Home Vacation Home Rentals By Owner In Winter Park, FL

Showing 20 Of 65 Vacation Rentals
Slider Thumb
Exceptional(4)

$119.62

/ Nightly
Private Vacation Home

Cozy Comfort Just 2 Blocks From Park Ave!

Winter Park, Florida, United States

This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very comfortable mattresses. brbrLocated just 3 blocks from PARK AVE to the east and 2 blocks from THE WINTER PARK VILLAGE to the west. Vast amounts of restaurants and shops within walking distance. Parks and museums within easy walking distance as well. We have bikes available on property for your use as well, free, of course. Cheesecake Factory and PF Chang's two blocks away. Publix Grocery two blocks, Whole Foods 1/2 mile and Trader Joes 3/4 mile away. And many fantastic local restaurants and shops within a pleasant walking distance.brbrThe Charles Hosmer Morse Museum of American Art is just three blocks away and the Scenic Boat Tour offers a boat tour through the canals to three of the five lakes on the Winter Park Chain of Lakes. The Winter Park Country Club nine hole golf course is just a few blocks away and open to the public.brbrThe property is professionally managed in a mom and pop fashion. Your privacy is respected and protected. The amenities are very nice with a lovely pool area that has a massive bouganvillea trellis hedge running atop a wall. The pool area also offers outside dining, a grill station for cooking outside and a hot tub. The pool is heated in winter. Everything is kept very clean. There are seven bikes, including one child's bike and two other relatively small ones available for guests in the fourteen unit complex.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb
Exceptional(4)

$133.12

/ Nightly
Private Vacation Home

LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!

Winter Park, Florida, United States

This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very comfortable mattresses. brbrLocated just 3 blocks from PARK AVE to the east and 2 blocks from THE WINTER PARK VILLAGE to the west. Vast amounts of restaurants and shops within walking distance. Parks and museums within easy walking distance as well. We have bikes available on property for your use as well, free, of course. Cheesecake Factory and PF Chang's two blocks away. Publix Grocery two blocks, Whole Foods 1/2 mile and Trader Joes 3/4 mile away. And many fantastic local restaurants and shops within a pleasant walking distance.brbrThe Charles Hosmer Morse Museum of American Art is just three blocks away and the Scenic Boat Tour offers a boat tour through the canals to three of the five lakes on the Winter Park Chain of Lakes. The Winter Park Country Club nine hole golf course is just a few blocks away and open to the public.brbrThe property is professionally managed in a mom and pop fashion. Your privacy is respected and protected. The amenities are very nice with a lovely pool area that has a massive bouganvillea trellis hedge running atop a wall. The pool area also offers outside dining, a grill station for cooking outside and a hot tub. The pool is heated in winter. Everything is kept very clean. There are seven bikes, including one child's bike and two other relatively small ones available for guests in the fourteen unit complex.
Bed 2

Bed

Bath 1

Bath

Sleep 4

Sleeps

Slider Thumb

$167.46

/ Nightly
Private Vacation Home

Brizzy 2BR/2BA Near Park Ave and Rollins, Perfect for Families and Long Stays.

