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From $514 per night (USD)
VRBO
**VILLA BAHAMA @ 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! VILLA BAHAMA ...
From $514 per night (USD)
VRBO
From $1856 per night (USD)
Expedia
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $1856 per night (USD)
Expedia
From $5147 per night (USD)
VRBO
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in th ...
From $5147 per night (USD)
VRBO
$**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...$
From $4751 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY VII** 7BR\/7BA & Pool + LAST KEY SERVICES...
Bedrooms:
8
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $4751 per night (USD)
Expedia
From $1098 per night (USD)
VRBO
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $1098 per night (USD)
VRBO
From $3278 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & 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! For a truly o ...
From $3278 per night (USD)
Expedia
From $735 per night (USD)
VRBO
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Finally, a la ...
From $735 per night (USD)
VRBO
From $493 per night (USD)
Expedia
**VILLA CUBANA @ OLD TOWN** Comfy Cottage Near Duval + 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! This colorful ...
From $493 per night (USD)
Expedia
From $456 per night (USD)
VRBO
**MAISON TROPICALE @ OLD TOWN** Historic Home + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine a tra ...
From $456 per night (USD)
VRBO
$**CONCH IN THE TREETOPS @ 1800 ATLANTIC** Beach Condo \/ Pool + LAST KEY SERVICES$
From $944 per night (USD)
Expedia
**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 $944 per night (USD)
Expedia
$**CASA SUITE CASA @ CASA MARINA** Lush Home \/ Pool + LAST KEY SERVICE...$
From $517 per night (USD)
VRBO
**CASA SUITE CASA @ CASA MARINA** Lush Home \/ Pool + LAST KEY SERVICE...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Imagine your ...
From $517 per night (USD)
VRBO
$**SOUTHERNMOST HOSPITALITY V** 5BR\/5BA & Pool + LAST KEY SERVICES...$
From $3739 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY V** 5BR\/5BA & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $3739 per night (USD)
Expedia
From $665 per night (USD)
VRBO
Our Nautical Home in Key West is available for amazing prices Summer of 2023
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1st floor garden-view unit, King in the master bedroom, A double and a single in the guest bedroom and a queen sleeper ...
From $665 per night (USD)
VRBO
$**CAYO CALYPSO @ HIGGS BEACH** Modern Home \/ Pool + LAST KEY SERVICES...$
From $436 per night (USD)
Expedia
**CAYO CALYPSO @ HIGGS BEACH** Modern Home \/ Pool + LAST KEY SERVICES...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Upscale islan ...
From $436 per night (USD)
Expedia
From $774 per night (USD)
VRBO
Poolside Breeze a Tropical Retreat has a wrap around Balcony best location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Poolside Breeze! Discover a beautifully decorated two-bedroom condominium on the first floor, ideally locate ...
From $774 per night (USD)
VRBO
From $1112 per night (USD)
Expedia
Find Sanity in the Heart of Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Experience the charm of this fantastic Old Town location surrounded by local businesses and restaurants, allowing you to ...
From $1112 per night (USD)
Expedia
From $1520 per night (USD)
VRBO
**CASITA ANGELITA @ OLD TOWN** Historic Condo by Duval + 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 Old Town ...
From $1520 per night (USD)
VRBO
$**SUNSET DREAMS @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...$
From $287 per night (USD)
Expedia
**SUNSET DREAMS @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUNSET DREAMS ...
From $287 per night (USD)
Expedia
From $367 per night (USD)
VRBO
Irish in Truman Annex Shipyard close to Historic Duval & Ft Zach State Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilt ...
From $367 per night (USD)
VRBO
From $1626 per night (USD)
Expedia
**PUERTA CORALINA @ OLD TOWN** Cottage Near Duval + LAST KEY SERVICE...
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This precious ...
From $1626 per night (USD)
Expedia
From $722 per night (USD)
VRBO
High Tide awaits your next visit upgraded condo close to Smathers Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1800 Atlantic Condominiums Unit B117 2 Bedroom Garden-View Condo at 1800 Atlantic Perfect for a family get-away or a gr ...
From $722 per night (USD)
VRBO
From $4168 per night (USD)
Expedia
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $4168 per night (USD)
Expedia
$**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES..$
From $890 per night (USD)
VRBO
**FOLLOW THE SUN @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! FOLLOW THE SU ...
From $890 per night (USD)
VRBO
From $2990 per night (USD)
Expedia
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
6
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located in Tr ...
