastefully designed space features midcentury modern amenities ensuring you have everything for a perfect getaway. Each bedroom offers serene views and plush bedding for a restful night’s sleep. Whether you seek adventure or relaxation, this is your ideal getaway. Book now for unforgettable memories!

Top guest favourite
Guest house in Orlando
4.97 out of 5 average rating, 382 reviews

Oasis Garden Cottage -cozy, chic, near everything!

Our cozy cottage is located within minutes of some of the best areas, restaurants, bars, and attractions Orlando has to offer. Winter Park and College Park are 3-5 minute drives, Disney and Universal only 20 minutes, etc. The interior is chic and inviting, with a homey feel. Enjoy the fireplace, play some board games, soak in bath salts in the claw foot tub, curl up on the porch with a coffee and read one of our provided books— it’s so peaceful you’ll have a hard time leaving for the day!

Guest favourite
A crystal-clear pool reflects the sunlight, with a spacious pergola providing shade nearby. Comfortable lounge chairs are positioned around the pool, creating a relaxing outdoor space surrounded by greenery.
Home in Casselberry
4.93 out of 5 average rating, 133 reviews

Villa with Guest House & Pool-Patio

Welcome to this Amazing House Pool-Patio with 4 Bedrooms + 2 Bathrooms and optional guest house to complete the 10 guests. True gem with covered summer kitchen, covered pergola, garage for two cars and a large driveway. 30 Minutes distance to Universal, Sea World, Volcano Bay and others. UCF in 15 minutes and Daytona beach/Cape Canaveral in 50’. Great restaurants and shops. The house is conveniently located for all attractions in Central Orlando. Airport is 25 minutes. SAFE NEIGHBORHOOD

Guest favourite
A sparkling swimming pool is set against a backdrop of lush greenery. Sun loungers and a shaded double canopy bed are positioned nearby. A spacious patio shelter is visible, providing a comfortable area for outdoor gatherings.
Home in Maitland
4.86 out of 5 average rating, 159 reviews

Bonheur Ala Maison

Bonheur A la Maison is the home that offers a beautiful, comfortable, spacious, convenient and all around happy feeling with the little extras and attention to detail to make you feel like you're basking in a lot of luxury for a simple price! Its everything you need from your blow dryer, to your plush robe and from your USB outlets at all bedsides to your built in wireless speakers for your music of choice. We tried to think of it all. Conveniently located near lots of shops and parks!

Top guest favourite
A serene pool area is surrounded by lush tropical plants and palm trees, providing a vibrant setting. A spacious pool is situated in the center, with a concrete deck and a charming thatched umbrella nearby. Comfortable outdoor seating is visible under a covered porch, enhancing relaxation.
Home in Maitland
4.95 out of 5 average rating, 184 reviews

Orlando area pool home in Maitland

Everyone finds our home fun & relaxing. We are close to tons of restaurants & shopping. Only 1 mile from the intersection of I-4 & 414 (Maitland Blvd). Home, it is fully stocked. Plus a gas grill. Towels & linens provided. Games and toys for all ages. Pets are welcome with pet fee. Guests have private use of property, 2 bedrooms & 2 full baths and all living areas, back yard and porch with pool . There is an optional third bedroom available for an additional $35 a night fee.

Top guest favourite
The screened-in pool area features a tranquil pool with a soft blue hue, surrounded by white decking. A small table holds a lit lantern beside two lounge chairs, providing a serene space for relaxation under the evening sky.
Home in Maitland
4.99 out of 5 average rating, 124 reviews

Florida Poolside Paradise a Great Place to Unwind!

Welcome to our exquisite 4-bedroom vacation rental in the heart of Maitland, Florida – a true gem where luxury meets convenience. This upscale home boasts fine furnishings and a private pool, making it the ideal retreat for families or groups seeking both comfort and style during their Sunshine State getaway. The house is located in a residential neighborhood with plenty of restaurants and shopping within a 5 minute drive. Convenient location off Rt 436. and half hour to the airport.

Superhost
A backyard swimming pool is surrounded by a natural landscape, featuring colorful floaties resting on the water's surface. Comfortable seating is arranged nearby, and palm trees provide a tropical touch to the serene outdoor setting, all under a softly lit evening sky.
Home in Altamonte Springs
4.88 out of 5 average rating, 130 reviews

Private Pool / Cozy Central Florida Home

Updated four-bedroom home in Altamonte Springs, ready for your stay! Perfect for groups. Plenty of free parking in the driveway and curb side. Only minutes from I-4, which means easy access to your favorite spots in and around Central Florida. Universal Studios, for example, is about 25 minutes away. SeaWorld is 30 and Disney Springs is about 35, depending on traffic. Plenty of sports complexes are nearby. Uptown Altamonte is just around the corner. No parties or events please.

Superhost
Home in Altamonte Springs
4.87 out of 5 average rating, 121 reviews

Renovated Peaceful Luxury Walk to Mall Park Publix

- Luxury 2 Bedroom/1Bath Style Renovated peaceful home with Fireplace, Skylights, 87 inch TV, Chandelier, & Full kitchen - Spacious bathroom - Americans with Disabilities Act (ADA) bars for shower and toilet & Smart mirror - Outdoor Gym with Kids Playground & Dedicated Laundry Room - 1 minute drive to major highway Orlando ( Disney, Universal, Aquatica, Beaches, Downtown ) Approximately 30 minutes away - Plenty of free private parking right in front of the house - Pet friendly

Popular amenities for rentals with a fireplace in Winter Park

When is the best time to visit Winter Park?

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Quick stats about holiday rentals with a fireplace in Winter Park

  • Total holiday rentals

    Explore 50 holiday rentals in Winter Park

  • Nightly prices starting at

    Winter Park holiday rentals start at €43 per night before taxes and fees

  • Verified guest reviews

    Over 1,950 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    50 of Winter Park holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winter Park rentals

  • 4.9 Average rating

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

  • Nearby attractions

    Winter Park’s top spots include Orlando Science Center, Harry P. Leu Gardens and Orlando Museum of Art

Destinations to explore