Airbnb Properties for Sale in Maitland, FL

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

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

Airbnb For Sale in Maitland, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2517 CAPER LANE #207 Maitland, FL One or more photo(s) has been virtually staged. Charming 1 Bedroom, 1 Bathroom condo in be...	1 beds \| 1 baths \| 550 sq.ft.	$120,000	Airbnb cash on cash: 8.64% Traditional cash on cash: 8.14% Airbnb Rental Income: $1832 Traditional Rental Income: $1280 Airbnb ROI: 8.64% Traditional ROI: 8.14%
1521 OXFORD ROAD Maitland, FL Under contract-accepting backup offers. Welcome to 1521 Oxford Rd - here's your opportunit...	4 beds \| 2 baths \| 1,925 sq.ft.	$468,900	Airbnb cash on cash: 6.9% Traditional cash on cash: 4.26% Airbnb Rental Income: $5007 Traditional Rental Income: $2826 Airbnb ROI: 6.9% Traditional ROI: 4.26%
1000 WINDERLEY PLACE #122 Maitland, FL Under contract-accepting backup offers. MOVE-IN READY FIRST-FLOOR OASIS AT SUN BAY CLUB! D...	2 beds \| 2 baths \| 1,164 sq.ft.	$279,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 1.98% Airbnb Rental Income: $2379 Traditional Rental Income: $1716 Airbnb ROI: 2.28% Traditional ROI: 1.98%
162 ORANGE PLACE Maitland, FL This beautiful 3/2 Maitland home has been meticulously cared for. It boast original hardwo...	3 beds \| 2 baths \| 1,624 sq.ft.	$599,900	Airbnb cash on cash: 3.16% Traditional cash on cash: 2.41% Airbnb Rental Income: $3440 Traditional Rental Income: $2261 Airbnb ROI: 3.16% Traditional ROI: 2.41%
824 TOWN CIRCLE #101 Maitland, FL Move-in ready two story townhome. This beautifully updated 3 bd 2.5 ba townhome is located...	3 beds \| 3 baths \| 1,565 sq.ft.	$290,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 3.9% Airbnb Rental Income: $3440 Traditional Rental Income: $2200 Airbnb ROI: 5.65% Traditional ROI: 3.9%
1375 LAKE SHADOW CIRCLE #11208 Maitland, FL Step into comfort and ease with this charming 2-bedroom, 1-bath condo at 1375 Lake Shadow ...	2 beds \| 1 baths \| 898 sq.ft.	$205,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 2.61% Airbnb Rental Income: $2379 Traditional Rental Income: $1449 Airbnb ROI: 4.38% Traditional ROI: 2.61%
2133 KORAT LANE Maitland, FL Exceptional Value New Reduced price $514,900 Great Style, great space, prime loca...	4 beds \| 3 baths \| 2,359 sq.ft.	$514,900	Airbnb cash on cash: 5.81% Traditional cash on cash: 4.28% Airbnb Rental Income: $5007 Traditional Rental Income: $3249 Airbnb ROI: 5.81% Traditional ROI: 4.28%
2525 CAPER LANE #205 Maitland, FL Condo features plenty of natural light, full side kitchen, bathroom with bathtub shower co...	1 beds \| 1 baths \| 550 sq.ft.	$125,000	Airbnb cash on cash: 6.18% Traditional cash on cash: 5.3% Airbnb Rental Income: $1832 Traditional Rental Income: $1232 Airbnb ROI: 6.18% Traditional ROI: 5.3%
505 LAKE SHORE DRIVE Maitland, FL Imagine mornings with the sunrise shimmering across Lake Faith, directly across the street...	4 beds \| 2 baths \| 2,317 sq.ft.	$600,000	Airbnb cash on cash: 5.58% Traditional cash on cash: 3.5% Airbnb Rental Income: $5007 Traditional Rental Income: $2823 Airbnb ROI: 5.58% Traditional ROI: 3.5%
