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Florida Keys Rentals

$Ocean Front Lower Keys on Stock Island, 3\/2 luxury condo at the Ocean's Edge!$
From $562 per night (USD)
VRBO
Ocean Front Lower Keys on Stock Island, 3\/2 luxury condo at the Ocean's Edge!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This ocean front 3/2 condominium is fully equipped with all the amenities you will need for a relaxing stay. The gated c ...
From $562 per night (USD)
VRBO
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Expedia
2-bedroom villa in fantastic Marathon with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to this serene 2-bedroom villa in Marathon. Relax in the gorgeous living room with a sofa bed, perfect for unwind ...
Click For Pricing
Expedia
From $217 per night (USD)
VRBO
Beautiful 2-bedroom canal home with peak-a-boo open water views in Cudjoe Key
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Escape to paradise in our charming Cudjoe Key rental home! This, small dog friendly beautiful property is nestled among ...
From $217 per night (USD)
VRBO
$Welcome to Sol y Sal - your 2 bedroom + den\/ 2 1\/2 bath coastal retreat$
From $227 per night (USD)
Expedia
Welcome to Sol y Sal - your 2 bedroom + den\/ 2 1\/2 bath coastal retreat
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Welcome to "Sol y Sal" in Buttonwood Bay. Brand new 2 bedrooms + den/ 2 1/2 bath townhouse. This unit was just redone a ...
From $227 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Keys to Paradise by AvantStay | Balcony, Pool, Golf
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This home is available for stays of 28 nights or longer. Welcome to Keys to Paradise, your Key West sanctuary nestled r ...
From $343 per night (USD)
VRBO
From $413 per night (USD)
Expedia
Duck Key house waterfront with 75 Lf of dock and a pool 3 bedrooms 3 bathrooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Located in Duck key, this marvelous house offers 3 bedrooms with a mix of queen, full, and twin beds. The property is fo ...
From $413 per night (USD)
Expedia
From $543 per night (USD)
VRBO
New! Ritaville - Waterfront with Private Pool!
Bedrooms:
3
Bathrooms:
4
Sleeps:
11
Summary: Discover the perfect retreat with this expansive two-story, 4-bedroom, 3-bathroom rental. Located in a serene w ...
From $543 per night (USD)
VRBO
From $448 per night (USD)
Expedia
*NEW* Sea La Vie-Pool & Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Sea la Vie located on Key Colony Beach. This Brand New Condo is walking distance to some of the very best res ...
From $448 per night (USD)
Expedia
$*NEW* Kokomo Views-Pool\/Beach$
From $339 per night (USD)
VRBO
*NEW* Kokomo Views-Pool\/Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Kokomo Views. This stunning BRAND NEW CONDO has it all! Located in the most beautiful and sought after Key Co ...
From $339 per night (USD)
VRBO
$*NEW* Casa Coco-Pool\/Tennis\/Ramp$
From $954 per night (USD)
Expedia
*NEW* Casa Coco-Pool\/Tennis\/Ramp
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Casa Coco, a stunning two-story retreat that embodies the perfect blend of comfort and luxury. Casa Coco's sl ...
From $954 per night (USD)
Expedia
$Friends' Retreat 2BR w\/ Ocean View, Pool & Beach$
From $348 per night (USD)
VRBO
Friends' Retreat 2BR w\/ Ocean View, Pool & Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $348 per night (USD)
VRBO
$Friends' Retreat 2BR w\/ Ocean View, Pool & Beach$
From $359 per night (USD)
Expedia
Friends' Retreat 2BR w\/ Ocean View, Pool & Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oceanfront resort with private sandy beach, marina, Jr. Olympic pool, hot tub, tennis, and more Located near Key Largo a ...
From $359 per night (USD)
Expedia
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VRBO
Upgraded 2-Bedroom Condo-Olympic size Pool- Fitness room-Beach-on Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful upgraded condo features vaulted ceilings and spacious living room, two bedrooms and a office/den for your use. ...
