Home Vacation Rentals By Owner In Winter Park, FL

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$134.96

/ Nightly
Mobile Home

Comfy Tiny Home @WP. Large Private Deck+Queen bed

Winter Park, Florida, United States

This memorable place is anything but ordinary. Welcome to our charming TINY house in the heart of Orlando! Nestled in a quiet neighborhood, this cozy retreat offers the perfect blend of comfort, privacy, and convenience. Whether you`re here for business or leisure, our centrally located TINY house is an ideal home base for exploring all that Orlando and Winter Park have to offer.brbr✅️Private Patiobr✅️Free Parking br✅️Deck with outdoor seatingbr 10-15 min from Universal br✈️20-22 min to airportbrbrStep into our thoughtfully designed TINY house and discover a world of comfort. The space is split into 2 buildings:brbr Main living area features a comfortable queen bed, ensuring a restful night`s sleep.brbr2nd building area features living/kitchen space.brbr The clever layout maximizes space, providing a cozy atmosphere without sacrificing functionality. You`ll find all the amenities you need for a comfortable stay, including a compact kitchenette, a clean and modern bathroom, and ample storage space.brbrThe Master Suite: Equipped with Queen bed, large bathroom with shower and also full size Washer/Dryer combination.brbrThe Living Room/Kitchen: Step outside into another private space as your full kitchen and living room area are just outside the master suite. brbrParking: Dedicated space for 2 vehicles just several yards from the entrance to the tiny home.brbrPatio/Deck: Enjoy a large wrap around private deck. Lava rock and crushed concrete surround the fenced area.brbrPrivacy:brEnjoy the luxury of privacy in our tiny house. Tucked away in a tranquil corner of the property, you`ll have the space all to yourself. Whether you`re a couple seeking a romantic getaway or a solo traveler in search of tranquility, our tiny house is the perfect escape.brbrOutdoor Oasis:brStep outside onto the large deck and soak up the Florida sunshine. The spacious deck is perfect for enjoying your morning coffee, reading a book, or simply unwinding after a day of exploring. Surrounded by lush greenery, this outdoor oasis provides a serene retreat right at your doorstep.brbrCentrally Located:brOur tiny house is strategically located, offering easy access to both downtown Orlando and the charming Winter Park area. Explore the vibrant city life, visit world-renowned attractions, or stroll through the historic streets of Winter Park—all within a short drive from your cozy retreat.brbrAmenities:brbr*Comfortable queen bedbr*Private bathroombr*Kitchenette with essential appliancesbr*Large deck with outdoor seatingbr*Central location near downtown Orlando and Winter Parkbr*Ample storage spacebr*Free parking on the premisesbrbrWhether you`re here for a weekend getaway or an extended stay, our tiny house provides a unique and memorable lodging experience. Book your stay now and discover the magic of Orlando from the comfort of our cozy retreat!brbrYou`ll have full access to the tiny home property inside the fence as well as access to the common lounge/bbq area.brbrThere are 4 units on the property. The tiny home is located in the rear of the property. You have 2 dedicated parking spaces available which will be described in detail at check in through the airbnb app instructions.brbrThe property is just blocks away from a supermarket, many restaurants, bars and shopping.brbrMini Split: When switching between heating and cooling, please allow 5 minutes before the mini split changes modes. This allows the system to heat/cool the area properly. For a link to using the system and remote, please send the CRASHPADS team a message through the Airbnb app.brbrThere are both ROKU and GOOGL TV`s in the property. Feel free to login to apps using your own personal code. At the end of your stay you will be conveniently logged out.brbr ✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brBy booking this property, you agree to the following:brbrNo PartiesbrNo AnimalsbrNo Smoking - $500 penalty - if you need to smoke, please do it outside and clean up after yourself (buds, waste etc)brbrBBQ area hours are 9am-9pm dailybrbrParking is limited so please ensure to park ONLY in your designated area.brbrService Animals - This property has 3 other neighboring units and. Any animals brought onto the property must remain on a leash for the safety and security of others, guest and neighbors.brbr ✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brbrQuiet hours 10pm - 7am
Bed 1

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Bath 1

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Sleep 3

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Exceptional(2)

