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From $450 per night (USD)
VRBO
BEACHFRONT-Coconut Beach Resort, 7 nights, May 10-17, or May 31-June 7, only.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Private tropical Paradise on the Atlantic Ocean in Key West, Florida. This condo unit is a 1 bedroom, with 2 full bathro ...
From $450 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Sweet Caroline Historic Seaport Key West Home Rental Floor 2
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-mi ...
From $450 per night (USD)
Expedia
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VRBO
Indoor / Outdoor Living in Old Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Our home is down a quiet lane in the heart of Key West. Walk to Duval Street, organic “fast food,” yoga, beer, fishin ...
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VRBO
From $1219 per night (USD)
Expedia
**CASA AMARILLA @ DUVAL** Old Town Cottage & Private Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The moment yo ...
From $1219 per night (USD)
Expedia
From $286 per night (USD)
VRBO
**THE POETIC PINEAPPLE @ OLD TOWN** Charming 2BR/2BA Cottage + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! You have many ...
From $286 per night (USD)
VRBO
From $288 per night (USD)
Expedia
~Reel Paradise~Beautiful private townhouse in a small gated community.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $288 per night (USD)
Expedia
From $759 per night (USD)
VRBO
~Butterfly Cottage~ Enjoy a hot tub, gourmet kitchen, and 2 king ensuites.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
PROPERTY: Enjoy your coffee on the front porch or listen to the birds while gliding on the swing. Either way, you will a ...
From $759 per night (USD)
VRBO
From $468 per night (USD)
Expedia
Classic Key West living w/ a full kitchen, balcony, & shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Baya House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $468 per night (USD)
Expedia
$\LA DOLCE VITA\, OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!$
From $399 per night (USD)
VRBO
\"LA DOLCE VITA\", OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
'La Dolce Vita' is located in Old Town, Key West!! Jus 3 short blocks to Southernmost Beach and Southernmost Point ...
From $399 per night (USD)
VRBO
From $613 per night (USD)
Expedia
Hyatt Windward Pointe 2 Bedroom
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Windward Pointe in Key West is a tranquil resort offering a luxurious escape on the island’s serene southeast coas ...
From $613 per night (USD)
Expedia
From $357 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo w/ a patio at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condo includes: 2 bedrooms 1 bath {queen and ...
From $357 per night (USD)
VRBO
From $281 per night (USD)
Expedia
Gulf Getaway | Condo w/Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $281 per night (USD)
Expedia
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VRBO
Luxurious top floor, end unit, within premier resort on the Atlantic Ocean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Relax in style at the Hyatt Windward Pointe Resort. This is the best location within the resort: Top floor, end unit. Lo ...
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VRBO
From $668 per night (USD)
Expedia
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
• Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • ...
From $668 per night (USD)
Expedia
From $909 per night (USD)
VRBO
Washer & Dryer, Near Downtown - The Mesa House
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $909 per night (USD)
VRBO
From $341 per night (USD)
Expedia
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w/ Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $341 per night (USD)
Expedia
Click For Pricing
VRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
VRBO
From $758 per night (USD)
Expedia
Balcony & Near Downtown - Cloud Suite on Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Cloud Suite On Duval is a beautifully updated 2 bed, 2.5 bath upper level condo located right in the heart of w ...
From $758 per night (USD)
Expedia
From $429 per night (USD)
VRBO
A PEACE OF PARADISE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Swanky condo in The Shipyard of Truman Annex! Luxury touches everywhere. This end unit was completely remodeled with fla ...
From $429 per night (USD)
VRBO
From $1152 per night (USD)
Expedia
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR/2BA Home & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $1152 per night (USD)
Expedia
From $453 per night (USD)
VRBO
**SERENITY ON SOUTHARD @ THE ANNEX** Condo Near Duval & Beach + LAST KEY SERVICE
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SERENITY ON S ...
From $453 per night (USD)
VRBO
From $243 per night (USD)
Expedia
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $243 per night (USD)
Expedia
From $275 per night (USD)
VRBO
THE MANGO TREE COTTAGE - Old Town Key West, Steps to Duval Street
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Location, Location, LOCATION!!! Perfectly located in Old Town Key West, this beautifully remodeled 3 bedroom, 2 bathroom ...
From $275 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Roosters Perch at Truman Annex- LOW SUMMER RATES!!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $317 per night (USD)
Expedia
From $234 per night (USD)
VRBO
Key West Hideaway, ½ Mile to Beach,Walkable, Peaceful, Well-Equipped!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR STORM POLICIES ...