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VRBO
$SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w\/ Pool!$
From $384 per night (USD)
Expedia
SATISFY MY SOUL ~ 3 BR, 3.5 Ba Newly Renovated Mid Town Home w\/ Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
AUTHENTIC KEY WEST AMBIENCE... This fully renovated mid-century jewel pairs modern allure with classic White Street Gall ...
From $384 per night (USD)
Expedia
$Charming 2-bedroom house with WiFi, AC in gorgeous Marathon.\n$
From $375 per night (USD)
VRBO
Charming 2-bedroom house with WiFi, AC in gorgeous Marathon.\n
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Unwind in Marathon at this welcoming house. With 2 soothing bedrooms - 2 full beds and 1 twin bed, plus a cozy living ro ...
From $375 per night (USD)
VRBO
From $406 per night (USD)
Expedia
Brand New Home on The Ocean, bring your boat and RV!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our Brand New Home on The Gulf of Mexico, built July 2023. 40’ Boat slip. Plenty of of room for your RV on the ea ...
From $406 per night (USD)
Expedia
$Exec Bay 3 Bedroom townhouse w\/heated pool, marina, tennis & more$
From $212 per night (USD)
VRBO
Exec Bay 3 Bedroom townhouse w\/heated pool, marina, tennis & more
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Come and experience the beauty and tranquility of the Florida Keys at Executive Bay Club! Enjoy gorgeous sunsets from th ...
From $212 per night (USD)
VRBO
From $161 per night (USD)
Expedia
Cozy-Steps from Pool-1st Floor, Key Largo Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to paradise in this inviting 2-bedroom, 2-bathroom Key Largo condo. Enjoy breathtaking pool views from your first ...
From $161 per night (USD)
Expedia
From $462 per night (USD)
VRBO
Enchanting dog-friendly waterfront retreat with pool, hot tub, & amazing views
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Ocean Oasis I Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $462 per night (USD)
VRBO
From $234 per night (USD)
Expedia
Open Water Access canal home, large kitchen, WIFI, central AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Fisherman's Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $234 per night (USD)
Expedia
From $445 per night (USD)
VRBO
Private pool, boat dock, water view, canal front, fully equipped kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The Endless Oasis Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $445 per night (USD)
VRBO
From $488 per night (USD)
Expedia
Speakeasy Inn-Room 3B- 2 Queen Beds
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The Speakeasy Inn is a quaint guesthouse located in an historic Key West conch style house. It is situated on upper Duva ...
From $488 per night (USD)
Expedia
From $285 per night (USD)
VRBO
Casa Tranquila - Fully-Renovated 2-bedroom Townhome in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Casa Tranquila! This 2-bedroom townhome is perfect for your escape to Key West. Located in Old Town just five ...
From $285 per night (USD)
VRBO
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Expedia
Charming 2-bedroom condo with WiFi and AC in delightful Key Largo
Bedrooms:
3
Bathrooms:
2
Sleeps:
8
This Key Largo condo boasts 2 inviting bedrooms, including 2 twin beds, 1 futon, and 1 king bed. With 3 bathrooms and a ...
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Expedia
$Room in Tranquil Resort by Ocean Spa w\/ Pool, 4 Restaurants & Fire Pits$
From $540 per night (USD)
VRBO
Room in Tranquil Resort by Ocean Spa w\/ Pool, 4 Restaurants & Fire Pits
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located just off Overseas Highway and mere steps from the Florida coast. Families will appreciate the proximity of Theat ...
From $540 per night (USD)
VRBO
From $540 per night (USD)
VRBO
Room in Elegant Beachfront Resort Ideal for Water Sports & Dolphin Swimming
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located just off Overseas Highway and mere steps from the Florida coast. Families will appreciate the proximity of Theat ...
From $540 per night (USD)
VRBO
$Relaxing Couple Retreat in the Florida Keys | Resort w\/ Scenic Waterfront View$
From $396 per night (USD)
VRBO
Relaxing Couple Retreat in the Florida Keys | Resort w\/ Scenic Waterfront View
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the ultimate waterfront retreat at Marathon, FL, where sea adventures and breathtaking views await! Dive into ...
