Vacation Home Rentals By Owner In Winter Park, FL

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

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

Winter Park, Florida, United States

Bed

Bath

6

Sleeps

$271.06

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.

Elegant & Spacious Historic Winter Park Home with Pool + Spa

Winter Park, Florida, United States

Bed

Bath

Sleeps

$235.88

Escape to our Citrus Oasis! This beautiful 4-bedroom, 2-bath home offers a fully equipped kitchen, spacious bedrooms, and an open layout. Step outside to a private pool, hot tub, two large hammocks in soft sand, and a cozy fire pit—perfect for relaxation. Whether lounging by the pool or enjoying nights by the fire, this home is the ultimate getaway. Please note that the umbrella pictured got destroyed in a recent storm and has not been replaced. Book now and make unforgettable memories!brAs an Airbnb Host, we aim to make your stay as comfortable as it can possibly be! Our mission is to help our guests create beautiful family memories in our cozy home. For us to do so, we would truly appreciate it if you can follow these house rules and confirm that is has been reviewed WITHIN 48 HOURS OF YOUR BOOKING. This is to ensure that if there is any reason the House Rules cannot be followed, you, our guest, will have the option of cancelling the booking penalty free as we have a Strict Cancellation policy. Thank you in advance and truly appreciate your cooperation!brbr br★☆ HOUSE RULES ☆★br☀ No smokingbr☀ No events, parties, or extra-large gatheringsbr☀ 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.brbrbr☀If guests are found to have had a party without host permission which results in extra cleaning, guests will be responsible for extra cleaning charges and in the unfortunate event of the disruptions alerting neighbors, GUESTS WILL BE ASKED TO VACATE THE PROPERTY IMMEDIATELY.brbr☀If guests are suspected of carrying and/or using illegal drugs of any kind, the authorities will be engaged, and GUESTS WILL BE ASKED TO VACATE THE PROPERTY IMMEDIATELY.brbrWe thank you for staying in our home and hope that you have a fun and relaxing stay. If you have any questions or concerns please do not hesitate to reach out.

Citrus Oasis: 4BR Pool Home

Winter Park, Florida, United States

Bed

Bath

Sleeps

$280.0

Enjoy a peaceful stay at this 5-bedroom house in Winter Park. The quaint space features three queen beds, two king beds, and a twin bed, perfect for families or groups. Guests find two bathrooms with showers and hair dryers for added convenience. The house offers heating and AC to keep everyone comfortable year-round. Whether relaxing indoors or exploring nearby spots, this delightful home provides an enjoyable retreat. We hope you enjoy what our place and Winter Park has to offer.

Cute 5-bedroom house in peaceful Winter Park

Winter Park, Florida, United States

5

Bed

Bath

11

Sleeps

$200.62

Your backyard oasis awaits you, with queen size 10in memory foam swing mattress, full outdoor kitchen, 65in TV along with a 2 hole putting green and flower wall. You can relax and enjoy the warm florida winters with a nice bbq.brbrWalking distance to phelps park, 1 mile from park ave, 1.5 mile from Rollins college and plenty more.

Winter Park Oasis

Winter Park, Florida, United States

Bed

Bath

Sleeps

$116.96

Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed and bunk beds. Easily sleeping 4. We are located very close to downtown Winter Park and steps off Park Ave. Museums, restaurants, golf and shopping are all within walking distance. There is a dedicated desk/work area for corporate guest. Designed to feel like home away from home we want to make sure your stay with us is enjoyable.

