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 $447 per night (USD)
VRBO
Watch dolphins play in Shelter Cove while swimming in our oversized pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Forget Fall and experience warm late summer waters and calm ocean for fishing! Relax in the private pool with your fa ...
From $447 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Stunning Panoramic 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 $336 per night (USD)
Expedia
From $581 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 $581 per night (USD)
VRBO
From $247 per night (USD)
Expedia
Canal front Fall Escape With 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 $247 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 ...
Click For Pricing
VRBO
From $430 per night (USD)
Expedia
🌸Home #2: THE REEL WORLD (Off Water Property-approximately 250 ft from Private beach entrance)- 🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Totally Private😉- Turn-Key and fully Stocked- Single Family Home 4BR/3BA with your own Heated-Cooled Private Swimming P ...
From $430 per night (USD)
Expedia
From $446 per night (USD)
VRBO
2 Ocean View Units w/ Full Kitchens! Enjoy Outdoor Swimming Pool & Beach Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Adore the infinite ocean view from your room in this one-bedroom suite that welcomes you with its family-friendly amenit ...
From $446 per night (USD)
VRBO
From $381 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 $381 per night (USD)
VRBO
From $315 per night (USD)
VRBO
El Tesoro a Beautiful 3 Bedroom 2 Bath Marathon Ho
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
VACA-23-40Saturday to Saturday booking only( Please ask before booking other dates, you will need prior approval or the ...
From $315 per night (USD)
VRBO
From $442 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 $442 per night (USD)
VRBO
From $218 per night (USD)
VRBO
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 $218 per night (USD)
VRBO
From $1553 per night (USD)
Expedia
Sublime Sunsets Waterfront Condo at The Truman Annex in Key West
Bedrooms:
4
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 $1553 per night (USD)
Expedia
From $569 per night (USD)
VRBO
Villa 5027 on Duck Key BOAT SLIP available
Bedrooms:
2
Bathrooms:
2
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 $569 per night (USD)
VRBO
From $160 per night (USD)
Expedia
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 $160 per night (USD)
Expedia
From $350 per night (USD)
VRBO
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 $350 per night (USD)
VRBO
From $363 per night (USD)
Expedia
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 $363 per night (USD)
Expedia
From $249 per night (USD)
VRBO
Private Tropical Beach • No Stairs • Pool • Fun Activities-Oceanside Restaurants
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Tropical Oceanfront Getaway | 2BR/2BA Condo w/ Private Beach, Pool & More Relax in tropical luxury just steps from your ...
From $249 per night (USD)
VRBO
From $240 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 $240 per night (USD)
Expedia
From $325 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 $325 per night (USD)
VRBO
From $393 per night (USD)
VRBO
Long Key florida,Beachfront Paradise, two bedroom ,3.5 bath, on Ocean, with Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Booking for August & September are at a discounted rate of 30%!!! Do not miss out....NEW LISTING. 30-day Minimum Stay. ...
From $393 per night (USD)
VRBO
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 $492 per night (USD)
Expedia
Coastal Key 3 bed 2 bath with pool kayaks, bikes,
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vaca-21-256Sombrero Beach area of Marathon. Beautifully decorated brand new home, located down the street from Sombrero ...
From $492 per night (USD)
Expedia
From $158 per night (USD)
VRBO
Rent a place in Paradise.
Bedrooms:
1
Bathrooms:
1
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 $264 per night (USD)
VRBO
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 $264 per night (USD)
VRBO
From $1172 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 $1172 per night (USD)
VRBO
From $138 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 $138 per night (USD)
Expedia
From $491 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 $491 per night (USD)
VRBO
From $486 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 $486 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 $800 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 $800 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Oceanfront, Snowbird-Friendly Home with High-Speed WiFi, Ocean Views, and Dock
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Humpty Dumpty Hacienda Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $274 per night (USD)
VRBO
From $194 per night (USD)
VRBO
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 $194 per night (USD)
VRBO
From $368 per night (USD)
VRBO
3BR/2BA Canalside Flamingo Island Home With Heated Pool, Jacuzzi, and 60' Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
License # VACA-23-219 - Discover paradise at this Flamingo Island retreat in Marathon boasting everything you'll need fo ...
From $368 per night (USD)
VRBO
From $306 per night (USD)
VRBO
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 $306 per night (USD)
VRBO
From $2741 per night (USD)
VRBO
**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
Bedrooms:
9
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 $2741 per night (USD)
VRBO
From $323 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 $323 per night (USD)
Expedia
From $251 per night (USD)
VRBO
Airy Top Floor Blue Heron Suite [Ocean Pointe 3407]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oc ...
