CielStay lists 136 homes for rent in Key West, run by independent hosts and property managers. All of them can be booked on the host's or manager's own website, across 8 booking sites. Some are also listed on Airbnb and Vrbo; each listing shows every place it can be booked.
The most common size is two bedrooms (38 homes). 50 homes sleep 10 or more.
Key West rentals at a glance
Counted from what hosts list. Check the listing before you book.
| Studio or 1 bedroom | 28 |
| 2 bedrooms | 38 |
| 3 bedrooms | 15 |
| 4 bedrooms | 25 |
| 5 or more bedrooms | 27 |
| Sleeps 10 or more | 50 |
| Air conditioning | 111 |
| Pool | 86 |
| Pets allowed | 53 |
| Hot tub | 7 |
| Fireplace | 5 |
| EV charger | 1 |
Planning a trip? Read our guide: Key West
Homes in Key West
Homes with the host's own booking site first. Prices can change and may not be exact; the asterisk shows what each one includes.
All 136 homes in Key West
- Shared Pool & Near Duval - Curry House Room 9 · 1 bd · sleeps 2
- Yellow Room at the Grand Maloney · 1 bd · sleeps 2
- Shared Pool & Parking - The Cottage at James House · 1 bd · sleeps 3
- Balcony, Pool, & Near Duval - Curry House Room 8 · 1 bd · sleeps 2
- The James Classic | Second Floor King · 1 bd · sleeps 2
- The Rigby House - Pool, One block from Duval St · 6 bd · sleeps 12
- Shared Heated Pool, Near Duval - Poolside Retreat · 1 bd · sleeps 4
- Island Time | Luxury Beach Condo w/ Pool & Hot Tub · 2 bd · sleeps 6
- Poolside Suite - Pool & Close to Duval Street · 2 bd · sleeps 6
- Curry House Room 1 - Near Duval, Pool & Balcony · 1 bd · sleeps 2
- The Maloney - Luxury Modern Downtown Penthouse · 2 bd · sleeps 6
- Private Heated Pool & Near Duval - The Curry House · 9 bd · sleeps 18
- Fish Camp | Old Florida canalfront getaway · 2 bd · sleeps 4
- Helluva Happy Place · 3 bd · sleeps 6
- Windsor Blue Private Pool and Off Street Parking · 2 bd · sleeps 4
- Cabana on Duval | Monthly studio w/ shared pool · sleeps 2
- Catchlight House at Lunara Bay · 6 bd · sleeps 16
- The Windrose Estate at Lunara Bay · 6 bd · sleeps 14
- Runaway Bills · 3 bd · sleeps 6
- Orchid Suite on Duval · sleeps 2
- Designer Waterfront Estate - Lunara Bay Collection · 4 bd · sleeps 10
- Balcony, Pool, & Near Duval - Curry House Room 7 · 1 bd · sleeps 2
- Curry House Room 6 - Balcony & Pool · 1 bd · sleeps 2
- Key Lime Hideaway · 2 bd · sleeps 6
- Rooftop Penthouse · 2 bd · sleeps 6
- Prime Tee Haven | Townhouse on golf course · 2 bd · sleeps 4
- Sky Suites Retreat - Balcony Overlooking Duval · 4 bd · sleeps 12
- The Joyrise House at Solaire Lunara Bay · 6 bd · sleeps 12
- GypsyGinny's Hideaway · 3 bd · sleeps 6
- Old Town Key West 4BR Home w/ Heated Pool · 4 bd · sleeps 8
- Luxury Residence in Old Town Key West w Pool · 4 bd · sleeps 10
- Lovely Cottage Downtown Key West · 3 bd · sleeps 6
- Studio Blu -Hip Studio/Old Town · 1 bd · sleeps 2
- Swarovski Sanctuary · 3 bd · sleeps 6
- Gulf Getaway | Condo w/Pool! · 2 bd · sleeps 6
- Ebberly & Windrose Estates at Lunara Bay · 12 bd · sleeps 28
- Keys Breeze - Walk to Duval, Private Pool · 3 bd · sleeps 6
- Tideview Haven- 5 bedroom with pool& dock · 5 bd · sleeps 10
- Blanco Luxury Villa · 4 bd · sleeps 8
- Curry House Room 2 - Near Duval, Pool & Balcony · 1 bd · sleeps 2
