Monroe Area, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Monroe Area, Florida on RentalSaver.com!

Monroe Area Rentals

From $398 per night (USD)
VRBO
Immaculate oceanfront townhouse with ocean view & private beach access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Duck Key Retreat Villa #5105 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $398 per night (USD)
VRBO
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Expedia
Modern Key Largo Waterfront Bayside Home - Dock your boat!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
WWW.MEETMEINKEYLARGO.COM Impeccable Waterfront Home in Key Largo on the bayside. This beautiful stilted home is new co ...
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Expedia
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VRBO
Affordable, Adorable home waiting for you in Cudjoe Key
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Adorable canal front 2 bed/2 bath home for rent in Cudjoe Key. This indoor/outdoor floor plan is complemented by 3 twelv ...
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VRBO
From $560 per night (USD)
Expedia
Waterfront luxury Villa (42) with sunset views and boat slip
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $560 per night (USD)
Expedia
From $472 per night (USD)
VRBO
The most setup home in BPK TIKI HUT,POOL ,GRILL ,CANAL FRONT, FREE UNLIMITED ICE
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
This Private Canal front Pool/TIKI home with Dock, sits in Port Pine Heights BIG PINE KEY FL. See key deer every day wa ...
From $472 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
The Sea Biscuit houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $354 per night (USD)
Expedia
$Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi$
From $520 per night (USD)
VRBO
Bright Key West House with Private Pool, Gas Grill, W\/D, Central AC, & Free WiFi
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
Tropical Vibes Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $520 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience elegant sophistication in this stunning 2-bedroom, 2-bathroom ocean-view condominium at the premier 1800 Atla ...
From $205 per night (USD)
Expedia
From $300 per night (USD)
VRBO
BOOK NOW FOR AMAZING DEALS FOR KEY WEST APRIL - SEPTEMBER $3750 A MONTH
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You will love our piece of paradise. Our home away from home is tiled throughout. All new furnishings in 2017. Large fla ...
From $300 per night (USD)
VRBO
From $614 per night (USD)
Expedia
409 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Instantly feel the warmth of the island spirit as you enter this recently renovated and refreshed 3-bedroom, 3-bath, tri ...
From $614 per night (USD)
Expedia
$Lux Key Largo Oceanfront 3 Bed \/ 3.5 Bath suite$
From $711 per night (USD)
VRBO
Lux Key Largo Oceanfront 3 Bed \/ 3.5 Bath suite
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Summary: The high-end ocean retreat features a custom gourmet kitchen with stainless steel appliances, granite counter t ...
From $711 per night (USD)
VRBO
From $292 per night (USD)
Expedia
Spacious Ocean View Suite with Private Kitchen & Balcony! Pool & Beach Access!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $292 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Nature Retreat Sailboat Escape
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
PLEASE READ! The Salty Conch is a 30ft monohull sailboat that was brought to Key Largo after sailing the Atlantic Oce ...
From $479 per night (USD)
VRBO
From $269 per night (USD)
Expedia
1 br Peaceful Ocean View Retreat in the Florida Keys!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key W ...
From $269 per night (USD)
Expedia
$Marathon 2BR Deluxe resort on the water w\/ Resort Amenities$
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VRBO
Marathon 2BR Deluxe resort on the water w\/ Resort Amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
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VRBO
From $1459 per night (USD)
Expedia
Private Parking & Pool, Near Duval - Contra House
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Summary: This captivating modern home with a striking exterior and vaulted ceilings makes for the perfect vacation home. ...
From $1459 per night (USD)
Expedia
From $470 per night (USD)
VRBO
Island Time Hideaway at Old Town Key West Historic Seaport - 3 Blocks to Duval
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
LOCATION, LOCATION, LOCATION! Located on a picturesque Old Town street, in one of the most desirable areas of the hist ...