From $2990 per night (USD)
Expedia
From $703 per night (USD)
VRBO
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
2 Bedroom 2 bath Island View King in the master bedroom, king in the the guest bedroom and a queen sleeper sofa in the ...
From $703 per night (USD)
VRBO
From $1221 per night (USD)
Expedia
Somewhere on the Beach a dream property all amenities included simply amazing
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Somewhere on the Beach has amazing views of the Atlantic Ocean and White Street Pier. The property was completely remode ...
From $1221 per night (USD)
Expedia
From $567 per night (USD)
VRBO
**THE ARTISTS' MUSE @ LOVE LANE** Immaculate Home & Pool + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For many, the ...
From $567 per night (USD)
VRBO
From $2547 per night (USD)
Expedia
**DIAMOND GIRL @ THE ANNEX** Elegant 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! Seals & Croft ...
From $2547 per night (USD)
Expedia
From $2206 per night (USD)
VRBO
**THE SMILING IBIS @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $2206 per night (USD)
VRBO
$**NATURES EDGE @ THE BEACH** Ocean Condo \/ Pool & Tennis + LAST KEY SERVICES...$
From $921 per night (USD)
Expedia
**NATURES EDGE @ THE BEACH** Ocean Condo \/ Pool & Tennis + 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! NATURE'S EDGE ...
From $921 per night (USD)
Expedia
From $2769 per night (USD)
VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool by Duval + LAST KEY SERVICES...
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $2769 per night (USD)
VRBO
$**SHANG-RI-LA @ THE BEACH** Oceanview Condo \/ Pool & Tennis + LAST KEY SERVICES.$
From $954 per night (USD)
Expedia
**SHANG-RI-LA @ THE BEACH** Oceanview Condo \/ Pool & Tennis + 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! SHANG-RI-LA i ...
From $954 per night (USD)
Expedia
$**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse \/ Pool + LAST KEY SERVICES.$
From $1425 per night (USD)
VRBO
**ATLANTIC REFLECTIONS @ THE BEACH** Ocean Penthouse \/ 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! ATLANTIC REFL ...
From $1425 per night (USD)
VRBO
From $4141 per night (USD)
Expedia
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
Bedrooms:
8
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $4141 per night (USD)
Expedia
From $638 per night (USD)
VRBO
Botanical Island Delight Key West fantastic discounts for Summer & Fall
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smather ...
From $638 per night (USD)
VRBO
From $709 per night (USD)
Expedia
**SALTWATER HARMONY @ THE ANNEX** Charming Condo & Pool + 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! SALTWATER HAR ...
From $709 per night (USD)
Expedia
From $1045 per night (USD)
VRBO
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely ...
From $1045 per night (USD)
VRBO
From $702 per night (USD)
Expedia
**LA PETITE PENTHOUSE @ THE ANNEX** Elegant Condo & Pool + 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! LA PETITE PEN ...
From $702 per night (USD)
Expedia
From $3815 per night (USD)
VRBO
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool near Duval + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CONCH CASA GR ...
From $3815 per night (USD)
VRBO
From $738 per night (USD)
Expedia
**LA GRANDE REUNION @ OLD TOWN** Estate & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling wit ...
From $738 per night (USD)
Expedia
From $1668 per night (USD)
VRBO
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! A stay in Key ...
From $1668 per night (USD)
VRBO
From $1017 per night (USD)
Expedia
**PROMENADE TO PARADISE @ THE ANNEX** Ocean Condo & Pool + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you dream ...
From $1017 per night (USD)
Expedia
From $976 per night (USD)
VRBO
Frost Free at 1800 Atlantic overlooking Smathers Beach top and the sunrise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1800 Atlantic 4th floor condominiums unit C439. Overlooking Smathers Beach and the Atlantic Ocean, this two bedroom, tw ...
From $976 per night (USD)
VRBO
From $295 per night (USD)
Expedia
**SUNDRENCHED REFLECTIONS @ SUNSET MARINA** Bayfront Condo + LAST KEY SERVICES..
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUNDRENCHED R ...
From $295 per night (USD)
Expedia
From $3095 per night (USD)
VRBO
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
Bedrooms:
4
Bathrooms:
5
Sleeps:
13
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This renovate ...
From $3095 per night (USD)
VRBO
From $1064 per night (USD)
Expedia
ROOFTOP PENTHOUSE- | 2 Bed, 1.5 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The high-end sophisticated Rooftop Penthouse is located directly above the famous Wyland Gallery on Duval Street. Enjoy ...