From $396 per night (USD)
VRBO
From $1188 per night (USD)
VRBO
Enjoy Breathtaking Water View from Our Outdoor Pool | 3 Family Ready Units
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Experience the ultimate waterfront retreat at Marathon, FL, where sea adventures and breathtaking views await! Dive into ...
From $1188 per night (USD)
VRBO
$Two Units Right tn the Heart of Florida Keys | Water Front Hotel w\/ Scenic View$
From $792 per night (USD)
VRBO
Two Units Right tn the Heart of Florida Keys | Water Front Hotel w\/ Scenic View
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience the ultimate waterfront retreat at Marathon, FL, where sea adventures and breathtaking views await! Dive into ...
From $792 per night (USD)
VRBO
From $396 per night (USD)
VRBO
Florida Keys Water Front Getaway | Near Historic Seven Miles Bridge
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Experience the ultimate waterfront retreat at Marathon, FL, where sea adventures and breathtaking views await! Dive into ...
From $396 per night (USD)
VRBO
$Close to Key West Canal-front retreat w\/ kayaks located on Little Torch Island$
From $348 per night (USD)
VRBO
Close to Key West Canal-front retreat w\/ kayaks located on Little Torch Island
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Introducing Aj’s Hideout – Welcome to your idyllic retreat in Little Torch Key, nestled in the heart of a charming fishi ...
From $348 per night (USD)
VRBO
From $170 per night (USD)
Expedia
Cozy keys getaway
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Your home away from home in Ramrod Key with 1 bedroom. This wonderful house is equipped with all the essentials for a co ...
From $170 per night (USD)
Expedia
From $1129 per night (USD)
VRBO
Spacious 6-bedroom- 2 kitchen Duplex with Cabana in beautiful Key Colony Beach
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Key Colony Beach is waiting for you at this 6-bedroom house. Upgraded Homes (duplex) on a large canal, each side has a 3 ...
From $1129 per night (USD)
VRBO
From $68 per night (USD)
Expedia
Charming shared 1-bedroom house with AC and WiFi in fabulous Ramrod Key
Bedrooms:
1
Bathrooms:
1
Sleeps:
1
Summerland Beauty located 35 min north of Key West. Many charming restaurants located nearby. Plenty of activities and f ...
From $68 per night (USD)
Expedia
$Ocean View Beautifully Remodeled 2\/2 at Seagulls$
From $318 per night (USD)
VRBO
Ocean View Beautifully Remodeled 2\/2 at Seagulls
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Beautiful ocean views, spacious interior, and recent renovations of the condo make it the perfect place for Florida Keys ...
From $318 per night (USD)
VRBO
From $372 per night (USD)
Expedia
HERE COMES THE SUN ~ 2 BR, 2 Ba Casa Marina Home with Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
CLASSIC CHARMER... Some of the best things come in small packages and this conch cutie is no exception. Nestled in the e ...
From $372 per night (USD)
Expedia
From $378 per night (USD)
VRBO
Paradise Palms | Ocean Pointe 1206
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Embrace Florida Keys style living in this wonderfully decorated 2 Bedroom Condo! You and your family will feel ...
From $378 per night (USD)
VRBO
From $642 per night (USD)
Expedia
Oceanfront Home - Marathon - 4BR, 3 Bath, Pool, Dock, Parking, Amazing Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
"Billy Ocean" is more than just an oceanfront home; it's an experience of the ultimate Keys lifestyle with outdoor livin ...
From $642 per night (USD)
Expedia
$Romantic Stay in Historic Key West: 1BR Suite w\/ King Bed & Pool$
From $1238 per night (USD)
VRBO
Romantic Stay in Historic Key West: 1BR Suite w\/ King Bed & Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $1238 per night (USD)
VRBO
$Key West Paradise: Minimalist King Room w\/ Balcony or Terrace! Enjoy the Breeze$
From $1026 per night (USD)
VRBO
Key West Paradise: Minimalist King Room w\/ Balcony or Terrace! Enjoy the Breeze
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $1026 per night (USD)
VRBO
From $1069 per night (USD)
VRBO
Stunning Key West Stay Perfect for a Romantic Escape! Outdoor Pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Enjoy vibrant Key West: steps to Duval Street's nightlife, historic sites, and serene beaches. Perfect for culture and s ...
