Key West and Florida Keys cottage, condo and vacation home directory

333 of 333 listings in Key West and Florida Keys

This is the full list of all 333 Key West and Florida Keys listings on BnB Search: 259 individual vacation rentals, 34 resorts, inns or lodging businesses, 39 rental companies, property managers or real estate offices. Rentals by area tag: Key West (182), Key Largo (25), Islamorada (21), Marathon (17), Big Pine Key (14). Words hosts use in rental titles: condo (22), house or home (38), hot tub (3), pool (36), lakefront or waterfront (17), beachfront, oceanfront or Gulf-front (12), pets or dogs (10). Confirm each feature with the host before you book.

Start here: Key West and Florida Keys vacation rentals map and guide · Key West and Florida Keys rentals with a pool (12) · Oceanfront rentals in Key West and Florida Keys (11) · Waterfront rentals in Key West and Florida Keys (10) · Key West and Florida Keys condo rentals (15).

Planning guides: Key West holidays: Thanksgiving to New Year’s · Key West vacation rental tips · Key West winter packing · Key West vs Hilton Head · Key West vs Outer Banks · Florida Keys Rentals with Pool Access.

Key West and Florida Keys vacation rentals: what to know

The waters around the Keys are part of NOAA’s Florida Keys National Marine Sanctuary. NOAA says it protects 4,539 square miles of water, from south of Miami west to the Dry Tortugas (not including Dry Tortugas National Park). It was designated on November 16, 1990.

Towns

Our listings are tagged Key West, Key Largo, Islamorada, Marathon or Big Pine Key. Our area tags are broad, so open the map pin to see where a rental actually is.

Boats, snorkeling and sanctuary rules

NOAA says the sanctuary starts at the mean high-water mark, so once you step into Keys waters you are in the sanctuary and its rules apply. If your rental comes with a dock or kayaks, read NOAA’s sanctuary regulations before you head out.

Pools and waterfront

The title counts above come from what hosts write. A title saying “pool” or “waterfront” doesn’t tell you whether the pool is private or shared, or whether the water is open ocean or a canal. Ask the host before you book.

Local vacation rental companies

Each of these companies’ own websites describes it as offering vacation rentals in Key West and the Florida Keys (checked October 2026). They are listed alphabetically, not ranked:

More: The Florida Keys vacation rental companies · The Florida Keys facts for rental guests (sources linked there) · Things to do in the Florida Keys.

