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
1327 Chipola Trl Maitland, FL This meticulously renovated home has so much to offer for an incredible price. The house ...	4 beds \| 2 baths \| 1,538 sq.ft.	$415,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 3.87% Airbnb Rental Income: $5007 Traditional Rental Income: $2123 Airbnb ROI: 8.65% Traditional ROI: 3.87%
448 STONEWOOD LANE Maitland, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-b...	4 beds \| 3 baths \| 3,308 sq.ft.	$624,990	Airbnb cash on cash: 3.82% Traditional cash on cash: 3.8% Airbnb Rental Income: $5007 Traditional Rental Income: $3970 Airbnb ROI: 3.82% Traditional ROI: 3.8%
1000 WINDERLEY PLACE #141 Maitland, FL Updated GROUND-FLOOR condo in the secluded gated community of Sun Bay Club in Maitland, Fl...	2 beds \| 2 baths \| 1,275 sq.ft.	$300,000	Airbnb cash on cash: 2.05% Traditional cash on cash: 2.02% Airbnb Rental Income: $2379 Traditional Rental Income: $1785 Airbnb ROI: 2.05% Traditional ROI: 2.02%
550 FLEMMING WAY #100 Maitland, FL Bright and well maintained 2 bedroom, 1 bath condo located in a desirable shopping and din...	2 beds \| 1 baths \| 1,051 sq.ft.	$139,000	Airbnb cash on cash: 6.41% Traditional cash on cash: 4.18% Airbnb Rental Income: $2379 Traditional Rental Income: $1496 Airbnb ROI: 6.41% Traditional ROI: 4.18%
1404 CARING COURT Maitland, FL "RARE OPPORTUNITY" MOVE-IN READY 3-BED, 2.5-BATH SINGLE FAMILY HOME IN THE "EXCLUSIVE GATE...	3 beds \| 3 baths \| 2,110 sq.ft.	$659,900	Airbnb cash on cash: 1.42% Traditional cash on cash: 1.41% Airbnb Rental Income: $3440 Traditional Rental Income: $2673 Airbnb ROI: 1.42% Traditional ROI: 1.41%
2642 BROOKSIDE COURT Maitland, FL Indulge in the epitome of modern living with this fully renovated masterpiece! Boasting a ...	5 beds \| 2 baths \| 2,360 sq.ft.	$629,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 2.96% Airbnb Rental Income: $5533 Traditional Rental Income: $2974 Airbnb ROI: 5.43% Traditional ROI: 2.96%
612 GREEN MEADOW AVENUE Maitland, FL Under contract-accepting backup offers. Welcome to a home that doesnât just check boxes ...	3 beds \| 2 baths \| 1,707 sq.ft.	$490,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 2.9% Airbnb Rental Income: $3440 Traditional Rental Income: $2396 Airbnb ROI: 3.52% Traditional ROI: 2.9%
200 Moseley Ave Maitland, FL Under contract-accepting backup offers. INVESTMENT OPPORTUNITY IS HERE. In the heart of h...	3 beds \| 2 baths \| 1,625 sq.ft.	$420,000	Airbnb cash on cash: 5.36% Traditional cash on cash: 1.94% Airbnb Rental Income: $3440 Traditional Rental Income: $1332 Airbnb ROI: 5.36% Traditional ROI: 1.94%
1291 Oxford Rd Maitland, FL Welcome to this thoughtfully updated one-story home in the established community of Englis...	3 beds \| 2 baths \| 1,370 sq.ft.	$419,000	Airbnb cash on cash: 4.85% Traditional cash on cash: 4.23% Airbnb Rental Income: $3440 Traditional Rental Income: $2434 Airbnb ROI: 4.85% Traditional ROI: 4.23%
1511 E HORATIO AVENUE Maitland, FL Welcome to your dream home located in the heart of Maitland, FL. This stunning 4-bedroom, ...	4 beds \| 3 baths \| 2,676 sq.ft.	$719,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.32% Airbnb Rental Income: $5007 Traditional Rental Income: $3559 Airbnb ROI: 3.95% Traditional ROI: 3.32%
2697 QUEEN MARY PLACE Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	3 beds \| 2 baths \| 1,558 sq.ft.	$520,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 2.31% Airbnb Rental Income: $3440 Traditional Rental Income: $2480 Airbnb ROI: 2.72% Traditional ROI: 2.31%
2155 FENNELL STREET Maitland, FL Welcome to 2155 Fennell Street, a beautifully renovated pool home nestled in the desirable...	3 beds \| 2 baths \| 1,822 sq.ft.	$489,900	Airbnb cash on cash: 4.11% Traditional cash on cash: 3.92% Airbnb Rental Income: $3440 Traditional Rental Income: $2589 Airbnb ROI: 4.11% Traditional ROI: 3.92%
