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 Under contract-accepting backup offers. Nestled in the highly desirable Druid Isle neighbo...	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%
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%
2338 Tuscarora Trl Maitland, FL *Charming Dommerich Hills Home with Scenic Lake Views and Modern Updates* Nestled in t...	4 beds \| 2 baths \| 1,700 sq.ft.	$680,000	Airbnb cash on cash: 4.55% Traditional cash on cash: 2.44% Airbnb Rental Income: $5007 Traditional Rental Income: $2640 Airbnb ROI: 4.55% Traditional ROI: 2.44%
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 Trl 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%
1150 Lake Shadow Cir #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.	$199,900	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 Pl #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: 1.95% Traditional cash on cash: 1.78% Airbnb Rental Income: $2379 Traditional Rental Income: $1743 Airbnb ROI: 1.95% Traditional ROI: 1.78%
1460 LAKE SHADOW CIRCLE #7204 Maitland, FL Under contract-accepting backup offers. OWNER MOTIVATED! PRICED TO SELL!! Resort style liv...	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 Under contract-accepting backup offers. Welcome to 920 Park Lake Circle in charming Maitla...	3 beds \| 3 baths \| 1,486 sq.ft.	$269,000	Airbnb cash on cash: 5.78% Traditional cash on cash: 4.25% Airbnb Rental Income: $3440 Traditional Rental Income: $2289 Airbnb ROI: 5.78% Traditional ROI: 4.25%
135 Roosevelt Pl Maitland, FL This charming home boasts a wealth of valuable upgrades and improvements, making it an ent...	3 beds \| 2 baths \| 2,426 sq.ft.	$549,900	Airbnb cash on cash: 5.54% Traditional cash on cash: 2.77% Airbnb Rental Income: $5007 Traditional Rental Income: $2560 Airbnb ROI: 5.54% Traditional ROI: 2.77%
2329 Shadow View Cir #2329 Maitland, FL Welcome to this stunning, fully renovated 3-Bedroom, 2.5-Bath home located in the desirab...	3 beds \| 2 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 St 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 Ln Maitland, FL Motivated Seller \| Renovated Pool Home in Prime Maitland Location This solid concrete bloc...	4 beds \| 2 baths \| 1,664 sq.ft.	$418,500	Airbnb cash on cash: 8.55% Traditional cash on cash: 4.5% Airbnb Rental Income: $5007 Traditional Rental Income: $2394 Airbnb ROI: 8.55% Traditional ROI: 4.5%
2632 DERBYSHIRE ROAD Maitland, FL Under contract-accepting backup offers. 2025 ROOF \| POOL HOME Start your new life ...	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 Trl Maitland, FL One or more photo(s) has been virtually staged. Welcome home to this well outfitted 4 Bed ...	4 beds \| 2 baths \| 1,845 sq.ft.	$550,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 3.49% Airbnb Rental Income: $5007 Traditional Rental Income: $3187 Airbnb ROI: 5.04% Traditional ROI: 3.49%
1074 Hamlet Dr 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 Ave #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: 1.07% Traditional cash on cash: 0.95% Airbnb Rental Income: $2379 Traditional Rental Income: $1745 Airbnb ROI: 1.07% Traditional ROI: 0.95%
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: 4.82% Traditional cash on cash: 3% Airbnb Rental Income: $3440 Traditional Rental Income: $2123 Airbnb ROI: 4.82% Traditional ROI: 3%
225 Quayside Cir Maitland, FL Discover the perfect blend of style and location in this beautifully updated 3-bedroom, 2....	3 beds \| 2 baths \| 1,734 sq.ft.	$595,000	Airbnb cash on cash: 1.37% Traditional cash on cash: 0.9% Airbnb Rental Income: $3440 Traditional Rental Income: $2414 Airbnb ROI: 1.37% Traditional ROI: 0.9%
1291 Blessing St Maitland, FL Welcome to Montacino, a gated community offering both convenience and charm. This updated ...	3 beds \| 2 baths \| 1,674 sq.ft.	$379,900	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 Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **...	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 Dr 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%