249 SPARTAN DRIVE Maitland, FL Discover Your Perfect Maitland Retreat! Tucked away on a quiet dead-end street, this deli...	4 beds \| 2 baths \| 1,579 sq.ft.	$349,900	Airbnb cash on cash: 9.6% Traditional cash on cash: 4.44% Airbnb Rental Income: $5007 Traditional Rental Income: $2287 Airbnb ROI: 9.6% Traditional ROI: 4.44%
2047 HOWELL BRANCH ROAD Maitland, FL Under contract-accepting backup offers. The home youâve been searching for has officiall...	4 beds \| 2 baths \| 2,960 sq.ft.	$1,499,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 0.6% Airbnb Rental Income: $5007 Traditional Rental Income: $3284 Airbnb ROI: 1.1% Traditional ROI: 0.6%
1434 WINSTON ROAD Maitland, FL Welcome to 1434 Winston Road, located in Seminole Countyâs desirable English Estates nei...	4 beds \| 2 baths \| 2,312 sq.ft.	$579,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 3.82% Airbnb Rental Income: $5007 Traditional Rental Income: $3252 Airbnb ROI: 5.17% Traditional ROI: 3.82%
1150 LAKE SHADOW CIRCLE #3104 Maitland, FL One or more photo(s) has been virtually staged. SELLER'S PREFERRED LENDER IS OFFERING UP T...	2 beds \| 2 baths \| 1,048 sq.ft.	$230,000	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.94% Airbnb Rental Income: $2379 Traditional Rental Income: $1602 Airbnb ROI: 3.82% Traditional ROI: 2.94%
2031 EATON STREET Maitland, FL 2.99% Assumable Mortgage Rate Available Welcome to 2031 Eaton Street, a modern haven wit...	4 beds \| 3 baths \| 2,518 sq.ft.	$424,000	Airbnb cash on cash: 8.07% Traditional cash on cash: 5.19% Airbnb Rental Income: $5007 Traditional Rental Income: $2838 Airbnb ROI: 8.07% Traditional ROI: 5.19%
1460 LAKE SHADOW CIRCLE #7204 Maitland, FL Resort style living in this sought after gated community located near the Maitland Exchang...	3 beds \| 2 baths \| 1,243 sq.ft.	$239,900	Airbnb cash on cash: 6.93% Traditional cash on cash: 3.55% Airbnb Rental Income: $3440 Traditional Rental Income: $1911 Airbnb ROI: 6.93% Traditional ROI: 3.55%
214 CHERRYWOOD DRIVE Maitland, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	3 beds \| 2 baths \| 1,178 sq.ft.	$345,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 4.74% Airbnb Rental Income: $3440 Traditional Rental Income: $2281 Airbnb ROI: 5.96% Traditional ROI: 4.74%
2350 DERBYSHIRE ROAD Maitland, FL Under contract-accepting backup offers. Thereâs a quiet confidence to this one. The kind...	4 beds \| 2 baths \| 2,359 sq.ft.	$590,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 3.01% Airbnb Rental Income: $5007 Traditional Rental Income: $2988 Airbnb ROI: 4.82% Traditional ROI: 3.01%
113 GEM LAKE DRIVE Maitland, FL Must remodel this 1939 home that was moved from Park Avenue many years ago but now rests i...	3 beds \| 2 baths \| 1,538 sq.ft.	$575,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 3.05% Airbnb Rental Income: $3440 Traditional Rental Income: $2328 Airbnb ROI: 3.7% Traditional ROI: 3.05%
240 PEOPLE STREET Maitland, FL Under contract-accepting backup offers. Short Sale. Short sale. List price is a bank appro...	3 beds \| 2 baths \| 1,287 sq.ft.	$243,380	Airbnb cash on cash: 8.29% Traditional cash on cash: 5.37% Airbnb Rental Income: $3440 Traditional Rental Income: $2007 Airbnb ROI: 8.29% Traditional ROI: 5.37%
404 BANYON TREE CIRCLE #200 Maitland, FL Welcome to this spacious 1,612 sq. ft. condo, perfectly located for both convenience and l...	3 beds \| 2 baths \| 1,612 sq.ft.	$197,000	Airbnb cash on cash: 7.7% Traditional cash on cash: 5.19% Airbnb Rental Income: $3440 Traditional Rental Income: $2208 Airbnb ROI: 7.7% Traditional ROI: 5.19%