From $234 per night (USD)
VRBO
Click For Pricing
Expedia
One bedroom in the heart of downtown w/ kitchen
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Truman at Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
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Expedia
From $611 per night (USD)
VRBO
The Secret Grotto
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Welcome to The Secret Grotto! This spacious 3,300 square foot home is located on nearly a 5,000 square foot lot and fea ...
From $611 per night (USD)
VRBO
From $881 per night (USD)
Expedia
The Gideon Lowe House - Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $881 per night (USD)
Expedia
From $339 per night (USD)
VRBO
Keys to Paradise - Shipyard Truman Annex - LOWEST RATES JUNE-SEPTEMBER!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $339 per night (USD)
VRBO
From $844 per night (USD)
Expedia
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $844 per night (USD)
Expedia
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VRBO
Oceanfront Condo at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
You won't find a better steal than a high-season stay in this beautiful and spacious second-floor condo on the Hyatt Win ...
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VRBO
From $762 per night (USD)
Expedia
Waterfront Home in Key Cove Landings
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $762 per night (USD)
Expedia
From $807 per night (USD)
VRBO
Waterfront luxury home with private pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for an upscale escape by the sea, 3/4 Time is your Key West hidden gem. Enjoy the island life in your ...
From $807 per night (USD)
VRBO
From $876 per night (USD)
Expedia
Luxury Waterfront Home with private pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $876 per night (USD)
Expedia
From $764 per night (USD)
VRBO
Modern Waterfront Luxury Home with Heated Pool!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
If you’re looking for a luxury escape on the water, Paris Mango is your island gem. Named after Jimmy's "Last Mango in P ...
From $764 per night (USD)
VRBO
From $1042 per night (USD)
Expedia
Conch style home in Oldtown with private pool AND dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1042 per night (USD)
Expedia
From $1078 per night (USD)
VRBO
Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1078 per night (USD)
VRBO
From $576 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $576 per night (USD)
Expedia
$Spec @107.lodg+ Aug & sept. \n10 min walk beach, close to all +\nfull kitch& patio$
From $196 per night (USD)
VRBO
Spec @107.lodg+ Aug & sept. \n10 min walk beach, close to all +\nfull kitch& patio
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SUMMER SPECIAL August and September Most dates @ 107. lodging plus extras per night. With 4 night stay 5th night FREE ...
From $196 per night (USD)
VRBO
From $618 per night (USD)
Expedia
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $618 per night (USD)
Expedia
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VRBO
Two Bedroom Condo, Key West, Ocean View 3054374
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
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VRBO
From $404 per night (USD)
Expedia
Curaçao Key West 2BR Condo w/ Pool&Waterfront Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home - Stay spacious in Key West. Boat ...
From $404 per night (USD)
Expedia
$Downtown Key West 2BR/2BA•Pool, Dock, Pet \Aruba\$
From $400 per night (USD)
VRBO
Downtown Key West 2BR/2BA•Pool, Dock, Pet \"Aruba\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Enjoy true space in Key West! This 1,200 sq ft waterfront condo offers a full kitchen, dining area, living room ...
From $400 per night (USD)
VRBO
From $1718 per night (USD)
VRBO
St. Johns Waterfront 4BR Penthouse•Pool•Dock•Park
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring the whole crew to this 2200 sqft waterfront penthouse—perfect for families & large groups! With 4 bedroom ...
From $1718 per night (USD)
VRBO
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $400 per night (USD)
VRBO
Old Town \"Eleuthera\" • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $400 per night (USD)
VRBO
From $285 per night (USD)
Expedia
Pool & Parking, & Pet Friendly - Hidden Oasis
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Hidden Oasis is a 28-night minimum rental, offering contemporary luxury in the heart of Midtown, Key West. It’s ...
From $285 per night (USD)
Expedia
From $623 per night (USD)
VRBO
**ISLAND BLISS @ CASA MARINA** Spacious Home / Pool + 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! ISLAND BLISS ...
From $623 per night (USD)
VRBO
From $279 per night (USD)
Expedia
Charming, updated home near Duval St. with enclosed patio & walkable location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Coral Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $279 per night (USD)
Expedia
Click For Pricing
VRBO
Hyatt Residence Club Windward Pointe Key West 2br/2ba/6ppl
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT Windward Pointe. Sleeps 6 people. 2 bedrooms (1King/1Quee ...
Click For Pricing
VRBO
From $233 per night (USD)
Expedia
2 Bedroom Townhome on Key West Golf Club
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Escape to paradise with this spacious 2-bedroom townhome in Key West. Ideal for families and couples alike, this propert ...