From $470 per night (USD)
VRBO
$Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar$
From $362 per night (USD)
Expedia
Key West Cabana-Old Town Key West- Steps to Duval Street w\/ Pool & Tiki Bar
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Key West Cabana welcomes you to our quaint 2 bedroom, 2 bathroom home with large private pool, assigned parking for 2 ca ...
From $362 per night (USD)
Expedia
From $491 per night (USD)
VRBO
Fishermen's Paradise- Private Pool, Hot Tub, Quick Access To Ocean, 60 ft Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
NO PETS. NO SMOKING. Vacation in Paradise in our spacious (approx 1,700 sq. ft living space 3 bedroom 2 bath ground l ...
From $491 per night (USD)
VRBO
From $418 per night (USD)
Expedia
Modern Nautical Townhome on Moonbay Key Largo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to a piece of paradise! This is a beautiful two-story townhouse that has been newly furnished. Upstairs you will ...
From $418 per night (USD)
Expedia
$Remodeled Townhome at EBC w\/ Beach, Pool and more - 20% OFF FOR THE SUMMER!$
From $210 per night (USD)
VRBO
Remodeled Townhome at EBC w\/ Beach, Pool and more - 20% OFF FOR THE SUMMER!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated and remodeled 1,359sf townhome at EXECUTIVE BAY CLUB in the heart of Islamorada REDUCED 20% MAY-AUGUST 2 ...
From $210 per night (USD)
VRBO
From $446 per night (USD)
Expedia
🌸Home(#3) BIKINI👙 BOTTOM (Partial View Property-approximately 200 ft from private beach entrance🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
#3: BIKINI BOTTOM 👙Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Coole ...
From $446 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Paradise 201 East Ocean Drive,Key Colony Beach 33051. Minutes to Marathon.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Competently remodeled from quartz countertops in kitchen and both full bathrooms. New doors throughout the unit with up ...
From $224 per night (USD)
VRBO
From $416 per night (USD)
Expedia
Gulf side Gem, 45 ft. Dock, pool , hot tub and more
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Spacious 3 Bedrooms and 3 Baths 1,600 sq ft home overlooking a canal with a brand new dock that spans the width of the ...
From $416 per night (USD)
Expedia
$DUPLEX IN DUCK KEY, 2 Bedroom \/2 Bath w\/40' Dock, Trailer Storage Incl.$
From $411 per night (USD)
VRBO
DUPLEX IN DUCK KEY, 2 Bedroom \/2 Bath w\/40' Dock, Trailer Storage Incl.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait an ...
From $411 per night (USD)
VRBO
From $763 per night (USD)
Expedia
Waterfront Luxury Villa (62) with sunset views and boat slip
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $763 per night (USD)
Expedia
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VRBO
Beautiful resort located just off the Florida Keys.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
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VRBO
From $992 per night (USD)
Expedia
Beautiful Ocean Front View
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Oceanfront 2BD/2BA and separate 1BD/1BA pool-side overlooking the Atlantic* Enter your paradise dream home with stunni ...
From $992 per night (USD)
Expedia
$Ocean view condo with balcony\/marina view$
From $461 per night (USD)
VRBO
Ocean view condo with balcony\/marina view
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in ...
From $461 per night (USD)
VRBO
$Venetian Tropics weekly Pvt home w\/heated Pool, 3 bedroom \/70ft dock w\/canal$
From $786 per night (USD)
Expedia
Venetian Tropics weekly Pvt home w\/heated Pool, 3 bedroom \/70ft dock w\/canal
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Vacation Rental License No VR-001 WEEKLY RENTAL Located on the peaceful upper Keys, in Islamorada, this home is situat ...
From $786 per night (USD)
Expedia
From $607 per night (USD)
VRBO
Watch dolphins play in Shelter Cove while swimming in our oversized pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Relax in the private pool with the Spectacular Shelter Bay in the background...Our home is located directly on Shelt ...
From $607 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Stunning rooftop views from this gulf side Tuscan style Villa
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
3 Bedroom 3 Bathroom Freestanding villa located in Bougainvillea, a Gated Community, with a pool exclusive to Bougain ...
