Monroe Area Rentals
From $357 per night (USD)VRBO
P11 - Charming 2 bedroom 2 bath duplex with private pool and dock -...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This lovely 2 bedroom, 2 bath home is located on the gulfside with immediate Gulf water access and near the Vaca Cut for ...
From $357 per night (USD)VRBO
From $686 per night (USD)Expedia
335 Mariners Club Key Largo | 3 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Infinite horizons...from this third floor, luxury, three-bedroom, two and one-half bath villa! A peaceful, relaxing get ...
From $686 per night (USD)Expedia
From $265 per night (USD)VRBO
Coral Club Condo - Your Slice of Paradise in the Sombrero Beach Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Coral Club Condo is your tropical haven in the serene Sombrero Beach Neighborhood, just a brief 10-minute walk from the ...
From $265 per night (USD)VRBO
From $717 per night (USD)Expedia
Beautiful Oceanside Mariner's 3 Bedroom Townhome
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This marina facing 3 bedroom townhome is spacious and beautifully decorated. Relax with the whole family at this peacef ...
From $717 per night (USD)Expedia
From $1008 per night (USD)VRBO
Waterfront, 100ft Boat Dock, Kayaks, Paddle boards, Bikes, Private Pool, Sunsets
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Coco Plum on the Bay, your private waterfront single family home in Marathon, FL. You will enjoy a spacious ...
From $1008 per night (USD)VRBO
From $300 per night (USD)Expedia
RV Camper in the heart of Key Largo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
A beautiful RV camper right in the middle of paradise. A beautiful ambiance with such friendly neighbors. You wake up an ...
From $300 per night (USD)Expedia
From $544 per night (USD)VRBO
Rent a Piece of Paradise, Best Location on the Island!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Rent a piece of paradise right in the heart of beautiful Old Town Key West. Walking distance to all major attraction (r ...
From $544 per night (USD)VRBO
From $1154 per night (USD)Expedia
W09 - New Luxury Property! Breathtaking Canal Front Pool Home - Sleeps 14
- Bedrooms:
- 7
- 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 $1154 per night (USD)Expedia
From $614 per night (USD)VRBO
**TIDEWATER VIEWS @ VENTURE OUT** 2BR\/2BA Cottage + 35’ Private Slip | 80’ Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! TIDEWATER VIE ...
From $614 per night (USD)VRBO
From $274 per night (USD)Expedia
Tropical Getaway in Paradise.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
3 Nite Minimum Stay! **7 day minimum for Lobster Fest, July 22-Aug. 13. ** This bright, freshly decorated, modern 2 bedr ...
From $274 per night (USD)Expedia
From $763 per night (USD)VRBO
Beautiful 4 Bedroom, 3 Bath, Spacious Pool\/SPA Home with 200' wide Canal.
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to Casa del Cielo. Enjoy breathtaking views of the Gulf and Ocean from this beautiful canal front home. Bring y ...
From $763 per night (USD)VRBO
From $333 per night (USD)Expedia
Little Island Pearl
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Have you been dreaming of a get away in the Florida Keys in Key Colony Beach. A little piece of heaven with a brand ne ...
From $333 per night (USD)Expedia
From $387 per night (USD)VRBO
B-105 Moon Bay | 3 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
7-night minimum stay requirement. Lovely bayside townhouse with 2 bedrooms, 1 1/2 baths on the main floor and a studio ...
From $387 per night (USD)VRBO
From $464 per night (USD)Expedia
Great Location , Great Vibes, Great Pool
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Quiet, secluded Keys house with a pool. Ideal for larger groups of friends and family's. Equal distance to Marathon an ...
From $464 per night (USD)Expedia
From $448 per night (USD)VRBO
The Palms...A beautiful space in the perfect place.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The perfect space in the perfect place. A quiet oasis on the 2nd floor nestled amongst palm trees in the shipyard secti ...
From $448 per night (USD)VRBO
From $440 per night (USD)Expedia
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community bui ...
From $440 per night (USD)Expedia
From $503 per night (USD)VRBO
Key Largo Ocean Shore Villa 1 with pool & boat slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the heart of the Florida Keys, this one-of-a-kind vacation rental offers the perfect combination of luxury an ...
From $503 per night (USD)VRBO
From $549 per night (USD)Expedia
TA Beach, Pool, Marina, family friendly, Kitchen, Jacuzzi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This listing is for a TROPICAL ISLAND villa, at Cocoplum Beach and Tennis Club and Marina, which is one of the 2 villas ...
From $549 per night (USD)Expedia
From $722 per night (USD)VRBO
A BANANA REPUBLIC in Old Town Key West
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
A Banana Republic Gem. This Old Town house may be the nicest property in Key West. Totally redone and professionally dec ...
From $722 per night (USD)VRBO
From $492 per night (USD)Expedia
Marina, Resort Pool, Tiki Bar & Restaurant, Pickleball, Beach, Waterfront & more
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE DAPPER DOLPIN updated coastal themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete ...
From $492 per night (USD)Expedia
From $774 per night (USD)VRBO
**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a month i ...
From $774 per night (USD)VRBO
From $560 per night (USD)Expedia
207 Mariners Club Key Largo | 3 Bed, 3 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Perfectly located along the picture perfect marina front overlooking the beautifully landscaped gardens of Mariners Club ...
From $560 per night (USD)Expedia
From $735 per night (USD)VRBO
611 Mariners Club Key Largo | 4 Bed, 4 Bath
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
This luxury Key Largo vacation townhome rental (Unit 611) is a 4 bedroom/4 bath unit. Ideal accommodations for the Flori ...
