Cottages in Lower Florida Keys
Florida
United States of America
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A coastal landscape with clear turquoise waters, a long bridge, and a small island with buildings.

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your current months are November, 2026 and December, 2026.

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Our top choices for Lower Florida Keys cottages

A floating houseboat with a covered deck and seating area, docked at a marina.

A row of houseboats docked at a marina with clear reflections in the water.

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina

2.5 star property

Punta Brisa

8.6 out of 10, Excellent, (382 reviews)

8.6/10

Excellent

(382 reviews)

"Very clean for Florida keys room - no complaints easy check in and out"

Anthony

The price is AED 257

AED 257

AED 805 total

includes taxes & fees

4 Dec - 5 Dec

Old Wooden Bridge Resort and Marina

A covered outdoor deck with a sofa and table, overlooking a marina with boats and palm trees.

A swimming pool with palm trees and a cloudy sky.

A dining area with a white table and chairs, a ceiling light fixture, and a compass wall decoration.

A modern living room with a ceiling fan, a sofa, a coffee table, and a TV mounted on the wall.

2. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key

8.8 out of 10, Excellent, (110 reviews)

8.8/10

Excellent

(110 reviews)

"The place was better than listed. Extremely well taken care. Highly recommend"

Joseph L.

The price is AED 1,047

AED 1,047

AED 1,934 total

includes taxes & fees

14 Nov - 15 Nov

Canal front, dockage, 2 bedroom, 2 bath

A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

A room with a ceiling fan, two windows with blinds, a sofa with patterned cushions, and a rustic coffee table.

A swimming pool with clear blue water, surrounded by lush greenery and palm trees.

A compact living space with a sofa, a coffee table, a kitchen area with cabinets, and a door.

3. OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4

Old Town Key West

9.4 out of 10, Exceptional, (63 reviews)

9.4/10

Exceptional

(63 reviews)

"The place is very clean and AC works great. Access to pool was super convenient. Pool is very nice. Landscaping is tropical and tidy."

Juan B.

The price is AED 582

AED 582

AED 2,084 total

includes taxes & fees

12 Nov - 13 Nov

OSPREY STUDIO @ The Colony-Sleeps up to 4

A two-story building with balconies, surrounded by lush greenery and palm trees.

A dining area with a round table, wicker chairs, a floral rug, and a chandelier.

A modern living room with a blue sofa, a dining table with wicker chairs, a chandelier, and artwork on the walls.

A bedroom with a large bed, a wooden floor, a white wall, and a window with blinds.

4. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Old Town Key West

10.0 out of 10, Exceptional, (37 reviews)

10/10

Exceptional

(37 reviews)

"Wonderful property! We enjoyed our stay! Property hosts were very attentive to every question we had. Highly recommend!"

Sheri J.

The price is AED 1,102

AED 1,102

AED 2,003 total

includes taxes & fees

29 Nov - 30 Nov

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Two small, single-story buildings with a red and yellow exterior, each with a door and windows, and surrounded by greenery and trees.

A bedroom with a bed, bedside tables, a TV, and a sliding glass door to the outside.

A thatched-roof bar area with a large island counter, bar stools, and a television screen.

A food truck parked in a lush garden with a brick pathway, surrounded by various plants and a white fence.

5. Tropical Cottages

Tropical Cottages

3.0 star property

Marathon

8.6 out of 10, Excellent, (1,014 reviews)

8.6/10

Excellent

(1,014 reviews)

"The family running the food truck and tiki hut were great. Felt like we were guests in their home."