From $251 per night (USD)
VRBO
From $285 per night (USD)
VRBO
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 $285 per night (USD)
VRBO
From $1309 per night (USD)
VRBO
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Key West has ...
From $1309 per night (USD)
VRBO
From $2934 per night (USD)
Expedia
1 Block to Duval St | Banana's Foster Guesthouse
Bedrooms:
7
Bathrooms:
7
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 $2934 per night (USD)
Expedia
From $490 per night (USD)
VRBO
Fully renovated Condo with Private Balcony, Shared Pool, Hot Tub and Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
*Brand New Listing* Welcome to Captains Choice The NICEST Unit at Sunrise Suites Resort in Key West- Unit 302. Tropical ...
From $490 per night (USD)
VRBO
From $445 per night (USD)
Expedia
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Bedrooms:
2
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 $445 per night (USD)
Expedia
From $424 per night (USD)
VRBO
Key Largo Treasure, 2 Master Suites 2 Kings Beds Marina Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
<p>🌴 Coastal Getaway ✔ONE STORY BRAND NEW SPACIOUS CONDO WITH ELEVATOR ✔BOAT SLIP AVAILABLE AT ADDITIONAL COST OF $4.25 ...
From $424 per night (USD)
VRBO
From $555 per night (USD)
Expedia
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 $555 per night (USD)
Expedia
From $274 per night (USD)
VRBO
Upscale end unit home @ Truman Annex close to Duval St
Bedrooms:
1
Bathrooms:
1
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 $274 per night (USD)
VRBO
From $287 per night (USD)
Expedia
**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 $287 per night (USD)
Expedia
From $420 per night (USD)
VRBO
Breezy Beach Waterfront home in Port Antigua
Bedrooms:
3
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)
VRBO
From $255 per night (USD)
Expedia
Waterfront 75’Dock POOL Kayaks Bikes SombreroBeach2mi OutdoorSpace WalkToStores
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
PARADISE AWAITS AT LUNA BAY BREEZE Experience the perfect Florida Keys getaway at this waterfront oasis where Atlantic ...
From $255 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Villa 5053 on Duck Key BOAT SLIP available
Bedrooms:
2
Bathrooms:
2
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 $360 per night (USD)
VRBO
From $564 per night (USD)
Expedia
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 $564 per night (USD)
Expedia
From $1288 per night (USD)
VRBO
Heated Pool, Steps to Duval St - Poolside Paradise
Bedrooms:
2
Bathrooms:
3
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 $1288 per night (USD)
VRBO
From $358 per night (USD)
Expedia
Shared Heated Pool, Near Duval - Poolside Retreat
Bedrooms:
1
Bathrooms:
1
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 $358 per night (USD)
Expedia
From $205 per night (USD)
VRBO
Lou & Mary`s Getaway ~ 2 bed 2 Bath home W/Dock, I
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Welcome to Your Perfect Florida Keys Retreat!Relax, fish, and enjoy the laid-back island lifestyle in this charming 2-be ...
From $205 per night (USD)
VRBO
From $560 per night (USD)
Expedia
Reel Sunset 3/2 with Pool and Canalfront in Duck K
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful 3 bedroom 2.5 bath canal front home with private pool. Seaside decor and casual elegance define this comfortab ...
From $560 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Keys Escape! Lovely Hammock View, Pools, Beach Access, Pets Allowed!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Oceanfront family-friendly property with direct beach access and pool This listing is for a room within a hotel. ✦ You ...
From $415 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Oceanview Condo in Key Colony Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Oceanview Condo is fully furnished and features two bedrooms, two bathrooms, a dining area, full kitchen, washer/dryer, ...
From $336 per night (USD)
Expedia
From $426 per night (USD)
VRBO
Yellowtail for Dinner
Bedrooms:
3
Bathrooms:
3
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 $426 per night (USD)
VRBO
From $985 per night (USD)
Expedia
Sunrise Paradise on Sombrero Brand New 4 bed 5 bat
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Are you looking for an upscale, top-of-the-line, out of this world property? Then look no further than Sunrise Paradise. ...
From $985 per night (USD)
Expedia
From $396 per night (USD)
VRBO
Casa De Tiki in Marathon
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Casa De Tiki is a spacious 4-bedroom, 3-bathroom half duplex located just minutes from the stunning Sombrero Beach. Insi ...
From $396 per night (USD)
VRBO
From $265 per night (USD)
Expedia
Comfy Condo in Marathon
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This updated one-bedroom condo, centrally located in Marathon, offers convenient access to historical sites such as Cran ...