1074 HAMLET DRIVE Maitland, FL Welcome to this beautifully maintained 3-bedroom, 2-bathroom home that blends comfort, con...	3 beds \| 2 baths \| 1,076 sq.ft.	$308,000	Airbnb cash on cash: 7.35% Traditional cash on cash: 5.91% Airbnb Rental Income: $3440 Traditional Rental Income: $2262 Airbnb ROI: 7.35% Traditional ROI: 5.91%
67 CYPRESS LANE Maitland, FL Under contract-accepting backup offers. Welcome to 67 Cypress Lane, a stunning single-owne...	4 beds \| 3 baths \| 2,292 sq.ft.	$999,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.11% Airbnb Rental Income: $5007 Traditional Rental Income: $3379 Airbnb ROI: 2.76% Traditional ROI: 2.11%
1033 Hamlet Dr Maitland, FL 1033 Hamlet Dr, Maitland, FL 32751 \| Single Family Residential	3 beds \| 2 baths \| 1,146 sq.ft.	$350,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 3.98% Airbnb Rental Income: $3440 Traditional Rental Income: $2078 Airbnb ROI: 5.81% Traditional ROI: 3.98%
2453 Worthington Rd Maitland, FL 2453 Worthington Rd, Maitland, FL 32751 \| Single Family Residential	4 beds \| 2 baths \| 1,959 sq.ft.	$560,000	Airbnb cash on cash: 5.55% Traditional cash on cash: 2.91% Airbnb Rental Income: $5007 Traditional Rental Income: $2598 Airbnb ROI: 5.55% Traditional ROI: 2.91%
140 E Faith Ter Maitland, FL 140 E Faith Ter, Maitland, FL 32751 \| Single Family Residential	4 beds \| 3 baths \| 2,748 sq.ft.	$500,000	Airbnb cash on cash: 6.44% Traditional cash on cash: 5.29% Airbnb Rental Income: $5007 Traditional Rental Income: $3448 Airbnb ROI: 6.44% Traditional ROI: 5.29%
2040 Geronimo Trl Maitland, FL 2040 Geronimo Trl, Maitland, FL 32751 \| Single Family Residential	3 beds \| 2 baths \| 2,375 sq.ft.	$749,900	Airbnb cash on cash: 1.81% Traditional cash on cash: 1.26% Airbnb Rental Income: $3440 Traditional Rental Income: $2289 Airbnb ROI: 1.81% Traditional ROI: 1.26%
623 GREEN MEADOW AVENUE Maitland, FL Welcome to this beautifully maintained two-owner concrete block home offering the perfect ...	4 beds \| 2 baths \| 1,909 sq.ft.	$500,000	Airbnb cash on cash: 6.91% Traditional cash on cash: 5.39% Airbnb Rental Income: $5007 Traditional Rental Income: $3272 Airbnb ROI: 6.91% Traditional ROI: 5.39%
551 RUFFEL STREET Maitland, FL Under contract-accepting backup offers. Situated at the end of a cul-de-sac in the Eatonvi...	3 beds \| 2 baths \| 1,162 sq.ft.	$299,900	Airbnb cash on cash: 8.02% Traditional cash on cash: 6.92% Airbnb Rental Income: $3440 Traditional Rental Income: $2369 Airbnb ROI: 8.02% Traditional ROI: 6.92%
1776 BOBTAIL DRIVE Maitland, FL Welcome to 1776 Bobtail Drive â the kind of home that doesnât just check boxesâ¦ it c...	4 beds \| 3 baths \| 2,344 sq.ft.	$519,999	Airbnb cash on cash: 6.47% Traditional cash on cash: 4.61% Airbnb Rental Income: $5007 Traditional Rental Income: $3079 Airbnb ROI: 6.47% Traditional ROI: 4.61%
1100 LAKE SHADOW CIRCLE #2307 Maitland, FL One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 2-b...	2 beds \| 2 baths \| 1,111 sq.ft.	$200,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 2.65% Airbnb Rental Income: $2379 Traditional Rental Income: $1662 Airbnb ROI: 3.34% Traditional ROI: 2.65%
1000 WINDERLEY PLACE #226 Maitland, FL *PRICE IMPROVEMENT*Welcome to this beautifully maintained 3-bedroom, 2-bath condo loca...	3 beds \| 2 baths \| 1,538 sq.ft.	$315,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 3.32% Airbnb Rental Income: $3440 Traditional Rental Income: $2082 Airbnb ROI: 5.33% Traditional ROI: 3.32%