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 Cir #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: 6.61% Traditional cash on cash: 2.97% Airbnb Rental Income: $3440 Traditional Rental Income: $1825 Airbnb ROI: 6.61% Traditional ROI: 2.97%
633 Magnolia Dr 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 Cir #C Maitland, FL Welcome to refined living in The Moorings! This beautifully updated 3-bedroom, 2.5-bath to...	3 beds \| 2 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%
2065 Derbyshire Rd Maitland, FL Beautifully renovated and move-in ready, this 3-bedroom, 2-bath home offers modern design ...	3 beds \| 2 baths \| 1,430 sq.ft.	$499,990	Airbnb cash on cash: 4.21% Traditional cash on cash: 3.14% Airbnb Rental Income: $3440 Traditional Rental Income: $2175 Airbnb ROI: 4.21% Traditional ROI: 3.14%
67 Cypress Ln Maitland, FL Welcome to 67 Cypress Lane, a stunning single-owner custom residence nestled among majesti...	4 beds \| 3 baths \| 2,292 sq.ft.	$1,339,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 1.05% Airbnb Rental Income: $5007 Traditional Rental Income: $3028 Airbnb ROI: 1.81% Traditional ROI: 1.05%
1325 Lake Shadow Cir #12202 Maitland, FL Welcome to this beautifully maintained 2-bedroom, 2-bath condominium offering comfort, sty...	2 beds \| 2 baths \| 1,111 sq.ft.	$235,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 2.57% Airbnb Rental Income: $2379 Traditional Rental Income: $1637 Airbnb ROI: 3.24% Traditional ROI: 2.57%
210 MAGNOLIA ROAD #106 Maitland, FL RARE 3-BEDROOM GROUND FLOOR UNIT IN MAITLAND HOUSE. Enter this unit just steps from the as...	3 beds \| 2 baths \| 1,394 sq.ft.	$399,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 0.24% Airbnb Rental Income: $3440 Traditional Rental Income: $1955 Airbnb ROI: 2.17% Traditional ROI: 0.24%
1933 SOUTH BOULEVARD Maitland, FL Under contract-accepting backup offers. Perfectly positioned in the highly sought-after Ma...	5 beds \| 3 baths \| 2,376 sq.ft.	$600,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 3.09% Airbnb Rental Income: $5533 Traditional Rental Income: $2720 Airbnb ROI: 6.13% Traditional ROI: 3.09%
185 BIRCHWOOD DRIVE Maitland, FL Under contract-accepting backup offers. Welcome to 185 Birchwood Drive, a rare Maitland SK...	4 beds \| 3 baths \| 2,253 sq.ft.	$800,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 1.56% Airbnb Rental Income: $5007 Traditional Rental Income: $2258 Airbnb ROI: 3.88% Traditional ROI: 1.56%

Vacation Rentals in Maitland

There are 61 vacation rental properties available for sale in the city of Maitland . The median list price of Airbnb properties available for sale in Maitland is $419,900 and the average price per square foot is $239. 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 61 Airbnb properties available for sale in Maitland.

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

In February 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%

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%

2338 Tuscarora Trl

Maitland, FL

4 beds | 2 baths | 1,700 sq.ft.

$680,000

Airbnb cash on cash: 4.55%

Traditional cash on cash: 2.44%

Airbnb Rental Income: $5007

Traditional Rental Income: $2640

Airbnb ROI: 4.55%

Traditional ROI: 2.44%

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 Trl

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%

1150 Lake Shadow Cir #3104

Maitland, FL

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

$199,900

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 Pl #222

Maitland, FL

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

$309,000

Airbnb cash on cash: 1.95%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $2379

Traditional Rental Income: $1743

Airbnb ROI: 1.95%