From $265 per night (USD)
Expedia
From $566 per night (USD)
VRBO
Happy’s Houseboat Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This beautiful houseboat is the best way to stay in Key West. Recently Featured in Old Dominion‘s music video “I was on ...
From $566 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Canal front, Dock, Hot Tub and Cabana Club Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Orchid House, a lushly landscaped canal front home located on the beautiful island of Key Colony Beach. Th ...
From $243 per night (USD)
Expedia
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VRBO
Key Largo Getaway
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Beautiful, 2-bedroom, 1 bathroom property located at the entrance to the Florida Keys. Property features full kitchen, 2 ...
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VRBO
From $433 per night (USD)
Expedia
🌸Home #2: THE REEL WORLD (Off Water Property-approximately 250 ft from Private beach entrance)- 🌸
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming P ...
From $433 per night (USD)
Expedia
$Relax and Unwind! 2 Family-Friendly Suites To Stay w\/ Swimming Pool Access$
From $484 per night (USD)
VRBO
Relax and Unwind! 2 Family-Friendly Suites To Stay w\/ Swimming Pool Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Escape to a tropical paradise and experience the ultimate beachfront retreat! Nestled in the heart of Key Largo, this pr ...
From $484 per night (USD)
VRBO
$El Tesoro a Beautiful 3 Bedroom 2 Bath Marathon Home w\/ Private Pool & Dock$
From $451 per night (USD)
Expedia
El Tesoro a Beautiful 3 Bedroom 2 Bath Marathon Home w\/ Private Pool & Dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
VACA-23-40 Friday to Friday booking only( Please ask before booking other dates, you will need prior approval or the res ...
From $451 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Florida Keys Escape! Two Elegant Rooms for 8 Guests, Pool, FREE Breakfast
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is p ...
From $479 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Private Paradise with Heated Waterfall Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Time to sit back and relax! Paradise found in this completely redone home in Key West. Private outdoor heated pool, show ...
From $241 per night (USD)
Expedia
From $1537 per night (USD)
VRBO
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
Breathtaking waterfront view from this 4 bedroom, 4.5 bath condominium in Harbour Place in the Truman Annex is ready to ...
From $1537 per night (USD)
VRBO
From $573 per night (USD)
Expedia
Villa 5027 on Duck Key BOAT SLIP available
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $573 per night (USD)
Expedia
From $174 per night (USD)
VRBO
Centrally located cottage apartment with patio - walk to beach & dining
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Bottoms Up Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $174 per night (USD)
VRBO
$Waterfront home with 35-foot dock, Cabana Club membership with pool\/beach access$
From $469 per night (USD)
Expedia
Waterfront home with 35-foot dock, Cabana Club membership with pool\/beach access
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Dream in the Keys Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $469 per night (USD)
Expedia
From $401 per night (USD)
VRBO
Bonefish Bungalow: 3 BR, 3 BA Townhouse in MARATHON, Sleeps 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Bonefish Bungalow offers an idyllic vacation experience in the captivating Florida Keys, overlooking the picturesque Key ...
From $401 per night (USD)
VRBO
Click For Pricing
Expedia
Cozy condo with free WiFi & fantastic location in central Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Truman at Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
Click For Pricing
Expedia
From $271 per night (USD)
VRBO
Private Tropical Beach-No Stairs-Great Location-Heated Pool-Wifi-It's LOADED!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Ask me about my Covid-19 cancellation policy. Note: I have been listed on VRBO-Homeaway since 2009. Situated on a Pr ...
From $271 per night (USD)
VRBO
From $243 per night (USD)
Expedia
Beautiful vacation mobile home at the Florida keys.
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
You can enjoy a spacious terrace with built in kitchen/bbq, TV and Bluetooth speakers, in a campground resort with plent ...