$278.81

/ Nightly
Private Vacation Home

Tranquil Oasis: 4BR Pool Home

Winter Park, Florida, United States

Welcome to our spacious 4-bedroom, 2-bath home in Winter Park, FL! Perfect for families or groups, this inviting retreat features a private pool and hot tub, ensuring relaxation and fun for everyone. Enjoy ample indoor and outdoor space, including a fully equipped kitchen, cozy living areas, and a screened-in patio. Located in a quiet neighborhood, you're just minutes from local attractions like Park Avenue shopping and dining, museums, and parks. Only 16 mins to UCF!brbrProperty Highlights:brSpacious Living Areas:brStep into a beautifully designed interior with an open floor plan that includes a cozy living room and a fully-equipped modern kitchen. The abundant natural light and tasteful decor create a welcoming atmosphere for relaxation and entertainment.brbrPrivate Fenced Backyard:brThe highlight of this property is the expansive fenced backyard, offering complete privacy and a safe space for children and pets to play. The lush landscaping and ample seating areas make it a perfect spot for outdoor activities or simply unwinding with a good book.brbrInviting Pool and Hot Tub:brDive into the crystal-clear waters of your private pool or soak in the rejuvenating hot tub after a day of exploring the area. Whether you’re swimming laps, floating under the stars, or enjoying a glass of wine in the hot tub, the outdoor amenities are designed for your ultimate comfort and enjoyment.brbrComfortable Bedrooms:brThe home features four spacious bedrooms, each thoughtfully furnished to ensure a restful night’s sleep. The master suite includes a luxurious king-sized bed, an en-suite bathroom, and direct access to the backyard oasis. The additional bedrooms are equally inviting, with plush beds and ample storage.brbrConvenient Location:brLocated in a quiet, family-friendly neighborhood, 7002 Citrus Point Ct is just minutes away from local attractions, shopping centers, and dining options. Enjoy easy access to parks, golf courses, and scenic nature trails, making it an excellent base for exploring the area.brbr★☆ NEARBY ATTRACTIONS, LANDMARK & RESTAURANTS☆★br☀ Park Avenue (10 min drive)br☀ Rollins College (10 min drive)br☀ University of Central FL (16 min drive)br☀ Winter Park Farmers' Market (10 min drive)br☀ Mead Botanical Garden (10 min drive)br☀ The Ravenous Pig (10 min drive)br☀ Prato (10 min drive)br☀ Bosphorous Turkish Cuisine (10 min drive)br☀ 4 Rivers Smokehouse (10 min drive)brbrbr★☆ KEY FEATURES ☆★br☀ Poolbr☀ Patio and Outdoor Furniturebr☀ Hot Tubbrbrbr★☆ BEDROOM ARRANGEMENT☆★brBR1: 1 King BedbrBR2: 1 Queen BedbrBR3: 2 TwinsbrBR3: 2 Twinsbrbr★☆ LIVING ROOM ☆★brAs you step inside, you'll find modern, open spaces adorned with contemporary furnishings.brbr★☆ KITCHEN & DINING ☆★brThe kitchen, fully equipped. Enjoy your culinary creations in the stylish dining area or take the dining experience outdoors to the charming patio, offering a view of the shimmering pool.brbr★☆ PARKING ☆★br☀ 2 parking spaces in the drivewaybrbr★☆ HOUSE RULES ☆★br☀ No smokingbr☀ No events, parties, or extra-large gatheringsbr☀No sitting outside after 10 pmbr☀Lights outside should be turned off after 10br☀ Must be at least 25 years old to bookbr☀ Please report any damages that occur during staybr☀ Late Check Out Fees are as follows: $50 for the first hour, $100 for two hours, and $500 for any extended time.br☀ These fees ensure fair compensation for our cleaners or any subsequent guests affected by delays. If you need a late checkout, please inquire in advance. Depending on upcoming bookings, we might accommodate you, though a fee might still apply.br☀ Extra Guests: If more guests than permitted are found at the property, we reserve the right to deny entry based on AirBnB’s policies. Extra guests will be treated as trespassers. An additional fee of $50/night per extra guest may apply, or we might request that you vacate the property.br☀ If uncertain about guest numbers or daytime visitors, please reach out. We aim to prevent any misunderstandings.brbr★☆ Book Now & Let Us Take Care Of You! ☆★.brOther things to notebrThe guest will not have to use the garage or washer and dryer.
Bed 4

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Bath 2

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Sleep 8

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Exceptional(2)

