Key West Rentals
From $452 per night (USD)VRBO
Newly-Built, Dog-Friendly Home with Shared Pool - Walk to Beach & Dining
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cabana Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $452 per night (USD)VRBO
From $532 per night (USD)Expedia
Cheery Beach Getaway Near Local Attractions - Pool & Easy Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shipyard Perch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $532 per night (USD)Expedia
From $580 per night (USD)VRBO
**SOUTHERNMOST PALMS @ THE ANNEX** 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! When you thin ...
From $580 per night (USD)VRBO
From $263 per night (USD)Expedia
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Cayo Coco Suite 208 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $263 per night (USD)Expedia
From $368 per night (USD)VRBO
Penthouse with WiFi, Private Hot Tub, & Shared Pool - Close to Beaches
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Duval Square Penthouse R19 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply en ...
From $368 per night (USD)VRBO
From $235 per night (USD)Expedia
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Antigua Suite 312 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $235 per night (USD)Expedia
From $289 per night (USD)VRBO
Tropical Condo with Pool & Private Patio - Walk to Beaches & Duval Street
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Salty Air Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $289 per night (USD)VRBO
From $266 per night (USD)Expedia
Sunny Dog-Friendly Condo with WiFi, Hot Tub, Pool & Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Sunrise Suites - Big Kahuna Suite 202 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $266 per night (USD)Expedia
From $275 per night (USD)VRBO
Family Friendly Condo with WiFi, Pool, & Hot Tub - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Saint Lucia Suite 201 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $275 per night (USD)VRBO
From $501 per night (USD)Expedia
Colorful Condo with Deck, Balcony, & Pool - Near Downtown & Beaches
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Cubana @ Duval Square R14 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $501 per night (USD)Expedia
From $3463 per night (USD)VRBO
Six Dog-Friendly Homes in Quiet Neighborhood with Private Pool & Hot Tub
- Bedrooms:
- 9
- Bathrooms:
- 12
- Sleeps:
- 34
Tropical Village Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $3463 per night (USD)VRBO
From $190 per night (USD)Expedia
Condo in Historic District with Shared Hot Tub - Two Blocks to Ocean, Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Duval Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $190 per night (USD)Expedia
From $229 per night (USD)VRBO
Island-Themed, Dog-Friendly Oasis with Shared Pool & Walkable Locale
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Tropical Village - Utopia Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ent ...
From $229 per night (USD)VRBO
From $523 per night (USD)Expedia
Spacious Key West Conch Cottage with WiFi & Private Hot Tub - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Hemingway's View Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $523 per night (USD)Expedia
From $225 per night (USD)VRBO
Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Flamingo Hideaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $225 per night (USD)VRBO
From $283 per night (USD)Expedia
Updated Corner Condo with Pool, Hot Tub, WiFi, Covered Parking - Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Sea Breeze Suite 101 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $283 per night (USD)Expedia
From $301 per night (USD)VRBO
Sunrise Suites Condo w/ Balcony, Pool & Hot Tub, Tennis & Covered Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Tahiti Suite 104 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $301 per night (USD)VRBO
From $144 per night (USD)Expedia
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 $144 per night (USD)Expedia
From $227 per night (USD)VRBO
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 $227 per night (USD)VRBO
From $233 per night (USD)Expedia
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 $233 per night (USD)Expedia
From $302 per night (USD)VRBO
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $302 per night (USD)VRBO
From $347 per night (USD)Expedia
Family Friendly Condo with Pool, Hot Tub, Tennis, & Parking Space
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Cristobal Suite 411 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $347 per night (USD)Expedia
From $651 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 $651 per night (USD)VRBO
From $432 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 $432 per night (USD)Expedia
From $301 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 $301 per night (USD)VRBO
From $256 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 $256 per night (USD)Expedia
From $243 per night (USD)VRBO
Cozy Cottage with Porch, WiFI, AC, & Amazing Walking Locale - Small Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Audubon House #6 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $243 per night (USD)VRBO
From $269 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 $269 per night (USD)Expedia
From $786 per night (USD)VRBO
Elegant Home with Patio & Shared Pool - Walk to Beaches & Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Mangrove Lagoon Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $786 per night (USD)VRBO
From $127 per night (USD)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 ...
