Airbnb Properties for Sale in Winter Park, FL

Looking for a vacation rental investment in Winter Park, FL with high ROI ?

Explore a range of newly added short-term rental homes in Winter Park, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winter Park, FL

Q: How to get Winter-park, FL Airbnb data?

Airbnb data on vacation rentals in Winter-park, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter-park, FL market insights, guest information and booking details, seasonality trends and historical Winter-park, FL Airbnb performance data .

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2607 Lafayette Ave Winter Park, FL Welcome to 2607 Lafayette Avenueâa stunning custom home in one of Winter Parkâs most d...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,095,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 1.34% Airbnb Rental Income: $5745 Traditional Rental Income: $3752 Airbnb ROI: 2.17% Traditional ROI: 1.34%
151 N ORLANDO AVENUE #101 Winter Park, FL Welcome home to this beautiful 2-bedroom, 1-bath gem in the heart of Winter Park! Nestled ...	2 beds \| 1 baths \| 804 sq.ft.	$260,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 3.63% Airbnb Rental Income: $3260 Traditional Rental Income: $1551 Airbnb ROI: 7.61% Traditional ROI: 3.63%
3018 NORTHWOOD BOULEVARD Winter Park, FL One or more photo(s) has been virtually staged. "MOVE-IN READY", 3-BED, 2-FULL BATHS, SING...	3 beds \| 2 baths \| 1,761 sq.ft.	$734,000	Airbnb cash on cash: 2.97% Traditional cash on cash: 2.29% Airbnb Rental Income: $4337 Traditional Rental Income: $2958 Airbnb ROI: 2.97% Traditional ROI: 2.29%
1608 BOMI CIRCLE Winter Park, FL Your beautifully upgraded home in Winter Park with NO HOA is waiting for you! Centrally lo...	3 beds \| 2 baths \| 1,807 sq.ft.	$475,000	Airbnb cash on cash: 6.12% Traditional cash on cash: 4.18% Airbnb Rental Income: $4337 Traditional Rental Income: $2563 Airbnb ROI: 6.12% Traditional ROI: 4.18%
2774 BRIGHT BIRD LANE Winter Park, FL Motivated seller! Brand new townhouse professionally decorated, and available today! Built...	3 beds \| 3 baths \| 1,907 sq.ft.	$465,000	Airbnb cash on cash: 5.48% Traditional cash on cash: 3.45% Airbnb Rental Income: $4337 Traditional Rental Income: $2540 Airbnb ROI: 5.48% Traditional ROI: 3.45%
1660 WALNUT AVENUE Winter Park, FL Under Construction. Elegant and modern new construction home perfectly situated in beautif...	4 beds \| 4 baths \| 2,172 sq.ft.	$1,759,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 0.67% Airbnb Rental Income: $5745 Traditional Rental Income: $3477 Airbnb ROI: 1.35% Traditional ROI: 0.67%
2033 CANNY COVE Winter Park, FL Step into this stunning townhome and be greeted by an open-concept kitchen, dining, and li...	3 beds \| 3 baths \| 1,907 sq.ft.	$432,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 2.6% Airbnb Rental Income: $4337 Traditional Rental Income: $2540 Airbnb ROI: 4.79% Traditional ROI: 2.6%
625 BRECHIN DRIVE Winter Park, FL PICTURE PERFECT HOME IN WINTER PARKâS KENILWORTH SHORES! Homes of this quality and prese...	3 beds \| 2 baths \| 1,827 sq.ft.	$765,000	Airbnb cash on cash: 3.32% Traditional cash on cash: 1.99% Airbnb Rental Income: $4337 Traditional Rental Income: $2479 Airbnb ROI: 3.32% Traditional ROI: 1.99%
720 N PENNSYLVANIA AVENUE Winter Park, FL Nestled in one of Winter Parkâs most sought-after locations, this 3-bedroom, 2-bathroom ...	3 beds \| 2 baths \| 1,115 sq.ft.	$550,000	Airbnb cash on cash: 4.56% Traditional cash on cash: 1.6% Airbnb Rental Income: $4337 Traditional Rental Income: $1903 Airbnb ROI: 4.56% Traditional ROI: 1.6%