From $233 per night (USD)
Expedia
From $965 per night (USD)
VRBO
Ideal Family Stay in Great Location, 4 Pools, Shuttle Service, Near Airport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $965 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Beautiful Water Views! Minutes to Southernmost Point! Parking, Onsite Pools!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $428 per night (USD)
VRBO
From $474 per night (USD)
VRBO
Experience Key West w/ Poolside Bar, Private Terraces & Free Shuttle Service!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Indulge in an island escape at this tropical haven. Wake up to Gulf of Mexico views, savoring breakfast on your private ...
From $474 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W/D
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $280 per night (USD)
Expedia
From $472 per night (USD)
VRBO
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR/3.5BA Condo & Pool + LAST KEY SERVI
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! MODERN MAJEST ...
From $472 per night (USD)
VRBO
From $308 per night (USD)
Expedia
The Elizabeth Suite | 1 bed, 1 bath w/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Experience the charm of historic Key West with a stay at The Elizabeth Suite, a recently renovated 1 bedroom, 1 bathroom ...
From $308 per night (USD)
Expedia
From $497 per night (USD)
VRBO
The Fleming Suite | 1 bed, 1 bath condo w/shared pool, monthly rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to The Fleming Suite, a beautifully refreshed 1 bedroom, 1 bathroom vacation rental located at The Bayview House ...
From $497 per night (USD)
VRBO
Click For Pricing
Expedia
New Listing-Golf Course Charmer!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
As you make your way into The Sweet Tee, an immediate sense of relaxation and vacation mode envelops you. The carefully ...
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Expedia
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VRBO
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
About this space Experience the paradise of Southern Skies, an elegant 3 bedroom and 2.5 bath home nestled in the heart ...
Click For Pricing
VRBO
From $401 per night (USD)
Expedia
The Speakeasy Inn - Room 1A (1 Queen Bed & 1 Single Bed)
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $401 per night (USD)
Expedia
From $345 per night (USD)
VRBO
Room 2 (1 Queen Bed & Single Sleeper Sofa)
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $345 per night (USD)
VRBO
From $338 per night (USD)
Expedia
Speakeasy Inn -Room 1B-1 Queen Bed
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $338 per night (USD)
Expedia
From $319 per night (USD)
VRBO
Starr's Suite - 2 person K Suite w/Private Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, ...
From $319 per night (USD)
VRBO
Click For Pricing
Expedia
**KESTRAL KOVE @ THE GOLF CLUB** Townhome w/ Community Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Dreaming of va ...
Click For Pricing
Expedia
From $284 per night (USD)
VRBO
Breezy Key West First-Floor Condo w/ Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $284 per night (USD)
VRBO
From $380 per night (USD)
Expedia
**THE OSPREY'S NEST @ SUNRISE SUITES** 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! Want to be in ...
From $380 per night (USD)
Expedia
From $227 per night (USD)
VRBO
Poolside tropical paradise in Key West! The Salty Conch
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
The Salty Conch is tucked away in the gated community of The Key West Golf Club with 24/7 security for your peace of min ...
From $227 per night (USD)
VRBO
From $647 per night (USD)
Expedia
Craig & Cindy Key West Truman Annex Shipyard Condo with balcony at Mile Marker 0
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $647 per night (USD)
Expedia
From $500 per night (USD)
VRBO
Our Piece of Paradise-
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to your ideal Key West getaway! Perfect for families and ideally situated between Old Town, New Town, and Duval ...
From $500 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-ti ...
From $408 per night (USD)
Expedia
From $181 per night (USD)
VRBO
Monkey House by AvantStay | Pool, by Duval Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Monkey House is a two-bedroom Key West escape that ...
From $181 per night (USD)
VRBO
From $212 per night (USD)
Expedia
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
*Please note that this home is available for 28+ night stays only.* Tennessee Williams is a one-of-a-kind Key West esca ...
From $212 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Speakeasy Inn - 1C (1 Queen Bed & Sleeper Sofa)
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $349 per night (USD)
VRBO
From $334 per night (USD)
Expedia
Speakeasy Inn - Room 1A (1 King Bed & 1 Single Sleeper Sofa)
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $334 per night (USD)
Expedia
From $607 per night (USD)
VRBO
BE AS YOU ARE - 3 Bedroom / 3 Bathroom - Mid Town KEY WEST w/ POOL
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Elegantly renovated and furnished with guest comfort and enjoyment in mind we would like to welcome you to “Be as you ar ...