From $1069 per night (USD)
VRBO
From $433 per night (USD)
Expedia
Luxury Oceanfront Villa with Private Dockage, Stunning Views and Top Amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Exquisite 3-bedroom, 3 full bathroom, with 3 balconies, including one off the master bedroom. Every angle offers a stun ...
From $433 per night (USD)
Expedia
From $607 per night (USD)
VRBO
Mystic Waters ~ Luxury Open Ocean Views, Private Pool!
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Mystic Waters Welcome to Mystic Waters, your exclusive retreat in Marathon, Florida, where luxury meets the serenity of ...
From $607 per night (USD)
VRBO
$Key West Oasis-1Br\/2Ba Loft Town Home in a Resort$
From $313 per night (USD)
Expedia
Key West Oasis-1Br\/2Ba Loft Town Home in a Resort
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Experience the perfect balance of excitement and tranquility in this charming loft town home. Minutes from downtown, ye ...
From $313 per night (USD)
Expedia
$Tranquil Tides ~ Luxury Waterfront Pool Home w\/ Expansive Water Views, 75` Boat$
From $572 per night (USD)
VRBO
Tranquil Tides ~ Luxury Waterfront Pool Home w\/ Expansive Water Views, 75` Boat
Bedrooms:
5
Bathrooms:
5
Sleeps:
8
Tranquil Tides Welcome to this stunning new home that captures the irresistible charm of the Keys with a modern and coz ...
From $572 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Indigo Reef #23~ Lionfish Lodge- Waterfront Unit in Gated Resort, 31` Boat Slip!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
#23 Lionfish Lodge at Indigo Reef Experience the serenity of Lionfish Lodge, a stunning Florida Keys vacation rental wh ...
From $396 per night (USD)
Expedia
From $273 per night (USD)
VRBO
Waterfront home in Pirates Cove offers a blend of serenity and adventure
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A vacation bayside home in Key Largo on a canal offers a perfect blend of relaxation and adventure. Nestled along the tr ...
From $273 per night (USD)
VRBO
From $244 per night (USD)
Expedia
Charming 2-bedroom house in Key West with Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Embrace the Enchantment of Old Key West Charm! Escape to the enchanting world of Key West Hideaway, where history meets ...
From $244 per night (USD)
Expedia
From $380 per night (USD)
VRBO
Key Largo Condo - Community Pool, Marina & Beach!
Bedrooms:
3
Bathrooms:
3
Sleeps:
4
Experience the best of the Florida Keys at this 2-bedroom, 2.5-bath vacation rental in sunny Key Largo. Nestled in Moon ...
From $380 per night (USD)
VRBO
$Ocean Pointe Ocean View w\/heated pool beach marina$
From $453 per night (USD)
Expedia
Ocean Pointe Ocean View w\/heated pool beach marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean Pointe Suites is an all-suite resort located directly on the Atlantic. Enjoy the many activities our resort has to ...
From $453 per night (USD)
Expedia
From $735 per night (USD)
VRBO
Key Lime Breeze Ocean Retreat
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to Key Lime Breeze Retreat! Immerse yourself in the ultimate tropical getaway at our oceanside condo located at ...
From $735 per night (USD)
VRBO
From $934 per night (USD)
Expedia
Sombrero Reef-Tortugas Harbor Suites | Traveling with a group? Share these 2 condos, pool
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
The Tortugas Harbor and Sombrero Reef Lighthouse Suites are two separate and NON-Connecting suites on the same level tha ...