Winter Park charm. Close to Park Ave

Winter Park, Florida, United States

Bed

Bath

Sleeps

$5115.13

Welcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortably accommodating over 20 guests. With its prime location near CP, WP and DT Orlando, you’ll have access to the best areas!brbrStep inside to tall ceilings and expansive living spaces, designed for ultimate comfort and style. Enjoy a movie night in the dedicated movie room with a state-of-the-art projector, or relax on the screened-in patio featuring a Jacuzzi tub that seats 6.brbrWelcome to your perfect Orlando getaway! This stunning new home boasts 5 spacious bedrooms and 4 modern baths, comfortably accommodating over 20 guests. With its prime location near College Park, Winter Park, and downtown Orlando, you’ll have easy access to the best dining, shopping, and entertainment in the area.brbrStep inside to tall ceilings and expansive living spaces, designed for ultimate comfort and style. Enjoy a movie night in the dedicated movie room with a state-of-the-art projector, or relax on the screened-in patio featuring a Jacuzzi tub that seats 6.brbrEach room is equipped with a TV and Roku, offering endless entertainment options. Whether you`re planning a family reunion, group vacation, or corporate retreat, this luxurious home offers ample space and modern amenities for everyone in your group.brbrBook now for an unforgettable stay in the heart of Orlando!brbrTHE SPACE:br1st FLOORbrMaster Bedroom:brbrLarge tall 12ft ceilings and a KING bed. En suite bathroom with separate tub and shower, double sink vanity and 2 walk in closets. Sliding glass door access to screened in patio and jacuzzi tub. Sleeps 2brbrOpen floorplan with large dinning table, open kitchen with island and bar stool seating, large sectional, separate breakfast table, lounge chairs and 80+ inch Roku enabled TV. Sleeps 2 small adults/kidsbrbrExtra Guest Bathroom Downstairs with large Shower.brbr2nd FLOOR:brbrBonus Area/Movie room area - equipped with 4k projector and Roku, large sectional sofa, Arcade game machine.brbrBedroom 2 - Equipped with 55` Roku smart TV, Queen bed and plenty of storage + closet space. Sleeps 2.brbrBedroom 3 - 55` roku smart tv, queen bed, storage space and large closet.brbrBedroom 4 - 55` roku smart tv, queen bed, storage space and large closet.brbrBedroom 5 - `The BLUEROOM` - Large bedroom setup with 4 full size bunk beds (x4). En suite bathroom with large shower and double closets sleeps 8.brbrLaundry area - has full size washer and dryer with overhead storage cabinetsbrbrPatio - Screened in patio, lots of outdoor seating and 6 person jacuzzi tub. Backyard, paver bbq area with overhead canopy cover to keep you shielded from the sun and elements. Large fenced in backyard.brbrGarage - 1-2 vehicles and also has workout space with bench and workout equipment.brbrGuest has access to the full home for the exception of the staff storage closets labeled accordingly.brbrInteraction from guests is as needed or upon request.brbrHot tub - temperature does not exceed 103F for safety reasons. See hot tub info and rules under house rules for more details.brbrPropane & Grill - please let us know in advance if you`ll be needing propane. Tank fee per stay is $10brbrAir Mattress - please notify host in advance if you`ll need onebrbr ✅ 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, Guest agree to follow house rules :brbr Please do not park inside the garage/Gameroombrbr- Do not move gameroom games outdoors as may be damaged if left outsidebrbr No parties, events or professional photographybrbr No Smoking or Vaping. Smoke-free property. $550 remediation fee applies.brbr No Pets. No Animals -- $350 animal remediation and cancellation of the reservation - non refundablebrbr - Parking for 3-4 vehicles - ONLY ON DRIVEWAYbrbr - For stays 10+ days we require a complimentary weekly tidy clean.brbr Yard is serviced once per week. Landscapers will need access to front and back yard to cut grass.brbr Hot tub is also serviced once per week, they will need access to the back patio for weekly cleanings and service. NO MORE THAN 6 PEOPLE max occupancy in the Hot tub at a time.br-Please shower before entering hot tubbr-no food or glass drink in hot tubbr-no children underage unattended br-please do not shut off the hot tub heater as it takes several days to heat and can affect other guest experience br-failure to follow care/instructions here or posted on site can lead to damaging the hot tub and or parts. Guest are responsible for remediation cost of hot tub repair/damages.brbr Follow all hot tub rules in house manual. 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).brbrRunning business activity like Massage services, salon or any other kind of business services traffic at the property is strictly prohibited and can result in non refundable cancelation of your reservation

