Key West Rentals
From $430 per night (USD)VRBO
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Fam ...
From $430 per night (USD)VRBO
From $435 per night (USD)Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $435 per night (USD)Expedia
From $2234 per night (USD)VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $2234 per night (USD)VRBO
From $605 per night (USD)Expedia
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $605 per night (USD)Expedia
From $667 per night (USD)VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside Condo & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $667 per night (USD)VRBO
From $305 per night (USD)Expedia
Sumptuous Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $305 per night (USD)Expedia
From $434 per night (USD)VRBO
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When your vac ...
From $434 per night (USD)VRBO
From $402 per night (USD)Expedia
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SET SAIL cele ...
From $402 per night (USD)Expedia
Click For PricingVRBO
Cozy studio cottage in Old Town Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
Click For PricingVRBO
From $574 per night (USD)Expedia
Welcome to the Shady Palms - Private Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $574 per night (USD)Expedia
From $875 per night (USD)VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! While Old Tow ...
From $875 per night (USD)VRBO
From $549 per night (USD)Expedia
SOUTHERNMOST SWIM AND SOCIAL CLUB
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your Home Away from Home in Beautiful Key West Welcome to Southernmost Swim & Social Club — where you and your loved on ...
From $549 per night (USD)Expedia
From $365 per night (USD)VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $365 per night (USD)VRBO
From $784 per night (USD)Expedia
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $784 per night (USD)Expedia
From $587 per night (USD)VRBO
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $587 per night (USD)VRBO
From $278 per night (USD)Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $278 per night (USD)Expedia
From $1060 per night (USD)VRBO
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $1060 per night (USD)VRBO
From $861 per night (USD)VRBO
Key West's Crown Jewel
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Key West's Crown Jewel is a penthouse condominium at 1800 Atlantic Condominium development with two-bedroom, two-bath wi ...
From $861 per night (USD)VRBO
From $511 per night (USD)VRBO
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! It is not so ...
From $511 per night (USD)VRBO
From $586 per night (USD)Expedia
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you’re loo ...
From $586 per night (USD)Expedia
From $669 per night (USD)VRBO
Flirty Flamingo Key West
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $669 per night (USD)VRBO
From $577 per night (USD)Expedia
Henry's Piece of Paradise on the Ocean in Key West - Weekly / Nightly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $577 per night (USD)Expedia
Click For PricingVRBO
Sunset views at the Galleon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
Click For PricingVRBO
From $1216 per night (USD)Expedia
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites & Marina - NO CLEANING FEE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1216 per night (USD)Expedia
From $463 per night (USD)VRBO
2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $463 per night (USD)VRBO
From $219 per night (USD)Expedia
Upscale Townhome w/ Golf, Garden & Lake Views, Shared Pool, WiFi - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Tipsy Mermaid at Key West Golf Club Our calendar is updated in real-time & our nightly rates are accurately display ...
From $219 per night (USD)Expedia
From $912 per night (USD)VRBO
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $912 per night (USD)VRBO
From $1047 per night (USD)Expedia
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1047 per night (USD)Expedia
From $746 per night (USD)VRBO
3 Bed 3 Bath Condo @ Bayfront Suites - NO CLEANING FEE (Non-Waterfront)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $746 per night (USD)VRBO
From $1055 per night (USD)Expedia
4-Bed, 3-Bath Waterfront Condo at Bayfront Suites & Marina - NO CLEANING FEE
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1055 per night (USD)Expedia
From $1190 per night (USD)VRBO
4-Bed, 4.5 Bath Condo & Bayfront Suites - NO CLEANING FEE (Non-Waterfront)
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1190 per night (USD)VRBO
From $771 per night (USD)Expedia
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina - NO CLEANING FEE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $771 per night (USD)Expedia
From $572 per night (USD)VRBO
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $572 per night (USD)VRBO
From $727 per night (USD)Expedia
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. **Beginning January, 2026, Fair Winds will be a MONTHLY (28 ni ...