1511 GLASTONBERRY ROAD Maitland, FL This AMAZING!, spacious 5-bedroom, 3-bath split-level home is located in a fantastic neigh...	5 beds \| 3 baths \| 2,376 sq.ft.	$549,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 5.59% Airbnb Rental Income: $5533 Traditional Rental Income: $3653 Airbnb ROI: 7.08% Traditional ROI: 5.59%
444 BANYON TREE CIRCLE #202 Maitland, FL Beautifully well-maintained 3 bedroom, 2 bathroom condo located in the desirable Maitland ...	3 beds \| 2 baths \| 1,428 sq.ft.	$239,900	Airbnb cash on cash: 6.64% Traditional cash on cash: 3.55% Airbnb Rental Income: $3440 Traditional Rental Income: $1976 Airbnb ROI: 6.64% Traditional ROI: 3.55%
9001 LAKE CHARITY DRIVE Maitland, FL Welcome to a rare opportunity in the beautiful neighborhood of Druid Hills in Maitlandât...	3 beds \| 2 baths \| 1,623 sq.ft.	$575,000	Airbnb cash on cash: 3.48% Traditional cash on cash: 2.88% Airbnb Rental Income: $3440 Traditional Rental Income: $2355 Airbnb ROI: 3.48% Traditional ROI: 2.88%
2154 FENNELL STREET Maitland, FL Under contract-accepting backup offers. Welcome to this meticulously maintained, one-owner...	3 beds \| 2 baths \| 1,642 sq.ft.	$420,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 3.89% Airbnb Rental Income: $3440 Traditional Rental Income: $2205 Airbnb ROI: 5.09% Traditional ROI: 3.89%
499 JULIAN LANE Maitland, FL Location, Location, Location. Welcome to your new home in Maitland! This conviently loca...	3 beds \| 3 baths \| 1,596 sq.ft.	$455,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.23% Airbnb Rental Income: $3440 Traditional Rental Income: $2216 Airbnb ROI: 4.32% Traditional ROI: 3.23%
2040 BOBTAIL DRIVE Maitland, FL Cute home alert! Finally â an updated, move-in ready home in an amazing Maitland locatio...	3 beds \| 2 baths \| 1,382 sq.ft.	$370,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.71% Airbnb Rental Income: $3440 Traditional Rental Income: $2038 Airbnb ROI: 5.56% Traditional ROI: 3.71%
541 MANOR ROAD Maitland, FL Tucked between the shores of Lake Nina and Lake Maitland, this beautifully reimagined Cali...	5 beds \| 3 baths \| 3,400 sq.ft.	$1,599,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 1.23% Airbnb Rental Income: $5533 Traditional Rental Income: $4358 Airbnb ROI: 1.27% Traditional ROI: 1.23%
457 FORESTWOOD LANE Maitland, FL Under contract-accepting backup offers. From the moment you step inside, youâre welcomed...	4 beds \| 3 baths \| 2,610 sq.ft.	$849,000	Airbnb cash on cash: 2.91% Traditional cash on cash: 2.32% Airbnb Rental Income: $5007 Traditional Rental Income: $3516 Airbnb ROI: 2.91% Traditional ROI: 2.32%
1140 S ORLANDO AVENUE #I14 Maitland, FL One or more photo(s) has been virtually staged. Where Maitland's pristine waters meet a mo...	2 beds \| 2 baths \| 816 sq.ft.	$325,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 0.9% Airbnb Rental Income: $2379 Traditional Rental Income: $1464 Airbnb ROI: 1.98% Traditional ROI: 0.9%
1191 WILLOWBROOK TRAIL Maitland, FL Under contract-accepting backup offers. Don't miss this rare opportunity to purchase your ...	4 beds \| 2 baths \| 2,287 sq.ft.	$765,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 2.17% Airbnb Rental Income: $5007 Traditional Rental Income: $2785 Airbnb ROI: 3.86% Traditional ROI: 2.17%
1781 TONTO TRAIL Maitland, FL Under contract-accepting backup offers. Welcome to 1781 Tonto Trail, a 4-bedroom home in o...	4 beds \| 2 baths \| 1,880 sq.ft.	$600,000	Airbnb cash on cash: 5.54% Traditional cash on cash: 3.05% Airbnb Rental Income: $5007 Traditional Rental Income: $2584 Airbnb ROI: 5.54% Traditional ROI: 3.05%
2494 Castlewood Rd Maitland, FL 2494 Castlewood Rd, Maitland, FL 32751 \| Single Family Residential	4 beds \| 2 baths \| 2,482 sq.ft.	$570,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 2.27% Airbnb Rental Income: $5007 Traditional Rental Income: $2306 Airbnb ROI: 5.42% Traditional ROI: 2.27%