5/4 King bed LUX Arcade near WP/CP & DT Orlando ‼️

Winter Park, Florida, United States

Bed

Bath

Sleeps

$267.13

Enjoy a stylish experience at this centrally-located place. MillsHouse is conveniently located for a foodie adventure. The best of Winter Park and Mills 50 is just blocks away.brbrbr✅ minutes to Lake Eola, Park Ave, Mills 50, shopping, parks and highwaysbrbr✅ Covid-19 enhanced cleaningbrbr✅ Walk to many winter park restaurants brbr✅ 25min to theme parksbrbr✅ Free Parking ️brbr✅ Se Habla Españolbrbr❌ Strict No Pets Allowedbrbr❌ No Smokingbrbr⭐ Stylish and comfortable living room - wifi TV equipped with Roku so you can login/stream from your favorite services. The couch serves as an optional futon to sleep ️ an additional 2 guest.brbr ️ - Dinning Table and bar topbrbr ‍ - Kitchen fully stocked including coffee maker, coffee microwave, dishwasher, toaster and refrigeratorbrbr ‍♂️ ‍♀️ - Master bedroom: The tranquiltiy suite with queen bed, 55` roku tv, ensuite bathroom and washer dryer space brbr - Bedroom 2: The Black & Gold room with queen bed, vintage lighting, 55` roku tv and wall design.brbr - Bedroom 3: The Quad with 2 sets of bunk beds, sleeps 5 (3 twins, 1 full) also has a dedicated work space.brbr - Living room with 55`RokuTV and 2 sofa couches. PLEASE NOTE sleeping here is best suited for children and not full size adultsbrbr - Backyard: Large rock paved yard off the master suite with BBQ grill.brbr - Covered Porch entry way facing the rock paved driveway. there is parking for 4 vehicles. brbrGuest have full use of the property as well as fenced in backyard.brbr ️Parking can accommodate 3-4 vehicles and is located to the left of the home when looking at the front doorbrbrWe are available via messenger in the airbnb app and so are our cohost.brbrThe property is located just off the main mills area which is packed with restaurants, bars, gastropubs, and more. brbrYou`ll enjoy plenty of privacy as the home is nestled in the rear of a larger resort complex . Our guest say they enjoy the close proximity to both College Park, Winter Park, Downtown Orlando and the Mills50 zone. You`re also just a few minutes from I-4 and expressway.brbrThis area is growing quickly and has become the `Foodie Zone` of Orlando. There are restaurants of all types catering to sit down and also quick bites.brbrRecently a vibrant nightlife with over 10 pubs, bars and social lounges nearby.brbrBus stop is a few blocks away on MillsbrbrParking - please ensure to park in the designated parking to the left of the home. Parking in front of the entrance to the home is prohibited as it will block access to the neighbors home.brbrPlease ensure NOT to park in front of the entryway as this will block access to the neighbors parking area.brbrMASTER BEDROOM - PENDANT LIGHTS: Lights are always on, to turn off simply unplug from the wall connections at the nightstands. At departure We just ask you plug them back in.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).br 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. $500 fine applied for the cleaning mitigation of any animal.brbr - No parking vehicles in backyard. If you need additional parking, please contact us to make arrangements with host.brbrbrRunning business activity like Massage services, salon or any other kind of business services traffic at the property is strictly prohibited and can result in non refundable cancelation of your reservationbrbr - 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.

Mills House @WP. Sleeps 11 Renovated. Queen beds

Winter Park, Florida, United States

Bed

Bath

Sleeps

$263.18

Located in Winter Park, this charming house with 3 queen beds is a dream. The adorable living room with a cozy sofa bed is perfect for relaxing after a day of exploring. With 2 bathrooms equipped with showers and hair dryers, guests will feel right at home. Enjoy the convenience of amenities like AC, WiFi, and a washing machine. On the second floor there is a comfortable space dedicated to office work. We're happy to assist with any questions while you stay at our house.

Charming 3-bedroom house with WiFi, AC in Winter Park

Winter Park, Florida, United States

Bed

Bath

Sleeps

$304.35

NEW CONSTRUCTION Luxury Home north of Downtown Orlando in the heart of Winter Park steps from Winter Park Village near the Famous Park Ave where you'll find unlimited entertainment choices including dining, shopping, nightlife, axe throwing, etc…brbr❤️❤️ You WILL LOVE this custom home!! ❤️❤️brbrNO CAR Needed! Walk to beautiful parks, train stations, major highways, and public bicycle and scooter sharing on several corners.

LUXURY ℂ ᴠᴀᴄᴀᴛɪᴏɴ in

Winter Park, Florida, United States

Bed

Bath

Sleeps

$151.18

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.

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

Winter Park, Florida, United States

Bed

Bath

7

Sleeps

$135.93

Experience Winter Park like a local in this superb 1-bedroom bungalow. This enchanting property offers all the comforts you need, from AC to WiFi. We're happy to assist with any questions while you stay at our bungalow.

