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$Gulf Getaway | Condo w\/Pool!$
From $251 per night (USD)
VRBO
Gulf Getaway | Condo w\/Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Summary: Conveniently situated in the picturesque Truman Annex gated Community, Gulf Getaway is a charming 2 bedroom 2.5 ...
From $251 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $820 per night (USD)
VRBO
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Bedrooms:
3
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 $820 per night (USD)
VRBO
From $1022 per night (USD)
Expedia
Washer & Dryer, Near Downtown - The Mesa House
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: Family-friendly home with a huge front lounging porch, two kitchens, steps from the ocean and everything else t ...
From $1022 per night (USD)
Expedia
$SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!$
From $427 per night (USD)
VRBO
SCARLET ~ Adult Only, 2nd Floor Suite, 1 Bedroom Unit w\/ Shared Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Exquisite 2nd floor king suite... DELIGHT IN OLD WORLD ALLURE... Bask in the charming ambience of the adults-only Scarl ...
From $427 per night (USD)
VRBO
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Expedia
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
Expedia
From $732 per night (USD)
VRBO
Balcony & Near Downtown - Cloud Suite on Duval
Bedrooms:
3
Bathrooms:
3
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 $732 per night (USD)
VRBO
From $385 per night (USD)
Expedia
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 $385 per night (USD)
Expedia
$**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE$
From $871 per night (USD)
VRBO
**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 $871 per night (USD)
VRBO
From $389 per night (USD)
Expedia
**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 $389 per night (USD)
Expedia
From $265 per night (USD)
VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $265 per night (USD)
VRBO
From $275 per night (USD)
Expedia
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)
Expedia
From $385 per night (USD)
VRBO
Roosters Perch at Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to Roosters Perch in Truman Annex, Porter Lane. This large corner duplex is full of natural light and windows. ...
From $385 per night (USD)
VRBO
From $293 per night (USD)
Expedia
Atlantic Ocean view across from Smathers Beach - La Brisa - Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open floor plan, 2 bedroom, 2 bath condo at La Brisa. Gated condo community. Large deep pool with saunas in the pool b ...
From $293 per night (USD)
Expedia
$Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen\n$
From $195 per night (USD)
VRBO
Spec.@159.+ 5-14 to 16 and 5-19 to 21 + extras Close to beach plus kitchen\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $195 per night (USD)
VRBO
$One bedroom in the heart of downtown w\/ kitchen$
Click For Pricing
Expedia
One bedroom in the heart of downtown w\/ kitchen
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Truman at Duval - Unit B Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
Click For Pricing
Expedia
From $611 per night (USD)
VRBO
The Secret Grotto
Bedrooms:
5
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 $786 per night (USD)
Expedia
The Gideon Lowe House - Old Town Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $786 per night (USD)
Expedia
From $389 per night (USD)
VRBO
Keys to Paradise - Shipyard Truman Annex
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Welcome to Keys to Paradise located in the Shipyard Condominium Complex at the beautiful Truman Annex! This quaint, we ...
From $389 per night (USD)
VRBO
From $870 per night (USD)
Expedia
Luxury 3-Bedroom Waterfront Home with Pool AND Dock!
Bedrooms:
5
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 $870 per night (USD)
Expedia
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VRBO
Oceanfront Condo at Hyatt Windward Pointe
Bedrooms:
2
Bathrooms:
3
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 $847 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 $847 per night (USD)
Expedia
From $1038 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 $1038 per night (USD)
VRBO
From $1216 per night (USD)
Expedia
Luxury Waterfront Home with private pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $1216 per night (USD)
Expedia
From $1110 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 $1110 per night (USD)
VRBO
From $1207 per night (USD)
Expedia
Conch style home in Oldtown with private pool AND dock!
Bedrooms:
4
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 $1207 per night (USD)
Expedia
From $1201 per night (USD)
VRBO
Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
5
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 $1201 per night (USD)
VRBO
From $362 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 $362 per night (USD)
Expedia
$May Spec 159.+\n5-19-23 & 5-26-29 NEWLY Redone. Not shown in current pics I\n$
From $177 per night (USD)
VRBO
May Spec 159.+\n5-19-23 & 5-26-29 NEWLY Redone. Not shown in current pics I\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
New Pics coming soon. GREAT LOCATION Close to beach and All! REASONABLE RATES. W. KITCHEN AND PATIO Come splash in ...
From $177 per night (USD)
VRBO
From $723 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 $723 per night (USD)
Expedia
Click For Pricing
VRBO
Two Bedroom Condo, Key West, Ocean View 3054374
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Hyatt Residence Club Key West – Windward Pointe Two Bedroom Condo – Partial Ocean Views Partial ocean views and lavish ...
Click For Pricing
VRBO
$Curaçao Key West 2BR Condo w\/ Pool&Waterfront Dock$
From $392 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 $392 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 $1773 per night (USD)
Expedia
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 $1773 per night (USD)
Expedia
$Old Town \Eleuthera\ • 2BR Waterfront Corner Condo$
From $692 per night (USD)
VRBO
Old Town \"Eleuthera\" • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just ...