From $127 per night (USD)Expedia
From $823 per night (USD)VRBO
**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 $823 per night (USD)VRBO
From $375 per night (USD)Expedia
Licence #CND5403292 Apt A-403, 2022 IS THE FINAL YEAR.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2022 IS THE FINAL YEAR. This property will be listed with All Florida Keys Vacation Rentals Effective Jan 1st 2023. ...
From $375 per night (USD)Expedia
From $402 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 $402 per night (USD)VRBO
From $729 per night (USD)Expedia
Forever ocean front views expansive 3 Bedroom Tropical Key West Paradise
- 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 $729 per night (USD)Expedia
From $250 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 $250 per night (USD)VRBO
From $1705 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 $1705 per night (USD)Expedia
From $144 per night (USD)VRBO
**MARA-VILLA @ OLD TOWN** Private Conch Home & Hot Tub + 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! MARA-VILLA is ...
From $144 per night (USD)VRBO
From $223 per night (USD)Expedia
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 $223 per night (USD)Expedia
From $375 per night (USD)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 ...
From $375 per night (USD)VRBO
From $223 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 $223 per night (USD)Expedia
From $323 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 $323 per night (USD)VRBO
From $150 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 $150 per night (USD)Expedia
From $151 per night (USD)VRBO
Sunny Condo w/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Frontier Flat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $151 per night (USD)VRBO
From $142 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 $142 per night (USD)Expedia
From $228 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 $228 per night (USD)VRBO
From $396 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 $396 per night (USD)Expedia
From $298 per night (USD)VRBO
Old town condo with hot tub and pool access - a quick away from Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Caribe at Duval Square, Unit R9 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $298 per night (USD)VRBO
From $204 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 $204 per night (USD)Expedia
From $324 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 $324 per night (USD)VRBO
From $226 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 $226 per night (USD)Expedia
From $355 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 $355 per night (USD)VRBO
From $198 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 $198 per night (USD)Expedia
From $229 per night (USD)VRBO
Queen’s Lair Rockhouse
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Cook in your bright and open kitchen overlooking an 8ft marble table in the dining room. Climb the floating stairs to t ...
From $229 per night (USD)VRBO
From $204 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 $204 per night (USD)Expedia
From $672 per night (USD)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 ...
From $672 per night (USD)VRBO
From $202 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 $202 per night (USD)Expedia
From $323 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 $323 per night (USD)VRBO
From $266 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 $266 per night (USD)Expedia
From $108 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 $108 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 $324 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 $324 per night (USD)VRBO
From $121 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 $121 per night (USD)Expedia
From $289 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 $289 per night (USD)VRBO
From $355 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 $355 per night (USD)Expedia
From $111 per night (USD)VRBO
Cute Dog-friendly Tropical Condo with AC, WiFi, & Shared Pool - Snowbirds OK
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Paradise Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $111 per night (USD)VRBO
From $510 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 $510 per night (USD)Expedia
From $1783 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 $1783 per night (USD)VRBO
From $268 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 $268 per night (USD)Expedia
From $1155 per night (USD)VRBO
Southernmost View - Pool, Sundeck & Water 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 $1155 per night (USD)VRBO
From $837 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 $837 per night (USD)Expedia
From $280 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 $280 per night (USD)VRBO
From $299 per night (USD)Expedia
Lovely Condo w/ Pool & Hot Tub, Right by the Beach - Family Friendly, Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Grenada Suite 209 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $299 per night (USD)Expedia
From $318 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 $318 per night (USD)VRBO
From $304 per night (USD)Expedia
Comfortable Condo with WiFi, Pool & Lush Gardens - in Old Town
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Bonita @ Duval Square R1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $304 per night (USD)Expedia
From $201 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 $201 per night (USD)VRBO
From $397 per night (USD)Expedia
Bright Condo with Private Hot Tub & Shared Pool - Amazing Walkable Locale
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Havana @ Duval Square R22 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...