Quaint Key West Pool Bungalow

Winter Park, Florida, United States

Bed

Bath

Sleeps

$459.53

Experience serene luxury in this spacious Japandi-style home in beautiful Winter Park. Blending Scandinavian warmth with Japanese minimalism, this modern retreat sleeps 12 comfortably with 4 stylish bedrooms and 3 full bathrooms. Enjoy open-concept living, a fully equipped kitchen, calming interiors, and clean, modern design. Perfect for family getaways, ski trips, or peaceful retreats—just minutes from local attractions and nature.brbrSpacious Modern Japandi Retreat - Winter ParkbrbrEscape to the Modern Japandi Retreat, a custom-built, Parade of Homes award-winning masterpiece, designed to provide an intimate, luxurious retreat. Perfect for those seeking privacy, comfort, and top-tier amenities, this property offers everything you need to unwind and enjoy a world-class experience.brbrKey Features:brbr100% Custom-Built, Parade of Homes WinnerbrOutdoor Kitchen with Grill brFully Equipped Chef's KitchenbrLarge Smart TVs in Living Room and Master Bedroom brOutdoor Patio with Seating & FireplacebrStocked Gourmet Coffee BarbrbrAbout the Space:brbr2000 sq ft air-conditioned indoor space brAdditional 1000 sq ft of outdoor entertainment and lounge areas br4 Bedrooms, 3 Full Bathrooms: Ideal for multi-family stays with plenty of space and privacy for everyone. brbrbrAdditional Perks:brbrPet-Friendly: Pets are welcome with a $100 Flat Fee.br6-Person Jacuzzi: No Additional FeebrNeighborhood: Quiet, Residential.brWork-Friendly: Dedicated workspace.brSafety & Comfort: Entry via keypad deadbolt for ease and security.brbrLocation:brbr20 minutes from Universal Studios and International Drivebr20 miles from DisneybrClose to downtown, offering a perfect balance of relaxation and proximity to Orlando’s best attractions.brbrWhether you’re here for a weekend getaway or a longer retreat, Modern Japandi Retreat is the perfect place to relax, rejuvenate, and create unforgettable memories.

Top 1% Modern Japandi Retreat - Jacuzzi No Fee

Winter Park, Florida, United States

4

Bed

Bath

12

Sleeps

$138.84

Charming Farmhouse Themed cottage in beautiful Winter Park, FL. This home is centrally located near Rollins College (4 miles), UCF (6.5 miles), and Full Sail University (1.8 miles) as well as just a short drive away from Park Avenue in Winter Park (4.5 miles) and a hop, skip and a jump away from 417 which takes you to Downtown Orlando (11 miles) and Disney's theme parks (34 miles). This house has 3 bedrooms and 2 bathrooms with a large fenced in back yard. The kitchen is fully furnished with a stainless steel fridge, electric oven, dishwasher and microwave. You will have everything you need including pots, pans, utensils, dishware, coffee station, linens, towels, and complimentary shampoo and conditioner in bathrooms. Dogs are welcome with a $100 pet fee and will love the big fenced in back yard! there is no garage, however, there is plenty of space for 2-4 vehicles. All bedrooms have a queen bed. The house is beautifully furnished with farmhouse decor.

Charming Winter Park Fully Furnished & Pet Friendly Farmhouse Bungalow

Winter Park, Florida, United States

Bed

Bath

Sleeps

$252.93

This comfortable and modernized 3 bed 2 bath home in WInter Park is perfect for those traveling for a family event such as a wedding, or family get-together. Enjoy all the homes amenities including a gym, fenced yard, full kitchen, dedicated workspaces, and washer/dryer. Work or stream your favorite shows over our fast 300mbps wifi. Located in a quiet, middle-class neighborhood and centrally located to all Central Florida's offerings: Park Ave (10 mins), Downtown Orlando (15 mins), UCF (10 mins), and the Theme parks (30 mins).

