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From $1207 per night (USD)
VRBO
**CASA OLIVIANA @ SOLARES HILL** Home & Pool + Last Key White Glove Service...
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 $1207 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Beautiful Modern House in Key Largo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Open layout of the living area, dining room and kitchen. Large, screened patio offers the tropical 'out of doors and fre ...
From $222 per night (USD)
Expedia
From $557 per night (USD)
VRBO
Coral Hammock Poolside Home 3 bdrm 3 bath10 minute drive to Old Town Key West
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Coral Hammock – 3BR/3BA Home with Pool Views in Coral Hammock 3 Bedrooms | 3 Full Bathrooms | Sleeps up to 8 | Backs to ...
From $557 per night (USD)
VRBO
From $459 per night (USD)
Expedia
**CONCH IN THE TREETOPS** Beach Condo / Pool + Last Key White Glove Service...
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 $459 per night (USD)
Expedia
From $511 per night (USD)
VRBO
**CASA SUITE CASA @ CASA MARINA** Home / Pool + Last Key White Glove Service...
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine your ...
From $511 per night (USD)
VRBO
From $1562 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + Last Key White Glove Service...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1562 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Our Nautical Home Key West prime location & amenities. Last minute specials.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to paradise in this spacious first-floor garden-view condo in beautiful Key West — the perfect setting for a rela ...
From $469 per night (USD)
VRBO
From $350 per night (USD)
Expedia
**CAYO CALYPSO @ HIGGS BEACH** Home / Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Upscale islan ...
From $350 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Poolside Breeze Retreat, Tropical flare, Key West spectacular getaway.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Poolside Breeze is a nicely decorated two bedroom 1st floor condominium with an excellent location very close to the poo ...
From $492 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Flamingo Nook. Renovated, Private Pool, Canal & Cabana Club Access!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The ultimate Florida Keys getaway! The Flamingo Nook located at Key Colony Beach near Marathon. Privacy is what separate ...
From $292 per night (USD)
Expedia
From $527 per night (USD)
VRBO
**HAVANA HOUSE @ OLD TOWN** Cottage Near Duval + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located on So ...
From $527 per night (USD)
VRBO
From $794 per night (USD)
Expedia
**WINDSWEPT PALMS** Seaside / Pool & Jacuzzi + Last Key White Glove 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 $794 per night (USD)
Expedia
From $1119 per night (USD)
VRBO
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For the ultim ...
From $1119 per night (USD)
VRBO
From $492 per night (USD)
Expedia
**SHANG-RI-LA** Oceanview Condo/ Pool & Tennis + Last Key White Glove Service...
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 $492 per night (USD)
Expedia
From $597 per night (USD)
VRBO
**ATLANTIC REFLECTIONS @ THE BEACH** Penthouse + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical f ...
From $597 per night (USD)
VRBO
From $2083 per night (USD)
Expedia
**THE IBIS & THE CRANE @ OLD TOWN** Compound + Last Key White Glove Service...
Bedrooms:
7
Bathrooms:
6
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Dreaming of a ...
From $2083 per night (USD)
Expedia
From $494 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 $494 per night (USD)
VRBO
From $247 per night (USD)
Expedia
**SALTWATER HARMONY @ THE ANNEX** Condo & Pool + Last Key White Glove Service...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SALTWATER HAR ...
From $247 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Atlantic Paradise Found modern luxury Best pool in Key West fine finishes
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely ...
From $538 per night (USD)
VRBO
From $247 per night (USD)
Expedia
**LA PETITE PENTHOUSE** Elegant Condo & Pool + Last Key White Glove Service...
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! LA PETITE PEN ...
From $247 per night (USD)
Expedia
From $1659 per night (USD)
VRBO
**CONCH CASA GRANDE** Home+ Pool near Duval + Last Key White Glove Service...
Bedrooms:
6
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! CONCH CASA GR ...
From $1659 per night (USD)
VRBO
From $722 per night (USD)
Expedia
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + Last Key White Glove Service...
