Stays for 6+ guests in Florida Keys & Key West, FL
Stays for 6+ guests in Florida Keys & Key West, FL, from $125 a night. Book direct on each manager's site, no OTA fee.
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Stays, best documented first
Reel Escape
House · 3 bed · 2 bath · sleeps 8
Marathon, FL
From $375 a night
- cleaning products
- oven
- conditioner
- carbon monoxide detector
Exact location
Book direct on Paradise Found Escapes
Villa De Madera
Villa · 3 bed · 3 bath · sleeps 8
Marathon, FL
From $375 a night
- kayak
- fire pit
- hot water
- heated pool
Exact location
Book direct on Paradise Found Escapes
The Hideaway
House · 3 bed · 2 bath · sleeps 8
Marathon, FL
From $450 a night
- first aid kit
- bathtub
- smart tv
- stove
Exact location
Book direct on Paradise Found Escapes
The Toasted Coconut
House · 3 bed · 2 bath · sleeps 8
Marathon, FL
From $450 a night
- hot water
- essentials
- barbeque utensils
- dining table
Exact location
Book direct on Paradise Found Escapes
Tiki Time
House · 3 bed · 2 bath · sleeps 8
Marathon, FL
From $650 a night
- board games
- fenced pool
- stove
- body soap
Exact location
Book direct on Paradise Found Escapes
Life is a Marathon
House · 4 bed · 3 bath · sleeps 10
Marathon, FL
From $700 a night
- pots pans
- water view
- free parking
- conditioner
Exact location
Book direct on Paradise Found Escapes
Serenity Oasis
House · 3 bed · 2 bath · sleeps 8
Marathon, FL
From $1,000 a night
- near ocean
- air filter
- lock on bedroom
- cleaning products
Exact location
Book direct on Paradise Found Escapes
Paradise Point
House · 3 bed · 2.5 bath · sleeps 8
Marathon, FL
From $1,200 a night
- shampoo
- conditioner
- pool all year
- dishwasher
Exact location
Book direct on Paradise Found Escapes
Paradise Palms
House · 3 bed · 2 bath · sleeps 8
Marathon, FL
From $1,400 a night
- air filter
- free parking
- laptop friendly
- essentials
Exact location
Book direct on Paradise Found Escapes
The Oasis
House · 1 bed · 1.5 bath · sleeps 8
Islamorada, FL
From $1,400 a night
- fireplace
- air conditioning
- central heating
- linens provided
Exact location
Book direct on YourKeys.Vacations
Paradise Palms | 2 Balconies | Ocean Pointe 1206
Villa · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $199 a night
- air conditioning
- bbq grill
- baking sheet
- barbeque utensils
City-level location
Book direct on Oasis Vacation Rentals
Keys Bohemian | Renovated 2BR | Ocean Pointe 1312
Villa · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $229 a night
- air conditioning
- bbq grill
- baking sheet
- barbeque utensils
City-level location
Book direct on Oasis Vacation Rentals
Across from Pool | Sleeps 6 | Ocean Pointe 3212
Villa · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $239 a night
- air conditioning
- bbq grill
- bathtub
- beach
City-level location
Book direct on Oasis Vacation Rentals
Aqua Vista | Ocean View 2BR | Ocean Pointe 3307
Villa · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $239 a night
- air conditioning
- bbq grill
- beach
- beach access
City-level location
Book direct on Oasis Vacation Rentals
Ocean View 2BR | Sleeps 6 | Ocean Pointe 2307
Villa · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $239 a night
- air conditioning
- bbq grill
- bathtub
- beach
City-level location
Book direct on Oasis Vacation Rentals
Sunrise Sanctuary | Top Floor | Ocean Pointe 2415
Villa · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $263 a night
- air conditioning
- bbq grill
- bathtub
- beach
City-level location
Book direct on Oasis Vacation Rentals
Corner Penthouse | Ocean Views | Ocean Pointe 5416
Villa · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $289 a night
- air conditioning
- bbq grill
- bathtub
- beach
City-level location
Book direct on Oasis Vacation Rentals
Blu-3BR Home, Pool/Kid-friendly
House · 1 bed · 1 bath · sleeps 6
Key West, FL
From $335 a night
- air conditioning
- dishes and silverware
- hair dryer
- dedicated workspace
Exact location
Book direct on CielStay
107 Pelican Rd, Tavernier, FL 33070
House · 3 bed · 1 bath · sleeps 6
Tavernier, FL
From $500 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Select Housing, LLC
Waterfront Condo | Pool, Dock, Parking, Sleeps 8
Condo · 2 bed · 2 bath · sleeps 8
Key West, FL
From $650 a night
- air conditioning
- bbq grill
- baking sheet
- barbeque utensils
Exact location
Book direct on CielStay
The Ebberly Estate at Lunara Bay
Bungalow · 6 bed · 6.5 bath · sleeps 14
Key West, FL
From $1,200 a night
- air conditioning
- bbq grill
- bathtub
- bed linens
Exact location
Book direct on CielStay
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
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Villa · 2 bed · 2 bath · sleeps 6
Key West, FL
From $1,045 a night
- air conditioning
- coffee/tea maker
- deck or patio
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Calypso Corner - Little Torch Key
House · 2 bed · 2 bath · sleeps 6
Little Torch Key
From $185 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Barracuda Bungalow - Big Pine Key
Bungalow · 3 bed · 2 bath · sleeps 6
Big Pine Key
From $200 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Reel Paradise in Little Torch Key
House · 3 bed · 2 bath · sleeps 6
Little Torch Key
From $215 a night
Exact location
Book direct on infinitypropertymanagement.net
Turtle Nest 1 Private beach, Pool, 2bed 2bath
Condo · 2 bed · 2 bath · sleeps 6
Tavernier
From $235 a night
Exact location