From $934 per night (USD)
Expedia
From $1136 per night (USD)
VRBO
An Ocean Serenity in Truman Annex, Key West
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
A luxury, ocean front, 2 bedroom, (king in master, queen in guest bedroom) 2.5 bath condo at Harbour Place in the award ...
From $1136 per night (USD)
VRBO
From $1174 per night (USD)
Expedia
Alligator Reef & American Shoal Suites: Traveling with a group? Share these 2 condos
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
The Alligator Reef and American Shoal Lighthouse Suites are two separate and NON-Connecting suites on the same level tha ...
From $1174 per night (USD)
Expedia
From $4583 per night (USD)
VRBO
Wander Islamorada Island
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Wander Islamorada Island is an extraordinary private oasis nestled in the Florida Keys. This gated Caribbean-style retre ...
From $4583 per night (USD)
VRBO
From $581 per night (USD)
Expedia
Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
You and your guests will have exclusive use of this 40ft yacht all to yourselves. The yacht stays docked, the entire res ...
From $581 per night (USD)
Expedia
$2BR Apt in Oceanview Resort w\/ Sunset Cruises & Poolside Relaxation$
From $1854 per night (USD)
VRBO
2BR Apt in Oceanview Resort w\/ Sunset Cruises & Poolside Relaxation
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $1854 per night (USD)
VRBO
From $1545 per night (USD)
VRBO
2 Suites Oceanview Balcony King at Oceans Edge Key West, Full Service Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $1545 per night (USD)
VRBO
From $772 per night (USD)
VRBO
Oceanview Balcony King Suite at Oceans Edge Key West, Sunset Cruises
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $772 per night (USD)
VRBO
From $717 per night (USD)
VRBO
Ocean View Balcony King Room at Oceans Edge, Panoramic Water Views, Pets Welcome
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $717 per night (USD)
VRBO
$Serene Retreat w\/ Waterfront Balcony & Easy Access to Paddleboarding$
From $926 per night (USD)
VRBO
Serene Retreat w\/ Waterfront Balcony & Easy Access to Paddleboarding
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $926 per night (USD)
VRBO
$Room in Coastal Resort w\/ Oceanview - Six Pools & Pvt Oceanview Balcony$
From $733 per night (USD)
VRBO
Room in Coastal Resort w\/ Oceanview - Six Pools & Pvt Oceanview Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $733 per night (USD)
VRBO
$Elegant Resort Room w\/ Paddleboards, Kayaks & Breathtaking Oceanviews$
From $824 per night (USD)
VRBO
Elegant Resort Room w\/ Paddleboards, Kayaks & Breathtaking Oceanviews
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $824 per night (USD)
VRBO
$2 Suites 2 Queen w\/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools$
From $1482 per night (USD)
VRBO
2 Suites 2 Queen w\/ Oceanview at Oceans Edge Resort, Kayak Rentals, 6 Pools
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $1482 per night (USD)
VRBO
From $686 per night (USD)
VRBO
Oceanview Balcony 2 Queen Room at Oceans Edge Resort, Six Saltwater Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $686 per night (USD)
VRBO
From $1646 per night (USD)
VRBO
2 Cozy Resort Rooms Perfect for Family Vacations, Enjoy Pools & Water Activities
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $1646 per night (USD)
VRBO
From $1371 per night (USD)
VRBO
Ocean View Balcony 2 Queen at Oceans Edge Key West, Saltwater Pools - 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $1371 per night (USD)
VRBO
$2 Charming Oceanfront Rooms w\/ Full-Service Marina & Bike Rentals - Pets Welcome$
From $1778 per night (USD)
VRBO
2 Charming Oceanfront Rooms w\/ Full-Service Marina & Bike Rentals - Pets Welcome
Bedrooms:
2
Bathrooms:
2
Sleeps:
12
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $1778 per night (USD)
VRBO
$Comfortable Family Resort Room w\/ Ocean Views, Kayak Rentals & Six Pools$
From $860 per night (USD)
VRBO
Comfortable Family Resort Room w\/ Ocean Views, Kayak Rentals & Six Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $860 per night (USD)
VRBO
From $916 per night (USD)
Expedia
Spacious 6-bedroom waterfront pool estate in awesome Key Largo
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
This stunning 6-bedroom, 4-bathroom home is the perfect sanctuary for those seeking a blend of elegance, comfort, and t ...
