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From $167 per night (USD)
VRBO
Breezy Florida Home with Shared Pool, Dog & Snowbird-Friendly - Walk to Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
The Headquarters Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $167 per night (USD)
VRBO
From $137 per night (USD)
Expedia
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Barbados Suite 204 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $137 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Dog-Friendly Cottage with Private Hot Tub & Garden - Great Downtown Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Windward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $192 per night (USD)
VRBO
From $501 per night (USD)
Expedia
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $501 per night (USD)
Expedia
From $986 per night (USD)
VRBO
Dog-Friendly Home with Patio and Private Hot Tub - Walk to the Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Southernmost Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $986 per night (USD)
VRBO
From $566 per night (USD)
Expedia
Charming cottage with private hot tub - one block to Duvall Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Conch Casa Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $566 per night (USD)
Expedia
From $491 per night (USD)
VRBO
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Panama Suite 310 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $491 per night (USD)
VRBO
From $154 per night (USD)
Expedia
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Cozumel Suite 112 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $154 per night (USD)
Expedia
From $530 per night (USD)
VRBO
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Audubon House #6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $530 per night (USD)
VRBO
From $139 per night (USD)
Expedia
Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Catalina Suite 311 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $139 per night (USD)
Expedia
Click For Pricing
Expedia
Dog-friendly home with central AC, fast WiFi, washer/dryer, and private hot tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Seafoam Escape Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
Click For Pricing
Expedia
From $1031 per night (USD)
Expedia
**VILLA ANGELITA @ OLD TOWN** Renovated Condo Off Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This modern O ...
From $1031 per night (USD)
Expedia
From $487 per night (USD)
VRBO
**SUZY'S PARROT PERCH @ OLD TOWN** Cozy 2nd Floor Condo + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUZY'S PARROT ...
From $487 per night (USD)
VRBO
From $1000 per night (USD)
Expedia
Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breeze ...
From $1000 per night (USD)
Expedia
From $342 per night (USD)
VRBO
**VIVA MARGARITA! @ OLD TOWN** Large Home & Pool Near Duval + LAST KEY SERVICES.
Bedrooms:
5
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West is t ...
From $342 per night (USD)
VRBO
From $2297 per night (USD)
Expedia
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & 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! Resembling a ...
From $2297 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Dog-friendly home w/ large private pool only a short walk to Historic Seaport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Seaport Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $296 per night (USD)
VRBO
From $403 per night (USD)
Expedia
Little Paradise, Historic Harbor Old Town Key West 2/2
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom One and a half bath home is nestl ...
From $403 per night (USD)
Expedia
Click For Pricing
VRBO
7 Nights - Hyatt Sunset Harbor 2 bed/2bath/Kitchen/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
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VRBO
From $265 per night (USD)
Expedia
Beautiful Condo with Deck, Patio, & Pool - Walk to Duval Street & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Secret Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $265 per night (USD)
Expedia
From $808 per night (USD)
VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $808 per night (USD)
VRBO
From $340 per night (USD)
Expedia
Great Family Vacation Rental.
Bedrooms:
3
Bathrooms:
2
Sleeps:
7
Family friendly vacation rental just outside of Key West with everything you need to enjoy a great getaway just 10 minut ...
From $340 per night (USD)
Expedia
From $137 per night (USD)
VRBO
Sunny Condo w/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Frontier Flat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $137 per night (USD)
VRBO
From $140 per night (USD)
Expedia
Stylish Dog-Friendly Condo with Balcony - In Heart of the Historic District
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Kingfish Keep On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $140 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Condo on Duval with WiFi, Hot Tub, & Private Parking - Dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Duval Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $266 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Charming Condo w/ Entertainment & Private Parking - Great In-Town Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $132 per night (USD)
Expedia
From $617 per night (USD)
VRBO
Tranquil Dog-friendly Getaway with Shared Pool, WiFi, & AC - Snowbirds Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropical Village - Tropical Cottage Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $617 per night (USD)
VRBO
From $356 per night (USD)
Expedia
Contemporary Seaside Cottage with a Private Hot Tub & Shared, Heated Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Heron Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $356 per night (USD)
Expedia
From $368 per night (USD)
VRBO
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Saint Barts Suite 303 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $368 per night (USD)
VRBO
From $125 per night (USD)
Expedia
Elegant Condo with Entertainment & Private Parking - Great Central Location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $125 per night (USD)
Expedia
From $275 per night (USD)
VRBO
Queen’s Lair Rockhouse
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
(((Third bedroom is an awesome open loft with a queen size bed- it is upstairs above the living room and master suite an ...