From $243 per night (USD)
Expedia
From $291 per night (USD)
VRBO
Gorgeous Home with Lush Patio & Private Pool - Two Blocks to Higgs Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Sunshine Drive Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $291 per night (USD)
VRBO
From $395 per night (USD)
Expedia
Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
Bedrooms:
4
Bathrooms:
4
Sleeps:
6
Booking for August & September are at a discounted rate of 30%!!! Do not miss out....NEW LISTING. 30-day Minimum Stay. ...
From $395 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Winter Special - Beautiful Waterfront Pool Home
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
“A Little Slice of Heaven”- completely renovated and updated in December 2020 waterfront pool home in paradise. This is ...
From $258 per night (USD)
VRBO
From $710 per night (USD)
Expedia
Coastal Key 3 bed 2 bath with pool kayaks, bikes, paddlebooards and dock
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Vaca-21-256 Sombrero Beach area of Marathon. Beautifully decorated brand new home, located down the street from Sombrero ...
From $710 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Rent a place in Paradise.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A private, Charming 1 bed 1 bath Condo with a full kitchen, heated pool, and spectacular views of the Sunset right from ...
From $158 per night (USD)
VRBO
From $241 per night (USD)
Expedia
A+ Location in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
The house has beautiful vaulted high ceilings. Along with the en-suite there is also another bathroom on the 1st floor a ...
From $241 per night (USD)
Expedia
From $1054 per night (USD)
VRBO
Affordable yacht charters. Limited time Discount! 25% off for May and June 2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This is a private yacht charter. Only your family and friends aboard along with your captains. License To Chill is back ...
From $1054 per night (USD)
VRBO
From $147 per night (USD)
Expedia
Fish Camp | Old Florida canalfront getaway close to Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Escape to this Old Florida-style cottage offering a quintessential retreat for fishing enthusiasts and nature lovers ali ...
From $147 per night (USD)
Expedia
From $608 per night (USD)
VRBO
Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the bedroo ...
From $608 per night (USD)
VRBO
From $604 per night (USD)
Expedia
Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This house is a 3 bedroom stand alone unit with 2 king bedrooms upstairs with balconies and own bathrooms and the b ...
From $604 per night (USD)
Expedia
Click For Pricing
VRBO
Studio in the heart of the Florida Keys, snowbird community
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
400 sq ft fully equipped studio,full bathroom & kitchenette. Chase sofa with sleeper. On wide private canal to the Ocea ...
Click For Pricing
VRBO
From $725 per night (USD)
Expedia
AFTERNOON DELIGHT at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This amazing 2 bedroom/2 bath condo has one of the best views in Key West. Located in the historic Mills Place in Truman ...
From $725 per night (USD)
Expedia
From $349 per night (USD)
VRBO
Oceanfront, Snowbird-Friendly Home with High-Speed WiFi, Ocean Views, and Dock
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Humpty Dumpty Hacienda Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $349 per night (USD)
VRBO
$3BR\/3BA Duck Key Island Retreat With Private Pool$
From $304 per night (USD)
Expedia
3BR\/3BA Duck Key Island Retreat With Private Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
In the Heart of the Florida Keys, this three bedroom and three bath Duck Key retreat is located within just minutes of t ...
From $304 per night (USD)
Expedia
$3BR\/2BA Canalside Flamingo Island Home With Heated Pool, Jacuzzi, and 60' Boat Slip$
From $562 per night (USD)
VRBO
3BR\/2BA Canalside Flamingo Island Home With Heated Pool, Jacuzzi, and 60' Boat Slip
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
License # VACA-23-219 - Discover paradise at this Flamingo Island retreat in Marathon boasting everything you'll need fo ...
From $562 per night (USD)
VRBO
$2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool$
From $339 per night (USD)
Expedia
2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features ...
From $339 per night (USD)
Expedia
$**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…$
From $2717 per night (USD)
VRBO
**SWEET AMERICANA @ OLD TOWN** 8BR\/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
10
Bathrooms:
8
Sleeps:
20
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! It doesn't ge ...