From $607 per night (USD)
VRBO
From $601 per night (USD)
Expedia
New Years special in gorgeous Bahama Village 4Bd 4.5 Ba all ensuite, 2x parking!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to Moveable Feast, a dreamy home in the heart of Bahama Village that sleeps 10 comfortably. Located on a quiet, ...
From $601 per night (USD)
Expedia
From $746 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $746 per night (USD)
VRBO
From $378 per night (USD)
VRBO
Romantic Retreat - 2 person K Suite, Pvt deck/Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottage ...
From $378 per night (USD)
VRBO
From $587 per night (USD)
VRBO
Key West Lighthouse Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Key West Lighthouse Suite offers a cozy queen bungalow home with a unique queen loft and sle ...
From $587 per night (USD)
VRBO
From $532 per night (USD)
Expedia
American Shoal Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape the Ordinary.... The American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely ...
From $532 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Tortugas Harbor Light Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Tortugas Harbor Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 g ...
From $445 per night (USD)
VRBO
From $451 per night (USD)
Expedia
Sombrero Reef Light Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape the Ordinary... The Sombrero Reef Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 gue ...
From $451 per night (USD)
Expedia
From $533 per night (USD)
VRBO
Alligator Reef Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape the Ordinary... The Alligator Reef Lighthouse Suite offers separate King and Queen bedrooms and was completely r ...
From $533 per night (USD)
VRBO
From $984 per night (USD)
Expedia
~CALIFORNIA DREAMING~ Enjoy an extended vacation in this posh home and pool.
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $984 per night (USD)
Expedia
From $427 per night (USD)
VRBO
**THE COZY STARFISH @ THE ANNEX** Condo Near Duval & Beach + 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! THE COZY STAR ...
From $427 per night (USD)
VRBO
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Expedia
Studio Unit in quiet resort adjacent to Old Town Key West!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
With a coveted location in the heart of Old Town and magnificent views of the Gulf of Mexico, Sunset Harbor is the ultim ...
Click For Pricing
Expedia
From $202 per night (USD)
VRBO
Beautifully Renovated Paradise with Pool and Tropical Gardens in Old Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into paradise in this clean and impeccably appointed 2 bedroom, 2 bathroom house in Old Town. Located just 2 blocks ...
From $202 per night (USD)
VRBO
From $432 per night (USD)
VRBO
Quaint Bungalow w/ Private Outdoor Space Near Duval Street | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $432 per night (USD)
VRBO
From $602 per night (USD)
VRBO
Celebrate History in Key West: Tropical Free Breakfast and Pool Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $602 per night (USD)
VRBO
From $449 per night (USD)
VRBO
Serene Bungalow with Outdoor Pool Access | Free Breakfast Onsite!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $449 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Romantic Getaway with Plush Turkish Robes & Inviting Pools! Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $465 per night (USD)
VRBO
From $922 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool, Free Breakfast!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $922 per night (USD)
VRBO
From $428 per night (USD)
VRBO
Serene Bungalow in Key West: Poolside Refreshers & Free Breakfast!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $428 per night (USD)
VRBO
From $836 per night (USD)
VRBO
Tranquil Bungalow w/ an Artistic Vibe in Vibrant Key West | Breakfast Included
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $836 per night (USD)
VRBO
From $436 per night (USD)
VRBO
Stylish Room in the Heart of Old Town w/ Access to Outdoor Pool | Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $436 per night (USD)
VRBO
From $528 per night (USD)
VRBO
Historical Charm in a Room Surrounded by Key West's Best: Free Breakfast!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town Key West with nearby landmarks like the Ernest Hemingway Home and Museum or stroll down lively Duval S ...
From $528 per night (USD)
VRBO
From $530 per night (USD)
VRBO
Bohemian Key West Boutique Inn with Pool & Free Breakfast | Near Sunset Pier
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover the heart of Old Town Key West! This hotel is located steps from Duval Street and Hemingway's home. Stroll to S ...
From $530 per night (USD)
VRBO
From $588 per night (USD)
Expedia
Palms and Pool Paradise
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to our luxurious Key West retreat in the heart of midtown! This spacious house boasts a private pool, soothing h ...
From $588 per night (USD)
Expedia
$Hemmingways Paradise \nJust a short stroll to all Key West has to offer.$
Click For Pricing
VRBO
Hemmingways Paradise \nJust a short stroll to all Key West has to offer.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You will fall in love with this beautifully renovated old town historic home. Located on one of old towns coveted quiet ...
Click For Pricing
VRBO
From $237 per night (USD)
Expedia
Seaside Serenity-2BD 2BA condo w/ pool, parking, tennis courts, near beaches
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $237 per night (USD)
Expedia

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