From $275 per night (USD)
VRBO
From $189 per night (USD)
Expedia
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Tierra Bomba Suite 403 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $189 per night (USD)
Expedia
Click For Pricing
VRBO
Fresh Getaway w/ Private Pool & Rooftop Patio - Great Location, Steps from Beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Hueso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
Click For Pricing
VRBO
From $132 per night (USD)
Expedia
Condo on Duval Street - Walk to Beach & Southernmost Point, Dogs OK
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Yellowfin Ledge On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $132 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Sunny Tropical Condo with WiFi & Pool - Close to Beachside Action
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Seashore at the Shipyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $424 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Amazing condo with pool & hot tub - ideal for exploring Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sunrise Suites - Cat Island Suite 205 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $331 per night (USD)
Expedia
From $109 per night (USD)
VRBO
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Paradise Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $109 per night (USD)
VRBO
From $327 per night (USD)
Expedia
Dog-Friendly Retreat in Casa Marina with Shared Pool, WiFi, and Walkable Locale
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Tropical Village - Toon Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $327 per night (USD)
Expedia
From $2483 per night (USD)
VRBO
Spacious dog-friendly retreat with 3 hot tubs - near Duval Street & the beach
Bedrooms:
6
Bathrooms:
6
Sleeps:
24
Southernmost Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $2483 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Breezy Condo with Pool & Hot Tub, Private Parking & Great Location - Dog OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Bonaire Suite 210 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $446 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Comfortable Condo with Pool, Private Balcony, & Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Ocean View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $283 per night (USD)
VRBO
From $191 per night (USD)
Expedia
Contemporary Dog-Friendly Cottage with Easy Beach Access & Shared Pool
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Old Town Garden Villas - Andros Suite Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $191 per night (USD)
Expedia
From $210 per night (USD)
VRBO
Welcoming & Conveniently Located Dog-Friendly Home - Walk to Everything
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Olivia Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $210 per night (USD)
VRBO
From $377 per night (USD)
Expedia
Dog-Friendly Gulf-Front Condo w/ WiFi, Dock/Boat Slip, Gulf Views, & Shared Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Flagler's Crossing Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $377 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Dog-friendly resort condo with pool & hot tub, private parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Saint Croix Suite 212 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $220 per night (USD)
VRBO
From $764 per night (USD)
Expedia
Dog-friendly condo in prime location - walk to dining & sights, near the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Frontier Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $764 per night (USD)
Expedia
From $653 per night (USD)
VRBO
Southernmost View by Brightwild | Pool & H20 Views
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fro ...
From $653 per night (USD)
VRBO
From $1354 per night (USD)
Expedia
Lovely Dog-Friendly Home w/ Guest Cottage - Great Location, Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Bahama House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $1354 per night (USD)
Expedia
From $428 per night (USD)
VRBO
Serene dog-friendly haven with pool access, central AC, & walkable locale
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropical Village - Southern Cross Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $428 per night (USD)
VRBO
Click For Pricing
Expedia
Dante's Marina Townhouse 2 bed 1.5 bath unit with a 5 minute walk to Duval!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
A short walk, just blocks away from all the sought-after action on Duval Street and near the infamous Dante's Pool at th ...
Click For Pricing
Expedia
From $291 per night (USD)
VRBO
Dog-friendly Key West Cottage with Private Hot Tub & Unbeatable Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Amelia House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $291 per night (USD)
VRBO
From $317 per night (USD)
Expedia
Comfortable condo with WiFi & lush gardens - in Old Town
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Casa Bonita at Duval Square R1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $317 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Leeward Isle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $333 per night (USD)
VRBO
From $835 per night (USD)
Expedia
Bright condo with private hot tub - amazing walkable locale
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Casa Havana at Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
From $835 per night (USD)
Expedia
From $461 per night (USD)
VRBO
CONCH GET ENOUGH at The Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Enjoy an early morning cup of coffee on your private bedroom balcony after being gently woken by the crowing of a wild r ...
From $461 per night (USD)
VRBO
From $2000 per night (USD)
Expedia
Key West Oasis - Truman Annex Estate
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Welcome to Key West Oasis! This beautiful and sophisticated estate checks all the boxes and is located on one of the mos ...
From $2000 per night (USD)
Expedia
From $185 per night (USD)
VRBO
Modern 2BR Condo Old Town/Balcony & Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close to all the action ...