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 $722 per night (USD)
Expedia
From $537 per night (USD)
VRBO
**PROMENADE TO PARADISE** Ocean Condo & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! If you dream ...
From $537 per night (USD)
VRBO
From $454 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 $454 per night (USD)
Expedia
From $309 per night (USD)
VRBO
**SUNSET POINT @ SUNSET MARINA** Condo / Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET POINT ...
From $309 per night (USD)
VRBO
From $513 per night (USD)
Expedia
**SEA CAPTAIN'S HAVEN** Luxury Villa & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SEA CAPTAIN'S ...
From $513 per night (USD)
Expedia
From $496 per night (USD)
VRBO
**THE MELLOW MACAW** Cozy Condo Near Duval + Last Key White Glove Service...
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $496 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Hemingways Atlantic Retreat overlooks Smathers Beach upgrades galore Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**About...** Hemingway Atlantic Retreat is a two-bedroom condo conveniently located near beaches and restaurants, just ...
From $515 per night (USD)
Expedia
From $651 per night (USD)
VRBO
**NEPTUNE'S PENTHOUSE** Oceanside Condo / Pool + Last Key White Glove 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 $651 per night (USD)
VRBO
From $542 per night (USD)
VRBO
Best Deals in Duck Key . 2 Bedroom /2 Bath w/40' 'Dock, Trailer Storage Incl,
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*** This property is completely renovated on the inside and out! We cordially invite you to our property and enjoy the v ...
From $542 per night (USD)
VRBO
From $517 per night (USD)
VRBO
**CASITA ANGELITA @ OLD TOWN** Condo by Duval + Last Key White Glove Service...
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 $517 per night (USD)
VRBO
From $274 per night (USD)
Expedia
**SUNSET DREAMS @ SUNSET MARINA** Condo / Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNSET DREAMS ...
From $274 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Truman Annex Gem Shipyard 2BR C Walk to Beach & Bars, Best of Old Town
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Pool Closure The Shipyard Pool will be closed starting August 1, 2026, for the Pool Deck Replacement Project. W ...
From $229 per night (USD)
VRBO
$\Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\$
From $288 per night (USD)
Expedia
\"Canal-Front Paradise in Big Pine Key-Relax &Explore the keys\"
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
-Remodeling house 3 bedroom and 3 bath. -Please note that there is a 28 minimum rental period for this property. - D ...
From $288 per night (USD)
Expedia
From $704 per night (USD)
VRBO
**PUERTA CORALINA @ OLD TOWN** Cottage + Last Key White Glove 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 $704 per night (USD)
VRBO
From $490 per night (USD)
Expedia
High Tide awaits your next visit upgraded condo close to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 Bedroom Garden-View Condo at 1800 Atlantic – Key West, FL Your Tropical Getaway Awaits! Experience the ultimate in c ...
From $490 per night (USD)
Expedia
From $1554 per night (USD)
VRBO
**CASA VICTORIA @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! CASA VICTORIA ...
From $1554 per night (USD)
VRBO
From $460 per night (USD)
Expedia
**FOLLOW THE SUN** Ocean Condo / Pool & Tennis + Last Key White Glove Service...
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 $460 per night (USD)
Expedia
From $2211 per night (USD)
VRBO
**NOONA'S MANSION @ THE ANNEX** Home & Pool + Last Key White Glove Service...
Bedrooms:
5
Bathrooms:
6
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located in Tr ...
From $2211 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Tranquility by Smathers and 10 minute bike downtown Key West value savings
Bedrooms:
2
Bathrooms:
2
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 $408 per night (USD)
Expedia
From $676 per night (USD)
VRBO
Somewhere on the Beach a dream property all amenities included simply amazing
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Somewhere on the Beach – Oceanfront 2-Bedroom Condo in Key West Location, Location, Location... Welcome to Somewhere on ...
