Lake Maitland Rentals
From $124 per night (USD)VRBO
Stay near Winter Park action at our 2-bedroom apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In the heart of Winter Park, this charming 2-bedroom apartment offers non-stop chances for unwinding and exploring. Unwi ...
From $124 per night (USD)VRBO
From $140 per night (USD)Expedia
Three Blocks to Park Ave, 2 Blocks to WP Village!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two block ...
From $140 per night (USD)Expedia
From $156 per night (USD)VRBO
Mid Century Luxury, 1 block from Park Ave (#3)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This 2nd floor apartment is nestled under oaks on a quiet cobblestone street in downtown Winter Park. There are only 3 u ...
From $156 per night (USD)VRBO
From $156 per night (USD)Expedia
Mid Century Luxury, 1 block from Park Ave (#2)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This ground floor apartment is nestled under oaks on a cobblestone street in downtown Winter Park. There are only 3 unit ...
From $156 per night (USD)Expedia
From $155 per night (USD)VRBO
Winter Park charm. Close to Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Private 2 bedroom guest suite with its own entry and a separate sitting room. Tandem bedroom include 1 queen sized bed ...
From $155 per night (USD)VRBO
From $235 per night (USD)VRBO
2-bedroom vacation home on Lake, NON-SMOKERS only please
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
In our charming accommodations in exclusive Maitland neighborhood, you can easily reach all the popular spots in Orlando ...
From $235 per night (USD)VRBO
From $169 per night (USD)VRBO
Luxury Living Just 3 Blocks From Park Ave!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautiful Acacia wood flooring, with marble in the bathrooms and porcelain tile in the kitchen. Quartz countertops, ceil ...
From $169 per night (USD)VRBO
From $244 per night (USD)Expedia
Cute bungalow minutes walk from Park Avenue.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just what you have been waiting for; beautiful cottage home in the heart of Winter Park! 2 bedroom/2 bath only steps aw ...
From $244 per night (USD)Expedia
From $199 per night (USD)VRBO
Temporary living that feels like home where you can relax and be yourself.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Fully furnished, charming and comfortable, 4 bedroom - 2 bath, short-term home has new linens, new beds (1 King, 2 queen ...
From $199 per night (USD)VRBO
From $172 per night (USD)Expedia
Winter Park Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy your stay at the Winter Park Oasis! This cozy 2 bedroom private unit, is in a charming and historic neighborhood! ...
From $172 per night (USD)Expedia
From $183 per night (USD)VRBO
Modern Elegance In The Heart Of Winter Park - 2 beds\/2 baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Location!!! Beautifully appointed 2 bedroom, 2 bath second floor apartment overlooking a beautiful pool area with balcon ...
From $183 per night (USD)VRBO
From $201 per night (USD)Expedia
Winter Park Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Your backyard oasis awaits you, with queen size 10in memory foam swing mattress, full outdoor kitchen, 65in TV along wit ...
From $201 per night (USD)Expedia
From $208 per night (USD)VRBO
Just 3 Blocks to Park Ave Shops\/ Restaurants, 2 From The Winter Park Village!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Second floor penthouse unit overlooking the pool area. Gorgeous acacia wood floors, quartz c ...
From $208 per night (USD)VRBO
From $150 per night (USD)Expedia
LUXURY AND LOCATION!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Great Location! If you haven't explored Winter Park's Park Avenue, then you must! Three blocks to Park Ave and two block ...
From $150 per night (USD)Expedia
From $116 per night (USD)VRBO
Cozy and Chic Winter Park Studio which is conveniently located just for you
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Light, airy, and perfectly appointed studio. Enjoy this fully furnished and centrally-located location. This space provi ...
From $116 per night (USD)VRBO
From $286 per night (USD)VRBO
LUXURY 𝕄𝕚𝕕 ℂ𝕖𝕟𝕥𝕦𝕣𝕪 𝕄𝕠𝕕𝕖𝕣𝕟 ᴠᴀᴄᴀᴛɪᴏɴ in 𝒲𝒾𝓃𝓉𝑒𝓇 𝒫𝒶𝓇𝓀
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
NEW CONSTRUCTION Luxury Home north of Downtown Orlando in the heart of Winter Park steps from Winter Park Village near t ...
From $286 per night (USD)VRBO
From $250 per night (USD)VRBO
Modern, Charming Home in the heart of Winter Park- Perfect for a couples retreat or small group!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Escape to our charming 3BD/1BA home in Winter Park, FL—modern, cozy, and pet-friendly! Perfect for families, couples, an ...
From $250 per night (USD)VRBO
From $178 per night (USD)Expedia
Beautiful Mid Term Home in the Elegance of Winter Park!\n\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This newly renovated mid century split level home has all the modern ammenities of today with the charm and craftsmanshi ...
From $178 per night (USD)Expedia
From $112 per night (USD)VRBO
Modern Cuartito by Winter Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Cuartito is located near all major attractions the Orlando area has to offer. Below is a list of the top attraction ...
From $112 per night (USD)VRBO
From $130 per night (USD)Expedia
Charming 2BR\/2BA Winter Park Cottage, steps from Park Ave
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our charming 2-bedroom, 2-bathroom home nestled in the heart of Winter Park! Located just a short stroll away ...
From $130 per night (USD)Expedia
From $100 per night (USD)VRBO
Charming 4-bedroom House with WiFi, AC in welcome to Winter Park Area
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 1
Consider this house your home away from home while you visit Winter Park. This lovely property features 1 bedroom 1 Bath ...
From $100 per night (USD)VRBO
From $112 per night (USD)Expedia
Chris & Tish Cozy Apartment -2 bedroom and 4 bathrooms
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 4
Imagine a quiet, secluded- long driveway tucked away house. The Apartment is equipped with a full size Kitchen, washer ...