From $727 per night (USD)Expedia
From $193 per night (USD)VRBO
Paradise found at the Key West Golf Club!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee ...
From $193 per night (USD)VRBO
From $634 per night (USD)Expedia
Fantastic Fall Special Rates.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $634 per night (USD)Expedia
From $1057 per night (USD)VRBO
Historic Old Town Key West - Turtle House, Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $1057 per night (USD)VRBO
From $215 per night (USD)Expedia
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $215 per night (USD)Expedia
From $291 per night (USD)VRBO
Seaport Walkabout- the best location in town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Open to annual rental at lower rate Two hundred yards from Schooner Wharf and the seaport and steps from Pepe’s in the ...
From $291 per night (USD)VRBO
From $516 per night (USD)Expedia
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $516 per night (USD)Expedia
From $674 per night (USD)VRBO
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $674 per night (USD)VRBO
From $912 per night (USD)Expedia
Casa Papa Del Mar Ocean Front 1800 Atlantic spectacular view and Island charm
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $912 per night (USD)Expedia
From $562 per night (USD)VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $562 per night (USD)VRBO
From $227 per night (USD)Expedia
Charming Oceanfront Escape in Key West’s Historic District
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $227 per night (USD)Expedia
From $350 per night (USD)VRBO
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $350 per night (USD)VRBO
From $461 per night (USD)Expedia
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $461 per night (USD)Expedia
From $542 per night (USD)VRBO
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $542 per night (USD)VRBO
From $281 per night (USD)Expedia
Monthly historic old town rental Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem! Step back in time and experience Old Key West charm in this ...
From $281 per night (USD)Expedia
From $623 per night (USD)VRBO
Key West Beachfront Luxury 2/2 Condo A212
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sale on for June thru Aug construction by the pool. This Luxury unit is 1375 sq ft of breath taking beachfront living sp ...
From $623 per night (USD)VRBO
From $185 per night (USD)Expedia
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $185 per night (USD)Expedia
From $214 per night (USD)VRBO
Casa Coastal East – Morning Sunrises, Evening Vibes, Island Home in Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $214 per night (USD)VRBO
From $785 per night (USD)Expedia
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $785 per night (USD)Expedia
From $568 per night (USD)VRBO
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $568 per night (USD)VRBO
From $592 per night (USD)Expedia
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $592 per night (USD)Expedia
From $657 per night (USD)VRBO
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $657 per night (USD)VRBO
From $239 per night (USD)Expedia
Stunning Oceanfront Retreat with Panoramic Views & Private Balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $239 per night (USD)Expedia
From $208 per night (USD)VRBO
Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $208 per night (USD)VRBO
From $1453 per night (USD)Expedia
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $1453 per night (USD)Expedia
From $204 per night (USD)VRBO
Key West Getaway – Island Style Living with Ocean Views & Sunrises
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $204 per night (USD)VRBO
From $625 per night (USD)Expedia
Thirsty Mermaid - Large 4/3 Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $625 per night (USD)Expedia
From $181 per night (USD)VRBO
Old Town! Spacious Condo in Historic Home w/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $181 per night (USD)VRBO
From $229 per night (USD)Expedia
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $229 per night (USD)Expedia
From $1107 per night (USD)VRBO
**BRISA FRESCA @ THE ANNEX** Airy Home by Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A trip to Key ...
From $1107 per night (USD)VRBO
From $607 per night (USD)Expedia
**VILLA OLIVIETTA @ SOLARES HILL** Upscale Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This ultimate ...
From $607 per night (USD)Expedia
From $632 per night (USD)VRBO
**SMOOTH SAILING @ THE BEACH** Ocean Condo / Pool & Tennis + LAST KEY SERVICES..
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $632 per night (USD)VRBO
From $524 per night (USD)Expedia
**VILLA BAHAMA @ THE ANNEX** Villa Near Duval & Beach + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! VILLA BAHAMA ...