Winter Park: 3B 2B Home with King Bed, Gym, & Fenced Yard

Winter Park, Florida, United States

Bed

Bath

6

Sleeps

$173.25

Welcome to our Winter Park home behind East End Market ! You will fall in love with this area which is full of friendly and walkable restaurants, bars, boutique shops, yoga studio and a wellness center offering saunas, cryotherapy and massage - (search The Lovely, Domu, East End Market, Gideon's Bakehouse, The Salty, Sushi Lola's, Redlight Redlight, The Athlete Recovery Room, Warrior Yoga). Our neighborhood also has a gas station, 7-11 and ABC -all within 2 blocks walk. If you must get in a car, we are 30 minutes from Disney, 10 minutes from Downtown, 5 minutes from Rollins College, 5 minutes from Advent Health Winter Park /Advent Health Orlando, 2 minutes from Leu Gardens, 8 minutes from Orlando Science Museum and Museum of American Art minutes and an hour away from several of the best beaches on the coast.brThe home is a separate building on our property and has a very large living room, kitchen, laundry room and a separate bedroom with queen size bed and one bath. The unit also contains a full size washer dryer and your own private patio furnished with chairs and umbrella so you can enjoy our beautiful live oak trees and sunshine ! The kitchen comes fully equipped with all kitchen ware you need including fridge, coffee pot, microwave, induction cook top, toaster oven and dish washer. brTVs are in both the bedroom (32) and living room (65) equipped with internet and several movie channels (Netflix, Prime, Spectrum TV). Also, there is a separate and dedicated paved driveway for your vehicle.brWe live on the property as well so if you have any questions or need suggestions for dinner, music or shopping, we are available to make sure you are well prepared!brCheck in time: 3:00p.m.brCheck out time: 11:00p.m.

Quaint Winter Park East End Market Home

Winter Park, Florida, United States

Bed

Bath

Sleeps

$294.25

Charming 3BR Oasis with Private Pool in Winter ParkbrbrWelcome to your sunny Winter Park retreat — a spacious and family-friendly 3-bedroom, 2-bath home designed for relaxation, connection, and making memories.brbrWhether you're visiting for theme parks, college tours, family gatherings, or simply a Florida escape, this private pool home offers comfort, charm, and a peaceful neighborhood setting just minutes from the best of the area. brbrThe Space:brbrStep inside to a bright and welcoming living space with comfortable seating and a beautiful decorative fireplace that adds warmth and character to the home (please note: fireplace is not intended for use).brbrThe home features:brbr* 3 comfortable bedroomsbrbr* 2 full bathroomsbrbr* Fully equipped kitchen for home-cooked mealsbrbr* Open living and dining areas perfect for familiesbrbr* Private backyard with poolbrbrbrPrivate Pool & Outdoor Living:brbrEnjoy your own private, unscreened pool — perfect for cooling off after a day exploring Central Florida. The backyard offers space to relax, unwind, and soak up the Florida sunshine.brbrPlease note:brbrThe pool is not screenedbrbrAdult supervision is required at all times for childrenbrbrNo lifeguard on dutybrbrFlorida sunshine + a private pool = vacation mode activated.brbrbrbrLocation Highlights:brbrLocated in beautiful Winter Park, known for its tree-lined streets and charming atmosphere:brbrMinutes to Park Avenue (boutiques, restaurants, coffee shops)brbrNear the scenic campus of Rollins CollegebrbrApproximately 20–30 minutes to downtown OrlandobrbrEasy drive to Walt Disney World and other major attractionsbrbrYou’ll enjoy staying in a quieter, more relaxed neighborhood while still being close to everything Central Florida has to offer.brbrbrbrPerfect For:brbrFamilies visiting theme parksbrbrParents touring collegesbrbrSnowbirds escaping winterbrbrBusiness travelers wanting space and comfortbrbrSmall groups looking for a private pool homebrbrbrbrWhy Guests Love Staying Here:brbr✔ Private poolbr✔ Spacious 3BR layoutbr✔ Family-friendly setupbr✔ Quiet residential settingbr✔ Convenient location near attractionsbrbrWe can’t wait to host you and help make your Winter Park stay comfortable, relaxing, and memorable.brbrGuest accessbrGuests have full access to the entire home, including:brbrAll 3 bedrooms and 2 bathroomsbrbrFully equipped kitchen and dining areabrbrSpacious living roombrbrPrivate backyard with unscreened pool (adult supervision required at all times; no lifeguard on duty)brbrPatio seating for relaxing or dining outdoorsbrbrSafety Notes:brbrThe decorative fireplace is for ambiance only and not for use.brbrChildren must be supervised around the pool and backyard.brbr****There are 3 exterior security cameras (no indoor cameras) for general safety. One facing the front of the property, one facing the side entrance, and one facing the backyard/ pool. ****

Winter Park 3BR Oasis- Private Pool

Winter Park, Florida, United States

Bed

Bath

Sleeps

$220.08

Just what you have been waiting for; beautiful cottage home in the heart of Winter Park! 2 bedroom/2 bath only steps away from the art festival and all the wonderful shops and restaurants on Park Avenue. Newly renovated bright home with rich wood floors, updated kitchen and charm throughout. The convenience, comfort, and uniqueness of this bungalow make this a wonderful vacation home that we hope your family will enjoy.