726 N PENNSYLVANIA AVENUE Winter Park, FL Welcome to this beautifully designed 3-bedroom, 2-bathroom home, offering a blend of moder...	3 beds \| 2 baths \| 1,167 sq.ft.	$695,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 1.13% Airbnb Rental Income: $4337 Traditional Rental Income: $1931 Airbnb ROI: 3.43% Traditional ROI: 1.13%
726 And 720 N PENNSYLVANIA AVENUE Winter Park, FL Welcome to this exceptional duplex, a rare gem in Winter Park offering unmatched flexibili...	6 beds \| N/A baths \| 2,284 sq.ft.	$1,215,000	Airbnb cash on cash: 0.33% Traditional cash on cash: -0.02% Airbnb Rental Income: $3260 Traditional Rental Income: $2125 Airbnb ROI: 0.33% Traditional ROI: -0.02%
607 DUNBLANE DRIVE Winter Park, FL Welcome to this beautifully renovated 4-bedroom, 2.5-bath home in the heart of Winter Park...	4 beds \| 3 baths \| 2,046 sq.ft.	$675,000	Airbnb cash on cash: 4.98% Traditional cash on cash: 2.66% Airbnb Rental Income: $5745 Traditional Rental Income: $3136 Airbnb ROI: 4.98% Traditional ROI: 2.66%
101 S INTERLACHEN AVENUE #104 Winter Park, FL FIRST TIME ON THE MARKET! ULTRA-RARE GROUND FLOOR CONDO IN DOWNTOWN WINTER PARK'S LACHEN H...	2 beds \| 2 baths \| 949 sq.ft.	$635,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 0.77% Airbnb Rental Income: $3260 Traditional Rental Income: $1543 Airbnb ROI: 2.43% Traditional ROI: 0.77%
1360 FORMOSA AVENUE Winter Park, FL Discover a rare and lucrative opportunity at 1360 Formosa Ave, a corner lot triplex in the...	3 beds \| N/A baths \| 1,890 sq.ft.	$625,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 1.37% Airbnb Rental Income: $4337 Traditional Rental Income: $2251 Airbnb ROI: 3.39% Traditional ROI: 1.37%
1564 CAVENDISH ROAD Winter Park, FL Charming 3BR bungalow in sought-after Orwin Manor with timeless appeal and tons of potenti...	3 beds \| 1 baths \| 1,140 sq.ft.	$450,000	Airbnb cash on cash: 5.72% Traditional cash on cash: 1.95% Airbnb Rental Income: $4337 Traditional Rental Income: $1838 Airbnb ROI: 5.72% Traditional ROI: 1.95%
701 DENTON ROAD Winter Park, FL Motivated Seller! Contact us today. Welcome to this beautifully upgraded home in Winter Pa...	3 beds \| 2 baths \| 2,268 sq.ft.	$565,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 3.44% Airbnb Rental Income: $4337 Traditional Rental Income: $3016 Airbnb ROI: 4.22% Traditional ROI: 3.44%
2500 LEE ROAD #208 Winter Park, FL This charming two-bedroom, two-bathroom 2nd floor condo offers the perfect blend of comfor...	2 beds \| 2 baths \| 956 sq.ft.	$195,000	Airbnb cash on cash: 9.06% Traditional cash on cash: 5.06% Airbnb Rental Income: $3260 Traditional Rental Income: $1786 Airbnb ROI: 9.06% Traditional ROI: 5.06%
3601 MIDIRON DRIVE Winter Park, FL BUILD YOUR DREAM HOME IN WINTER PARK! Nestled directly across from the historic Dubsdread...	2 beds \| 1 baths \| 954 sq.ft.	$459,000	Airbnb cash on cash: 3.36% Traditional cash on cash: 1.18% Airbnb Rental Income: $3260 Traditional Rental Income: $1593 Airbnb ROI: 3.36% Traditional ROI: 1.18%
2487 HARBOUR WAY Winter Park, FL Unmissable opportunity in Winter Park! Beautiful house for sale with 3 bedrooms and 3 ...	3 beds \| 3 baths \| 1,803 sq.ft.	$319,900	Airbnb cash on cash: 8.38% Traditional cash on cash: 4.94% Airbnb Rental Income: $4337 Traditional Rental Income: $2390 Airbnb ROI: 8.38% Traditional ROI: 4.94%