Vacation Rentals in Maitland

There are 35 vacation rental properties available for sale in the city of Maitland . The median list price of Airbnb properties available for sale in Maitland is $564,708 and the average price per square foot is $265. The cash on cash return on vacation rentals in Maitland is 3.00%. 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 35 Airbnb properties available for sale in Maitland.

In 2026, the best neighborhood to buy short term rental property is Maitland.

In June 2026, 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

1327 Chipola Trl

Maitland, FL

4 beds | 2 baths | 1,538 sq.ft.

$415,000

Airbnb cash on cash: 8.65%

Traditional cash on cash: 3.87%

Airbnb Rental Income: $5007

Traditional Rental Income: $2123

Airbnb ROI: 8.65%

Traditional ROI: 3.87%

448 STONEWOOD LANE

Maitland, FL

4 beds | 3 baths | 3,308 sq.ft.

$624,990

Airbnb cash on cash: 3.82%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $5007

Traditional Rental Income: $3970

Airbnb ROI: 3.82%

Traditional ROI: 3.8%

1000 WINDERLEY PLACE #141

Maitland, FL

2 beds | 2 baths | 1,275 sq.ft.

$300,000

Airbnb cash on cash: 2.05%

Traditional cash on cash: 2.02%

Airbnb Rental Income: $2379

Traditional Rental Income: $1785

Airbnb ROI: 2.05%

Traditional ROI: 2.02%

550 FLEMMING WAY #100

Maitland, FL

2 beds | 1 baths | 1,051 sq.ft.

$139,000

Airbnb cash on cash: 6.41%

Traditional cash on cash: 4.18%

Airbnb Rental Income: $2379

Traditional Rental Income: $1496

Airbnb ROI: 6.41%

Traditional ROI: 4.18%

1404 CARING COURT

Maitland, FL

3 beds | 3 baths | 2,110 sq.ft.

$659,900

Airbnb cash on cash: 1.42%

Traditional cash on cash: 1.41%

Airbnb Rental Income: $3440

Traditional Rental Income: $2673

Airbnb ROI: 1.42%

Traditional ROI: 1.41%

2642 BROOKSIDE COURT

Maitland, FL

5 beds | 2 baths | 2,360 sq.ft.

$629,000

Airbnb cash on cash: 5.43%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $5533

Traditional Rental Income: $2974

Airbnb ROI: 5.43%

Traditional ROI: 2.96%

612 GREEN MEADOW AVENUE

Maitland, FL

3 beds | 2 baths | 1,707 sq.ft.

$490,000

Airbnb cash on cash: 3.52%

Traditional cash on cash: 2.9%

Airbnb Rental Income: $3440

Traditional Rental Income: $2396

Airbnb ROI: 3.52%

Traditional ROI: 2.9%

200 Moseley Ave

Maitland, FL

3 beds | 2 baths | 1,625 sq.ft.

$420,000

Airbnb cash on cash: 5.36%

Traditional cash on cash: 1.94%

Airbnb Rental Income: $3440

Traditional Rental Income: $1332

Airbnb ROI: 5.36%