Winter Park, Florida, United States

Discover this 2-bedroom house in Winter Park. The bedrooms feature a queen bed and a king bed, offering plenty of comfort for guests. Two bathrooms include a bathtub and a bidet, adding a touch of luxury to your stay. The living room provides extra sleeping options with a sofa bed and a twin bed, perfect for families or friends Near Park Ave dining, shops, cafés, and scenic strolls.brbr• Minutes to Rollins College & Full Sail Universitybrbr• Easy access with free parking close to the entrancebrbr• Fast Wi-Fi plus a work-ready space for remote workbrbr• Fully equipped kitchen with complimentary breakfast items, snacks, bottled water, and light dinner essentialsbrbr• Ideal for visiting family, medical trips, college visits, or brlonger stays. br brWHY GUESTS LOVE ITbrbr• Clean, light, modern design with an open living, dining, and kitchen layoutbr• Easy self check-in with keypad (no key handoffs)br• Private fenced patio for coffee, fresh air, and relaxing eveningsbr• In-unit washer and dryer so you can pack lighterbr• Fully equipped kitchen plus a coffee setupbrbr• Complimentary starter groceries: breakfast items, snacks, bottled water, plus a few ready-to-use dinner essentials so you can settle in immediatelybr• Shower heads with built-in water filters for a cleaner, softer shower experience.brbrSLEEPING ARRANGEMENTS (SLEEPS UP TO 6)br• Bedroom 1: King bedbr• Bedroom 2: Queen bedbr• Living room: Single sleeper (great for one adult or a child)br• Pull Out Sleeper Sofa (great for one adult or a child)brbrTHE SPACEbrThis is a private side of a duplex with its own entrance and exclusive access to the full interior plus the fenced outdoor space. The layout is simple and comfortable:br• Living room with TV and comfortable seatingbr• Open kitchen and dining area (easy for meals and conversation)br• Two full bathroomsbr• Laundry in-unit for conveniencebrbrKITCHEN AND DININGbrCook a full meal or keep it simple.br• Fully equipped kitchen with cookware and essentialsbr• Coffee and tea setupbr• Grill available for easy outdoor mealsbrbrWORK-FRIENDLY SETUPbrPerfect for solo business travelers, traveling nurses, and small work trips.br• Fast WiFibr• Extra Monitor, Keyboard and Mousebr• Dedicated workspacebr• Quiet, residential feelbrbrPARKINGbrFree parking on site. Please follow the posted parking guidance and keep access areas clear so everyone has an easy stay.brbrLOCATION, WITHOUT THE TOURIST CHAOSbrYou get the convenience of being close to the best of Winter Park and Orlando while staying in a calm neighborhood:br• Park Ave area, dining, shopping, and scenic walks nearbybr• Full Sail University close bybr• Quick access to major roads for downtown Orlando, attractions, and the airportbrbrGOOD TO KNOW BEFORE YOU BOOKbr• Check-in: after 4:00 PMbr• Check-out: before 11:00 AMbr• No smoking anywhere on the property (inside or outside)br• No petsbr• No shoes inside the homebr• Please keep food and drinks off the bedsbr• For everyone’s safety, there is an exterior security camera on the propertybrbrWe host with a focus on cleanliness, clear communication, and a smooth stay from start to finish. If you have questions before booking, message us. We are happy to help.
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(36)

$206.13

/ Nightly
Private Vacation Home

Great Family Home

Winter Park, Florida, United States

Our home has high quality furniture, linens, cookware and tableware for your family dinners. There are large and small appliances (including airfryer) to help with preparation. brEnjoy a fully-furnished 3 bedrooms, 2 baths, 1600 square-foot, single-story house in the heart of Winter Park, a wonderful town that is adjacent to Orlando and that is home to an array of restaurants, galleries, museums, up-scale shops, businesses, professional offices, parks, lakes and hiking and biking trails. Rollins College is just minutes away from the house by car. Address: 1827 Mizell Ave. (Between Lakemont and Phelps)brbrThe house has hardwood or tile flooring in most rooms; a large fenced backyard with a brick patio, lawn furniture, and a grille; front covered porch; and a concrete circular driveway. It has SpectrumTV, Wi-Fi; a printer/fax/copier/scanner machine; and DVD/CD player with DVDs and CDs. There are central heating and air conditioning systems; ceiling fans; smoke alarms; and a lawn sprinkler system. Lawn and landscaping care is provided. Traditional decor also available during the holiday season!brbrDowntown Winter Park has an Amtrak station. Getting to or from Orlando Airport from the house takes about 30 minutes by car. Both I-4 and 436 (Semoran Boulevard) exits are about 10 minutes away. Grocery and drug stores, Winter Park Hospital, and the Crosby wellness center are all within walking distance, as is a bus stop. Baldwin Park and Winter Park's public golf courses are minutes away by car. The Atlantic Ocean beaches, Walt Disney World, Universal Studios and other major attractions are about a 45 minute drive away.brbrWe are a professional couple -- a retired architect and a university professor -- who live in Pennsylvania. Our daughter-in-law lives down the street from the house and manages it for us. We love the house and intend to use and enjoy it more fully in the future. We believe that you will like spending time in it. Contact us for additional information and availability. Community outdoor pool and beautiful YMCA are both available within one mile. YMCA honors reciprocal agreements with many other Ys. Check with yours before leaving home.brbr
Bed 3