1399 ALOMA AVENUE Winter Park, FL *Price Adjustment * Charming 1948 Winter Park Home! This 3-bedroom, 2-bathroom gem is ...	3 beds \| 2 baths \| 1,804 sq.ft.	$665,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.68% Airbnb Rental Income: $4337 Traditional Rental Income: $2575 Airbnb ROI: 4.06% Traditional ROI: 2.68%
151 N ORLANDO AVENUE #204 Winter Park, FL One or more photo(s) has been virtually staged. Investors Dream with Minimal Lease Restric...	2 beds \| 1 baths \| 710 sq.ft.	$229,000	Airbnb cash on cash: 6.81% Traditional cash on cash: 3.41% Airbnb Rental Income: $3260 Traditional Rental Income: $1790 Airbnb ROI: 6.81% Traditional ROI: 3.41%
541 W CANTON AVENUE Winter Park, FL Timeless elegance meets boutique craftsmanship at 541 W Canton Avenueâan exceptional new...	4 beds \| 4 baths \| 3,553 sq.ft.	$2,935,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 0.46% Airbnb Rental Income: $5745 Traditional Rental Income: $4490 Airbnb ROI: 0.5% Traditional ROI: 0.46%
311 E MORSE BOULEVARD #7-5 Winter Park, FL Major Price Improvement! Here is your rare opportunity to own a studio apartment in Whispe...	1 beds \| 1 baths \| 482 sq.ft.	$359,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 1.77% Airbnb Rental Income: $2412 Traditional Rental Income: $1343 Airbnb ROI: 3.19% Traditional ROI: 1.77%
151 N ORLANDO AVENUE #118 Winter Park, FL Investment opportunity! Discover this hidden gemâa 2-bed, 1-bath condo nestled in the he...	2 beds \| 1 baths \| 710 sq.ft.	$299,999	Airbnb cash on cash: 6.61% Traditional cash on cash: 3.36% Airbnb Rental Income: $3260 Traditional Rental Income: $1610 Airbnb ROI: 6.61% Traditional ROI: 3.36%
2835 BONGART ROAD Winter Park, FL Seller is Motivated, must sell NOW! - Welcome to your spectacular pool home in Winter Park...	3 beds \| 3 baths \| 1,880 sq.ft.	$449,900	Airbnb cash on cash: 6.4% Traditional cash on cash: 5.97% Airbnb Rental Income: $4337 Traditional Rental Income: $3245 Airbnb ROI: 6.4% Traditional ROI: 5.97%
225 LEWFIELD CIRCLE #225 Winter Park, FL One or more photo(s) has been virtually staged. **This property qualifies for a closing co...	2 beds \| 2 baths \| 953 sq.ft.	$200,000	Airbnb cash on cash: 8.6% Traditional cash on cash: 3.28% Airbnb Rental Income: $3260 Traditional Rental Income: $1518 Airbnb ROI: 8.6% Traditional ROI: 3.28%
151 N ORLANDO AVENUE #212 Winter Park, FL Experience luxury lakefront living in this stunning and truly unique 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 1,875 sq.ft.	$570,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 1.41% Airbnb Rental Income: $4337 Traditional Rental Income: $2846 Airbnb ROI: 2.5% Traditional ROI: 1.41%
2500 LEE ROAD #243 Winter Park, FL Reasons you'll love this condo: convenient, cozy and quiet, you can't beat this community ...	1 beds \| 1 baths \| 645 sq.ft.	$145,000	Airbnb cash on cash: 8.17% Traditional cash on cash: 5.62% Airbnb Rental Income: $2412 Traditional Rental Income: $1467 Airbnb ROI: 8.17% Traditional ROI: 5.62%
2922 REEF KNOT PLACE Winter Park, FL One or more photo(s) has been virtually staged. Stunning Lakefront Living in an Exclusive ...	4 beds \| 4 baths \| 3,153 sq.ft.	$1,295,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 1.63% Airbnb Rental Income: $5745 Traditional Rental Income: $4439 Airbnb ROI: 1.76% Traditional ROI: 1.63%
446 ALBERTA DRIVE Winter Park, FL Charming Opportunity in Prime Winter Park â 446 Alberta Drive, Winter Park, FL! First t...	4 beds \| 3 baths \| 3,263 sq.ft.	$1,750,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.84% Airbnb Rental Income: $5745 Traditional Rental Income: $3714 Airbnb ROI: 1.39% Traditional ROI: 0.84%
