Key West Rentals
From $594 per night (USD)VRBO
**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach 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! This freshly ...
From $594 per night (USD)VRBO
From $180 per night (USD)Expedia
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 $180 per night (USD)Expedia
From $126 per night (USD)VRBO
Cozy Dog-Friendly Suite with WiFi, Balcony, Hot Tub, Pool, & Private Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Jamaica Suite 102 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $126 per night (USD)VRBO
From $883 per night (USD)Expedia
Stylish Condo with Swimming Pool - Minutes from Popular Attractions
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Truman's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $883 per night (USD)Expedia
From $248 per night (USD)VRBO
Dog & Snowbird-Friendly Home with Private Pool - Walk to Parks & Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Casa Atlantic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $248 per night (USD)VRBO
From $369 per night (USD)Expedia
Dog-Friendly Oasis with Patio, Central AC, Private Pool, and Walkable Locale
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Mermaid Manor Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $369 per night (USD)Expedia
From $114 per night (USD)VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $114 per night (USD)VRBO
From $352 per night (USD)Expedia
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 $352 per night (USD)Expedia
From $332 per night (USD)VRBO
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 $332 per night (USD)VRBO
From $95 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 $95 per night (USD)Expedia
From $402 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 $402 per night (USD)VRBO
From $155 per night (USD)Expedia
Sunny Dog-Friendly Condo with WiFi, Hot Tub, Pool & Tennis
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Big Kahuna Suite 202 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $155 per night (USD)Expedia
From $354 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 $354 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 $2376 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 $2376 per night (USD)VRBO
From $149 per night (USD)Expedia
Condo in Historic District with Shared Hot Tub - Two Blocks to Ocean, Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Southernmost Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $149 per night (USD)Expedia
From $253 per night (USD)VRBO
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 $253 per night (USD)VRBO
From $69 per night (USD)Expedia
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 $69 per night (USD)Expedia
From $200 per night (USD)VRBO
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 $200 per night (USD)VRBO
From $301 per night (USD)Expedia
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)Expedia
From $166 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 $166 per night (USD)VRBO
From $726 per night (USD)Expedia
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 $726 per night (USD)Expedia
From $436 per night (USD)VRBO
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 $436 per night (USD)VRBO
From $1052 per night (USD)Expedia
Dog-Friendly Home with Patio and Private Hot Tub - Walk to the Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Duval Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $1052 per night (USD)Expedia
From $425 per night (USD)VRBO
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 $425 per night (USD)VRBO
From $167 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 $167 per night (USD)Expedia
From $157 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 $157 per night (USD)VRBO
From $131 per night (USD)Expedia
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 $131 per night (USD)Expedia
From $117 per night (USD)VRBO
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 $117 per night (USD)VRBO
From $181 per night (USD)Expedia
Cozy Cottage with Porch, WiFI, AC, & Amazing Walking Locale - Small Dogs OK
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Audubon House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $181 per night (USD)Expedia
From $112 per night (USD)VRBO
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 $112 per night (USD)VRBO
From $786 per night (USD)Expedia
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)Expedia
From $375 per night (USD)VRBO
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)VRBO
From $552 per night (USD)Expedia
**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 $552 per night (USD)Expedia
From $750 per night (USD)VRBO
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 $750 per night (USD)VRBO
From $317 per night (USD)Expedia
**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 $317 per night (USD)Expedia
From $2777 per night (USD)VRBO
**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 $2777 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 $1134 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 $1134 per night (USD)VRBO
From $190 per night (USD)Expedia
**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 $190 per night (USD)Expedia
From $105 per night (USD)VRBO
Sunny Condo with Pool, Hot Tub, Tennis & Private Balcony - 1 Dog OK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sunrise Suites - Grand Bahama Suite 106 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $105 per night (USD)VRBO
From $237 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 $237 per night (USD)Expedia
From $325 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 $325 per night (USD)VRBO
From $259 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 $259 per night (USD)Expedia
From $626 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 $626 per night (USD)VRBO
From $231 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 $231 per night (USD)Expedia