From $676 per night (USD)
VRBO
From $565 per night (USD)
Expedia
**THE ARTISTS' MUSE @ LOVE LANE** Home & Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! For many, the ...
From $565 per night (USD)
Expedia
From $681 per night (USD)
VRBO
**DIAMOND GIRL @ THE ANNEX** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Seals & Croft ...
From $681 per night (USD)
VRBO
From $782 per night (USD)
Expedia
**THE SMILING IBIS @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $782 per night (USD)
Expedia
From $471 per night (USD)
VRBO
**NATURES EDGE** Ocean Condo / Pool & Tennis + Last Key White Glove Service...
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 $471 per night (USD)
VRBO
From $537 per night (USD)
Expedia
**OCTOPUS'S GARDEN @ CORAL HAMMOCK** Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OCTOPUS'S GAR ...
From $537 per night (USD)
Expedia
From $515 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 $515 per night (USD)
VRBO
From $314 per night (USD)
Expedia
**SUNDRENCHED REFLECTIONS** Bayfront Condo + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! SUNDRENCHED R ...
From $314 per night (USD)
Expedia
From $1115 per night (USD)
VRBO
**SWEET HOME ANGELITA @ OLD TOWN** Home + Last Key White Glove Service...
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 $1115 per night (USD)
VRBO
From $961 per night (USD)
Expedia
Rooftop Penthouse
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Summary: Rooftop Penthouse- Luxury Penthouse in prime Downtown location The Space: The high-end sophisticated Rooft ...
From $961 per night (USD)
Expedia
From $355 per night (USD)
VRBO
Island Therapy
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautiful 2BD/2BA vacation home features open water views and a full size 35' seawall for docking a boat. Amenities incl ...
From $355 per night (USD)
VRBO
From $302 per night (USD)
Expedia
Truman Annex, two blocks from Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Available for monthly, or longer, rentals this three-story townhouse is located on a picturesque street in the beautiful ...
From $302 per night (USD)
Expedia
From $325 per night (USD)
VRBO
**SOUTHERNMOST PALMS @ THE ANNEX** Villa + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! When you thin ...
From $325 per night (USD)
VRBO
From $359 per night (USD)
Expedia
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The spacious two bedroom vacation rental is ideal for fishermen, families, friends and pets. You can bring your own boat ...
From $359 per night (USD)
Expedia
From $493 per night (USD)
VRBO
*Summer Special $2,775 Week* with a private chilled pool & 75' of dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Gorgeous and welcoming ground level home directly on the canal! Located in the renowned city of Key Colony Beach, Mile M ...
From $493 per night (USD)
VRBO
From $697 per night (USD)
Expedia
**VILLA ANGELITA @ OLD TOWN** Condo Off Duval + Last Key White Glove Service...
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 $697 per night (USD)
Expedia
From $460 per night (USD)
VRBO
**SUZY'S PARROT PERCH @ OLD TOWN** Condo + Last Key White Glove Service...
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 $460 per night (USD)
VRBO
From $780 per night (USD)
Expedia
Mar Y Sol –Luxurious oceanfront Key West Breathtaking Atlantic Sunrise Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Mar Y Sol – Luxury Oceanfront Condo in Key West Breathtaking Views. Unbeatable Comfort. Perfect Location. Welcome to Ma ...
From $780 per night (USD)
Expedia
From $448 per night (USD)
VRBO
Sombrero Beach Villa with Private Pool and Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This beautiful villa was built in 2017, making it one of the newest and modern homes in the Florida Keys. There are nume ...
From $448 per night (USD)
VRBO
From $153 per night (USD)
VRBO
Key Largo Waterfront Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The property is located in Pirates Cove (mile marker 99 bayside), which is an early Key Largo development that is quiet ...
From $153 per night (USD)
VRBO
From $607 per night (USD)
VRBO
Little Paradise, Historic Harbor Old Town Key West 2/1.5
Bedrooms:
1
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 $607 per night (USD)
VRBO
From $562 per night (USD)
Expedia
208 Mariners Club - Newly Renovated 3 bedroom, 3 Bath Townhome
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Newly renovated! This tri-level townhouse has a laid-back, welcoming Florida Keys vibe, pristine decor, sleek new kitch ...
From $562 per night (USD)
Expedia
From $900 per night (USD)
VRBO
Marina Villa 212 3/3 Pools, Marina and Ocean views
Bedrooms:
3
Bathrooms:
3
Sleeps:
7
Best vacation rental to explore the Florida keys. Marina Villa 212 (3b/3b) with Marina and ocean views. Escape to pa ...
From $900 per night (USD)
VRBO
From $446 per night (USD)
Expedia
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
You will know you're on vacation when you enter this luxurious townhome! This beautiful home is located in Kawama Yacht ...