Douglas

The price is AED 364

AED 364

AED 409 total

includes taxes & fees

12 Nov - 13 Nov

Tropical Cottages

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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B&B in Cow Key
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Resorts in Little Torch Key
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Hotels with Free Parking in Stock Island
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B&B in Cudjoe Key
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Wyndham Hotels in Stock Island
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5 Star Hotels in Dredgers Key
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Hilton Hotels in Cudjoe Key
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Condo Rentals in Cow Key
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Cabin Rentals in Fleming Key
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Hilton Hotels in Sugarloaf Shores
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Rv Parks in Cudjoe Key
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Vacation Homes in Key West
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Motels in Ramrod Key
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Houseboats in Stock Island
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Highgate Independent Hotels in Cudjoe Key
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Motels in Key West
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Vacation Homes in Cow Key
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B&B in Key West
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Motels in Cudjoe Key
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Inns in Cow Key
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Condo Rentals in Stock Island
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Marriott Hotels & Resorts in Sugarloaf Key
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B&B in Raccoon Key
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Noble House Hotels in Stock Island
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Apartments in Dredgers Key
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Rv Parks in Summerland Key
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Resorts in Sugarloaf Key
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Guest Houses in Cudjoe Key
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Best Western Hotels in Sugarloaf Key
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Houseboats in Raccoon Key
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Apartments in Raccoon Key
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Beach Hotels in Cudjoe Key
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Hostels in Key West
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Vacation Homes in Ramrod Key
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5 Star Hotels in Sugarloaf Shores
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Cottages in Raccoon Key
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Houseboats in Dredgers Key
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Golf Hotels in Stock Island
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Remington Hotels in Sugarloaf Shores
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Aparthotels in Key West
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Marriott Hotels & Resorts in Sugarloaf Shores
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Vacation Homes in Little Torch Key
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3 Star Hotels in Raccoon Key
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Resorts in Stock Island
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Guest Houses in Ramrod Key
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Flights from Red Bluff (RBL) to Key West (EYW)
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Flights from Santiago (STI) to Key West (EYW)
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Flights from Grand Island (GRI) to Key West (EYW)
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Flights from Charleston (CHS) to Key West (EYW)
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Flights from Corpus Christi (CRP) to Key West (EYW)
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Flights from Princeton (PCT) to Key West (EYW)
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Flights from Tanga (TGT) to Key West (EYW)
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Flights from Cudjoe Key
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Flights from Aberdeen (ABZ) to Key West (EYW)
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Flights from Oakland (OAK) to Key West (EYW)
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Flights from Ixtapa (ZIH) to Key West (EYW)
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Flights from Monterrey (MTY) to Key West (EYW)
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Flights from Belleville (BLV) to Key West (EYW)
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Flights from Youngstown (YNG) to Key West (EYW)
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Flights from Great Harbour Cay (GHC) to Key West (EYW)
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Flights from Moline (MLI) to Key West (EYW)
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Flights from Tashkent (TAS) to Key West (EYW)
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Flights from Toulon (TLN) to Key West (EYW)
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Flights from Inverness (INV) to Key West (EYW)
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Flights from Dayton (DAY) to Key West (EYW)
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Flights from Mount Holly (LLY) to Key West (EYW)
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Flights from Truk (TKK) to Key West (EYW)
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Flights from Pontiac (PTK) to Key West (EYW)
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Flights from Harlingen (HRL) to Key West (EYW)
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Flights from Raccoon Key
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Flights from Eugene (EUG) to Key West (EYW)
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Flights from Tyler (TYR) to Key West (EYW)
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Flights from Orlando (SFB) to Key West (EYW)
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Flights from Longview (GGG) to Key West (EYW)
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Flights from The Valley (AXA) to Key West (EYW)
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Flights from Altamira (ATM) to Key West (EYW)
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Flights from Madurai (IXM) to Key West (EYW)
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Flights from Cincinnati (CVG) to Key West (EYW)
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Flights from Dallas (DFW) to Key West (EYW)
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Flights from Key West Intl.
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Flights from Duluth (DLH) to Key West (EYW)
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Flights from Marietta (MGE) to Key West (EYW)
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Flights from Desroches Island (DES) to Key West (EYW)
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Flights from Luxor (LXR) to Key West (EYW)
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Flights from Santa Rosa (STS) to Key West (EYW)
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Flights from Cortina d'Ampezzo (CDF) to Key West (EYW)
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Flights from Brandon (YBR) to Key West (EYW)
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Flights from Riverside (RAL) to Key West (EYW)
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Flights from Lazaro Cardenas (LZC) to Key West (EYW)
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Flights from Dera Ismail Khan (DSK) to Key West (EYW)
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Flights from Rockford (RFD) to Key West (EYW)
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Flights from Blacksburg (BCB) to Key West (EYW)
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Flights from La Fortuna (FON) to Key West (EYW)
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Flights from Clemson (CEU) to Key West (EYW)
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Flights from Istanbul (IST) to Key West (EYW)
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Flights from Victoria Falls (VFA) to Key West (EYW)
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Flights from DuBois (DUJ) to Key West (EYW)
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Flights from Seward (SWD) to Key West (EYW)
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Cutthroat Harbor Estates Vacations
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Search Cottages in Lower Florida Keys

Change your mind

Treat yourself

Be picky

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Lower Florida Keys cottages

1. Old Wooden Bridge Resort and Marina

2. Canal front, dockage, 2 bedroom, 2 bath

3. OSPREY STUDIO @ The Colony-Sleeps up to 4

4. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

5. Tropical Cottages

Learn more about Lower Florida Keys

Explore a world of travel with Expedia