From $692 per night (USD)
VRBO
From $355 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 $355 per night (USD)
Expedia
$**ISLAND BLISS @ CASA MARINA** Spacious Home \/ Pool + LAST KEY SERVICES...$
From $354 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 $354 per night (USD)
VRBO
From $372 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 $372 per night (USD)
Expedia
$Hyatt Residence Club Windward Pointe Key West 2br\/2ba\/6ppl$
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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
$Experience Key West w\/ Poolside Bar, Private Terraces & Free Shuttle Service!$
From $699 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 $699 per night (USD)
VRBO
From $1060 per night (USD)
Expedia
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 $1060 per night (USD)
Expedia
From $470 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 $470 per night (USD)
VRBO
$Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D$
From $296 per night (USD)
Expedia
Coconut Cottage | Colorful abode with a full kitchen, enclosed patio, AC, & W\/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Coconut Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $296 per night (USD)
Expedia
$**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI$
From $472 per night (USD)
VRBO
**MODERN MAJESTY @ THE ANNEX** Oceanside 3BR\/3.5BA Condo & Pool + LAST KEY SERVI
Bedrooms:
4
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
$The Elizabeth Suite | 1 bed, 1 bath w\/shared pool$
From $556 per night (USD)
Expedia
The Elizabeth Suite | 1 bed, 1 bath w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Elizabeth Suite at The Bayview House, a nightly rental with shared pool. One of 4 units ...
From $556 per night (USD)
Expedia
$The Fleming Suite | 1 bed, 1 bath condo w\/shared pool$
From $556 per night (USD)
VRBO
The Fleming Suite | 1 bed, 1 bath condo w\/shared pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are pleased to introduce The Fleming Suite at The Bayview House, a 1-bedroom, 1-bathroom nightly rental with a shared ...
From $556 per night (USD)
VRBO
Click For Pricing
Expedia
New Listing-Golf Course Charmer!
Bedrooms:
2
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
Click For Pricing
VRBO
Southern Skies, Stylish Home in Old Town Key West
Bedrooms:
3
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 $346 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 $346 per night (USD)
Expedia
From $349 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 $349 per night (USD)
VRBO
From $334 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 $334 per night (USD)
Expedia
$Starr's Suite - 2 person K Suite w\/Private Spa!$
From $441 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 $441 per night (USD)
VRBO
$**KESTRAL KOVE @ THE GOLF CLUB** Townhome w\/ Community Pool + LAST KEY SERVICES…$
From $253 per night (USD)
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 ...
From $253 per night (USD)
Expedia
$Breezy Key West First-Floor Condo w\/ Pool Access$
From $158 per night (USD)
VRBO
Breezy Key West First-Floor Condo w\/ Pool Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Experience your next seaside vacation in style at this 2-bedroom, 2-bathroom Key West vacation rental. This 1st-floor co ...
From $158 per night (USD)
VRBO
From $373 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 $373 per night (USD)
Expedia
$BE AS YOU ARE - 3 Bedroom \/ 3 Bathroom - Mid Town KEY WEST w\/ POOL$
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 $227 per night (USD)
Expedia
Poolside tropical paradise in Key West! The Salty Conch
Bedrooms:
2
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)
Expedia
From $361 per night (USD)
VRBO
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 $361 per night (USD)
VRBO
From $405 per night (USD)
Expedia
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 $405 per night (USD)
Expedia
From $398 per night (USD)
VRBO
Midnight Cowboy by AvantStay | 3 Artistic Spaces
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
*Please note that this home is available for 28+ night stays only.* Midnight Cowboy is a one-of-a-kind Key West escape ...
From $398 per night (USD)
VRBO
From $182 per night (USD)
Expedia
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 $182 per night (USD)
Expedia
From $207 per night (USD)
VRBO
Tennessee Williams by AvantStay | Funky Design + Pool
Bedrooms:
3
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 $207 per night (USD)
VRBO
From $346 per night (USD)
Expedia
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 $346 per night (USD)
Expedia
From $338 per night (USD)
VRBO
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 $338 per night (USD)
VRBO
From $451 per night (USD)
Expedia
Gorgeous Bahama Village 4Bd 4Ba ensuite, parking, backyard oasis, perf locale!
Bedrooms:
5
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 $451 per night (USD)
Expedia
From $916 per night (USD)
VRBO
Rooftop Penthouse, Walk to Duval - KAMP
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Stay in this one-of-a-kind penthouse and Jimmy Buffet's former Margaritaville Headquarters as well as David "Mr ...
From $916 per night (USD)
VRBO
From $673 per night (USD)
Expedia
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 $673 per night (USD)
Expedia
From $920 per night (USD)
VRBO
American Shoal Light Suite
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape the Ordinary.... The American Shoal Lighthouse Suite offers separate King and Queen bedrooms and was completely ...
From $920 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Tortugas Harbor Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape the Ordinary... The Tortugas Harbor Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 g ...
From $669 per night (USD)
Expedia
$Romantic Retreat - 2 person K Suite, Pvt deck\/Spa!$
From $471 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 $471 per night (USD)
VRBO
From $669 per night (USD)
Expedia
Sombrero Reef Light Suite
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape the Ordinary... The Sombrero Reef Lighthouse Suite offers a luxury king bedroom that can accommodate up to 4 gue ...