$156.75

/ Nightly
Private Vacation Home

Charming home @wp. Patio +Gazebo. close to highwys

Winter Park, Florida, United States

Keep it simple at this peaceful and centrally-located home. This special place is close to everything, making it easy to plan your visit. The Mills50 property is a convenient place to stay during your visit to Orlando, Winter Park and so much more!brbr Close to highwaysbrbr7 min to downtownbr2 min to winter parkbrbr15-20 minutes to wekiva springsbr50 min to ⛱️ beachesbrbr15-20 min to Universal Studios br30-35 min to Disneybrbr5 min to College ParkbrbrThis charming 850sq ft home is the perfect central lunch point to explore Orlando, Winter Park and surroundings areas. Only 5-7 min from Downtown, College Park, Mills50 District or Winter Park. You`ll find endless dining options, some even walkable from our location that make this the `Foodie area` of the town!brbrThe Space:brbrParking for 2 vehicles.brbrLiving Room - 55` Roku , bartop for dining seating 6. TV tables also provided for an additional4 guest. Sofa sleeper.brbrKitchen ‍ ‍ - Refrigerator, dishwasher, microwave and dedicated ice maker. Fully stocked including cookware, pots, pans and also has free in unit washer and dryer (stackable).brbrMaster Bedroom - sleeps 2 guests . Equipped with full bed, 55` Ggle TV and sleep sound machine for your convenience. En suite full bathroom with shower.brbrGuest Bedroom - the Quad. Sleeps 4 guests with a double bunk bed setup, 42` Roku TV, sleep sound machine and en suite bathroom with shower.brbrBackyard - fully fenced in private backyard with Gazebo and patio set to seat 4 guests + small table. For lounging or snacking outside. Gazebo cones with built in mosquito net.brbrWe take guest security and safety seriously No fraud bookings, must complete an easy, online hotel-style check-in with a Rental Agreement, ID check, and a refundable hold. Or you can opt for a damage waiver for stays under 10 nights, whichever you prefer! Full details in the House Rules.brBY BOOKING THIS PROPERTY YOU AGREE AND CONFIRM HOUSE RULES BELOW:brbr No parties, events or professional photographybrbr No Smoking or Vaping indoors. Smoke-free property - non refundable $300 smoke remediation fee and grounds for cancelation of the reservation brbr NO PETS - BE RESPECTFUL, please do not circumvent this rule. $250 FEE applied for the deep cleaning mitigation of any animal.brbr - No parking vehicles in backyard. If you need additional parking, please contact us to make arrangements with host.brbr - For stays 10+ days we require a complimentary weekly tidy clean.brbr ️ - Do not park inside the backyard as their is a drain fieldbrbr ✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of (which is not a traditional security deposit, just a pending transaction). As an optional alternative to the security hold, you may opt in to purchase a damage waiver provided by a third-party insurance company. The optional damage waiver is for stays up to 10 nights, with an additional $2 per day for stays longer than 10 nights. Damage waiver purchases are optional.brbrTo make this process easy for you, we use a secure and very simple, app-free platform called Happy Guest. It is not an app, and you do not have to sign up for an account - it’s a safe and secure website. It also gives you a guest portal with all the info about the home and all of my favorite local spots.brbrYour guest portal includes advertisements with third-party upgrades that you may want to enhance your stay. These upgrades are optional for things like early check in (when available).brbr Yard is serviced once per week. Landscapers will need access to front and back yard to cut grass.
Bed 2

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Bath 2

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Sleep 7

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Exceptional(20)

$148.44

/ Nightly
Condo

Dog-Friendly Apt w/ Fenced Yard in Winter Park

Winter Park, Florida, United States

The gateway to your dream Florida vacation, this charming studio stay is nestled near Walt Disney World, the airport, and downtown historic Winter Park. When you want to play in the sand and the surf, you can easily take a day trip to the beach, about 45 minutes away.brbr-- THE PROPERTY --brbrWhen you're ready to relax, unwind, and recuperate, lounge on the plush sofas while tuning into a movie on the large TV. The kitchenette comes well-equipped with a small fridge/freezer, a coffee maker, a microwave, a hot plate, and a toaster.brbrAdditionally inside you will find a phone-controlled mirror, central air-conditioning, and free WiFi. Outside, the small fenced-in yard provides the perfect space for the furry members of your family to stretch their legs.brbrThere are two pull-out sofas.brbr-- THE LOCATION --brbrbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $100 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- Quiet hours are from 10:00 PM to 8:00 AMbr- This property is not equipped with a washer and dryerbr- A single cot with a mattress is available upon requestbr- Your safety matters. The property features 2 exterior security cameras on the exterior of the house. All cameras are outward facing and do not look into interior spaces, are on and not motion activated, and record video
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Bath 1

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Sleep 6

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Exceptional(2)