1221 THUNDER TRAIL Maitland, FL Don't miss out on this AMAZING Maitland home for under $450k! NEW roof in 2023 and HVAC 20...	3 beds \| 2 baths \| 1,908 sq.ft.	$440,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 4.02% Airbnb Rental Income: $3440 Traditional Rental Income: $2377 Airbnb ROI: 4.75% Traditional ROI: 4.02%
380 BANYAN DRIVE Maitland, FL Charming 3BR/2BA Home with Updated Interior This move-in ready home features 3 bedrooms...	3 beds \| 2 baths \| 1,404 sq.ft.	$469,000	Airbnb cash on cash: 4.64% Traditional cash on cash: 3.22% Airbnb Rental Income: $3440 Traditional Rental Income: $2055 Airbnb ROI: 4.64% Traditional ROI: 3.22%
711 THOMPSON AVENUE Maitland, FL Come see this beautifully remodeled 3-bedroom, 1-bath home near the heart of Maitland! Thi...	3 beds \| 1 baths \| 1,056 sq.ft.	$289,000	Airbnb cash on cash: 8.24% Traditional cash on cash: 4.6% Airbnb Rental Income: $3440 Traditional Rental Income: $1687 Airbnb ROI: 8.24% Traditional ROI: 4.6%
2329 SHADOW VIEW CIRCLE #2329 Maitland, FL Welcome to this stunning, fully renovated 3-Bedroom, 2.5-Bath home located in the desirab...	3 beds \| 3 baths \| 1,583 sq.ft.	$325,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 2.7% Airbnb Rental Income: $3440 Traditional Rental Income: $2169 Airbnb ROI: 4.37% Traditional ROI: 2.7%
530 RUFFEL STREET Maitland, FL Great property to add to your investment portfolio. This 3 bed 1 1/2 bath with family room...	3 beds \| 2 baths \| 1,449 sq.ft.	$249,900	Airbnb cash on cash: 9.1% Traditional cash on cash: 6.74% Airbnb Rental Income: $3440 Traditional Rental Income: $2122 Airbnb ROI: 9.1% Traditional ROI: 6.74%
385 LIME STREET Maitland, FL Wonderful investment opportunity in historic Eatonville. Large corner lot. The roof was re...	4 beds \| N/A baths \| 1,680 sq.ft.	$419,900	Airbnb cash on cash: 4.89% Traditional cash on cash: 3.38% Airbnb Rental Income: $3440 Traditional Rental Income: $2082 Airbnb ROI: 4.89% Traditional ROI: 3.38%
1913 POINSETTA LANE Maitland, FL Motivated Seller â Stylishly Renovated 4-Bedroom Home in Prime Maitland Location! Donâ...	4 beds \| 2 baths \| 1,664 sq.ft.	$449,500	Airbnb cash on cash: 7.9% Traditional cash on cash: 4.12% Airbnb Rental Income: $5007 Traditional Rental Income: $2394 Airbnb ROI: 7.9% Traditional ROI: 4.12%
1325 LAKE SHADOW CIRCLE #12303 Maitland, FL Welcome to carefree living in the sought-after Visconti community of Maitland! This beauti...	2 beds \| 2 baths \| 1,048 sq.ft.	$215,000	Airbnb cash on cash: 4.37% Traditional cash on cash: 3.48% Airbnb Rental Income: $2379 Traditional Rental Income: $1614 Airbnb ROI: 4.37% Traditional ROI: 3.48%
2031 Warrens Avenue Maitland, FL Ready for a weekend project with big upside? With a little love and light renovations, 203...	2 beds \| 1 baths \| 520 sq.ft.	$169,900	Airbnb cash on cash: 8.62% Traditional cash on cash: 6.33% Airbnb Rental Income: $2379 Traditional Rental Income: $1423 Airbnb ROI: 8.62% Traditional ROI: 6.33%
1470 WINSTON ROAD Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Se...	4 beds \| 2 baths \| 2,090 sq.ft.	$450,000	Airbnb cash on cash: 7.61% Traditional cash on cash: 5.24% Airbnb Rental Income: $5007 Traditional Rental Income: $2982 Airbnb ROI: 7.61% Traditional ROI: 5.24%