From $185 per night (USD)
VRBO
From $589 per night (USD)
Expedia
Green Goddess - 4 BD/3 BA Amazing 360 Degree Rooftop Views! RealKeyWest
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the beauty of Key West's famous sunsets from the comfort of your own vacation home at The Green Goddess. This ...
From $589 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Lil Bit by Brightwild | Cottage in Quiet Area!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: - "Lil Bit" is a rare find in the historic Bahama Village neighborhood. - This historic beach home is modern a ...
From $202 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Key to Paradise by Brightwild | Pool w/Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Key to Paradise is a large townhome located in the gated Windward Park community off of Truman Avenue. Not only ...
From $244 per night (USD)
Expedia
From $1158 per night (USD)
VRBO
Sky Suite on Duval by Brightwild | Condo w/Balcony
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $1158 per night (USD)
VRBO
From $1858 per night (USD)
Expedia
**ENDLESS SUMMER @ OLD TOWN** New Villa & 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! All year long ...
From $1858 per night (USD)
Expedia
From $803 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Sleeps 4
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
OVERVIEW The Cigar House is a 100+ year old“Cigar maker’s house”. The recently completely renovated house is charming, ...
From $803 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Duval Dream Loft by Brightwild | Right on Duval!
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! This un ...
From $402 per night (USD)
Expedia
From $461 per night (USD)
VRBO
The Collins on Duval by Brightwild
Bedrooms:
1
Bathrooms:
2
Sleeps:
10
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $461 per night (USD)
VRBO
From $861 per night (USD)
Expedia
Old Town Key West Historic Cigarmaker's Cottage - Sleeps 5
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Conch House is a 100+ year old “Cigarmaker’s house. The house is recently renovated, charming, spacious, secluded a ...
From $861 per night (USD)
Expedia
Click For Pricing
Expedia
Waterfront views in beautiful Key West. Quality resort with fabulous amenities.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious two bedroom condo with full kitchen and balcony. Manicured grounds, right on the Atlantic Ocean, watch the sun ...
Click For Pricing
Expedia
From $212 per night (USD)
Expedia
Fairway Villa w/ Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to Fairway Villa a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one of a ...
From $212 per night (USD)
Expedia
From $710 per night (USD)
VRBO
**CARIBBEAN CHARM @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICES…
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! The sound of ...
From $710 per night (USD)
VRBO
From $165 per night (USD)
Expedia
**BACKCOUNTRY VIEWS @ SUNSET MARINA** Picturesque Waterfront Condo + LAST KEY SE
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! BACKCOUNTRY V ...
From $165 per night (USD)
Expedia
From $5788 per night (USD)
VRBO
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
Bedrooms:
15
Bathrooms:
13
Sleeps:
32
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Coordinating ...
From $5788 per night (USD)
VRBO
From $129 per night (USD)
Expedia
Central walk-up studio with partial ac - walk to Duval Street bars/dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Truman @ Duval - Unit E Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $129 per night (USD)
Expedia
From $1966 per night (USD)
VRBO
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool & Balcony over Duval + LAST KEY
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Walking along ...
From $1966 per night (USD)
VRBO
From $500 per night (USD)
Expedia
**CARSTEN CONCH COTTAGE @ OLD TOWN** Quaint Cottage + LAST KEY SERVICE…
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CARSTEN CONCH ...
From $500 per night (USD)
Expedia
From $814 per night (USD)
VRBO
Duval's Duet on Duval by Brightwild
Bedrooms:
2
Bathrooms:
4
Sleeps:
18
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! Duval's ...
From $814 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Old Town home a short walk to Duval/Couples Oasis
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Summary: Add this listing to your wishlist by clicking the ♥ in the upper right hand corner. This 1 bedroom/1.5 bathroom ...
From $260 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Relaxing island home/Great location/Stylish
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Summary: Only 4 short blocks to Duval, this 1 bedroom/1.5 bathroom home is walking distance to your favorite Key West sp ...
From $225 per night (USD)
VRBO
From $305 per night (USD)
Expedia
NEW! Completely Renovated / Close to Everything
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in the Heart of Historic Old Town Monthly Rental Pet Friendly. Up to 2 dogs, 40 lbs. max each. La Cala is a ...
From $305 per night (USD)
Expedia
From $1050 per night (USD)
VRBO
MILLIONAIRES ROW GREAT PRICES 4 BR, pool, free wifi, convenient to Duval St.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
You will love our GREAT PRICES and newly renovated 4 BR 3 1/2 bath home. 4th bedroom and a full bath is located in the g ...
