Stays for 8+ guests in Florida Keys & Key West, FL
Stays for 8+ guests in Florida Keys & Key West, FL, from $257 a night. Book direct on each manager's site, no OTA fee.
Find stays in Florida Keys & Key West, FL
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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
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
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
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
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
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
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
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
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
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
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
Turtle Nest Islamorada 30ft dock 28 day 4bed 5bath
House · 4 bed · 5 bath · sleeps 8
Islamorada
From $550 a night
Exact location
Book direct on AOVRentals.com
Mariner's Club 210 Key Largo Marina Villa Rental
Villa · 3 bed · 3 bath · sleeps 8
Key Largo
From $584 a night
Exact location
Book direct on Keys Life Vacations
Vaca Cut w/60' dock, 4br/4ba, 2 kitchens
House · 4 bed · 4 bath · sleeps 10
Marathon
From $589 a night
Exact location
Book direct on Melbourne Space Coast Vacation Rentals
Kawama G12 Key Largo Vacation Rental | 2 Bedroom Villa
Villa · 2 bed · 2 bath · sleeps 8
Key Largo
From $593 a night
Exact location
Book direct on Keys Life Vacations
Kawama L4 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 10
Key Largo
From $593 a night
Exact location
Book direct on Keys Life Vacations
Seabreeze Marathon Oceanside 4/3 Pool Boat Dock
House · 4 bed · 3 bath · sleeps 8
Key Colony Beach
From $600 a night
Exact location
Book direct on Seabreeze Stay Vacation Rentals
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
House · 3 bed · 3 bath · sleeps 8
Key Largo
From $600 a night
Exact location
Book direct on Luxury Fort Lauderdale Vacation Rental
Private Pool Tropical Oasis - Centrally Located
House · 3 bed · 2 bath · sleeps 8
Duck Key, FL
From $605 a night
Exact location
Book direct on House Swap for Airbnb Hosts, No Nightly Rates
Kawama K5 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 8
Key Largo
From $690 a night
Exact location
Book direct on Keys Life Vacations
Kawama P6 Key Largo Vacation Rental | 3 Bedroom Villa
Villa · 3 bed · 3 bath · sleeps 8
Key Largo
From $690 a night
Exact location
Book direct on Keys Life Vacations
Key Largo Oasis Oceanfront with Pool & Hot Tub
House · 3 bed · 3 bath · sleeps 9
Key Largo
From $789 a night
Exact location
Book direct on Luxury Fort Lauderdale Vacation Rental
Waterfront 3BR Retreat: Pool, Spa & Kayaks
House · 3 bed · 2 bath · sleeps 9
Key Largo
From $789 a night
Exact location
Book direct on Luxury Fort Lauderdale Vacation Rental
Chic Ocean Hideaway with Grill
House · 3 bed · 2 bath · sleeps 10
Key Largo
From $799 a night
Exact location
Book direct on Luxury Fort Lauderdale Vacation Rental
New Oceanside Paradise with Pool and Waterfront Views!
House · 3 bed · 3 bath · sleeps 9
Key Largo
From $799 a night
Exact location
Book direct on Luxury Fort Lauderdale Vacation Rental
Luxury Private Home w/ Heated Pool in Key West
House · 4 bed · 3 bath · sleeps 10
Key West
From $800 a night
Exact location
Book direct on Trautman Short Term Rentals Champaign-Urbana
Ocean's Edge Retreat
House · 3 bed · 3 bath · sleeps 8
Key Colony Beach
From $859 a night
Exact location
Book direct on Ocean Isles Vacation Rentals
Coconut Palm - Steps from Duval with Private Pool
House · 3 bed · 2 bath · sleeps 8
Key West, FL
From $1,023 a night
Exact location
Book direct on CielStay
Amelia Home by AvantStay | In Historic Old Town w/ Pool
House · 2 bed · 2.5 bath · sleeps 10
Key West, FL
From $1,171 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
Just steps to Duval- Sleeps 10- Pool House
House · 3 bed · 2.5 bath · sleeps 10
Key West, FL
From $1,171 a night
- air conditioning
- bathtub
- coffee/tea maker
- cookware, dishware, and utensils
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
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
Blue Island
Beach house · 6 bed · 6 bath · sleeps 14
Marathon
From $1,525 a night
Exact location
Book direct on Blue Island Marathon / Oceanfront Vacation Rental
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
House · 4 bed · 4 bath · sleeps 10
Key West
From $1,658 a night
Exact location
Book direct on Center Court Key West
DUVAL SQUARE PENTHOUSE! A gorgeous condo on Duval St with room for everyone!
Condo · 2 bed · sleeps 9
Key West, FL
From $347 a night
- air conditioning
- balcony
- bedsheets provided
- coffee/tea maker
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
Key West Cockadoodle Cottage on Duval
Cottage · 2 bed · sleeps 14
Key West, FL
From $361 a night
- air conditioning
- bedsheets provided
- coin laundry
- dining area
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
Sunny Condo w/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
Condo · 1 bath · sleeps 8
Key West, FL
From $454 a night
- air conditioning
- balcony
- coffee/tea maker
- cookware, dishware, and utensils
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
Key West Hideaway, Sleeps 10, 4BR/4BA, Q Sl. Sofa!
House · 2 bed · sleeps 10
Key West, FL
From $631 a night
- air conditioning
- balcony
- barbecue grill
- coffee/tea maker
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Tropical Island Retreat Near Florida Beaches with Pool & Views
House · 4.5 bath · sleeps 10
Key West, FL
From $631 a night
- air conditioning
- bedsheets provided
- breakfast included
- english
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
Salvador's Seclusion | Cozy Studio Retreat with a Heated Pool!
Studio · sleeps 15
Key West, FL
From $363 a night
- air conditioning
- bedsheets provided
- dryer
- free wifi
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
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 2026-10-30 09:14 UTC. Prices and facts are whatever the manager published on their own site.