From $916 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Charming 2-bedroom townhome with WiFi, AC in enjoyable Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Your Islamorada adventure begins at this 2-bedroom townhome. Inside, guests will find a delightful mix of comfort and st ...
From $231 per night (USD)
VRBO
$Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar$
From $963 per night (USD)
VRBO
Stylish Boutique Room w\/ 2 Queen Beds - Access Pool & Poolside Bar
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $963 per night (USD)
VRBO
From $446 per night (USD)
VRBO
Renovated Waterfront 3-bedroom House in Key Largo with Pool and Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Experience Key Largo like a local in this newly renovated waterfront home located on the oceanside at MM 96. The home fe ...
From $446 per night (USD)
VRBO
$Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street$
From $886 per night (USD)
VRBO
Relax in Romantic Lodge w\/ Pool Minutes from Vibrant Duval Street
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $886 per night (USD)
VRBO
$Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun$
From $660 per night (USD)
VRBO
Modern Lodge w\/ Outdoor Pool Near Attractions Ideal for Family Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $660 per night (USD)
VRBO
$2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums$
From $1324 per night (USD)
VRBO
2 Rooms for the whole family w\/ Pool access! Near Duval St. and Museums
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $1324 per night (USD)
VRBO
$2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West$
From $1022 per night (USD)
VRBO
2 Bedroom Suite w\/ Outdoor Pool in Old Town Key West
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $1022 per night (USD)
VRBO
$Beautiful Room w\/ Outdoor Pool & Close to Duval St. Restaurants$
From $645 per night (USD)
VRBO
Beautiful Room w\/ Outdoor Pool & Close to Duval St. Restaurants
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Discover Old Town charm, plunge into vibrant Duval Street life, and dive deep into Key West's treasures. We're footsteps ...
From $645 per night (USD)
VRBO
From $543 per night (USD)
VRBO
New Build Paradise Vacation Home in Key Largo
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
NEW Paradise Vacation Home! Relaxation awaits you the minute you enter this new build Key Largo vacation home with a can ...
From $543 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Mermaid Hideaway: Charming 2BR Canal Front Home with Pool, Tiki, Dockage, and Dog-Friendly Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to Mermaid Hideaway, an updated 2BR canal front home on Big Coppitt Key, offering an ideal retreat for your Flor ...
From $247 per night (USD)
Expedia
From $340 per night (USD)
VRBO
Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Castaway Cove! Nestled in the vibrant New Town area of Key West, Castaway Cove is your perfect home away from ...
From $340 per night (USD)
VRBO
From $587 per night (USD)
Expedia
Heron Hideaway - Charming 1st-Floor Unit, Shared Pool, Spa, Pet-Friendly, Near Duval St & Beaches
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to Heron Hideaway, a charming 1st-floor condo nestled in the desirable Meadows area of Key West. Just six blocks ...
From $587 per night (USD)
Expedia
From $317 per night (USD)
VRBO
Spacious 4-bedroom house with AC, WiFi in wonderful Key Largo
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Make yourself at home in this 4-bedroom Key Largo retreat. This wonderful house boasts 1 king bed, 2 queen beds, and 2 b ...
From $317 per night (USD)
VRBO
$Charming 2-bedroom guest house with Pool, A\/C, & WiFi in Key West, near Duval St$
From $778 per night (USD)
VRBO
Charming 2-bedroom guest house with Pool, A\/C, & WiFi in Key West, near Duval St
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Key West is waiting for you at this clean and spacious 2-bedroom guest house. With 2 queen beds and 3 bathrooms equippe ...
From $778 per night (USD)
VRBO
From $2877 per night (USD)
VRBO
Spacious 5-bdrm 5 bathroom house in charming Key West with AC, WiFi, Plunge Pool
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Located in Key West and about 6 blocks away from Duval Street, enjoy what this 5-bedroom house has to offer. This beauti ...