From $112 per night (USD)Expedia
From $98 per night (USD)VRBO
Chris & Tish Cozy Apartment 2 bedrooms, a bonus room. 2 beds for 3 people. Q&T
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Imagine a quiet, secluded-long driveway tucked away house. This apartment overseas the entire property. The apartment ...
From $98 per night (USD)VRBO
From $162 per night (USD)Expedia
Cozy 4-bedroom house with WiFi, AC in peaceful Winter Park
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this lovely house in Winter Park. With 4 bedrooms, including 3 queen beds and 1 king bed, this fantastic prop ...
From $162 per night (USD)Expedia
From $380 per night (USD)VRBO
Casa Jardin
- Bedrooms:
- 6
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedrooms with 3 bathrooms home overlooking an extra large backyard with a mature landscape surrounding the pool area. ...
From $380 per night (USD)VRBO
From $222 per night (USD)Expedia
Unit A Cheerful 2 Bedroom
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located place in the Heart of Maitland. Close to dining options, Enzian The ...
From $222 per night (USD)Expedia
From $320 per night (USD)VRBO
Unit B 2 Bedroom with Herb Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located place in the Heart of Maitland. Close to dining options, Enzian The ...
From $320 per night (USD)VRBO
From $110 per night (USD)Expedia
6 Mi to Downtown Orlando: Quiet Home w\/ Sunroom
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Soak up the Florida sun and explore the Orlando area with ease from this 2-bed, 1-bath vacation rental in Winter Park! Y ...
From $110 per night (USD)Expedia
From $115 per night (USD)VRBO
LOCATION! COZY COMFORT 2 BLOCKS FROM PARK AVE W POOL, HOT TUB AND GRILL STATION!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very com ...
From $115 per night (USD)VRBO
From $120 per night (USD)Expedia
Cozy Comfort Just 2 Blocks From Park Ave!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This duplex unit is cozy and comfortable. It's updated with all new appliances, is tastefully decorated and has very com ...
From $120 per night (USD)Expedia
From $125 per night (USD)VRBO
Light, Bright and Full of Delight! 2 Blocks to Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy this PRIVATE and Sparkling clean entire home, first floor 2 bedroom/1 full bath luxury apartment near Park Avenue! ...
From $125 per night (USD)VRBO
From $144 per night (USD)Expedia
Walk To Park Ave, Heated Pool, Hot Tub, Grill Station, Modern and Comfortable!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $144 per night (USD)Expedia
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A DEAL By The Month! Walk to Rollins & Park Ave
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
It's your own private one-room structure with a private entrance next to a parking space. It's much like a hotel room in ...
Click For PricingVRBO
From $246 per night (USD)Expedia
You're Pampered Here - Just 3 Blocks From Park Avenue!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, clean and unique. Fastest internet speed available: 139MBPS download and 21.5 MBPS upload! Second floor penthous ...
From $246 per night (USD)Expedia
From $122 per night (USD)VRBO
Walk The Downtown Village of Winter Park!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a downstairs end apartment with a back door that opens directly onto the pool deck near the hot tub. The apartme ...
From $122 per night (USD)VRBO
From $373 per night (USD)VRBO
Contemporary Award Winning Hotel w\/Rooftop Close to Parks & Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our 323 square foot King Room is appointed with handsome contemporary furnishings, including an armoire, mini fridge, fl ...
From $373 per night (USD)VRBO
From $375 per night (USD)VRBO
ADA Compliant Room - Contemporary Furnishings - Rooftop Pool - Close to Parks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our Classic King ADA is wheelchair-accessible. The room is appointed with handsome contemporary furnishings, including a ...
From $375 per night (USD)VRBO
From $408 per night (USD)VRBO
Private Balcony in Award Winning Hotel, Roof-top Pool, Close to Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Classic King with Balcony room measures 323 square feet and has the added feature of a balcony with French doors tha ...
From $408 per night (USD)VRBO
From $380 per night (USD)VRBO
Award Winning Boutique Hotel Close to Parks & Rollins College, Rooftop Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Classic Queen room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens and handsome c ...
From $380 per night (USD)VRBO
From $414 per night (USD)VRBO
Private Balcony - Award Winning Accommodations w\/Rooftop Pool, Close to Parks!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our Classic Queen with Balcony room is 358 square feet and appointed with two pillowtop Queen size beds, luxury linens a ...
From $414 per night (USD)VRBO
From $442 per night (USD)VRBO
Rooftop Pool, Close to Parks & Rollins College - Award Winning Accommodations
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $442 per night (USD)VRBO
From $488 per night (USD)VRBO
Large Room Award Winning Hotel w\/Rooftop Pool - Close to Parks & Rollins College
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our Parlor King is a larger room at 435 square feet and features a separate Parlor seating area with a sleeper sofa and ...
From $488 per night (USD)VRBO
From $449 per night (USD)VRBO
ADA Compliant Room in Award Winning Hotel w\/Rooftop Pool - Close to Parks!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Our Premier ADA Queen is a larger room at 448 square feet and is wheelchair-accessible. The room features an additional ...
From $449 per night (USD)VRBO
From $11422 per night (USD)VRBO
Queen Room Near All Saints Episcopal Church ORL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Winter Park, Florida, This property offers free WiFi and an outdoor pool. Rollins College is located 650 metr ...
From $11422 per night (USD)VRBO
From $237 per night (USD)VRBO
Lake Front Home near Winter Park!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Beautiful Casita Eulalia located north of Downtown Orlando in the heart of Maitland FL. This Casita is the pe ...
From $237 per night (USD)VRBO