From $265 per night (USD)
Expedia
From $641 per night (USD)
VRBO
Sweet Retreat! 4 bedroom 2.5 Baths Sombrero Beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Do you love the Tropical Waters of the Florida Keys? This vacation home is calling to you. Located on the water in the e ...
From $641 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Tropical Oasis Home in Key Colony 3 bedrooms 2
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Rentals are Saturday Saturdayunless prior agent and guest agreement made or calendar matched to other reservations alre ...
From $186 per night (USD)
Expedia
From $241 per night (USD)
VRBO
Castaway 2/2 w/ 50` Ft. Dock on the Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
VACA-22-4197-night minimum, NO ExceptionsMax Occupancy: 5 (No Matter the age) Per the city of Marathon's rule.**Castaway ...
From $241 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Palm Point in Marathon
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Palm Point presents a breathtaking 3-bedroom, 2-bathroom single-family residence located in Marathon on the gulf side of ...
From $475 per night (USD)
Expedia
$Luxurious, Elegant Home, Waterfront\nWith Dockage$
From $916 per night (USD)
VRBO
Luxurious, Elegant Home, Waterfront\nWith Dockage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oasis getaway, 3 bedroom, 3 bath, including chefs kitchen. This home has all the amenities on the water, located in a q ...
From $916 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Waves of the Sea, Ocean View Home with Dock, Priva
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
VACA-22-260Booking Min age is 25 and must be present for the duration of the reservation. Max occupancy is 8 no matter a ...
From $402 per night (USD)
Expedia
From $707 per night (USD)
VRBO
Mariners Club # 314 3 Bed 2.5 Bath Key Largo Beac
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Every one will love this luxurious and spacious 3 bedroom and 2.5 bathroom condo in the exclusive Mariner's Club gated c ...
From $707 per night (USD)
VRBO
From $574 per night (USD)
Expedia
Ocean View Gem 3/2.5 Home 70` Dock Cabana Club inc
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Easy Breezy Oceanside home on the Atlantic Ocean, just one house in from open water, with easy deep water access by boat ...
From $574 per night (USD)
Expedia
From $759 per night (USD)
VRBO
Shangri-La 3 Bedroom 3 Baths Gulf Front Estate
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
VACA-22-258Rentals would be Saturday Saturdayunless prior agent and guest agreement made or calendar matched to other r ...
From $759 per night (USD)
VRBO
From $687 per night (USD)
Expedia
Coral Lagoon#8 3 Bed 2.5 bath 35` optional boat slip MKB~Blanco
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This Coral Lagoon Resort & Marina townhome in a quaint Key West village style atmosphere. 1450 sq ft and Built in 200 ...
From $687 per night (USD)
Expedia
From $427 per night (USD)
VRBO
A Pirates Great Escape ~ 3bed/2baths Ocean View B
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada.The condo h ...
From $427 per night (USD)
VRBO
From $582 per night (USD)
Expedia
Beachy Keen House 3/2 Water View Pool Home with Do
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Vaca-21-258Beachy Keen House! This home is just one house up from the white sands of Sombrero Beach. Three bedrooms, two ...
From $582 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Blue Marlin 2/2 Pool home with 35` Dock Easy Acces
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VACA-21-257-night minimum, NO Exceptions Friday to Friday booking Only (for alternate dates message agent) We can do Mon ...
From $252 per night (USD)
VRBO
From $506 per night (USD)
Expedia
Compelling Canal Home with Pool & Large Dock on each side-Cabana Club Included
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
DUPLEX, THIS LISTING NUMBER IS 561552 OTHER SIDE LISTING IS 1275459. EACH SIDE HAS 4 BEDROOMS 3 BATHS, YOUR OWN POOL AND ...
From $506 per night (USD)
Expedia
From $1366 per night (USD)
VRBO
Old Town Retreat near Upper Duval St
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Casa Caribe! When you think of the Caribbean, you think of tranquil blue green waters and a fun vibe. That's the feel wh ...
From $1366 per night (USD)
VRBO
From $181 per night (USD)
Expedia
Canal-front condo with amazing views & convenient location
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sombrero Siesta Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $181 per night (USD)
Expedia
From $342 per night (USD)
VRBO
Dog-friendly condo with pool & hot tub - walk or bike to beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Sunrise Suites - Paradise Escape 407 Our calendar is updated in real-time & our nightly rates are accurately displayed. ...
From $342 per night (USD)
VRBO
From $515 per night (USD)
Expedia
Oceanside home, dock,kayaks,bikes,pool,fishing,111
Bedrooms:
4
Bathrooms:
2
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $515 per night (USD)
Expedia
From $431 per night (USD)
VRBO
Sea Breeze Cottage 2 Large Decks, pool, free parking/wifi in Truman Annex
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Sea Breeze Cottage Cottage is a private, tropical, stand alone cottage located in the prestigious Truman Annex. This is ...