From $2877 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Charming 2-bedroom mobile home with AC, WiFi in Key Largo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy a peaceful stay at this fabulous 2-bedroom mobile home in Key Largo. The cozy bedrooms feature a queen bed and a t ...
From $243 per night (USD)
Expedia
From $376 per night (USD)
VRBO
Charming 3-bedroom 2-bathroom house with Boat Ramp and Dockage in Marathon
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Your home away from home in Marathon with 3 delightful bedrooms. Each room is tastefully furnished with 1 king bed and 2 ...
From $376 per night (USD)
VRBO
From $879 per night (USD)
VRBO
Ocean View Balcony 2 Queen Suite at Oceans Edge Resort, Marina Access, 6 Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Located in Stock Island, a tropical paradise inside Key West. Enjoy fine dining w/ outstanding landscaping just around t ...
From $879 per night (USD)
VRBO
$Island Dream in the heart of the Florida Keys ~ Private, Spacious 3\/2 + Sofa bed$
From $238 per night (USD)
VRBO
Island Dream in the heart of the Florida Keys ~ Private, Spacious 3\/2 + Sofa bed
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Marathon, enjoy what this 3-bedroom house has to offer. With 3 queen beds and 2 bathrooms equipped with showe ...
From $238 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Wake up to Amazing View 2-bedroom condo in Key Largo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stay comfortably in Tavernier at this 2-bedroom condo. This awesome property features 1 queen bed and 1 twin bed, perfec ...
From $418 per night (USD)
Expedia
$Outstanding Room w\/ King Bed & Patio just steps from Duval St - Key West Bliss$
From $982 per night (USD)
VRBO
Outstanding Room w\/ King Bed & Patio just steps from Duval St - Key West Bliss
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $982 per night (USD)
VRBO
$1BR Suite w\/ Spacious Living Area and Access to Heated Pool, Near Duval St$
From $1150 per night (USD)
VRBO
1BR Suite w\/ Spacious Living Area and Access to Heated Pool, Near Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1150 per night (USD)
VRBO
$Welcoming 2 Queen Room w\/ Patio- Heart of Key West$
From $1005 per night (USD)
VRBO
Welcoming 2 Queen Room w\/ Patio- Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1005 per night (USD)
VRBO
$Room w\/ Queen Bed w\/ Patio in the Heart of Key West - Duval St steps away$
From $1050 per night (USD)
VRBO
Room w\/ Queen Bed w\/ Patio in the Heart of Key West - Duval St steps away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1050 per night (USD)
VRBO
From $2436 per night (USD)
VRBO
Stunning 2 Floor Loft in Vibrant Key West Ideal for Romantic Weekends - Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $2436 per night (USD)
VRBO
From $1237 per night (USD)
VRBO
Vibrant 2 Floor Loft Ideal for Relaxing Escape in Key West - Near Duval St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $1237 per night (USD)
VRBO
$Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away$
From $981 per night (USD)
VRBO
Elegant Boutique Room w\/ Private Patio & Garden - Duval Street steps away
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Explore, dine, and relax in downtown Key West! We're steps from the Hemingway Home, Duval Street nightlife, and Southern ...
From $981 per night (USD)
VRBO
From $1181 per night (USD)
Expedia
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $1181 per night (USD)
Expedia
From $435 per night (USD)
VRBO
Yacht Primary Guest Quarters - Key West Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This 1-bedroom Primary Guest Suite in Key West is perfect for your escape. The bright bedroom features a nice queen bed, ...
From $435 per night (USD)
VRBO
From $5438 per night (USD)
Expedia
NEW! The Rigby House - Pvt Pool, Amazing Location!
Bedrooms:
7
Bathrooms:
6
Sleeps:
12
Summary: Escape to paradise with this stunning 6-bedroom, 6.5 bathroom home nestled in the heart of historic Key West. W ...
From $5438 per night (USD)
Expedia

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