240 KILLARNEY BAY COURT #4 Winter Park, FL Welcome to Killarney BayâWinter Parkâs best-kept secret for tranquil lakeside living, ...	2 beds \| 3 baths \| 1,536 sq.ft.	$399,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 3.01% Airbnb Rental Income: $3260 Traditional Rental Income: $2209 Airbnb ROI: 3.86% Traditional ROI: 3.01%
3110 HEARTLEAF PLACE Winter Park, FL Beautiful pool home with an open great room plan with high vaulted ceilings and master on ...	4 beds \| 3 baths \| 2,860 sq.ft.	$619,988	Airbnb cash on cash: 5.64% Traditional cash on cash: 4.52% Airbnb Rental Income: $5745 Traditional Rental Income: $3952 Airbnb ROI: 5.64% Traditional ROI: 4.52%
3115 HEARTLEAF PLACE Winter Park, FL One or more photo(s) has been virtually staged. Back on the market as previous buyers fina...	4 beds \| 3 baths \| 2,846 sq.ft.	$610,000	Airbnb cash on cash: 6.16% Traditional cash on cash: 4.07% Airbnb Rental Income: $5745 Traditional Rental Income: $3409 Airbnb ROI: 6.16% Traditional ROI: 4.07%
150 KILLARNEY BAY COURT #5 Winter Park, FL Tucked away in the hidden gem of Killarney Bay, this move-in ready condo offers the perfec...	2 beds \| 2 baths \| 1,140 sq.ft.	$355,000	Airbnb cash on cash: 4.66% Traditional cash on cash: 2.33% Airbnb Rental Income: $3260 Traditional Rental Income: $1751 Airbnb ROI: 4.66% Traditional ROI: 2.33%
3425 FERNDELL DRIVE Winter Park, FL Fully Renovated Gem in Winter Park! Welcome to your dream home in one of Central Floridaâ...	3 beds \| 2 baths \| 1,516 sq.ft.	$409,000	Airbnb cash on cash: 6.77% Traditional cash on cash: 3.46% Airbnb Rental Income: $4337 Traditional Rental Income: $2155 Airbnb ROI: 6.77% Traditional ROI: 3.46%
1713 W CHERYL DRIVE Winter Park, FL Pool Rescreen coming! Welcome to Winter Park luxury living in the sought-after Carolyn Est...	4 beds \| 2 baths \| 2,030 sq.ft.	$525,000	Airbnb cash on cash: 7.29% Traditional cash on cash: 4.37% Airbnb Rental Income: $5745 Traditional Rental Income: $3164 Airbnb ROI: 7.29% Traditional ROI: 4.37%
1849 VIBURNUM LANE Winter Park, FL Nestled near the highly sought-after Winter Park area, this beautifully updated 4-bedroom,...	4 beds \| 2 baths \| 1,627 sq.ft.	$425,000	Airbnb cash on cash: 9.46% Traditional cash on cash: 3.75% Airbnb Rental Income: $5745 Traditional Rental Income: $2323 Airbnb ROI: 9.46% Traditional ROI: 3.75%
3019 ANTIQUE OAKS CIRCLE #124 Winter Park, FL Investment Opportunity calling you!! Are you looking to start a portfolio of properties wi...	1 beds \| 1 baths \| 749 sq.ft.	$158,500	Airbnb cash on cash: 6.94% Traditional cash on cash: 5.92% Airbnb Rental Income: $2412 Traditional Rental Income: $1666 Airbnb ROI: 6.94% Traditional ROI: 5.92%
Lot #21 KAROLINA AVE Winter Park, FL Pre-Construction. To be built. Step into a life where charm meets convenience in the heart...	4 beds \| 4 baths \| 2,662 sq.ft.	$916,050	Airbnb cash on cash: 4.04% Traditional cash on cash: 2.83% Airbnb Rental Income: $5745 Traditional Rental Income: $3560 Airbnb ROI: 4.04% Traditional ROI: 2.83%
1981 BLUE RIDGE ROAD Winter Park, FL One or more photo(s) has been virtually staged. **This house comes with a REDUCED RATE thr...	4 beds \| 2 baths \| 2,750 sq.ft.	$1,199,900	Airbnb cash on cash: 2.74% Traditional cash on cash: 1.06% Airbnb Rental Income: $5745 Traditional Rental Income: $2726 Airbnb ROI: 2.74% Traditional ROI: 1.06%