From $431 per night (USD)
VRBO
From $350 per night (USD)
Expedia
Charming Studio in Historic Key West, 5-Min Bike Ride to Beach & Bikes Included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...
From $350 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,109
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $469 per night (USD)
VRBO
From $919 per night (USD)
Expedia
3 bedroom 2 bath Ocean front condo on marina with opt boat slip.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
3 bedroom 2 bathroom Ocean front condo. Full service marina on site. Restaurant/bar on site. Pool and spa Optional 50 ...
From $919 per night (USD)
Expedia
From $466 per night (USD)
VRBO
Oceanside home, dock,kayaks,bikes,pool,fishing,107
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built i ...
From $466 per night (USD)
VRBO
From $462 per night (USD)
Expedia
Ocean Front Modern Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands ...
From $462 per night (USD)
Expedia
From $276 per night (USD)
VRBO
'LA DOLCE VITA' OLD TOWN! STEPS TO DUVAL! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
La Dolce Vita is located in the heart of Old Town Key West and just steps to Duval Street in the heart of the Hi ...
From $276 per night (USD)
VRBO
From $444 per night (USD)
Expedia
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Here in Key West we believe in One Human Family where everyone is welcome and treated like family. Key West! .....it’s ...
From $444 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Galleon Resort efficiency
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This unit has a queen size bed. Updated ceramic stand up shower. The unit is an efficiency.It has a small refrigerator, ...
From $390 per night (USD)
VRBO
From $148 per night (USD)
Expedia
Key Largo Oasis.
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Relax with the whole family at this peaceful place to stay. The upstairs of the home features 3 bedrooms, 1 and half bat ...
From $148 per night (USD)
Expedia
From $304 per night (USD)
VRBO
Beautiful Key Largo awaits
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy this lavishly decorated 2 bedroom 2 bathroom ground floor unit in beautiful Buttonwood Bay. Unit is a smoke free, ...
From $304 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #14 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $187 per night (USD)
Expedia
Click For Pricing
VRBO
3 blocks from waterfront and 1 block off Duval in heart of Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get away from it all” but still be in the heart of Olde Town Key West with everything you need right there? Th ...
Click For Pricing
VRBO
From $374 per night (USD)
Expedia
PLUNGE POOL VILLA ON BLUE WATER LAGOON DUCK Key/MARATHON, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
In Duck Key/Marathon, Florida's sun-kissed beaches, you can find total relaxation at our beautiful two-bedroom house. Ne ...
From $374 per night (USD)
Expedia
From $812 per night (USD)
VRBO
Seaside Retreat: Waterfront Home with private heated pool & lush landscaping
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Luxurious furnishings and spacious interiors centered around the expansive water views perfectly compliment the beautifu ...
From $812 per night (USD)
VRBO
From $541 per night (USD)
Expedia
Marathon Keys Coral Lagoon Unit 2 Waterfront Villa
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
***A quick update regarding the property. The community has scheduled construction to begin on the seawall in our backya ...
From $541 per night (USD)
Expedia
Click For Pricing
VRBO
3 blocks from waterfront and 1 block off Duval in Old Town Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Want to “ Get Away from it all” but still in the heart of Old Town Key West with everything you need within walking dist ...
Click For Pricing
VRBO
From $821 per night (USD)
Expedia
W08 - New Luxury Property! Stunning Canal Front Pool Home - Sleeps 14
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Welcome to paradise! Escape to this luxurious 6 bedroom/6.5 bathroom home designed for VIP guests. Each bedroom i ...
From $821 per night (USD)
Expedia
From $252 per night (USD)
VRBO
Key Largo Getaway [ Ocean Pointe 1316 ]
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
In beautiful Tavernier, you'll find our impressive 2-bedroom condo waiting for your escape. Nestled just a short 19-minu ...
From $252 per night (USD)
VRBO
From $812 per night (USD)
Expedia
Hidden Gem Sunset Views-Marlin Bay Resort & Marina
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $812 per night (USD)
Expedia
From $418 per night (USD)
VRBO
🌸Home #1: “ANCHORS ⚓ AWAY” (Off Water-approximately 300 ft from beach entrance)- 🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Home #1: “ANCHORS ⚓ AWAY” (Off Water-approximately 300 ft from beach entrance)- 🌸 Totally Private😉- Turn-Key and fully ...
From $418 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderfu ...
From $408 per night (USD)
Expedia

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