From $524 per night (USD)Expedia
From $920 per night (USD)VRBO
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $920 per night (USD)VRBO
From $1850 per night (USD)Expedia
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $1850 per night (USD)Expedia
From $1731 per night (USD)VRBO
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 7
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1731 per night (USD)VRBO
From $1342 per night (USD)Expedia
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $1342 per night (USD)Expedia
From $2524 per night (USD)VRBO
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $2524 per night (USD)VRBO
From $775 per night (USD)Expedia
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $775 per night (USD)Expedia
From $495 per night (USD)VRBO
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $495 per night (USD)VRBO
From $483 per night (USD)Expedia
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine a tra ...
From $483 per night (USD)Expedia
From $527 per night (USD)VRBO
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo / Pool + LAST KEY SERVICES
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $527 per night (USD)VRBO
From $554 per night (USD)Expedia
**CASA SUITE CASA @ CASA MARINA** Lush Home / Pool + LAST KEY SERVICE...
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine your ...
From $554 per night (USD)Expedia
From $1459 per night (USD)VRBO
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1459 per night (USD)VRBO
From $622 per night (USD)Expedia
Our Nautical Home Key West prime location & amenities. Last minute specials.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $622 per night (USD)Expedia
From $409 per night (USD)VRBO
**CAYO CALYPSO @ HIGGS BEACH** Modern Home / Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Upscale islan ...
From $409 per night (USD)VRBO
From $533 per night (USD)Expedia
Poolside Breeze Retreat Key West – Your Tropical Getaway Awaits
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $533 per night (USD)Expedia
From $391 per night (USD)VRBO
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $391 per night (USD)VRBO
From $830 per night (USD)Expedia
**WINDSWEPT PALMS @ THE BEACH** Oceanfront / Pool & Jacuzzi + LAST KEY SERVICE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $830 per night (USD)Expedia
From $1086 per night (USD)VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1086 per night (USD)VRBO
From $523 per night (USD)Expedia
**SHANG-RI-LA @ THE BEACH** Oceanview Condo / Pool & Tennis + LAST KEY SERVICES.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $523 per night (USD)Expedia
From $594 per night (USD)VRBO
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse / Pool + LAST KEY SERVICES.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $594 per night (USD)VRBO
From $2467 per night (USD)Expedia
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2467 per night (USD)Expedia
From $513 per night (USD)VRBO
Botanical Island Delight Key West fantastic discounts for Summer & Fall
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $513 per night (USD)VRBO
From $580 per night (USD)Expedia
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SALTWATER HAR ...
From $580 per night (USD)Expedia
From $687 per night (USD)VRBO
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $687 per night (USD)VRBO
From $381 per night (USD)Expedia
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! LA PETITE PEN ...
From $381 per night (USD)Expedia
From $1925 per night (USD)VRBO
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $1925 per night (USD)VRBO
From $1032 per night (USD)Expedia
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Traveling wit ...
From $1032 per night (USD)Expedia
From $1023 per night (USD)VRBO
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $1023 per night (USD)VRBO
From $586 per night (USD)Expedia
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $586 per night (USD)Expedia
From $988 per night (USD)VRBO
Find Sanity in the Heart of Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $988 per night (USD)VRBO
From $754 per night (USD)Expedia
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This Old Town ...
From $754 per night (USD)Expedia
From $338 per night (USD)VRBO
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool & Spa + LAST KEY SERVICES...
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET DREAMS ...
From $338 per night (USD)VRBO
From $416 per night (USD)Expedia
Truman Annex Gem • 2BR Condo • Walk to Beach & Bars
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Best Deal in Truman Annex – Céad Míle Fáilte! 2 Bedroom | 1 Bathroom | Sleeps Up to 5 Guests Welcome to Innis-free, ou ...
From $416 per night (USD)Expedia
From $964 per night (USD)VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $964 per night (USD)VRBO
From $596 per night (USD)Expedia
High Tide awaits your next visit upgraded condo close to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $596 per night (USD)Expedia