736 FOREST GLEN COURT Maitland, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-b...	4 beds \| 2 baths \| 1,647 sq.ft.	$499,999	Airbnb cash on cash: 6.31% Traditional cash on cash: 3.38% Airbnb Rental Income: $5007 Traditional Rental Income: $2614 Airbnb ROI: 6.31% Traditional ROI: 3.38%
1277 BLESSING STREET Maitland, FL This is a well-located townhome in the gated community of Montacino. The unit has been ref...	3 beds \| 3 baths \| 1,751 sq.ft.	$399,990	Airbnb cash on cash: 3.25% Traditional cash on cash: 2.28% Airbnb Rental Income: $3440 Traditional Rental Income: $2314 Airbnb ROI: 3.25% Traditional ROI: 2.28%
2155 FENNELL STREET Maitland, FL This is a three-bedroom two-bathroom pool house well located that needs some tender love a...	3 beds \| 2 baths \| 1,822 sq.ft.	$395,000	Airbnb cash on cash: 5.35% Traditional cash on cash: 5.11% Airbnb Rental Income: $3440 Traditional Rental Income: $2589 Airbnb ROI: 5.35% Traditional ROI: 5.11%
305 WEST LAKE FAITH DRIVE #139 Maitland, FL This impeccable first-floor corner unit features an abundance of natural lighting that cre...	3 beds \| 2 baths \| 1,739 sq.ft.	$305,000	Airbnb cash on cash: 5.21% Traditional cash on cash: 3.7% Airbnb Rental Income: $3440 Traditional Rental Income: $2243 Airbnb ROI: 5.21% Traditional ROI: 3.7%
2220 DERBYSHIRE ROAD Maitland, FL Under contract-accepting backup offers. Welcome to 2220 Derbyshire Road, located in the hi...	4 beds \| 2 baths \| 2,220 sq.ft.	$515,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 4.33% Airbnb Rental Income: $5007 Traditional Rental Income: $3158 Airbnb ROI: 6.05% Traditional ROI: 4.33%
125 WHITE OAK CIRCLE Maitland, FL One or more photo(s) has been virtually staged. Welcome to 125 White Oak Circleâa rare o...	4 beds \| 3 baths \| 2,524 sq.ft.	$825,000	Airbnb cash on cash: 2.88% Traditional cash on cash: 1.94% Airbnb Rental Income: $5007 Traditional Rental Income: $3259 Airbnb ROI: 2.88% Traditional ROI: 1.94%
1140 S ORLANDO AVENUE #I-5 Maitland, FL Be the first to explore this brand new to the market, first time available in years. Disc...	2 beds \| 1 baths \| 816 sq.ft.	$190,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 2.84% Airbnb Rental Income: $2379 Traditional Rental Income: $1414 Airbnb ROI: 4.94% Traditional ROI: 2.84%
2491 LAUDER DRIVE Maitland, FL Nestled on a spacious corner lot in the highly sought-after Dommerich/Highland Park neighb...	5 beds \| 3 baths \| 2,695 sq.ft.	$695,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.58% Airbnb Rental Income: $5533 Traditional Rental Income: $3942 Airbnb ROI: 4.32% Traditional ROI: 3.58%
449 FORESTWOOD LANE Maitland, FL STONEWOOD. This desirable community is located in Maitland, Seminole County City limits. T...	4 beds \| 2 baths \| 2,532 sq.ft.	$575,000	Airbnb cash on cash: 4.89% Traditional cash on cash: 3.18% Airbnb Rental Income: $5007 Traditional Rental Income: $3068 Airbnb ROI: 4.89% Traditional ROI: 3.18%
2132 TORTOISE SHELL DRIVE Maitland, FL Under contract-accepting backup offers. Welcome to this beautifully maintained 4-bedroom, ...	4 beds \| 2 baths \| 1,809 sq.ft.	$425,000	Airbnb cash on cash: 8.21% Traditional cash on cash: 4.26% Airbnb Rental Income: $5007 Traditional Rental Income: $2412 Airbnb ROI: 8.21% Traditional ROI: 4.26%