Bed

Bath 2

Bath

Sleep 5

Sleeps

Slider Thumb

$195.19

/ Nightly
Private Vacation Home

Cozy home 5min to Park Ave and Downtown Orlando

Winter Park, Florida, United States

Welcome to your perfect getaway! This stylish 2-bedroom, 1-bath home is just 5 minutes from Park Avenue in Winter Park, where you’ll find top-rated restaurants, boutique shopping, and charming cafés. Plus, you’re less than 7 minutes from downtown Orlando!brbrUnwind in a spacious living area with vaulted ceilings and 50” Roku TVs, a dedicated office space and patio. With comfortable sleeping arrangements for up to 6 guests, this home is perfect for families, couples, or business travelers.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.brbr✅ This property has special local compliance requirements which include a signed rental agreement, verification, and a security hold of $1k(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 non refundable 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.brBy booking you agree to respect the house rules herein:brbr No Smoking, Vaping or E cigarettes brbr No Animals brbr No parties or Events - Reservation can be cancelled and is non refundable brbr Mail/Packages - we do not accept mail or packages. we are not responsible for any misplaced or lost packages. it`s recommended to mail to local post office or amazon locker if needed. brbr Do not tamper with security devices, cameras, fire or carbon monoxide sensors/alarms.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).brbr⛔️ Left storage area is off limits and used only by staff or maintenance team between stays. The Ladder is only for decor purposes. DO NOT CLIMB
Bed 2

Bed

Bath 1

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$124.56

/ Nightly
Private Vacation Home

Sleek, Spacious & Central – Your Ideal Getaway

Winter Park, Florida, United States

Looking for a peaceful getaway This is the ideal spot in Winter Park, FL.brbrThis beautifully updated entire downstairs unit offers a cozy living room, a remodeled modern kitchen, Smart TV, a clean bedroom with a comfortable queen-sized bed, and a full bathroom. brbrEnjoy free Wi-Fi, one dedicated parking spot per booking, and a convenient location close to everything and privacy in a quiet, upscale residential neighborhood. brbrLong-term stay available!brbrYOUR PROPERTY:brbr*Guests have the whole downstairs unit to themselves. This usually includes a bedroom, a bathroom, and a kitchen. Entire downstairs unit featuring a cozy living room, a remodeled modern kitchen, a clean bedroom with a comfortable queen-sized bed, and a full bathroom. brbr*Conveniently located just minutes from Winter Park Downtown, Orlando Downtown, Baldwin Lake, Rollins College, Full Sail University, shopping plazas, grocery stores, and a wide variety of restaurants. Whether you're visiting for leisure or here for work, this space offers the comfort and convenience you need.brbrGUEST ACCESS:brbr* Private downstairs unit with its own living room, kitchen, bathroom, and separate entrance. brbrShared Yard with the other tenants and guests.brbrADDITIONAL RULES:brbr* One pet is allowed per booking at no extra charge. Additional pets will incur a $50 fee each. Any damage caused by pets will result in additional fees.brbr* Your pets must be leashed and supervised by you at all times while in the yard, as it is a shared space with other tenants. brbr*Loud noises, smoking and heavy drinking is strictly prohibited in or around the property.brbr* Free yard parking in front of premises available for ONE car on each booking.brbr*We need picture ID to provide access to the property. Please take a picture of your valid ID and the person who is coming with you and send it to us one day prior your arrival.brbr*No outside visitors allowed. brbr*Smoking is strictly prohibited inside or around the premises.brbr*Any unapproved late checkouts may result in additional fees.brbr* Unable to receive packages or mail because it is a Domestic security issue. (but that long-term guests can ask permission first)brbr*$200 fee for each house rule broken.brbrThe property has outdoor and common areas security cameras for your safety and anyone caught breaking these rules will be escorted off the premises without refund and will forfeit their deposit.
Bed 1

Bed

Bath 1

Bath

Sleep 2

Sleeps

Slider Thumb
Exceptional(2)

$209.07

/ Nightly
Private Vacation Home

Comfortable & Quiet 2BR/2BA, Near Park Ave & Rollins, Extended Stays Welcome.