From $2717 per night (USD)
VRBO
$Dog-friendly home on a wide canal w\/ WiFi & amazing water views$
From $332 per night (USD)
Expedia
Dog-friendly home on a wide canal w\/ WiFi & amazing water views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tarpon Cove Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $332 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Airy Top Floor Blue Heron Suite [Ocean Pointe 3407]
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oc ...
From $302 per night (USD)
VRBO
From $204 per night (USD)
Expedia
Julia's Secret
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Best location in Key West! Just steps from the world class shops and restaurants of world famous Duval Street. There are ...
From $204 per night (USD)
Expedia
From $1126 per night (USD)
VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + 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! Key West has ...
From $1126 per night (USD)
VRBO
From $2924 per night (USD)
Expedia
Banana's Foster Guesthouse | 1 Block to Duval St
Bedrooms:
8
Bathrooms:
9
Sleeps:
19
Summary: Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large histori ...
From $2924 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $451 per night (USD)
VRBO
From $450 per night (USD)
Expedia
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
VRL# 25-0132 we are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with di ...
From $450 per night (USD)
Expedia
From $471 per night (USD)
VRBO
VOTED TRIPADVISOR'S #1 KEY LARGO DESTINATION: 2 KING SUITES, POOLS TENNIS
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Please check out our other properties in Mariners,Kawama and Ocean Point by entering the following property numbers in ...
From $471 per night (USD)
VRBO
From $359 per night (USD)
Expedia
~Bahari House, Seaport~Walk to the harbor from this quintessential conch home
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $359 per night (USD)
Expedia
$Luxury Key Largo Home w\/ Guest House & Pool!$
From $439 per night (USD)
VRBO
Luxury Key Largo Home w\/ Guest House & Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Total relaxation awaits you at this Key Largo vacation rental. Located in prestigious Buccaneer Point, this 3-bedroom, 4 ...
From $439 per night (USD)
VRBO
From $291 per night (USD)
Expedia
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $291 per night (USD)
Expedia
From $798 per night (USD)
VRBO
Dream Vacation! 3 Awesome Units, Pool, On-Site Bar, Gym, Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $798 per night (USD)
VRBO
From $740 per night (USD)
Expedia
Ultimate Key West Adventure! 3 Serene Units, Pool, Parking, Bar, Restaurant!
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $740 per night (USD)
Expedia
From $233 per night (USD)
VRBO
King Bed Accommodation at The Gates Hotel Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $233 per night (USD)
VRBO
From $233 per night (USD)
Expedia
Escape to the Beach! Pool, Restaurant, Gym, Bike Rentals, Parking!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $233 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Pool View Two Queen Beds at The Gates Hotel Key West, Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $266 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Pool View King at The Gates Hotel Key West, Onsite Swimming Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Offering a relaxing tropical atmosphere, this Key West property greets guests with a welcome cocktail and is just a few ...
From $249 per night (USD)
Expedia
From $222 per night (USD)
VRBO
**DRIFTWOOD DREAMS @ 1800 ATLANTIC** Beachside Condo & Pool + LAST KEY SERVICES.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - There will be concrete restoration happening in this complex through Summer 2026. This constructio ...
From $222 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Breezy Beach Waterfront home in Port Antigua
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept ...
From $420 per night (USD)
Expedia
From $366 per night (USD)
VRBO
Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
PARADISE AWAITS AT LUNA BAY BREEZE Experience the perfect Florida Keys getaway at this waterfront oasis where Atlantic ...
From $366 per night (USD)
VRBO
From $573 per night (USD)
Expedia
Villa 5053 on Duck Key BOAT SLIP available
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa b ...
From $573 per night (USD)
Expedia
From $630 per night (USD)
VRBO
403 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Starlight star bright...first star I see tonight...I wish I may I wish I might have the wish I wish tonight… And I wish ...
From $630 per night (USD)
VRBO
From $1271 per night (USD)
Expedia
Poolside Paradise | Heated Pool, Steps to Duval St!