Vacation Rentals in Maitland

There are 50 vacation rental properties available for sale in the city of Maitland . The median list price of Airbnb properties available for sale in Maitland is $463,950 and the average price per square foot is $245. The cash on cash return on vacation rentals in Maitland is 4.00%. The average monthly short term rental income in Maitland is $3,440.

Maitland, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 50 Airbnb properties available for sale in Maitland.

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

In September 2025, the average Airbnb occupancy rate in Maitland is 68%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Maitland, FL

2517 CAPER LANE #207

Maitland, FL

1 beds | 1 baths | 550 sq.ft.

$120,000

Airbnb cash on cash: 8.64%

Traditional cash on cash: 8.14%

Airbnb Rental Income: $1832

Traditional Rental Income: $1280

Airbnb ROI: 8.64%

Traditional ROI: 8.14%

1521 OXFORD ROAD

Maitland, FL

4 beds | 2 baths | 1,925 sq.ft.

$468,900

Airbnb cash on cash: 6.9%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $5007

Traditional Rental Income: $2826

Airbnb ROI: 6.9%

Traditional ROI: 4.26%

1000 WINDERLEY PLACE #122

Maitland, FL

2 beds | 2 baths | 1,164 sq.ft.

$279,000

Airbnb cash on cash: 2.28%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $2379

Traditional Rental Income: $1716

Airbnb ROI: 2.28%

Traditional ROI: 1.98%

162 ORANGE PLACE

Maitland, FL

3 beds | 2 baths | 1,624 sq.ft.

$599,900

Airbnb cash on cash: 3.16%

Traditional cash on cash: 2.41%

Airbnb Rental Income: $3440

Traditional Rental Income: $2261

Airbnb ROI: 3.16%

Traditional ROI: 2.41%

824 TOWN CIRCLE #101

Maitland, FL

3 beds | 3 baths | 1,565 sq.ft.

$290,000

Airbnb cash on cash: 5.65%

Traditional cash on cash: 3.9%

Airbnb Rental Income: $3440

Traditional Rental Income: $2200

Airbnb ROI: 5.65%

Traditional ROI: 3.9%

1375 LAKE SHADOW CIRCLE #11208

Maitland, FL

2 beds | 1 baths | 898 sq.ft.

$205,000

Airbnb cash on cash: 4.38%

Traditional cash on cash: 2.61%

Airbnb Rental Income: $2379

Traditional Rental Income: $1449

Airbnb ROI: 4.38%

Traditional ROI: 2.61%

2133 KORAT LANE

Maitland, FL

4 beds | 3 baths | 2,359 sq.ft.

$514,900

Airbnb cash on cash: 5.81%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $5007

Traditional Rental Income: $3249

Airbnb ROI: 5.81%

Traditional ROI: 4.28%

2525 CAPER LANE #205

Maitland, FL

1 beds | 1 baths | 550 sq.ft.

$125,000

Airbnb cash on cash: 6.18%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $1832

Traditional Rental Income: $1232

Airbnb ROI: 6.18%