Key West 237

Happy In The Keys

★★★★★5

beachfishinggrill

73 Coco Plum Dr, Marathon, FL 33050

1001 Whitehead St, Key West, FL 33040

Eleanor's Place Vacation Rental - Key West

★★★★★5

beachdeckkitchen

Vacation Rental - Blu on White

★★★★★5

Casa Feliz Florida Keys

★★★★★5

balconybeachdeck

Barry Beach

★★★★★5

Bluescape Real Estate and Vacation Rentals

★★★★4.9

beachpool

Lunara Bay

★★★★4.9

beachpool

2 Shoreline Rd, Key West, FL 33040

Torchview

★★★★4.9

3236 Catherine St, Summerland Key, FL 33042

Alamar on the Bay

★★★★4.9

beachdeck

Key West Vacation Properties and Realty

★★★★4.9

beach

Duval Street Suites

★★★★4.9

dishwasherdryerkitchen

Orchid Bay Condo

★★★★4.9

beachjacuzzikitchen

Venetian Shores

★★★★4.9

Key Lime Cottage

★★★★4.9

Seabird Key

★★★★4.9

beachbunk beddeck

Coral Lagoon Vacation Rentals by Coco Plum

★★★★4.8

accessiblebeachfishing

Island Breeze Vacations | Vacation Rentals

★★★★4.8

beachfishingkitchen

Seaside Place Key West - Vacation Rental

★★★★4.8

beachkitchenparking

Key West Vacation Homes

★★★★4.8

beachkitchenpet friendly

Marrero's Guest Mansion

★★★★4.8

beachdeckpool

Speakeasy Inn

★★★★4.8

beachkitchenparking

The Mermaid and The Alligator

★★★★4.8

beachpool

Key Colony Beach Vacation Rentals

★★★★4.8

beachdeckfishing

Keys Holiday Rentals

★★★★4.7

beachdeckdryer

VHKW - Vacation Homes of Key West

★★★★4.7

beachparkingpool

507 Whitehead St, Key West, FL 33040

Brightwild

★★★★4.7

beach

Historic Hideaways

★★★★4.7

Grassy Flats Resort and Beach Club

★★★★4.7

beachdeckhot tub

Knowles House Vacation Rental

★★★★4.7

parkingpool

Anglers Reef Vacation Rental

★★★★4.7

beachdishwasherdryer

Truman Annex Condominium Rentals

★★★★4.6

pool

Key West Island Rentals Inc

★★★★4.6

beachkitchen

28 Key Haven Rd, Key West, FL 33040

Harbor Walk Hideaways

★★★★4.6

fishingpool

Courtney's Place

★★★★4.6

720 Whitmarsh Ln, Key West, FL 33040

The Duval House

★★★★4.6

1800 Atlantic/All Florida Keys Property Management

★★★★4.5

balconybbqbeach

Keys Ocean Vacation Rentals

★★★★4.5

beachfishing

Key West Resort Rentals

★★★★4.5

balconybeachdeck

Sunset Cove Beach Resort

★★★★4.5

Sombrero Beach

★★★★4.5

beachparkingplayground

2130 Sombrero Beach Rd, Marathon, FL 33050

Boyd's Key West Campground

★★★★4.5

bbqbeachfishing

William Skelton Home

★★★★4.5

beachgrillkitchen

Bud N' Mary's Marina

★★★★4.5

Key Colony Beach Realty Florida Keys

★★★★4.4

beachfishing

Florida Keys Vacation Cottages

★★★★4.4

beachfishing

Steamplant Key West

★★★★4.4

beachdeckfitness

Lime Tree Bay Resort

★★★★4.4

accessiblebeachfishing

Edgewater Lodge

★★★★4.4

accessiblebbqbeach

Rose Lane Villas

★★★★4.4

fishingkitchenparking

Key West Hideaways

★★★★4.3

hot tubkitchenpet friendly

Coconut Palms of Key West

★★★★4.3

beachwater view

Chesapeake Beach Resort

★★★★4.3

balconybeachfishing

Parrot Key Hotel and Villas

★★★★4.3

accessiblebalconybeach

2801 N Roosevelt Blvd, Key West, FL 33040

Key West by the Sea Association, Inc.

★★★★4.2

beachpooltennis

2601 S Roosevelt Blvd Apt 220C, Key West, FL 33040

Coconut Mallory Resort And Marina By Kees Vacations

★★★★4.2

beachdeckfishing

1445 S Roosevelt Blvd, Key West, FL 33040

Sunshine Key RV Resort and Marina

★★★★4.2

basketballbeachcreek

Heron House

★★★★4.2

beachdeckhot tub

Wicker Guesthouse

★★★★4.1

jacuzziparkingpet friendly

Playa Largo Ocean Residences Vacation Rentals

★★★★4.1

pet friendlypoolwater view

Key West Breeze Vacations

★★★★4

beachpet friendlywifi

Looe Key Reef Resort

★★★★4

beachdeckgrill

Waterfront Keys Realty, Inc.

★★★3.9

beachdeckdryer

Banana Bay Resort

★★★3.8

balconybeachfishing

Altair House

Key West and Florida Keys cottage, condo and vacation home directory

Key West and Florida Keys vacation rentals: what to know

Towns

Boats, snorkeling and sanctuary rules

Pools and waterfront

Local vacation rental companies

Key West 237

Happy In The Keys

Beach Houses Key West

Cozy Coves

Colocada Vacation Rentals @ Sunrise Suites Resort

Seven Keys Vacations

Eleanor's Place Vacation Rental - Key West

Vacation Rental - Blu on White

Casa Feliz Florida Keys

Barry Beach

Bluescape Real Estate and Vacation Rentals

Lunara Bay

Torchview

Alamar on the Bay

Key West Vacation Properties and Realty

Duval Street Suites

Orchid Bay Condo

Venetian Shores

Key Lime Cottage

Seabird Key

Coral Lagoon Vacation Rentals by Coco Plum

Island Breeze Vacations | Vacation Rentals

Seaside Place Key West - Vacation Rental

Key West Vacation Homes

Marrero's Guest Mansion

Speakeasy Inn

The Mermaid and The Alligator

Key Colony Beach Vacation Rentals

Keys Holiday Rentals

VHKW - Vacation Homes of Key West

Brightwild

Historic Hideaways

Grassy Flats Resort and Beach Club

Knowles House Vacation Rental

Anglers Reef Vacation Rental

Truman Annex Condominium Rentals

Key West Island Rentals Inc

Harbor Walk Hideaways

Courtney's Place

The Duval House

1800 Atlantic/All Florida Keys Property Management

Keys Ocean Vacation Rentals

Key West Resort Rentals

Sunset Cove Beach Resort

Sombrero Beach

Boyd's Key West Campground

William Skelton Home

Bud N' Mary's Marina

Key Colony Beach Realty Florida Keys

Florida Keys Vacation Cottages

Steamplant Key West

Lime Tree Bay Resort

Edgewater Lodge

Rose Lane Villas

Key West Hideaways

Coconut Palms of Key West

Chesapeake Beach Resort

Parrot Key Hotel and Villas

Key West by the Sea Association, Inc.

Coconut Mallory Resort And Marina By Kees Vacations

Sunshine Key RV Resort and Marina

Heron House

Wicker Guesthouse

Playa Largo Ocean Residences Vacation Rentals

Key West Breeze Vacations

Looe Key Reef Resort

Waterfront Keys Realty, Inc.

Banana Bay Resort

Altair House

Beach Club Brokers

FOLLOW THE SUN @ THE BEACH Ocean Condo / Pool and Tennis + LAST KEY SERVICES..

Ocean Front Suite with Direct Beach Access

The Tortuga at Sunrise Suites - Balcony and Pool

Waterfront and Heated Pool - Away Awai Floating Villa