Houses for 12+ guests in Florida Keys & Key West, FL
Houses for 12+ guests in Florida Keys & Key West, FL, from $300 a night. Book direct on each manager's site, no OTA fee.
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The Windrose Estate at Lunara Bay
House · 6 bed · 6.5 bath · sleeps 14
Key West, FL
From $1,289 a night
- air conditioning
- bbq grill
- baking sheet
- bathtub
Exact location
Book direct on CielStay
Autograph House | 6BR Retreat w/Guest House, Private Pools & BBQ
House · 6 bed · 6.5 bath · sleeps 12
Key West, FL
From $1,664 a night
- body soap
- hot water
- dryer
- essentials
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Island Time - Open water view w. dock
House · 5 bed · 4 bath · sleeps 12
Marathon
From $300 a night
Exact location
Book direct on infinitypropertymanagement.net
THE FLAGLER ROOM @ The Inn on Fleming ~ 1st Floor King Room w/ Shared Pool!
House · 1 bath · sleeps 34
Key West, FL
From $347 a night
- air conditioning
- coffee/tea maker
- free wifi
- hair dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
The Andros | Incredible Views w/ Shared Pool
House · 2 bath · sleeps 23
Key West, FL
From $421 a night
- air conditioning
- cookware, dishware, and utensils
- dishwasher
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Coco's Poolside Retreat
House · 2.5 bath · sleeps 48
Key West, FL
From $405 a night
- air conditioning
- available in the house: free wifi
- balcony
- barbecue grill
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
La Brisa - Ocean Views Across from Smathers Beach
House · 2 bath · sleeps 22
Key West, FL
From $458 a night
- air conditioning
- available in the condo: free wifi
- balcony
- barbecue grill
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
~ POINCIANA TREETOP ~ Casual second floor duplex 2 blocks from Duval Street!
House · 1 bath · sleeps 52
Key West, FL
From $482 a night
- air conditioning
- balcony
- barbecue grill
- bathtub or shower
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Citrus Queen at Custom House Inn | Ideal Location On Duval!
House · 1 bath · sleeps 20
Key Wets, FL
From $570 a night
- air conditioning
- free wifi
- hair dryer
- in the city center
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Luxurious 3-Bedroom Key West Home with WiFi, EV charging, AC & Tropical Vibes!
House · 3 bath · sleeps 47
Key West, FL
From $1,259 a night
- 8 pets total
- air conditioning
- barbecue grill
- bathtub or shower
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Tranquility by AvantStay | Close to Duval St w/ BBQ & Shared Pool
House · sleeps 42
Key West, FL
From $494 a night
- air conditioning
- available in the house: free wifi
- barbecue grill
- children's dinnerware
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Chagall’s Corner | Newly Remodeled!
House · sleeps 35
Key West, FL
From $388 a night
- air conditioning
- bedsheets provided
- dryer
- free wifi
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Half block to Duval - Stay at the Bonaire Suite
House · sleeps 25
Key West, FL
From $413 a night
- air conditioning
- barbecue grill
- bedsheets provided
- coffee/tea maker
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Charming, updated home near Duval St. with enclosed patio & walkable location
House · sleeps 36
Key West, FL
From $551 a night
- air conditioning
- bedsheets provided
- dining area
- kitchen
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Pool, Laundry, and grilling area
House · sleeps 32
Key West, FL
From $551 a night
- bedsheets provided
- dryer
- free wifi
- iron/ironing board
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
ARIA~Adult Only, Treetop King Suite w/ Balcony & Shared Pool at Azul Mansion!
House · sleeps 17
Key West, FL
From $801 a night
- air conditioning
- balcony
- bedsheets provided
- free wifi
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Escape to the wonderful Cuban Paradise!
House · sleeps 43
Key West, FL
From $871 a night
- air conditioning
- balcony
- children's dinnerware
- dining table
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Poinciana House in Key West
House · sleeps 52
Key West, FL
From $1,131 a night
- available in the house: wifi
- barbecue grill
- books
- dining table
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Architect's Personal Residence, Private Pool, 1 Blk. to Duval
House · sleeps 17
Key West, FL
From $1,171 a night
- air conditioning
- available in the house: wifi
- barbecue grill
- blender
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Excellent Choice! Family-friendly Room, Fantastic View, Outdoor Pool
House · sleeps 39
Key West, FL
From $1,171 a night
- air conditioning
- beach view
- breakfast available
- breakfast available for a fee
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Charming 2 room guest house, access to Pool, A/C, & WiFi, Key West, near Duval
House · sleeps 56
Key West, FL
From $1,172 a night
- air conditioning
- available in the house: free wifi
- children's games
- free wifi
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Emerald Tides
House · 12 bed · 4.5 bath · sleeps 12
Marathon, MA
No nightly rate published
- cleanliness
- self check in / check out
- safety features
- fire extinguisher
Exact location
Book direct on Florida Keys Vacation Rentals in Marathon
Sombrero Beach Beauty
House · 2 bed · 3 bath · sleeps 12
Marathon
No nightly rate published
- cleanliness
- self check in / check out
- safety features
- fire extinguisher
Exact location
Book direct on Florida Keys Vacation Rentals in Marathon
Tipsy Turtle
House · 2 bed · 4 bath · sleeps 12
Marathon, MA
No nightly rate published
- cleanliness
- self check in / check out
- safety features
- fire extinguisher
Exact location
Book direct on Florida Keys Vacation Rentals in Marathon
East Sister Rock Island - Exclusive Vacation Rental in Marathon, Florida Keys
House · 4 bed · 3 bath · sleeps 12
Marathon, FL
No nightly rate published
- private swimming pool
- helicopter landing pad
- 100-foot private boat dock
- pet friendly
Exact location
Book direct on Best Vacation Rental Marathon Florida Keys
Classic Key West Estate
House · 7 bed · 5 bath · sleeps 16
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- swimming pool
City-level location
Book direct on Key West Vacation Rentals
Emerald Horizon
House · 5 bed · 4 bath · sleeps 12
No nightly rate published
- cleanliness
- self check in / check out
- safety features
- fire extinguisher
Approximate area
Book direct on Florida Keys Vacation Rentals in Marathon
Family Reunion Compound: Flower Power House + Coco's Poolside Retreat
House · 9 bed · 6 bath · sleeps 21
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- swimming pool
City-level location
Book direct on Key West Vacation Rentals
Flower Power House
House · 5 bed · 4 bath · sleeps 13
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- swimming pool
City-level location
Book direct on Key West Vacation Rentals
Sombrero Beach | Canalfront Pool Home + Dock
House · 2 bed · 3 bath · sleeps 12
Marathon, FL
No nightly rate published
- air conditioning
- bathtub
- bbq grill
- bed linens
Exact location
Book direct on Vacation In The Florida Keys|Island Breeze Vacations
The Blue Llama Estate Compound
House · 7 bed · 7 bath · sleeps 14
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
Book your Chateau On The Ocean
House · 7 bed · sleeps 14
Islamorada
No nightly rate published
Exact location
Book direct on HōM
Luxury Oceanfront Estate | Private Dock • Pool
House · 5 bed · sleeps 12
Key Largo, FL
No nightly rate published
- air conditioning
- barbecue utensils
- bbq grill
- blender
Exact location
Book direct on Manage your vacation home with Fairly.
Front Beach, Paradise Villa, Islamorada FL Keys
House · 7 bed · 8 bath · sleeps 14
Islamorada, FL
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
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How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-30 06:39 UTC. Prices and facts are whatever the manager published on their own site.