- Duval's Duet - Double Balconies Duval Street · 4 bd · sleeps 16
- Triple Crown Villa- Boaters paradise with Pool · 4 bd · sleeps 8
- Commodore's Cove - One block from Duval St · 4 bd · sleeps 12
- Seaport Suite - Steps from Duval Street · 4 bd · sleeps 12
- Red Room at the Grand Maloney · 1 bd · sleeps 2
- Waterfront Dock Pool Near Duval St Penthouse · 4 bd · sleeps 15
- Curry House Room 3 & 4 - Near Duval · 2 bd · sleeps 4
- Carriage House at the Grand Maloney · 1 bd · sleeps 2
- Beautiful Key Haven Home with Pool, Dock &boat lift · 3 bd · sleeps 8
- Serenity Retreat- 2/2 Townhouse, Dock & Pool · 2 bd · sleeps 4
- Coastal Rose - Private Pool & Near Duval · 1 bd · sleeps 4
- Waterlane House at Lunara Bay · 4 bd · sleeps 10
- Azure Vista Penthouse · 2 bd · sleeps 6
- The Perch on Duval- Hip & Modern Duval Suite · 2 bd · sleeps 5
- The Ebberly Estate at Lunara Bay · 6 bd · sleeps 14
- Blu-3BR Home, Pool/Kid-friendly · 1 bd · sleeps 6
- KAMP - Rooftop Penthouse Overlooking Duval · 2 bd · sleeps 6
- Southernmost View - Private Pool · 4 bd · sleeps 8
- Sky Suite with Balcony Overlooking Duval Street · 2 bd · sleeps 6
- Villa del Sol · 6 bd · sleeps 12
- Doc`s Paradise · 3 bd · sleeps 6
- Waterfront Condo | Pool, Dock, Parking, Sleeps 8 · 2 bd · sleeps 8
- The Fairhaven House at Solaire Lunara Bay · 8 bd · sleeps 16
- The Collins - On Duval Street · 2 bd · sleeps 8
- Floralee House at Lunara Bay · 6 bd · sleeps 16
- Nate's Place in Key West · 3 bd · sleeps 5
- The Mesa House - One block from Duval St · 3 bd · sleeps 10
- The Bartlum - Steps to Duval Street · 1 bd · sleeps 4
- Altair House at Lunara Bay · 6 bd · sleeps 14
- Cool Change · 3 bd · sleeps 6
- Sea Breeze - One Block from Duval Street · 2 bd · sleeps 6
- Duval Dream Loft - On Duval street · 2 bd · sleeps 8
- Joyrise & Fairhaven House at Solaire Lunara Bay · 14 bd · sleeps 28
- Gated Parking, Heated Pool - Villa Positano · 2 bd · sleeps 6
- Island Links Escape · 2 bd · sleeps 5
- Heated Rooftop Pool, Gated Parking - Casa Caribe · 2 bd · sleeps 6
- Larkshine House at Lunara Bay · 8 bd · sleeps 18
- Waterfront Dock Pool Downtown Near Duval Pet · 2 bd · sleeps 8
- Rose Key Cottage - Private Pool & Near Duval · 2 bd · sleeps 6
- Sunnyside Up - Shared Pool · 2 bd · sleeps 9
- Waterfront Dock Pool Penthouse Near Duval St · 4 bd · sleeps 16
- Waterfront Dock Pool Pet Friendly Near Duval St · 4 bd · sleeps 16
- Penthouse Waterfront Dock Pool Condo Near Duval St · 4 bd · sleeps 16
- Poolside Paradise - Heated Pool & Steps to Duval St · 3 bd · sleeps 10
- The Shellstone House at Solaire Lunara Bay · 8 bd · sleeps 16
- Waterfront Dock Pool Condo Near Duval St Pet OK · 2 bd · sleeps 8
- Fairhaven & Shellstone House at Solaire Lunara Bay · 16 bd · sleeps 32
- Mirador House at Lunara Bay · 5 bd · sleeps 16
- Capmar House at Lunara Bay · 4 bd · sleeps 10
- The Fleming Suite | 1 bedroom condo w/shared pool · 1 bd · sleeps 4
- Mastway House at Lunara Bay - Wellness Home · 4 bd · sleeps 12
- Spindrift House at Lunara Bay · 4 bd · sleeps 12
- Curry House Room 5 - First Floor · 1 bd · sleeps 2
- Aquaria House at Lunara Bay · 4 bd · sleeps 10
- The Elizabeth Suite | 1 bedroom condo, shared pool · 1 bd · sleeps 4
- Contra House - Private Pool & Steps to Duval St. · 4 bd · sleeps 12