From $446 per night (USD)
Expedia
From $704 per night (USD)
VRBO
Relaxing Pool Home on Open Gulf with Fantastic Panoramic View
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Our home in Marathon at M.M.51, is located in a tropical setting on the open gulf surrounded by lush palms. Marathon is ...
From $704 per night (USD)
VRBO
From $1439 per night (USD)
VRBO
Gated Vacation Oasis Luxury Home Sunset Point Key Largo
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Escape to a one of a kind gated vacation oasis and experience the relaxing breezes of the bay from every room and around ...
From $1439 per night (USD)
VRBO
From $1029 per night (USD)
VRBO
Islamorada Boaters Paradise with 70' Dock and private beach access..
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $1029 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Keys Kottage & Bayside Villa W/ free onsite boat ramp marina & trailer parking.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $350 per night (USD)
Expedia
From $394 per night (USD)
VRBO
water at your back door
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
**We Have Everything You Need For A lovely Getaway** We welcome you to our Beautifully Furnished 2 bedroom, 2 bath home ...
From $394 per night (USD)
VRBO
From $318 per night (USD)
VRBO
Queen’s Lair Rockhouse 28 day minimum rental
Bedrooms:
2
Bathrooms:
3
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 $318 per night (USD)
VRBO
From $371 per night (USD)
VRBO
Seas the Day – 3bed/2.5bath Modern Townhome with Swim Spa in Marathon
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Seas the Day – Modern Townhome with Swim Spa in Marathon Welcome to Seas the Day, a beautifully designed 3-bedroom, 2.5 ...
From $371 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Catch the Day, Toast the Night- Fish, Dive & Island Vibes!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Perched on the top floor (4th floor) of the second building, this charming oceanfront condo offers a peaceful ...
From $344 per night (USD)
Expedia
From $269 per night (USD)
VRBO
Southernmost View - Private Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Southernmost View is a modern, luxurious waterfront home in a private seven-home gated community just steps fr ...
From $269 per night (USD)
VRBO
From $277 per night (USD)
Expedia
200ft of Waterfront with Tiki & Heated Pool - Boaters Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Raised waterfront home at the start of the Florida Keys (Mile Marker 112) with all around views of waterway and Barnes S ...
From $277 per night (USD)
Expedia
From $252 per night (USD)
VRBO
BOOK YOUR DREAM VACATION at BEACON REEF - SPECIAL SUMMER DEAL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
August to November, take $500 off regular price! World Famous Beacon Reef Condo (a gated community) Oceanfront Islamorad ...
From $252 per night (USD)
VRBO
From $572 per night (USD)
Expedia
Key Largo Villa, Kawama K5, 3/3
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Keys Relaxing Getaway....Have fun with the whole family at this stylish place. Explore the Florida Keys from this centr ...
From $572 per night (USD)
Expedia
From $401 per night (USD)
VRBO
★Remodeled tropical delight townhome★private plunge pool close to fun activities
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This beautiful townhouse was remodeled in late 2021 with a modern tropical inspired scheme. High speed internet -1,000m ...
From $401 per night (USD)
VRBO
From $361 per night (USD)
Expedia
Conch Get Enough at The Truman Annex in Key West
Bedrooms:
2
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 $361 per night (USD)
Expedia
From $1723 per night (USD)
VRBO
Key West Oasis - Truman Annex Estate
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Welcome to Key West Oasis Luxury | Privacy | Iconic Location in Truman Annex Tucked away on one of the most exclusive ...
From $1723 per night (USD)
VRBO
From $742 per night (USD)
Expedia
Bayside Boaters Paradise w/Pool – Marlin Bay
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $742 per night (USD)
Expedia
From $300 per night (USD)
VRBO
Executive Bay Club Bayfront/Beachfront paradise
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $300 per night (USD)
VRBO
From $238 per night (USD)
VRBO
Modern 2BR Condo Old Town/Balcony & Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
*28 day min stay* Come enjoy this fully updated 2/BR condo in the heart of Old Town. The perfect balance of being close ...