From $1064 per night (USD)
Expedia
From $412 per night (USD)
VRBO
Truman Annex, two blocks from Duval
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Available for weekly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful ...
From $412 per night (USD)
VRBO
From $766 per night (USD)
Expedia
**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 $766 per night (USD)
Expedia
From $403 per night (USD)
VRBO
Dog-Friendly Sunrise Suites Condo with Pool, Hot Tub & Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Cayo Coco Suite 208 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $403 per night (USD)
VRBO
From $315 per night (USD)
Expedia
Dog-friendly home with pool & walk to parks & beach - snowbirds welcome
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Casa Atlantic Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $315 per night (USD)
Expedia
From $541 per night (USD)
VRBO
Bright Condo with Homey Feel, Entertainment & Private Parking - Beach Nearby
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Jasmine Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $541 per night (USD)
VRBO
From $593 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 $593 per night (USD)
Expedia
From $641 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 $641 per night (USD)
VRBO
From $519 per night (USD)
Expedia
Tropical Getaway with Private Balcony, Shared Pool & Hot Tub - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Antigua Suite 312 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $519 per night (USD)
Expedia
From $635 per night (USD)
VRBO
Sunny 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 $635 per night (USD)
VRBO
From $890 per night (USD)
Expedia
Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Top floor penthouse ocean-view condominium at 1800 Atlantic in the highly desirable B building. This unit has recently b ...
From $890 per night (USD)
Expedia
From $559 per night (USD)
VRBO
**BLUE HERON'S COVE @ THE ANNEX** Luxury Villa by Duval + 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! BLUE HERON'S ...
From $559 per night (USD)
VRBO
$**SUNSET POINT @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...$
From $322 per night (USD)
Expedia
**SUNSET POINT @ SUNSET MARINA** Condo \/ Pool & Spa + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SUNSET POINT ...
From $322 per night (USD)
Expedia
From $983 per night (USD)
VRBO
**THE MELLOW MACAW** Cozy Condo Near Duval + LAST KEY SERVICES...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This colorful ...
From $983 per night (USD)
VRBO
From $729 per night (USD)
Expedia
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This wonderful property has just received a major face lift and has been beautifully renovated. King bed in the master b ...
From $729 per night (USD)
Expedia
$**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.$
From $1273 per night (USD)
VRBO
**NEPTUNE'S PENTHOUSE @ THE BEACH** Oceanfront Condo \/ Pool + LAST KEY SERVICE.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! As Neptune wa ...
From $1273 per night (USD)
VRBO
$Dog-friendly condo with pool, hot tub, balcony, central AC, W\/D, & fitness room$
From $561 per night (USD)
Expedia
Dog-friendly condo with pool, hot tub, balcony, central AC, W\/D, & fitness room
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Saint Lucia Suite 201 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $561 per night (USD)
Expedia
Click For Pricing
VRBO
Colorful condo with deck & balcony - near downtown & beaches
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Casa Cubana at Duval Square R14 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simp ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Condo in Historic District with Shared Hot Tub - Two Blocks to Ocean, Dogs OK
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Duval Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
Click For Pricing
Expedia
From $383 per night (USD)
VRBO
**HAVANA HOUSE @ OLD TOWN** Elegant Cottage Near Duval + LAST KEY SERVICES...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Located on So ...
From $383 per night (USD)
VRBO
$**WINDSWEPT PALMS @ THE BEACH** Oceanfront \/ Pool & Jacuzzi + LAST KEY SERVICE$
From $1659 per night (USD)
Expedia
**WINDSWEPT PALMS @ THE BEACH** Oceanfront \/ Pool & Jacuzzi + 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! Imagine a hom ...
From $1659 per night (USD)
Expedia
From $695 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 $695 per night (USD)
VRBO
From $538 per night (USD)
Expedia
Updated Corner Condo with Pool, Hot Tub, WiFi, Covered Parking - Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Sea Breeze Suite 101 Our calendar is updated in real-time & our nightly rates are accurately displayed ...
