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.	$110,000	Airbnb cash on cash: 9.47% Traditional cash on cash: 8.93% Airbnb Rental Income: $1832 Traditional Rental Income: $1280 Airbnb ROI: 9.47% Traditional ROI: 8.93%
1301 DRUID ISLE ROAD Maitland, FL Nestled in the highly desirable Druid Isle neighborhood, this single-family residence offe...	4 beds \| 3 baths \| 2,162 sq.ft.	$649,990	Airbnb cash on cash: 4.37% Traditional cash on cash: 3.74% Airbnb Rental Income: $5007 Traditional Rental Income: $3600 Airbnb ROI: 4.37% Traditional ROI: 3.74%
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.	$195,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 2.79% Airbnb Rental Income: $2379 Traditional Rental Income: $1449 Airbnb ROI: 4.65% Traditional ROI: 2.79%
500 BANYON TREE CIRCLE #104 Maitland, FL One or more photo(s) has been virtually staged. Welcome to this beautifully renovated 3-be...	3 beds \| 2 baths \| 1,428 sq.ft.	$199,999	Airbnb cash on cash: 8.04% Traditional cash on cash: 5.94% Airbnb Rental Income: $3440 Traditional Rental Income: $2280 Airbnb ROI: 8.04% Traditional ROI: 5.94%
2270 DELORAINE TRAIL Maitland, FL Under contract-accepting backup offers. This beautifully updated 4-bedroom, 2-bath pool ho...	4 beds \| 2 baths \| 2,000 sq.ft.	$850,000	Airbnb cash on cash: 3.07% Traditional cash on cash: 1.67% Airbnb Rental Income: $5007 Traditional Rental Income: $2871 Airbnb ROI: 3.07% Traditional ROI: 1.67%
708 THUNDER TRAIL Maitland, FL Welcome to 708 Thunder Trail in beautiful Maitland, Florida â a stunning 4-bedroom, 2-ba...	4 beds \| 2 baths \| 1,907 sq.ft.	$635,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 2.76% Airbnb Rental Income: $5007 Traditional Rental Income: $3074 Airbnb ROI: 4.3% Traditional ROI: 2.76%
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.	$345,000	Airbnb cash on cash: 9.75% Traditional cash on cash: 4.51% Airbnb Rental Income: $5007 Traditional Rental Income: $2287 Airbnb ROI: 9.75% Traditional ROI: 4.51%
1150 LAKE SHADOW CIRCLE #3104 Maitland, FL One or more photo(s) has been virtually staged. BIG NEWS! THE SELLERâS PREFERRED LENDER ...	2 beds \| 2 baths \| 1,048 sq.ft.	$215,000	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.21% Airbnb Rental Income: $2379 Traditional Rental Income: $1602 Airbnb ROI: 4.15% Traditional ROI: 3.21%
1000 WINDERLEY PLACE #222 Maitland, FL Discover Sun Bay Club â Maitlandâs Hidden Gem on Lake Destiny! Behind the signature b...	2 beds \| 2 baths \| 1,164 sq.ft.	$309,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.62% Airbnb Rental Income: $2379 Traditional Rental Income: $1743 Airbnb ROI: 3.79% Traditional ROI: 3.62%
1460 LAKE SHADOW CIRCLE #7204 Maitland, FL OWNER MOTIVATED! PRICED TO SELL!! Resort style living in this sought after gated community...	3 beds \| 2 baths \| 1,243 sq.ft.	$199,900	Airbnb cash on cash: 8.48% Traditional cash on cash: 4.44% Airbnb Rental Income: $3440 Traditional Rental Income: $1911 Airbnb ROI: 8.48% Traditional ROI: 4.44%
920 PARK LAKE CIRCLE #36 Maitland, FL Welcome to 920 Park Lake Circle in charming Maitland, FL â a beautifully updated 3 bedro...	3 beds \| 3 baths \| 1,486 sq.ft.	$269,000	Airbnb cash on cash: 7.9% Traditional cash on cash: 6.36% Airbnb Rental Income: $3440 Traditional Rental Income: $2289 Airbnb ROI: 7.9% Traditional ROI: 6.36%
2352 SIERRA LANE #2352 Maitland, FL Under contract-accepting backup offers. Experience the comfort and convenience of living i...	3 beds \| 2 baths \| 1,343 sq.ft.	$340,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 1.24% Airbnb Rental Income: $3440 Traditional Rental Income: $2039 Airbnb ROI: 3.24% Traditional ROI: 1.24%
135 Roosevelt Place Maitland, FL This charming home boasts a wealth of valuable upgrades and improvements, making it an ent...	4 beds \| 2 baths \| 2,426 sq.ft.	$564,900	Airbnb cash on cash: 5.37% Traditional cash on cash: 2.67% Airbnb Rental Income: $5007 Traditional Rental Income: $2560 Airbnb ROI: 5.37% Traditional ROI: 2.67%