From $238 per night (USD)
VRBO
From $465 per night (USD)
VRBO
Green Goddess - Sunsets Included - 4BD/3Bath - 360° Rooftop - Private Pool
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 $465 per night (USD)
VRBO
From $387 per night (USD)
Expedia
BeachHouse @ Sombrero & Ocean access w/45’ Dock, kayaks and Bikes.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your family will be close to everything when you stay at this centrally-located place. Our home is close to grocery stor ...
From $387 per night (USD)
Expedia
From $794 per night (USD)
VRBO
Sky Suite with Balcony Overlooking Duval Street
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sky Suite On Duval Street - a newly remodeled masterpiece that overlooks world famous Duval Street. ...
From $794 per night (USD)
VRBO
From $1248 per night (USD)
Expedia
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + Last Key White Glove Service...
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 $1248 per night (USD)
Expedia
From $859 per night (USD)
VRBO
Historic Old Town Key West Cigarmaker's Cottage - Cigar House, Sleeps 4
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
OVERVIEW The Cigar House is a 100+ year old “Cigar maker’s house”. The recently completely renovated house is charming, ...
From $859 per night (USD)
VRBO
From $990 per night (USD)
Expedia
525 Mariners Club - Luxury 4 bedroom ocean-front villa perfect for family and friends
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Discover an extraordinary oceanfront sanctuary where sophistication meets serenity in the heart of the Florida Keys. Thi ...
From $990 per night (USD)
Expedia
From $383 per night (USD)
VRBO
Luxury Condominium In Key Largo... Sunsets, Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
From your balcony in the Kawama Tower, you get stunning vistas of ocean and palm trees. Enjoy the view from this complet ...
From $383 per night (USD)
VRBO
From $676 per night (USD)
Expedia
Duval Dream Loft - On Duval street
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Summary: Located in the heart of world-famous Duval Street, this unique property offers an authentic downtown Key West ...
From $676 per night (USD)
Expedia
From $677 per night (USD)
VRBO
The Collins - On Duval Street
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! The Co ...
From $677 per night (USD)
VRBO
From $273 per night (USD)
Expedia
This Oceanfront Resort HAS IT ALL!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fantastic 2 bedroom, 2 bath condo resort. Enjoy the breathtaking view of the Atlantic Ocean from the patio just steps fr ...
From $273 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Enjoy Caribbean weather in the USA. Openings August 2026 forward!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
We have a big bright eat in fully stocked kitchen. Kitchen has many pots and pans, keurig, blender, glassware and most t ...
From $267 per night (USD)
VRBO
From $859 per night (USD)
Expedia
Historic Old Town Key West Cigarmaker's Cottage - Conch House, 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 $859 per night (USD)
Expedia
From $372 per night (USD)
VRBO
Mermaid Magic ground level 3bed/3bath half duplex in Kcb with dockage & cabana club
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Mermaid Magic, a beautiful and spacious ground-level 3-bedroom, 3-bath duplex in the heart of the Florida Key ...
From $372 per night (USD)
VRBO
From $436 per night (USD)
Expedia
Splash Pool- Key Colony Villa - KCB#4
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to our stunning waterfront unit in Key Colony Beach with its tropical outdoor living & instant ocean access from ...
From $436 per night (USD)
Expedia
From $643 per night (USD)
VRBO
New 4/3 Private Single Family - 2 min to ocean, kayaks, paddleboards, bicycles
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Blue Treasure at Sombrero Beach is a 2020 built single-family home on a large lot within walking distance to the beautif ...
From $643 per night (USD)
VRBO
From $767 per night (USD)
Expedia
Sunrise Escape - Ocean Front Villa - Sleeps 10
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-vie ...
From $767 per night (USD)
Expedia
From $742 per night (USD)
VRBO
612 Mariners Club - 4 bedroom Tri-level townhome with room for the whole family
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Three-story townhouse with over 2600 sq of living space...room for the whole family! Ground floor 1-bedroom (king bed) ...
From $742 per night (USD)
VRBO
From $316 per night (USD)
Expedia
Ocean Point Retreat ~ Immaculate Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Private Beach, Fishing Pier, Fish Cleaning Station, Jr. Olympic pool, Spa, Pickleball Court, BBQ grills, nature ...
From $316 per night (USD)
Expedia

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