Book direct on AOVRentals.com
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Condo · 2 bed · 2 bath · sleeps 6
Tavernier
From $249 a night
Exact location
Book direct on AOVRentals.com
Paradise Found | Pet friendly, boating on Cudjoe
House · 3 bed · 2 bath · sleeps 6
Cudjoe Key, FL
From $277 a night
Exact location
Book direct on CielStay
Sunset Landing - Little Torch Key
House · 3 bed · 2 bath · sleeps 6
Little Torch Key
From $285 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Island Escape - Big Pine Key
House · 3 bed · 2 bath · sleeps 6
Big Pine Key
From $300 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
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
Catch & Relax
House · 2 bed · 3 bath · sleeps 6
Marathon
From $305 a night
Exact location
Book direct on Seas the Keys
Paradise Blue - Little Torch Key
House · 3 bed · 2 bath · sleeps 6
Little Torch Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Paradise Palms - Cudjoe Key
House · 3 bed · 2 bath · sleeps 6
Summerland Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Reel Life - Cudjoe Key
House · 3 bed · 2 bath · sleeps 6
Cudjoe Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Summerland Key House - Summerland Key
House · 2 bed · 2 bath · sleeps 6
Summerland Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Blue Octopus Hideaway at OI! VACA-23-163
Apartment · 2 bed · 2 bath · sleeps 6
Marathon
From $325 a night
Exact location
Book direct on Ocean Isles Vacation Rentals
Serene Oceanfront Keys Condo
Condo · 2 bed · 2 bath · sleeps 6
Tavernier
From $328 a night
Exact location
Book direct on Keys Life Vacations
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
House · 2 bed · 2 bath · sleeps 6
Key West, FL
From $344 a night
- air conditioning
- balcony
- concierge services
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Seas the Keys Getaway with plunge pool/spa
Villa · 2 bed · 2 bath · sleeps 6
Marathon
From $345 a night
Exact location
Book direct on Seas the Keys
Key Largo Waterfront Condo with Pool & Boat Slip | Ocean Shore Villa 2
Villa · 2 bed · 2 bath · sleeps 8
Key Largo
From $353 a night
Exact location
Book direct on Keys Life Vacations
Oceanfront condo with beach access, pool, balcony, & tennis - marina available
Condo · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $355 a night
- air conditioning
- balcony
- communal pool
- deck or patio
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Key Largo Waterfront Condo with Pool & Boat Slip | Ocean Shore Villa 3
Villa · 2 bed · 2 bath · sleeps 8
Key Largo
From $377 a night
Exact location
Book direct on Keys Life Vacations
Key Largo Waterfront condo with Pool & Boat Slip | Ocean Shore Villa 1
Villa · 2 bed · 2 bath · sleeps 8
Key Largo
From $389 a night
Exact location
Book direct on Keys Life Vacations
Ocean view condo with balcony/marina view
Condo · 2 bed · 2 bath · sleeps 6
Tavernier, FL
From $391 a night
- air conditioning
- balcony
- barbecue grill
- bedsheets provided
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Casa Largo Vacation Rental | 2 Bedroom Florida Keys Stay
Villa · 2 bed · 2 bath · sleeps 8
Key Largo
From $433 a night
Exact location
Book direct on Keys Life Vacations
Oceanside home 107: dock-kayaks-bikes-pool-fishing
House · 2 bed · 3 bath · sleeps 6
Cudjoe Key
From $443 a night
Exact location
Book direct on Lower Keys Vacation Rentals
Kawama K1 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 10
Key Largo
From $448 a night
Exact location
Book direct on Keys Life Vacations
Ocean Breeze Oasis with great boating access VACA-23-410
House · 3 bed · 2 bath · sleeps 8
Marathon
From $449 a night
Exact location
Book direct on Ocean Isles Vacation Rentals
Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
Cottage · 2 bed · 2 bath · sleeps 6
Key West
From $450 a night
Exact location
Book direct on Center Court Key West
Kawama J3 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 10
Key Largo
From $450 a night
Exact location
Book direct on Keys Life Vacations
Kawama L1 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 10
Key Largo
From $450 a night
Exact location
Book direct on Keys Life Vacations
Reef House Islamorada
House · 2 bed · 3 bath · sleeps 6
Islamorada
From $450 a night
Exact location
Book direct on Keys Life Vacations
Kawama N2 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 10
Key Largo
From $459 a night
Exact location
Book direct on Keys Life Vacations
Kawama R5 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 10
Key Largo
From $459 a night
Exact location
Book direct on Keys Life Vacations
Oceanside home 109, dock,kayaks,bikes,pool,fishing
House · 2 bed · 3 bath · sleeps 6
Cudjoe Key
From $466 a night
Exact location
Book direct on Lower Keys Vacation Rentals
Endless Summer Key Largo Vacation Home | 5 Bedrooms
House · 5 bed · 3 bath · sleeps 10
Key Largo
From $475 a night
Exact location
Book direct on Keys Life Vacations
ATLANTIC HIDEAWAY- Key West
House · 2 bed · 2 bath · sleeps 6
Key West, FL
From $480 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
Seabreeze Key Largo Oceanside 4/2 Pool Boat Dock
House · 4 bed · 2 bath · sleeps 10
Key Largo
From $500 a night
Exact location
Book direct on Seabreeze Stay Vacation Rentals
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
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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 08:42 UTC. Prices and facts are whatever the manager published on their own site.