From $1050 per night (USD)
VRBO
Click For Pricing
VRBO
A BIT OF AQUA at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Welcome to The Foundry a Bostonian style, 3 level townhouses that have been refurbished with tropical flair. Vaulted cei ...
Click For Pricing
VRBO
From $193 per night (USD)
VRBO
The Emelina, Key West Monthly Rental
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Emelina is located in a beautiful historic home. This unit is luxuriously appointed with elegant materials and impe ...
From $193 per night (USD)
VRBO
From $224 per night (USD)
Expedia
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
SULTRY GARDEN SANCTUARY... Steal away from reality and find your way to the quintessential, tropical & adults only Trave ...
From $224 per night (USD)
Expedia
From $263 per night (USD)
VRBO
COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen & Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
BOTANICAL MAGIC AWAITS YOU... Only three blocks from all of the fine dining and entertainment of Duval Street, yet tucke ...
From $263 per night (USD)
VRBO
From $181 per night (USD)
Expedia
Charming 'Boho Breeze' Retreat w/ Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience crystal clear waters, picturesque beaches, and famous historic sites with a stay at 'Boho Breeze!' This 2-bed ...
From $181 per night (USD)
Expedia
From $181 per night (USD)
VRBO
ROYAL PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
ESCAPE TO A BOTANICAL HIDEAWAY... Immerse yourself at the charming adults only Travelers Palm Inn with unique suites and ...
From $181 per night (USD)
VRBO
From $467 per night (USD)
VRBO
ISLAND OASIS at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Island Oasis @ the Truman Annex is beautifully renovated town home in the historic Foundry. | The living area is the ent ...
From $467 per night (USD)
VRBO
From $374 per night (USD)
VRBO
Sea Esta Suite by Brightwild | Pool on Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Summary: - In the middle of Duval Street and walking distance to the Southernmost Point! - Bright & airy two-story townh ...
From $374 per night (USD)
VRBO
From $148 per night (USD)
Expedia
NEW MONTHLY RENTAL, Old Town, Duplex, private backyard, pets welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Sea Monkey and The Mermaid. Our home is a duplex located in Old Town and full of Key West charm. Walk to a ...
From $148 per night (USD)
Expedia
From $202 per night (USD)
VRBO
Conch Cottage by Brightwild | Quiet w/ Shared Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Escape to this cozy Key West Cottage and enjoy all the island has to offer! Whether you plan to stay in or go o ...
From $202 per night (USD)
VRBO
From $600 per night (USD)
Expedia
Enjoy Old Town Key West in this Beautifully furnished house
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We recently bought this house because we LOVE Key West! It is a 2 story Key West style house. The bedrooms are upstair ...
From $600 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Yellow Room at Grand Maloney by Brightwild
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $255 per night (USD)
VRBO
From $200 per night (USD)
Expedia
Blue Room at the Grand Maloney by Brightwild
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $200 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Green Room at the Grand Maloney by Brightwild
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $255 per night (USD)
VRBO
From $181 per night (USD)
Expedia
Home Away From Home-Beautiful Duval Duplex
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Come stay in paradise! Golf cart available for rent! We are perfectly located one block from Duval Street but in a tranq ...
From $181 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Poolside King Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Poolside King Room is a hotel-style room adjacent to the pool. It can sleep up to four persons, two in the king-size ...
From $279 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Poolside Queen Room Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
The Poolside Queen Room is a hotel-style bedroom and bath unit that offers the amenities of our Key West villas for thos ...
From $249 per night (USD)
Expedia
From $299 per night (USD)
VRBO
One Bedroom Deck Villa Steps from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Enjoy a wonderful Key West accommodation. Our One Bedroom Deck Villa features a living room, a separate bedroom with ki ...
From $299 per night (USD)
VRBO
From $537 per night (USD)
Expedia
VILLA AZURA THE BEST place to be in Key West!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to Villa Azura - this is Enjoy this gem on a quiet lane in the award-winning gated community of the Truman An ...
From $537 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Duval Street Suite on Duval Free Parking and Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Cuban Club Suite is a one bedroom (queen) 1 bath suite with a queen murphy bed and kitchen. Overlooking Duval ...
From $342 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Duval Street Suite full kitchen, parking, & pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic O ...
From $316 per night (USD)
Expedia

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