$198.37

/ Nightly
Private Vacation Home

Charming Home Winter Park, Near Rollins College, Lake Baldwin Park, Orlando FL

Winter Park, Florida, United States

Discover the convenience of this exceptional locale strategically situated just 5-7 minutes away from the vibrant Park Avenue, Lake Baldwin Park, 5 minutes to Rollins college, adorned with charming cafes and boutiques stores, and immerse yourself in the warmth of my luminous 3 bedroom residence, thought fully furnished for your Winter Park visit.brbrThe non smoking unit boasts modern amenities such as AC, wIFI, and security cameras by the front door, ensuring a seamless and comfortable stay. Step into the living room, featuring a generous television and expansive windows that usher in natural light, crafting a luminous and open ambiance. Your ideal Winter Park visit begins here.brbrUpon entering, you are greeted by a spacious living room, with a big TV, and large windows allow natural light to flood the space, creating a bright and airy atmosphere.br brThe sunny kitchen with stainless steel frig, a place for you to enjoy your meal or morning coffee. Each bedroom has a double bed, with a big closet and lots of storage and fans. The master bedroom has a dresser, big closet and an updated bathroom with a walking shower. The other bathroom has modern fixtures, a big mirror and a soaking tub for your relaxation. The bedroom #3 has a dresser, desk with chair and a comfortable futon double bed.brbrThe sunny backroom welcomes the warmth of sunlight, creating a bright and uplifting atmosphere. With a view of the fenced backyard. It has a piano and desk with chair.brbrIt offers a perfect balance of tranquility and accessibility. A great location for you to discover winter park the best way. We look forward to hosting you!
Bed 3

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Bath 2

Bath

Sleep 6

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$271.06

/ Nightly
Private Vacation Home

Elegant & Spacious Historic Winter Park Home with Pool + Spa

Winter Park, Florida, United States

Historic Winter Park home, located within a beautiful neighborhood. The home is spacious, charming and elegantly-appointed with serene, lush views. Out back is a gorgeous oasis, featuring a resort-style heated pool and spa, surrounded by a tropical garden. Longer-term inquiries welcome – please reach out directly for more information/pricing.brbrThe home is brimming with charm and surrounded by beautiful nature. Charming features, such as hardwood floors throughout, push-button light switches and original windows/doors, give the home character while modern touches like Nest thermostats, Brilliant home automation, Nest-protect smoke detectors, and smart locks bring it into the 21st century. The home also has very reliable internet with a wireless mesh network that extends into the backyard.brbrAn oversized front porch with a classic porch swing, sofa, and rocking chairs welcome you to the front entrance. A large, gated driveway accommodates three parking spots and provides access to a private side-entrance. brbrThe first story boasts a formal living room with fireplace and cozy seating, a family room with a flat-screen TV (equipped with Apple TV with Netflix, ad-free Hulu and a variety of other apps) and large sectional sofa, a formal dining room, spacious eat-in kitchen (complete with large refrigerator, microwave, dishwasher, and oven), a mud room with a built-in office space and a half bathroom. brbrThe second story features four spacious bedrooms and a laundry room right next to the master bedroom. Master suite includes a large walk-in closet, a flatscreen tv with roku, two built-in his-and-hers toiletry stations and a luxurious master bathroom.brbrThe master suite has a king-size bed with pillow-top mattress, the second bedroom has a queen bed with pillow-top mattress, the third has full-size bed with memory foam mattress and the fourth bedroom has both a twin-sized bed with memory foam mattress, as well as a convertible sleeper-sofa. brbrOut the back-door is a screened-in porch with an additional dining area. The backyard is centered around a large, resort-style sparkling heated pool and spa. Backyard also includes a summer kitchen with grill, lounge chairs, a hammock, outdoor table and chairs with giant umbrella, and an additional intimate seating area near the spa. In the back corner is a fenced-in, grassy area with a children's playground.brbrAll backyard/common areas are shared with the detached, private guest house, which is rented separately. Please inquire if you're interested in renting the guest house as well. Landscape and pool are maintained weekly.
Bed 4

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Bath 2

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Sleep 8

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Exceptional(4)

$374.98

/ Nightly
Private Vacation Home

Winter Park Pool home close to Lake Virginia, Rollins College & Park Ave.

Winter Park, Florida, United States

One month minimum to rent (30 nights). brbrA hidden gem, this meticulous sun-filled 3 BR + Office/2.5 bath home offers ultra- privacy, tucked in a wonderful and established neighborhood. Easy stroll to charming downtown Park Avenue for shopping, restaurants, cafes, bistros, wine bars, museums, Farmers market, Rollins college, Lake Virginia and much more. Just minutes drive to grocery stores, bank and parks. It is truly convenient for everything! Come see it for yourself! Home away from home. Welcome to Winter Park, Florida where the old and historical charm meets the new! brNot Just Any Ordinary Vacation Home...This is our home and this is Our Story. Traveling has always been our passion for all our lives. My husband had decided to retire in 2021 and our dream is to travel more now while we are able. This is our precious time to experience our exciting chapter... to live, travel and explore the world beyond our comfort levels! We love and adore our home and community. So, we decided that when our home is occupied by our guests, we will take that wonderful opportunity to travel. brWe love to garden as our gardens are tendered with love. We hope that you will have the chance to enjoy our humble well-loved home and explore Winter Park as it is truly a special place to call home when you are away from home.brbrSee also: https://www.travelandleisure.com/winter-park-florida-7255868br
Bed 3

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Bath 2

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Sleep 6

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