From $127 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 $127 per night (USD)VRBO
From $120 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 $120 per night (USD)Expedia
From $392 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 $392 per night (USD)VRBO
From $429 per night (USD)Expedia
Little Paradise, Historic Seaport 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 $429 per night (USD)Expedia
From $189 per night (USD)VRBO
Old Town, dog-friendly condo w/ hot tub & pool access - walk to Duval Street
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Caribe @ Duval Square R9 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $189 per night (USD)VRBO
From $100 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 $100 per night (USD)Expedia
From $385 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 $385 per night (USD)VRBO
From $400 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 $400 per night (USD)Expedia
From $511 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 $511 per night (USD)VRBO
From $117 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 $117 per night (USD)Expedia
From $325 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 $325 per night (USD)VRBO
From $436 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 $436 per night (USD)Expedia
From $683 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 $683 per night (USD)VRBO
From $95 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 $95 per night (USD)Expedia
From $128 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 $128 per night (USD)VRBO
From $334 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 $334 per night (USD)Expedia
From $198 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 $198 per night (USD)VRBO
From $190 per night (USD)Expedia
Dog-Friendly Gulf-Front Condo w/ WiFi, Dock/Boat Slip, Gulf Views, & Shared Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Flagler's Crossing Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $190 per night (USD)Expedia
From $149 per night (USD)VRBO
Resort Condo with Pool & Hot Tub, Private Parking - Dog OK, Family-Friendly
- 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 $149 per night (USD)VRBO
From $225 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 $225 per night (USD)Expedia
From $392 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 $392 per night (USD)VRBO
From $351 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 $351 per night (USD)Expedia
From $108 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 $108 per night (USD)VRBO
From $656 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 $656 per night (USD)Expedia
From $2447 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 $2447 per night (USD)VRBO
From $217 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 $217 per night (USD)Expedia
From $823 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 $823 per night (USD)VRBO
From $960 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 $960 per night (USD)Expedia
From $273 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 $273 per night (USD)VRBO
From $124 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 $124 per night (USD)Expedia
From $190 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 $190 per night (USD)VRBO
From $170 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 $170 per night (USD)Expedia
From $126 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 $126 per night (USD)VRBO
From $163 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 $163 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 $416 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 $416 per night (USD)Expedia
From $426 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 $426 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 $825 per night (USD)VRBO
Green Goddess - Amazing 360 Degree Rooftop Views! RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
You will be thrilled with this property's secluded location just off Whitehead Street. Less than a block from the Southe ...
From $825 per night (USD)VRBO
From $305 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 $305 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 $255 per night (USD)Expedia
Light House South- Luxurious w/ Shared Heated Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Lighthouse South is a large townhome located in the gated Windward Park community. Not only is it equipped with ...
From $255 per night (USD)Expedia
From $367 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 $367 per night (USD)VRBO
From $2007 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 $2007 per night (USD)Expedia
From $827 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 $827 per night (USD)VRBO
From $269 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 $269 per night (USD)Expedia
From $199 per night (USD)VRBO
The Collins- Two Story Loft w/ Balcony on Duval St
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: Located right in the heart of the World Famous Duval Street, enjoy a true downtown Key West experience! The Col ...
From $199 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 $881 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 $881 per night (USD)VRBO
From $493 per night (USD)Expedia
2021 Remodel! Luxury Couples Bathroom and more!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
New Remodel Fall 2021! New Luxury Bathroom including 2 rain shower heads with separate controls, a spacious bench, dou ...
From $493 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 $510 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 $510 per night (USD)Expedia
From $163 per night (USD)VRBO
**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 $163 per night (USD)VRBO
From $5863 per night (USD)Expedia
**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 $5863 per night (USD)Expedia