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.	$699,900	Airbnb cash on cash: 4.09% Traditional cash on cash: 3.44% Airbnb Rental Income: $5007 Traditional Rental Income: $3559 Airbnb ROI: 4.09% Traditional ROI: 3.44%
380 BANYAN DRIVE Maitland, FL Under contract-accepting backup offers. Charming 3BR/2BA Home with Updated Interior Thi...	3 beds \| 2 baths \| 1,404 sq.ft.	$429,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 3.61% Airbnb Rental Income: $3440 Traditional Rental Income: $2055 Airbnb ROI: 5.16% Traditional ROI: 3.61%
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.	$320,000	Airbnb cash on cash: 4.45% Traditional cash on cash: 2.76% Airbnb Rental Income: $3440 Traditional Rental Income: $2169 Airbnb ROI: 4.45% Traditional ROI: 2.76%
385 LIME STREET Maitland, FL Wonderful investment opportunity in historic Eatonville. Large corner lot. Roof was replac...	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! Stunningly Renovated 4-Bedroom Home in Prime Maitland Seize this rare op...	4 beds \| 2 baths \| 1,664 sq.ft.	$424,900	Airbnb cash on cash: 8.41% Traditional cash on cash: 4.41% Airbnb Rental Income: $5007 Traditional Rental Income: $2394 Airbnb ROI: 8.41% Traditional ROI: 4.41%
2632 DERBYSHIRE ROAD Maitland, FL 2025 ROOF \| POOL HOME Start your new life to one of Orlando's most prestigious sub...	4 beds \| 2 baths \| 1,770 sq.ft.	$525,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 3.68% Airbnb Rental Income: $5007 Traditional Rental Income: $2807 Airbnb ROI: 6.08% Traditional ROI: 3.68%
736 FOREST GLEN COURT Maitland, FL One or more photo(s) has been virtually staged. Huge Price Reduction!!!!! - Motivated Sell...	4 beds \| 2 baths \| 1,647 sq.ft.	$455,000	Airbnb cash on cash: 7.03% Traditional cash on cash: 3.81% Airbnb Rental Income: $5007 Traditional Rental Income: $2614 Airbnb ROI: 7.03% Traditional ROI: 3.81%
1024 KEWANNEE TRAIL Maitland, FL One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed ...	4 beds \| 3 baths \| 1,845 sq.ft.	$595,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 3.15% Airbnb Rental Income: $5007 Traditional Rental Income: $3187 Airbnb ROI: 4.59% Traditional ROI: 3.15%
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% Airbnb Rental Income: $3440 Traditional Rental Income: $1997 Airbnb ROI: 7.35% Traditional ROI: 5%
2318 CASTLEWOOD ROAD Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Yo...	4 beds \| 3 baths \| 2,335 sq.ft.	$580,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 4.61% Airbnb Rental Income: $5007 Traditional Rental Income: $3329 Airbnb ROI: 5.82% Traditional ROI: 4.61%
1140 S ORLANDO AVENUE #16 Maitland, FL Lovely direct waterfront condominium with large screen porch overlooking beautiful 451 acr...	2 beds \| 1 baths \| 816 sq.ft.	$459,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.32% Airbnb Rental Income: $2379 Traditional Rental Income: $1745 Airbnb ROI: 2.44% Traditional ROI: 2.32%
1000 WINDERLEY PLACE #142 Maitland, FL Wake up to water views, an abundance of natural light, and tropical serenity in this beaut...	3 beds \| 2 baths \| 1,538 sq.ft.	$325,000	Airbnb cash on cash: 6.72% Traditional cash on cash: 4.9% Airbnb Rental Income: $3440 Traditional Rental Income: $2123 Airbnb ROI: 6.72% Traditional ROI: 4.9%
225 QUAYSIDE CIRCLE Maitland, FL Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2....	3 beds \| 3 baths \| 1,734 sq.ft.	$595,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 2.66% Airbnb Rental Income: $3440 Traditional Rental Income: $2414 Airbnb ROI: 3.14% Traditional ROI: 2.66%
1291 BLESSING STREET Maitland, FL Welcome to Montacino, a gated community offering both convenience and charm. This updated ...	3 beds \| 3 baths \| 1,674 sq.ft.	$385,000	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.6% Airbnb Rental Income: $3440 Traditional Rental Income: $2159 Airbnb ROI: 4.03% Traditional ROI: 2.6%
