Monroe County, FL Short term rental properties for sale

Updated: Aug 12

Waterfront Duplex with Private Pool

219 Sombrero Beach Road, Marathon, FL 33050

$1,439,000

1,840 sqft 0.16 AC lot

1,840‑square‑foot waterfront duplex property built in 2017
Four bedrooms and three bathrooms
31 feet of private dockage
Private pool with deck, patio, porch, and cabana‑style outdoor area
Walkable access to Sombrero Beach

View details

Updated: Oct 9

Mixed-Use Property with Storefront

1011 Whitehead Street, Key West, FL 33040

$3,795,000

2,024 sqft 0.03 AC lot

Three one‑bedroom residences, each with a kitchen and transient rental license
Street‑level commercial storefront
2,024 square feet on a 0.03‑acre lot
Built in 1918
Decks and porches provide private outdoor areas

View details

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.

View details

Realmo Analytics Monitor Off-market properties and contact owners who are ready to sell. Many signals applied to make quality leads for you. Get Leads

Waterfront Resort With Private Marina

101910 Overseas Hwy, Key Largo, FL 33037

$12,900,000

16,840 sqft 2.60 AC lot

Bayside resort with guest accommodations, event flexibility, pools, beach access, and a private marina.

View details

Six-Unit Bed And Breakfast

223 Eanes Lane, Key West, FL 33040

$6,999,000

1,630 sqft 0.12 AC lot

Licensed transient lodging with private baths, tropical landscaping, and an outdoor pool.

View details

Canal-Front Duplex with Dockage

126 N Indies Drive, Duck Key, FL 33050

$1,875,000

2,544 sqft 0.18 AC lot

Two side-by-side units offer separate living spaces, balconies, and under-building storage.

View details

Four-Unit Quadplex with Pool

1501 Truman Avenue, Key West, FL 33040

$3,750,000

2,214 sqft 0.10 AC lot

Three units carry transient rental licenses, while the fourth is leased monthly.

View details

Short-Term Rental Property

1401 Atlantic Boulevard, Key West, FL 33040

$3,400,000

2,530 sqft

A three-residence setup pairs a monthly-rental home with two detached, transient-licensed guest suites.

View details

Renovated Waterfront Short-Term Rental

150 E 63rd Street Ocean, Marathon, FL 33050

$875,000

1,378 sqft 0.09 AC lot

Furnished half-duplex residence with direct ocean access, private dockage, and short-term rental eligibility.

View details

Waterfront Short-Term Rental Property

100 E 63rd Street Ocean, Marathon, FL 33050

$875,000

1,342 sqft 0.09 AC lot

Renovated, furnished half duplex with ocean access, updated systems, and short-term rentals permitted.

View details

Islamorada Waterfront Family Compound

110 Gulfview Drive, Islamorada, FL 33036

$3,524,000

3,524 sqft

Luxury multi-family property with income potential and resort-style amenities.

View details

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.

View details

Furnished Short-Term Rental Residences

104000 Overseas Highway, Key Largo, FL 33037

$279,000

2,300 sqft

Fractional-use residences feature resort amenities, private outdoor space, stocked kitchens, and access to two boats.

View details

Four-Unit Short-Term Rental Property

1501 Truman Avenue, Key West, FL 33040

$3,750,000

Three units hold transient licenses for nightly stays; the remaining unit is leased monthly.

View details

Fractional Resort Residences

104000 Overseas Highway, Key Largo, FL 33037

$289,000

2,300 sqft

Fractional ownership includes furnished residences, resort amenities, waterfront access, and use of two boats.

View details

Waterfront Duplex Compound

Islamorada, FL 33036

$3,524,000

3,524 sqft 0.16 AC lot

Canal-front property combines two upstairs residences with a separate finished lower-level living area and private waterfront amenities.

View details

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.

View details

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.

View details

Oceanfront Short-Term Rental Estate