Winter Park, Florida, United States

Enjoy a peaceful stay in this comfortable, easy-access 2BR/2BA home in a quiet Winter Park neighborhood near Park Avenue, Rollins College, and Full Sail University.brbrExtended stays are welcome. This home is a great fit for visiting family, work trips, traveling nurses, and guests who want a calm, convenient place with everything needed for a smooth stay. The layout is simple and functional, offering privacy, comfort, and a relaxed residential feel.brbrWHY GUESTS LOVE ITbrClean, light, modern design with an open living, dining, and kitchen layoutbrEasy self check-in with keypad (no key handoffs)brbrPrivate fenced patio for coffee, fresh air, and relaxing eveningsbrbrIn-unit washer and dryer so you can pack lighterbrbrFully equipped kitchen plus a coffee setupbrbrComplimentary starter groceries: breakfast items, snacks, bottled water, plus a few ready-to-use dinner essentials so you can settle in immediatelybrbrShower heads with built-in water filters for a cleaner, softer shower experiencebrbrSmart backyard lighting that also works as a Bluetooth speaker, connect your phone and enjoy music while you unwind outsidebrbrSLEEPING ARRANGEMENTS (SLEEPS UP TO 6)brBedroom 1: Queen bedbrBedroom 2: Queen bedbrbrLiving room: Single sleeper (great for one adult or a child)brPull-out sleeper sofa (great for one adult or a child)brbrTHE SPACEbrThis is a private side of a duplex with its own entrance and exclusive access to the full interior plus the fenced outdoor space. The home includes:brLiving room with TV and comfortable seatingbrOpen kitchen and dining area (easy for meals and conversation)brbrTwo full bathroomsbrbrLaundry in-unit for conveniencebrbrKITCHEN AND DININGbrCook a full meal or keep it simple.brFully equipped kitchen with cookware and essentialsbrCoffee and tea setupbrGrill available for easy outdoor mealsbrbrWORK-FRIENDLY SETUPbrIdeal for longer stays and business travel.brFast WiFibrExtra monitor, keyboard, and mousebrDedicated workspacebrQuiet, residential feelbrbrPARKINGbrFree parking on site. Up to 4 carsbrbrLOCATION, WITHOUT THE TOURIST CHAOSbrYou’ll be close to the best of Winter Park and Orlando while staying in a calm neighborhood:brPark Ave dining, shopping, and scenic walks nearbybrRollins College close bybrFull Sail University close bybrQuick access to major roads for downtown Orlando, attractions, and the airportbrbrGOOD TO KNOW BEFORE YOU BOOKbrCheck-in: after 4:00 PMbrCheck-out: before 11:00 AMbrNo smoking anywhere on the property (inside or outside)brNo petsbrNo shoes inside the homebrPlease keep food and drinks off the bedsbrbrFor everyone’s safety, there is an exterior security camera on the propertybrWe host with a focus on cleanliness, clear communication, and a smooth stay from start to finish. If you have any questions before booking, send a message. brbr We’re happy to help, extended stays are subject to long term lease polices
Bed 2

Bed

Bath 2

Bath

Sleep 6

Sleeps

Slider Thumb
Exceptional(1)

$190.86

/ Nightly
Private Vacation Home

Funky Remodeled Otown Bungalow Sleeps 8

Winter Park, Florida, United States

This special place is close to everything, making it easy to plan your visit. The MillsHouse property is a convenient place to stay during your visit to Orlando, Winter Park, shopping, restaurants, bars, mills 50 and so much more!brbr3Min to major highwaysbr20Min to Universal Studiosbr4Min to Winter Park Golf Couse and Park Avenuebr6Min to Downtown Orlandobr30Minuts to Disneybr30Minutes to AirportbrbrLiving area - sleeper sofa with 55` Roku TV and large fireplace.brbrBedroom - the Quad, has 4 beds (2 twin bunks) so sleeps 4 guests. Equipped with 55` roku TV.brbrHallway - Desk workstation dedicated for cpu or laptop device. Also found here is a high table bartop for dining at. Seats 3.brbrKitchen ‍ ‍ - Microwave dishwasher, range, refrigerator, full size washer and dryer, large island and seperate countertop bar with seating for meals. brbrLiving area 2 - shared along side the kitchen is a sleeper sofa, love seat and 55` Roku TV.brbrBathroom 1 - full size bath with shower.brbrBedroom - Master bedroom, the room with queen bed, 55` smart TV and full ensuite bath equipped with a shower.brbrPatio - located off the master suitebrbrGazebo is located outside the gated patio and is for your use. There is also a common space with seating and soon to be bbq grill area that is shared by 4 guest units. We just ask you be mindful and considerate of other guests utilizing the space.brbrThe property is just blocks away from a supermarket, many restaurants, bars and shopping.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).brNo AnimalsbrNo Smoking - $500 penaltybrbrNo Eventsbrbr ✅ 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
Bed 2

Bed

Bath 2

Bath

Sleep 8

Sleeps

Home Most popular vacation rentals in Winter Park