Cute bungalow minutes walk from Park Avenue.

Winter Park, Florida, United States

Bed

Bath

Sleeps

$251.95

Welcome to Your Dream Oasis at Charming Pads!brEscape to this stunning 4-bedroom pool home, where comfort, style, and entertainment come together in perfect harmony. Nestled in a tranquil neighborhood, this charming retreat is ideal for families or groups seeking a relaxing getaway with easy access to top attractions.brbrBedrooms:brIndulge in the luxury of space with four beautifully appointed bedrooms, each featuring a cozy queen bed for restful nights. The master suite includes a private en-suite bathroom, offering exclusivity and convenience during your stay.brbrPrivate Pool Paradise:brStep outside to your private oasis and enjoy sun-filled afternoons by the sparkling, heated pool. Whether you’re taking a refreshing dip, lounging on the pool deck with a cool drink, or soaking up the serene surroundings, this space will be a highlight of your vacation.brbrThoughtfully Designed Living Spaces:brThis home features a split floor plan for ultimate privacy:brbrTwo bedrooms and a bathroom on one side.brThe master suite on the other.brAt the heart of the home, you’ll find a spacious living room, dining area, and a fully equipped kitchen. A dedicated game zone ensures endless fun for movie nights, board games, or friendly competitions.brbrChef’s Kitchen Delight:brThe kitchen is fully stocked with modern appliances and plenty of counter space for preparing delicious meals. Dine together in the cozy indoor dining area or take your meals outdoors for a charming al fresco dining experience under the Florida sky.brbrEntertainment Galore:brCreate lasting memories with the abundance of entertainment options:brbrEnjoy a family game night in the game zone.brRelax in the comfortable living room with a movie or show.brFlexible Check-In & Check-Out:brWe know flexibility is key! Early check-in and late check-out are available upon request for just $20 per hour (up to 2 hours). Let us know in advance to make your stay even more convenient.brbrPrime Location:brLocated in Winter Park, this home offers easy access to the best of Orlando:brbrDisney and Universal Studios just a short drive away.brClose to shopping, dining, and local attractions.brWhether you’re exploring the vibrant neighborhood or using this charming home as a base for adventures, it’s the perfect location for your vacation.brbrBook Your Stay:brDon’t miss out on this incredible 4-bedroom pool home! Experience relaxation, luxury, and convenience at Charming Pads—your dream getaway awaits. Book now and start planning your unforgettable vacation!brHouse Rules for Your Enjoyable Stay:brbrNo Eating in the Bedrooms:brPlease refrain from eating in the bedrooms to maintain a clean and inviting living space.brbrGuest Policy:brOnly guests listed in the reservation are allowed on the property. If you plan to have more than 8 guests at the house (including both overnight and visiting guests), there will be an additional charge of $50 per person. Any reservation found to exceed this limit may be canceled.brbrSecurity Measures:brFor your safety and the security of the property, we have a surveillance system in place to monitor the exterior of the house. Please avoid tampering with any security devices, including exterior cameras or the internal base station. Any interference may result in the cancellation of your reservation.brbrQuiet Hours:brRespect the tranquility of the neighborhood and fellow guests by observing quiet hours from 10PM to 7 AM.brbrEarly Check-In and Late Check-Out:brEarly check-in or late check-out may be available upon approval, with an additional charge of $20 per hour. Please inform us in advance if you wish to request these services.brbrSmoking Policy:brSmoking is strictly prohibited inside the house. Please use designated outdoor areas and dispose of cigarette butts responsibly.brbrPet Policy:brWe allow pets on the premises.brbrIssue Resolution and Communication:brbrWe are dedicated to ensuring your comfort and satisfaction during your stay. If you encounter any issues or have concerns, please notify us immediately to allow us the opportunity to address and resolve them promptly. We value open and constructive communication.brbrNegative Reviews:brWe appreciate your feedback and encourage you to communicate any concerns directly with us. Leaving a negative review without allowing us the chance to address the matter first prevents us from ensuring your satisfaction. Your feedback is vital for our improvement and to guarantee a wonderful stay for future guests.brbrThank you for choosing our home for your stay. We are committed to providing a positive experience and are here to assist you throughout your time with us.

Winter Park Charmer - Heated Pool Home - Close to everything

Winter Park, Florida, United States

4

Bed