Vacation Rentals in Winter Park

There are 130 vacation rental properties available for sale in the city of Winter Park . The median list price of Airbnb properties available for sale in Winter Park is $565,000 and the average price per square foot is $271. The cash on cash return on vacation rentals in Winter Park is 5.00%. The average monthly short term rental income in Winter Park is $4,337.

Winter Park, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 130 Airbnb properties available for sale in Winter Park.

In 2025, the best neighborhood to buy short term rental property is Winter Park.

In December 2025, the average Airbnb occupancy rate in Winter Park is 86%.

Airbnb data on vacation rentals in Winter Park, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winter Park, FL market insights, guest information and booking details, seasonality trends and historical Winter Park, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winter Park, FL

2607 Lafayette Ave

Winter Park, FL

4 beds | 4 baths | 2,770 sq.ft.

$1,095,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $5745

Traditional Rental Income: $3752

Airbnb ROI: 2.17%

Traditional ROI: 1.34%

151 N ORLANDO AVENUE #101

Winter Park, FL

2 beds | 1 baths | 804 sq.ft.

$260,000

Airbnb cash on cash: 7.61%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $3260

Traditional Rental Income: $1551

Airbnb ROI: 7.61%

Traditional ROI: 3.63%

3018 NORTHWOOD BOULEVARD

Winter Park, FL

3 beds | 2 baths | 1,761 sq.ft.

$734,000

Airbnb cash on cash: 2.97%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $4337

Traditional Rental Income: $2958

Airbnb ROI: 2.97%

Traditional ROI: 2.29%

1608 BOMI CIRCLE

Winter Park, FL

3 beds | 2 baths | 1,807 sq.ft.

$475,000

Airbnb cash on cash: 6.12%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $4337

Traditional Rental Income: $2563

Airbnb ROI: 6.12%

Traditional ROI: 4.18%

2774 BRIGHT BIRD LANE

Winter Park, FL

3 beds | 3 baths | 1,907 sq.ft.

$465,000

Airbnb cash on cash: 5.48%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $4337

Traditional Rental Income: $2540

Airbnb ROI: 5.48%

Traditional ROI: 3.45%

1660 WALNUT AVENUE

Winter Park, FL

4 beds | 4 baths | 2,172 sq.ft.

$1,759,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 0.67%

Airbnb Rental Income: $5745

Traditional Rental Income: $3477

Airbnb ROI: 1.35%

Traditional ROI: 0.67%

2033 CANNY COVE

Winter Park, FL

3 beds | 3 baths | 1,907 sq.ft.

$432,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $4337

Traditional Rental Income: $2540

Airbnb ROI: 4.79%

Traditional ROI: 2.6%

625 BRECHIN DRIVE

Winter Park, FL

3 beds | 2 baths | 1,827 sq.ft.

$765,000

Airbnb cash on cash: 3.32%

Traditional cash on cash: 1.99%

Airbnb Rental Income: $4337

Traditional Rental Income: $2479

Airbnb ROI: 3.32%