- Evershore Estate at Lunara Bay | Wellness Home · 4 bd · sleeps 12
- Suncoast House at Lunara Bay · 5 bd · sleeps 14
- The Caroline Suite | 1 bedroom condo w/shared pool · 1 bd · sleeps 4
- The Tortuga at Sunrise Suites - Balcony & Pool · 2 bd · sleeps 6
- The Seagate Estate at Lunara Bay · 4 bd · sleeps 10
- Waterfront Condo Dock Pool Downtown Near Duval · 2 bd · sleeps 8
- Key West House🌴Private Pool👙Waterfront🛥️ · 3 bd · sleeps 6
- The Starboard House at Solaire Lunara Bay · 8 bd · sleeps 20
- The Grenada at Sunrise Suites - Shared Pool · 2 bd · sleeps 6
- Tony's Conch Retreat · 1 bd · sleeps 2
- The Margaret Suite · 1 bd · sleeps 3
- Waterfront Condo Dock Pool Near Duval St · 2 bd · sleeps 8
- Sandbar Suite | 2 bed near Duval & waterfront · 2 bd · sleeps 6
- Commodore's Compound - One block from Duval St · 8 bd · sleeps 24
- Palmgale Estate at Lunara Bay · 6 bd · sleeps 16
- Waterfront Condo + Pool Downtown + Boat Slip · 2 bd · sleeps 8
- Cloud Suite on Duval Street with Balcony · 2 bd · sleeps 6
- Mesa House Uno - One block from Duval St · 1 bd · sleeps 4
- Springtide House at Lunara Bay · 4 bd · sleeps 10
- Casa Azul - Private Pool · 2 bd · sleeps 4
- Coral Reef Suite | 1 bed near Duval & waterfront · 1 bd · sleeps 4
- Waterfront Dock Pool Key West Near Duval · 2 bd · sleeps 8
- Key West Happy Hideaway · 2 bd · sleeps 6
- Parking & Shared Pool - Casa Key West · 3 bd · sleeps 8
- Mesa House Dos - One block from Duval St · 2 bd · sleeps 6
- Blue Horizon Hideaway · 3 bd · sleeps 6
- The Dreamside House at Lunara Bay · 8 bd · sleeps 16
- Sailfish Suite on Duval · 2 bd · sleeps 4
- Takeover at the Grand Maloney · 6 bd · sleeps 16
- Crestwood House at Lunara Bay · 6 bd · sleeps 14
- The Solaire Collection - 4 Stunning Estates · 30 bd · sleeps 64
- Rose Petal Petite Suite - Near Duval Street · sleeps 2
- Harbor Luxe Celebration Suites · 8 bd · sleeps 20
- Bunk Room at the Grand Maloney · 1 bd · sleeps 4
- Tidelands House at Lunara Bay · 8 bd · sleeps 16
- Green Room at the Grand Maloney · 1 bd · sleeps 4
- Harbor House Penthouse- B · 4 bd · sleeps 10
- Blue Room at the Grand Maloney · 1 bd · sleeps 2
- Sky Loft - Steps from Duval Street & Shared Pool · 1 bd · sleeps 4
- Harbor House Penthouse- A · 4 bd · sleeps 12
Questions about renting in Key West
How many vacation rentals are there in Key West?
CielStay lists 136 homes in Key West, counted from the homes live today with an exact map location.
Can I book a vacation rental in Key West directly with the host?
Yes. Every home here can be booked on the host's or manager's own website. Each listing links to it, along with any other place the home is listed.
Are there pet-friendly rentals in Key West?
53 homes list pets as allowed. Pet fees and limits vary by host, so check the house rules on the listing.
Are there rentals in Key West for large groups?
50 homes sleep 10 or more, and 27 homes have five or more bedrooms.
How are prices shown?
Each home shows one price with a note on what it includes; the asterisk explains how we work it out. Prices can change and may not be exact. If a host hasn't shared a fee with us, we can't include it. The host's site or booking channel has the final total; taxes are extra.