Stays for 16+ guests in Florida Keys & Key West, FL
Stays for 16+ guests in Florida Keys & Key West, FL, from $214 a night. Book direct on each manager's site, no OTA fee.
Find stays in Florida Keys & Key West, FL
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Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
Cottage · 4 bed · 2 bath · sleeps 28
Key West, FL
From $1,172 a night
- air conditioning
- barbecue grill
- car not required
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
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
Yellowfin Ledge | Inviting Getaway On Duval! Balcony!
House · 1 bath · sleeps 59
Key West, FL
From $441 a night
- air conditioning
- pet-friendly
- shower
- towels provided
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Studio · 1 bath · sleeps 46
Key West, FL
From $475 a night
- air conditioning
- barbecue grill
- bedsheets provided
- free wifi
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Sunshine State at Custom House Inn | Bright Studio on Duval Street!
Studio · 1 bath · sleeps 20
Key West, FL
From $614 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
Paradise Place by AvantStay | Key West Old Town Condo w/ Shared Pool
Condo · 4.5 bath · sleeps 24
Key West, FL
From $395 a night
- air conditioning
- available in the house: free wifi
- coffee/tea maker
- cookware, dishware, and utensils
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
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Cottage · 1 bath · sleeps 37
Key West, FL
From $407 a night
- air conditioning
- coffee/tea maker
- cookware, dishware, and utensils
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
Townhome · 1.5 bath · sleeps 43
Key West, FL
From $413 a night
- air conditioning
- barbecue grill
- coffee/tea maker
- cookware, dishware, and utensils
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
3-22 to 3-24 195 lodg.+ close beach
House · sleeps 28
Key West, FL
From $214 a night
- air conditioning
- bedsheets provided
- car not required
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
~ SOLARIS COTTAGE ~ Live like a local in this bright and cozy retreat.
Cottage · sleeps 44
Key West, FL
From $394 a night
- air conditioning
- barbecue grill
- bedsheets provided
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Unique Home with loft @ Truman Annex
Loft · sleeps 53
Key West, FL
From $421 a night
- id: 25653
- bathrooms: sleeps
- type: condo
- air conditioning
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
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
Cottage · sleeps 60
Key West, FL
From $507 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
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Condo · sleeps 21
Key West, FL
From $601 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
Colorful beachfront condo w/ ocean view balcony & shared hot tub/pool/tennis
Condo · sleeps 32
Key West, FL
From $367 a night
- air conditioning
- available in the condo: wifi
- balcony
- coffee/tea maker
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
Exclusive Key West Beach Front - 3BR Luxury Condo w/Gym and Pool Access
Condo · sleeps 41
Key West, FL
From $471 a night
- air conditioning
- available in the condo: free wifi
- balcony
- coffee/tea maker
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Leo’s Lodge | Newly Updated!
Lodge · sleeps 25
Key West, FL
From $480 a night
- air conditioning
- bedsheets provided
- dryer
- free wifi
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
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
Cottage · sleeps 39
Key West, FL
From $781 a night
- air conditioning
- available in the cabin: wifi
- barbecue grill
- coffee/tea maker
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
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
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
Ocean's Edge Clubhouse
Resort · 0 bed · 2 bath
Key Largo, FL
No nightly rate published
- air conditioning
- lock on bedroom door
- wireless internet
- bed linens
City-level location
Book direct on Playa Largo Ocean Residences
Old Town Caribbean Estate
Cottage · 10 bed · 7 bath · sleeps 21
Key West, FL
No nightly rate published
- internet
- wireless
- air conditioning
- kitchen
City-level location
Book direct on Key West Vacation Rentals
✦Relax on your Oceanfront villa on Seapalm island✦
Villa · 5 bed · 5 bath · sleeps 16
Little Conch Key
No nightly rate published
Exact location
Book direct on goodness.house
Real World MTV House Key West — Oceanfront Private Resort, Sleeps 18–22.
House · 9 bed · sleeps 22
Key West, FL
No nightly rate published
City-level location
Book direct on Real World MTV House Key West
Thompson Island Key West — Private Island Estate
Cottage · sleeps 20
Key West, FL
No nightly rate published
City-level location
Book direct on Thompson Island Key West
Nearby
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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 2026-10-31 05:16 UTC. Prices and facts are whatever the manager published on their own site.