From $669 per night (USD)
Expedia
From $920 per night (USD)
VRBO
Alligator Reef Light Suite
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Escape the Ordinary... The Alligator Reef Lighthouse Suite offers separate King and Queen bedrooms and was completely r ...
From $920 per night (USD)
VRBO
From $382 per night (USD)
VRBO
L'Attitude Adjustment | 3 Bed, 2 Bath with pool in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Your Dream Getaway in Key West! Discover the ultimate monthly vacation rental in Key West. This stunning hom ...
From $382 per night (USD)
VRBO
From $956 per night (USD)
VRBO
~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 $956 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 $452 per night (USD)
VRBO
Private Pool & Parking - Atlantic Oasis
Bedrooms:
4
Bathrooms:
3
Sleeps:
10
Summary: Atlantic Oasis is a true Key West "Conch Style" townhome consisting of over 1900 sq. ft. of beautiful living sp ...
From $452 per night (USD)
VRBO
From $424 per night (USD)
Expedia
**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 $424 per night (USD)
Expedia
From $1596 per night (USD)
VRBO
Old Town Key West Retreat | Seaport Paradise Room with Pool Access | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1596 per night (USD)
VRBO
$Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity$
From $600 per night (USD)
VRBO
Spacious Key West Room w\/ Balcony | Outdoor Pools | Seaport Proximity
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $600 per night (USD)
VRBO
$Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools$
From $1939 per night (USD)
VRBO
Family Old Town Key Getaway | Four Rooms w\/ Balcony & Outdoor Pools
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1939 per night (USD)
VRBO
$Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony$
From $2124 per night (USD)
VRBO
Vibrant Key West Stay w\/ Outdoor Pools | Four Rooms w\/ Balcony
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2124 per night (USD)
VRBO
$Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools$
From $1071 per night (USD)
VRBO
Two Relaxing Rooms w\/ Balcony | Waterfront Resort w\/ Access to Outdoor Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1071 per night (USD)
VRBO
$2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools$
From $3121 per night (USD)
VRBO
2 BR Spacious Suite w\/ Living Area and Balcony | Outdoor Pools
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3121 per night (USD)
VRBO
From $1717 per night (USD)
VRBO
Seaport Paradise Room with Pools | Old Town Key West Retreat | 3 Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1717 per night (USD)
VRBO
$Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony$
From $636 per night (USD)
VRBO
Seaport Proximity | Resort w\/ Outdoor Pools | Spacious Key West Room w\/ Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $636 per night (USD)
VRBO
$Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available$
From $2475 per night (USD)
VRBO
Spacious 2 BR Suite w\/ Living Area and Balcony | Onsite Parking Available
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2475 per night (USD)
VRBO
$Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools$
From $3121 per night (USD)
VRBO
Two Bedrooms Family Suite with Balcony | Idyllic Resort w\/ Outdoor Pools
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3121 per night (USD)
VRBO
$Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best$
From $1144 per night (USD)
VRBO
Waterfront Getaway | 2 Spacious Family Rooms w\/ Balcony | Old Town Best
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1144 per night (USD)
VRBO
From $286 per night (USD)
Expedia
Old Town main house and guest house one block from Duval Street for the best of Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This luxury Old Town renovation is on a quiet end of Virginia street with no through traffic but located only one block ...
From $286 per night (USD)
Expedia
From $1175 per night (USD)
VRBO
**GARDEN OF EMMA @ THE ANNEX** Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Tranquility. ...
From $1175 per night (USD)
VRBO
$Quaint Bungalow w\/ Private Outdoor Space Near Duval Street | Free Breakfast$
From $374 per night (USD)
Expedia
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 $374 per night (USD)
Expedia
From $508 per night (USD)
VRBO
Celebrate History in Key West: Tropical Bungalow Retreat Ideal for Relaxation
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 $508 per night (USD)
VRBO
From $529 per night (USD)
VRBO
Spacious Bungalow with Patio | Near Ernest Hemingway Home – 7 Min Walk
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 $529 per night (USD)
VRBO
From $381 per night (USD)
VRBO
Serene Bungalow with Outdoor Pool Access | Near Historic Ernest Hemingway Museum
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 $381 per night (USD)
VRBO
From $465 per night (USD)
Expedia
Romantic Getaway with Plush Turkish Robes & Inviting Pools Near Duval Street
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)
Expedia
From $739 per night (USD)
VRBO
Key West Oasis: Retreat in Historical Bungalows with Pool Paradise
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 $739 per night (USD)
VRBO
From $673 per night (USD)
VRBO
Tropical Escape: Artistic-Vibe Bungalows with Balcony | Welcome Drinks Included
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 $673 per night (USD)
VRBO
From $597 per night (USD)
VRBO
Enchanting Hideaway Perfect for Couples Seeking Romantic Bliss
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 $597 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Serene Bungalow in Key West: Poolside Refreshers & Relaxing Amenities
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 $362 per night (USD)
Expedia

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