1601 GROVE STREET #552 Maitland, FL One or more photo(s) has been virtually staged. 2024 ROOF, 2025 HVAC FULLY RENOVATED T...	2 beds \| 2 baths \| 1,087 sq.ft.	$230,000	Airbnb cash on cash: 6.72% Traditional cash on cash: 6.04% Airbnb Rental Income: $2379 Traditional Rental Income: $1646 Airbnb ROI: 6.72% Traditional ROI: 6.04%
314 BANYAN DRIVE Maitland, FL Experience Modern Florida Living at Its Finest Step inside this fully remodeled 3-bedroom,...	3 beds \| 2 baths \| 1,234 sq.ft.	$400,000	Airbnb cash on cash: 5.56% Traditional cash on cash: 3.59% Airbnb Rental Income: $3440 Traditional Rental Income: $1940 Airbnb ROI: 5.56% Traditional ROI: 3.59%
400 BOYNTON ROAD Maitland, FL Special Opportunity in the heart of Maitland! Own a piece of history or build your dream ...	3 beds \| 2 baths \| 1,520 sq.ft.	$525,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.15% Airbnb Rental Income: $3440 Traditional Rental Income: $2286 Airbnb ROI: 3.95% Traditional ROI: 3.15%
105 OAKWOOD DRIVE Maitland, FL Back on Market Due to Buyer Financing â Seminole County Multifamily Alert! This rare 4-u...	4 beds \| N/A baths \| 1,248 sq.ft.	$300,000	Airbnb cash on cash: 7.36% Traditional cash on cash: 2.52% Airbnb Rental Income: $3440 Traditional Rental Income: $1310 Airbnb ROI: 7.36% Traditional ROI: 2.52%
2525 NATIVE COURT Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,240 sq.ft.	$599,000	Airbnb cash on cash: 5.45% Traditional cash on cash: 4.61% Airbnb Rental Income: $5007 Traditional Rental Income: $3512 Airbnb ROI: 5.45% Traditional ROI: 4.61%
1175 LAKE SHADOW CIRCLE #4105 Maitland, FL 3 Bedroom/2 Bath 1st Floor Condo in a Gated Community! Close to Genesis Health Club, Down...	3 beds \| 2 baths \| 1,243 sq.ft.	$248,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 5.18% Airbnb Rental Income: $3440 Traditional Rental Income: $1825 Airbnb ROI: 8.82% Traditional ROI: 5.18%
633 MAGNOLIA DRIVE Maitland, FL Welcome to this Maitland 3-bedroom, 2-bath pool home offering incredible potential on a de...	3 beds \| 2 baths \| 1,285 sq.ft.	$370,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 4.94% Airbnb Rental Income: $3440 Traditional Rental Income: $2295 Airbnb ROI: 6.04% Traditional ROI: 4.94%
223 QUAYSIDE CIRCLE #C Maitland, FL Welcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath to...	3 beds \| 3 baths \| 1,734 sq.ft.	$575,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 1.02% Airbnb Rental Income: $3440 Traditional Rental Income: $2547 Airbnb ROI: 1.26% Traditional ROI: 1.02%
2167 MOHAWK TRAIL Maitland, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ce...	3 beds \| 2 baths \| 2,162 sq.ft.	$625,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 1.74% Airbnb Rental Income: $3440 Traditional Rental Income: $2641 Airbnb ROI: 1.8% Traditional ROI: 1.74%
613 ORANGE TREE COURT #507 Maitland, FL Come to your new home centrally located between Downtown Maitland and Winter Park. Close ...	3 beds \| 2 baths \| 1,256 sq.ft.	$243,000	Airbnb cash on cash: 9.48% Traditional cash on cash: 5.82% Airbnb Rental Income: $3440 Traditional Rental Income: $1836 Airbnb ROI: 9.48% Traditional ROI: 5.82%
1447 CARING COURT Maitland, FL Beautiful move-in ready home in the highly sought-after gated community of Montacino, loca...	3 beds \| 3 baths \| 2,110 sq.ft.	$625,000	Airbnb cash on cash: 2.38% Traditional cash on cash: 2.29% Airbnb Rental Income: $3440 Traditional Rental Income: $2623 Airbnb ROI: 2.38% Traditional ROI: 2.29%
508 BANYON TREE CIRCLE #202 Maitland, FL Located in the quiet, established community of Carrington Park in the heart of Seminole Co...	2 beds \| 2 baths \| 1,206 sq.ft.	$125,000	Airbnb cash on cash: 7% Traditional cash on cash: 2.67% Airbnb Rental Income: $2379 Traditional Rental Income: $1272 Airbnb ROI: 7% Traditional ROI: 2.67%
1220 WINSTON ROAD Maitland, FL Welcome to this completely reimagined 4 bedroom, 2 bath, single story home in Maitland's E...	4 beds \| 2 baths \| 1,724 sq.ft.	$499,000	Airbnb cash on cash: 6.21% Traditional cash on cash: 2.93% Airbnb Rental Income: $5007 Traditional Rental Income: $2451 Airbnb ROI: 6.21% Traditional ROI: 2.93%