From $538 per night (USD)
Expedia
$Sunrise Suites Condo w\/ Balcony, Pool & Hot Tub, Tennis & Covered Parking$
From $560 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 $560 per night (USD)
VRBO
From $586 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 $586 per night (USD)
Expedia
From $716 per night (USD)
VRBO
Cozy, Dog-Friendly Townhome with Shared Pool & Courtyard - Walkable Locale
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Old Town Garden Villas - Abaco Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $716 per night (USD)
VRBO
From $2382 per night (USD)
Expedia
Dog-Friendly Home with Patio and Private Hot Tub - Walk to the Beach
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Southernmost Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $2382 per night (USD)
Expedia
From $709 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 $709 per night (USD)
VRBO
From $198 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 $198 per night (USD)
Expedia
From $655 per night (USD)
VRBO
Sunrise Suites Condo with Views, Pool, Hot Tub - Dogs Welcome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Barbados Suite 204 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $655 per night (USD)
VRBO
$Watch Sunsets from Your Deck, Shared Pool\/Hot Tub - Perfect for the Whole Family$
From $405 per night (USD)
Expedia
Watch Sunsets from Your Deck, Shared Pool\/Hot Tub - Perfect for the Whole Family
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Panama Suite 310 Our calendar is updated in real-time & our nightly rates are accurately displayed. Si ...
From $405 per night (USD)
Expedia
From $387 per night (USD)
VRBO
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Cozumel Suite 112 Our calendar is updated in real-time & our nightly rates are accurately displayed. S ...
From $387 per night (USD)
VRBO
From $432 per night (USD)
Expedia
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 $432 per night (USD)
Expedia
$Cozy Dog-Friendly Condo w\/ Shared Pool, Hot Tub, Private Deck & Parking$
From $407 per night (USD)
VRBO
Cozy Dog-Friendly Condo w\/ Shared Pool, Hot Tub, Private Deck & Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Catalina Suite 311 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $407 per night (USD)
VRBO
From $496 per night (USD)
Expedia
Elegant home with with patio & community 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 $496 per night (USD)
Expedia
From $1446 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 $1446 per night (USD)
VRBO
From $961 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 $961 per night (USD)
Expedia
From $1014 per night (USD)
VRBO
Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Mar Y Sol is a beautiful oceanfront condominium featuring three bedrooms and two and a half baths, located at 1800 Atlan ...
From $1014 per night (USD)
VRBO
From $3918 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 $3918 per night (USD)
Expedia
$Dog-friendly home w\/ large private pool only a short walk to Historic Seaport$
From $337 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 $337 per night (USD)
VRBO
$Little Paradise, Historic Harbor Old Town Key West 2\/2$
From $587 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 $587 per night (USD)
Expedia
$7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location$
Click For Pricing
VRBO
7 Nights - Hyatt Sunset Harbor 2 bed\/2bath\/Kitchen\/Sleeps 6. Fantastic Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Fantastic location!!! Sunday to Sunday 7 night rental at HYATT SUNSET HARBOR 2 bedrooms 2 bath full kitchen and common a ...
Click For Pricing
VRBO
From $432 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 $432 per night (USD)
Expedia
From $818 per night (USD)
VRBO
Comfortable Cottage with Private Pool & Lovely Garden - Great Location
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Key Lime Calypso Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $818 per night (USD)
VRBO
From $516 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 $516 per night (USD)
Expedia
$Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location$
From $853 per night (USD)
VRBO
Charming Condo w\/ Entertainment & Private Parking - Great In-Town Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gardenia Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $853 per night (USD)
VRBO
From $367 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 $367 per night (USD)
Expedia
From $708 per night (USD)
VRBO
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Saint Barts Suite 303 Our calendar is updated in real-time & our nightly rates are accurately displaye ...
From $708 per night (USD)
VRBO
From $397 per night (USD)
Expedia
Elegant Condo with Entertainment & Private Parking - Great Central Location
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Orchid Suite Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $397 per night (USD)
Expedia
From $306 per night (USD)
VRBO
Queen’s Lair Rockhouse
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
(((Third bedroom is an awesome open loft with a queen size bed- it is upstairs above the living room and master suite an ...
From $306 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Dog-Friendly Retreat with Pool, Hot Tub, Tennis - Balcony with Pool Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sunrise Suites - Tierra Bomba Suite 403 Our calendar is updated in real-time & our nightly rates are accurately display ...
From $406 per night (USD)
Expedia
$Fresh Getaway w\/ Private Pool & Rooftop Patio - Great Location, Steps from Beach$
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 $527 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 $527 per night (USD)
Expedia
$Sunny Condo w\/ Entertainment, Balcony, & Great Location Near Beach - Dogs OK$
From $463 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 $463 per night (USD)
VRBO
From $570 per night (USD)
Expedia
Stylish Dog-Friendly Condo with Balcony - In Heart of the Historic District
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kingfish Keep On Duval Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $570 per night (USD)
Expedia

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