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
Summary: This 3 bed 2 bath home with an amazing HEATED pool is located right off the quieter end of Duval St. The home c ...
From $1271 per night (USD)
Expedia
From $451 per night (USD)
VRBO
Poolside Retreat | Shared Heated Pool, Near Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Summary: Poolside Retreat is the PERFECT vacation home for a couple or small group of friends looking for a fun-filled g ...
From $451 per night (USD)
VRBO
$Lou & Mary`s Getaway ~ 2 bed 2 Bath home W\/Dock, Inch Beach & Cabana Club$
From $305 per night (USD)
Expedia
Lou & Mary`s Getaway ~ 2 bed 2 Bath home W\/Dock, Inch Beach & Cabana Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
**Welcome to Your Perfect Florida Keys Retreat!** Relax, fish, and enjoy the laid-back island lifestyle in this charmin ...
From $305 per night (USD)
Expedia
$Reel Sunset 3\/2 with Pool and Canalfront in Duck Key$
From $587 per night (USD)
VRBO
Reel Sunset 3\/2 with Pool and Canalfront in Duck Key
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Beautiful 3 bedroom 2.5 bath canal front home with private pool. Seaside decor and casual elegance define this comforta ...
From $587 per night (USD)
VRBO
Click For Pricing
Expedia
Updated home with private pool, patio, & grill in enclosed tropical backyard
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Margaret Street Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
Click For Pricing
Expedia
From $458 per night (USD)
VRBO
Keys Escape! Lovely Hammock View, Pools, Beach Access, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We are about getting out there and having fun in the unmatched beauty of bayside Key Largo. Take an early morning swim i ...
From $458 per night (USD)
VRBO
From $321 per night (USD)
Expedia
Oceanview Condo 2bed 2bath second floor with elevator & ocean views!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oceanview Condo is fully furnished and features two bedrooms, two bathrooms, a dining area, full kitchen, washer/dryer, ...
From $321 per night (USD)
Expedia
From $446 per night (USD)
VRBO
Yellowtail For Dinner 3bed 3bath updated single family home with private pool &
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Yellowtail For Dinner is a stunning 3bed/3bath that is it is only one house away from the mouth of a deep-water canal th ...
From $446 per night (USD)
VRBO
From $916 per night (USD)
Expedia
Sunrise Paradise on Sombrero Brand New 4 bed 5 bath Pool Jacuzzi Kayaks
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Plr2019-00051 Are you looking for an upscale, top-of-the-line, out of this world property? Then look no further than Sun ...
From $916 per night (USD)
Expedia
$Casa De Tiki 4bed\/3bath half duplex w\/ heated pool, dockage & more!$
From $513 per night (USD)
VRBO
Casa De Tiki 4bed\/3bath half duplex w\/ heated pool, dockage & more!
Bedrooms:
3
Bathrooms:
5
Sleeps:
8
Casa De Tiki is a spacious 4-bedroom, 3-bathroom half duplex located just minutes from the stunning Sombrero Beach. Insi ...
From $513 per night (USD)
VRBO
From $278 per night (USD)
Expedia
Boot Key Harbor Comfy Condo 1bed 1bath
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This updated one-bedroom condo, centrally located in Marathon, offers convenient access to historical sites such as Cran ...
From $278 per night (USD)
Expedia
From $715 per night (USD)
VRBO
Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach w Pool Jacuzzi, 37` dock 2
Bedrooms:
3
Bathrooms:
5
Sleeps:
10
Plr2019-00281 Do you love the Tropical Waters of the Florida Keys? This vacation home is calling to you. Located on the ...
From $715 per night (USD)
VRBO
From $208 per night (USD)
Expedia
Tropical Oasis Home in Key Colony 3 bedrooms 2 Baths
Bedrooms:
2
Bathrooms:
4
Sleeps:
5
Rentals are Saturday – Saturday unless prior agent and guest agreement made or calendar matched to other reservations a ...
From $208 per night (USD)
Expedia

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