From $397 per night (USD)Expedia
From $250 per night (USD)VRBO
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 ...
From $250 per night (USD)VRBO
From $379 per night (USD)Expedia
CONCH GET ENOUGH in the Truman Annex
- 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 $379 per night (USD)Expedia
From $303 per night (USD)VRBO
ISLAND BLISS - Old Town Key West 3/2 w- Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Calling all SUN SEEKERS & SNOWBIRDS!!! ISLAND BLISS Key West is ready to welcome you home. This newly remodeled 3-bedro ...
From $303 per night (USD)VRBO
From $185 per night (USD)Expedia
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)Expedia
From $543 per night (USD)VRBO
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 $543 per night (USD)VRBO
From $163 per night (USD)Expedia
Lil' Bit- Updated Cottage In Quiet Neighborhood!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: "Lil Bit" is a rare find in the historic Bahama Village neighborhood. This historic beach home is modern and re ...
From $163 per night (USD)Expedia
From $2000 per night (USD)VRBO
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)VRBO
From $228 per night (USD)Expedia
Key to Paradise - Heated Pool & Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Key to Paradise is a large townhome located in the gated Windward Park community on off of Truman Avenue. Not o ...
From $228 per night (USD)Expedia
From $554 per night (USD)VRBO
Sky Suite on Duval - Luxury Condo w/ Pvt Balcony!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: NEWLY RENOVATED AS OF January 2022! Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that ...
From $554 per night (USD)VRBO
From $1488 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 $1488 per night (USD)Expedia
From $782 per night (USD)VRBO
Historic Old Town Key West Cigarmaker's Cottage - Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
A few words about the pandemic… The health and safety of our guests and employees is our top priority. Our homes are pr ...
From $782 per night (USD)VRBO
From $538 per night (USD)Expedia
Duval Dream Loft- Pvt. Balcony Overlooking 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 $538 per night (USD)Expedia
From $540 per night (USD)VRBO
The Collins- Two Story Loft w/ Balcony on Duval St
- 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 $540 per night (USD)VRBO
From $400 per night (USD)Expedia
Key West Clubhouse w/ Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Key West Clubhouse a beautiful large 3 bedroom, 3 bathroom townhouse on the Key West Golf Course. This one ...
From $400 per night (USD)Expedia
From $804 per night (USD)VRBO
Old Town Key West Historic Cigarmaker's Cottage - Sleeps 5
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A few words about the 'damn'pandemic… The health and safety of our guests and employees is our top priority. Our homes ...
From $804 per night (USD)VRBO
From $328 per night (USD)Expedia
Find your Island Oasis in 2023!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Luxury Bathroom including 2 rain shower heads with separate controls, a spacious bench, double sink, and plenty of room ...
From $328 per night (USD)Expedia
From $350 per night (USD)VRBO
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 ...
From $350 per night (USD)VRBO
From $130 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 $130 per night (USD)Expedia
From $4058 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 $4058 per night (USD)VRBO
From $487 per night (USD)Expedia
**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 $487 per night (USD)Expedia
From $162 per night (USD)VRBO
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 $162 per night (USD)VRBO
From $1664 per night (USD)Expedia
**MAYA’S SECRET TREASURE @ DUVAL** Private Pool / Modern / Balcony over Duval +
- 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 $1664 per night (USD)Expedia
From $222 per night (USD)VRBO
**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 $222 per night (USD)VRBO
From $1073 per night (USD)Expedia
Duval Duo- Two Premier Lofts w/ Pvt Balconies!
- 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 D ...
From $1073 per night (USD)Expedia