Vacation Rentals in Maitland

There are 45 vacation rental properties available for sale in the city of Maitland . The median list price of Airbnb properties available for sale in Maitland is $417,450 and the average price per square foot is $247. 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 45 Airbnb properties available for sale in Maitland.

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

In January 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

2517 CAPER LANE #207

Maitland, FL

1 beds | 1 baths | 550 sq.ft.

$110,000

Airbnb cash on cash: 9.47%

Traditional cash on cash: 8.93%

Airbnb Rental Income: $1832

Traditional Rental Income: $1280

Airbnb ROI: 9.47%

Traditional ROI: 8.93%

1301 DRUID ISLE ROAD

Maitland, FL

4 beds | 3 baths | 2,162 sq.ft.

$649,990

Airbnb cash on cash: 4.37%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $5007

Traditional Rental Income: $3600

Airbnb ROI: 4.37%

Traditional ROI: 3.74%

1375 LAKE SHADOW CIRCLE #11208

Maitland, FL

2 beds | 1 baths | 898 sq.ft.

$195,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 2.79%

Airbnb Rental Income: $2379

Traditional Rental Income: $1449

Airbnb ROI: 4.65%

Traditional ROI: 2.79%

500 BANYON TREE CIRCLE #104

Maitland, FL

3 beds | 2 baths | 1,428 sq.ft.

$199,999

Airbnb cash on cash: 8.04%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $3440

Traditional Rental Income: $2280

Airbnb ROI: 8.04%

Traditional ROI: 5.94%

2270 DELORAINE TRAIL

Maitland, FL

4 beds | 2 baths | 2,000 sq.ft.

$850,000

Airbnb cash on cash: 3.07%

Traditional cash on cash: 1.67%

Airbnb Rental Income: $5007

Traditional Rental Income: $2871

Airbnb ROI: 3.07%

Traditional ROI: 1.67%

708 THUNDER TRAIL

Maitland, FL

4 beds | 2 baths | 1,907 sq.ft.

$635,000

Airbnb cash on cash: 4.3%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $5007

Traditional Rental Income: $3074

Airbnb ROI: 4.3%

Traditional ROI: 2.76%

249 SPARTAN DRIVE

Maitland, FL

4 beds | 2 baths | 1,579 sq.ft.

$345,000

Airbnb cash on cash: 9.75%

Traditional cash on cash: 4.51%

Airbnb Rental Income: $5007

Traditional Rental Income: $2287

Airbnb ROI: 9.75%

Traditional ROI: 4.51%

1150 LAKE SHADOW CIRCLE #3104

Maitland, FL

2 beds | 2 baths | 1,048 sq.ft.

$215,000

Airbnb cash on cash: 4.15%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $2379

Traditional Rental Income: $1602

Airbnb ROI: 4.15%