Monroe County, FL Short Term Rental Properties for Sale

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Updated: Aug 10

Furnished Fractional Residences

104000 Overseas Highway, Key Largo, FL 33037

$279,000

2,300 sqft

6 private, fully furnished residences, each with 3 bedrooms and 3 bathrooms
Approximately 2,300 +/- square feet per residence with a 450 sq ft balcony
Two boats available for use: 26' Sea Fox and 24' Contender
Ocean access, seawall, Blackwater Sound views, and a resort‑style pool
Fully stocked kitchens, Smart TVs, WIFI, elevator, and in‑unit laundry

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104000 Overseas Highway, Key Largo, FL 33037

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Est. Cap Rate

2.8%
NOI ÷ price
Est. NOI

$8K
Annual
Price @ 7% Cap

$112K
Suggested
Last Sold

Jan 2011
$3M
Property Type

Restaurant
Built 1945

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Updated: Aug 12

Waterfront Short-Term Rental Property

219 Sombrero Beach Road, Marathon, FL 33050

$1,439,000

1,840 sqft 0.16 AC lot

1,840‑square‑foot waterfront property with four bedrooms and three bathrooms
31 feet of private dockage near Sombrero Beach
Private pool with patio, deck, porch, and cabana‑style outdoor area
RM - Residential Medium zoning
Built in 2017 with central heating and central air

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Oceanfront Short-Term Rental Property

16 Seaside Avenue, Key Largo, FL 33037

$11,750,000

6,585 sqft 0.14 AC lot

Oceanfront residence with private dockage, pool, elevator, and eligibility for seven-day vacation rentals.

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Canal-Front Duplex with Private Dockage

126 N Indies Drive, Duck Key, FL 33050

$1,875,000

2,544 sqft 0.18 AC lot

Canal-front duplex on Duck Key with two side-by-side units, private balcony, in-unit washer and dryer, and new dockage.

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Private Island Mixed-Use Development

62250 Overseas Highway, #11, Conch Key, FL 33050

$5,750,000

2,478 sqft 3.74 AC lot

Private island in the Florida Keys with MU zoning, deep-water access, concrete seawall, and transient licensed entitlements.

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Half Duplex with Dockage for Short-Term Rentals

150 E 63rd Street Ocean, Marathon, FL 33050

$895,000

1,378 sqft 0.09 AC lot

Turnkey, fully renovated three-bedroom half duplex with direct ocean dockage and RM residential medium zoning.

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Waterfront Short-Term Rental Duplex

Key Colony Beach, FL 33051

$1,295,000

1,500 sqft 0.08 AC lot

Renovated waterfront half-duplex with private pool, dockage potential, and en-suite bedrooms.

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Waterfront Resort With Private Marina

101910 Overseas Hwy, Key Largo, FL 33037

$12,900,000

16,840 sqft

Waterfront resort featuring guest accommodations, swimming pools, private beach access, and direct bay access.

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Waterfront Development Land with Seawall

62250 Overseas Highway, Conch Key, FL 33050

$5,750,000

2,478 sqft 1.98 AC lot

Waterfront land with concrete seawall, deep-water boat basin, and mixed-use zoning, plus licensed transient entitlements.

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Short-Term Rental Residences with Elevator

104000 Overseas Highway, Key Largo, FL 33037

$289,000

2,300 sqft

Furnished residences in Fisherman's Cove include accessible elevator service and wraparound balconies, with ocean access and smart home comforts.

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Furnished Condo Suite with Balcony

500 BURTON DR, Tavernier, FL 33070

Contact for pricing

841 sqft

Fully furnished 2-bed, 2-bath suite with waterfront-facing primary bedroom and private balcony in Ocean Pointe.

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CBS Duplex with Dock on Deep Canal

427 89Th Street Ocean, Marathon, FL 33050

$675,000

945 sqft 0.07 AC lot

CBS half-duplex features a granite kitchen, central air, and a 2018 metal roof with a fenced, low-maintenance yard.

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Waterfront Duplex with Dock

440-442 48th Street Ocean, Marathon, FL 33050

$1,725,000

2,244 sqft

Two three-bedroom units feature separate utilities, fenced outdoor space, and canal access for flexible occupancy options.

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Short-Term Rental RV Lot

27-29859 Overseas Hwy, Big Pine Key, FL 33042

$209,900

Transient stays are permitted, with shared recreation and guest facilities available within Breezy Pines RV Estates.

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Waterfront Resort with Private Marina

101910 Overseas Hwy, Key Largo, FL 33037

$12,900,000

2.57 AC lot

Bayside hospitality property with guest accommodations, pools, beach access, and a private boat ramp.

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Three-Residence Short-Term Rental Property

2394 Coco Plum Drive, Marathon, FL 33050

$11,000,000

12,198 sqft 1.31 AC lot

Waterfront rental compound with private pools, docks, and RM - Residential Medium zoning for weekly rentals.

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Furnished 2-Bedroom RV Trailer

325 Calusa Street, Key Largo, FL 33037

$380,000

Fully furnished 2021 Forest River Salem trailer with two bedrooms, outdoor kitchen, and a detached insulated shed with second kitchen and A/C.

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Campground-Ready RV and Trailer Lot

325 Calusa Street, Key Largo, FL 33037

$390,000

0.04 AC lot

A fully set-up, rentable campground lot with a well-maintained trailer and resort-style amenities in Calusa Campground.

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Oceanfront Resort Residence Portfolio

231 E Shore Dr, Summerland Key, FL 33042

Contact for pricing

4,200 sqft

Seven newly constructed residences offer private infinity pools and assigned dockage with direct ocean access in a gated enclave.

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Key Largo Lot with RV

325 Calusa St #5, Key Largo, FL 33037

$319,000

0.03 AC lot

Lot with RV in Key Largo, short-term rentals allowed.

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Waterfront Rental Homes Compound

2394 Coco Plum Drive, Marathon, FL 33050

$11,000,000

Three professionally built waterfront residences with private pools and docks, zoned for weekly rentals.

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Waterfront Residential Income Property

Key Colony Beach, FL 33051

$889,000

975 sqft 0.05 AC lot

Renovated two-bedroom home with a dock and permitted seven-day rentals.

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Waterfront Condominium Development

1 Kyle Way S, Marathon, FL 33050

Contact for pricing

Pre-construction waterfront condos in Marathon offer deeded boat slips and deeded transient rental licenses with nightly rental allowance.

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Canal-Front Duplex With Pool

Key Colony Beach, FL 33051

$2,845,000

4,478 sqft 0.19 AC lot

Canal-front duplex with two units, impact windows and doors, and a heated pool with spa and dockage.

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Monroe County, FL Short Term Rental Properties Market Trends and Statistics

Explore 33 short term rental properties for sale in Monroe County, FL, showcased through 33 active listings on our real estate platform. These investment opportunities span a total of 72,161 square feet of properties for sale, with an estimated market value of $100,104,895.

Sale prices for short term rental properties in Monroe County, FL start at $150,000, averaging $3,850,188, and reaching up to $12,900,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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