From $735 per night (USD)VRBO
From $1842 per night (USD)Expedia
**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Throughout Ke ...
From $1842 per night (USD)Expedia
From $308 per night (USD)VRBO
P63 - Beautiful, waterfront Key Colony Duplex. Short walk to the Cabana Beach...
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $308 per night (USD)VRBO
From $501 per night (USD)Expedia
M12 - Beautiful house in Key Colony offering 4 bedrooms, pool and dockage!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom, 3 bathroom home in the heart of the Florida Keys is located in the very desirable Key Colony Beach and w ...
From $501 per night (USD)Expedia
From $277 per night (USD)VRBO
M18 - Spacious 3 bedroom, 2 bath Gulf side condo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Spacious 3 bedroom, 2 bathroom, second floor condo, with split floor plan. Large screened wrap around porc ...
From $277 per night (USD)VRBO
From $203 per night (USD)Expedia
M123 - Cabana Beach Duplex! Premier location across the street from Cabana...
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This comfy, cozy 2 bedroom, 2 bathroom duplex is ideally located in the heart of the Keys in Key Colony Beach. ...
From $203 per night (USD)Expedia
From $620 per night (USD)VRBO
Luxury and Lovely Water Front House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
If you're looking for a low-key vacation, Big Pine Key is the place for you. In Big Pine Key, about 100 miles south of M ...
From $620 per night (USD)VRBO
From $411 per night (USD)Expedia
Florida keys Waterfront,Forever Summer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $411 per night (USD)Expedia
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Fully Furnished Condo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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Fully Furnished Condo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Large Living Room with water view. Park you boat at the private Boat Dock. Swim in the heated Pool. Grill you fresh cau ...
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Fully Furnished Condo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Large living room with water view and deck. Deck off Master Bedroom overlooking the Adams cut waterway and pool. Relax ...
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Water front property with bar, tennis, market place, and restaurants close by.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Comfortable home with 2 bedrooms and a bath on both upper level and lower level. Great for fishing and kayaking, has a d ...
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![Boaters Delight [Ocean Pointe 5301]](https://d1g8n4w8yie14k.cloudfront.net/lodging/61000000/60260000/60255900/60255808/b77b5c68.jpg?impolicy=ccrop&w=350&h=233&q=medium)
From $325 per night (USD)VRBO
Boaters Delight [Ocean Pointe 5301]
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
With thoughtful and creative touches both inside and out mixed with a keen attention to the smallest of details, this oc ...
From $325 per night (USD)VRBO
From $532 per night (USD)Expedia
The Barbados | Balcony & Pool View!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $532 per night (USD)Expedia
From $418 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 $418 per night (USD)VRBO
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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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From $678 per night (USD)VRBO
Harbor Walk Hideaways - Atocha Cottage | Downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Atocha is part of the quiet complex called "Harbor Walk Hideaways," located in the Historic Seaport district of ...
From $678 per night (USD)VRBO
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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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From $537 per night (USD)VRBO
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 $537 per night (USD)VRBO
From $488 per night (USD)Expedia
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 $488 per night (USD)Expedia
From $179 per night (USD)VRBO
Summerland Cove Paradise Waterfront Deep Water Canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bed 2 bath Florida Keys home. In need of a serene getaway with the ocean at arms reach? This 3 bedroom, 2 bathroom hom ...
From $179 per night (USD)VRBO
From $394 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 $394 per night (USD)Expedia
From $705 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 $705 per night (USD)VRBO
From $234 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 $234 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 $662 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 $662 per night (USD)Expedia
From $587 per night (USD)VRBO
Lux Key Largo Oceanfront 3 Bed \/ 3.5 Bath all suite w Private Beach & Boat Dock
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This Oceanfront Luxury Home features 3 bedroom, 3 1/2 bath vacation home with private beach on the gulf in beautiful Key ...
From $587 per night (USD)VRBO
From $312 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 $312 per night (USD)Expedia
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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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From $322 per night (USD)VRBO
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 $322 per night (USD)VRBO
From $364 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 $364 per night (USD)VRBO
From $3772 per night (USD)Expedia
Contra House | Luxury Home w\/Pool
- 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 $3772 per night (USD)Expedia
From $471 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 $471 per night (USD)VRBO
From $587 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 $587 per night (USD)Expedia
From $463 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 $463 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
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WaterFront community in Islamorada w\/ Marina\/Pool\/Tennis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
20% OFF FROM APRIL-JUNE!!! This 3 bed/2 bath features an open and spacious floor plan! Enjoy king beds, great sound sys ...
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Remodeled Townhome with Beach, Pool, Tennis and Marina!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated and remodeled 1,359sf townhome at EXECUTIVE BAY CLUB in the heart of Islamorada REDUCED 20% APRIL-JUNE!! ...
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From $515 per night (USD)VRBO
🌸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 $515 per night (USD)VRBO
From $180 per night (USD)Expedia
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 $180 per night (USD)Expedia
From $520 per night (USD)VRBO
The Andros | 4th Floor Sunset View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: - Welcome to the quiet Sunrise Suites community located on the southeast side of Key West. - Just 1 mile from t ...
From $520 per night (USD)VRBO
From $420 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 $420 per night (USD)Expedia
From $1007 per night (USD)VRBO
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 $1007 per night (USD)VRBO
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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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From $1085 per night (USD)VRBO
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 $1085 per night (USD)VRBO
From $458 per night (USD)Expedia
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 $458 per night (USD)Expedia
From $804 per night (USD)VRBO
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 $804 per night (USD)VRBO
From $651 per night (USD)Expedia
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 $651 per night (USD)Expedia
From $430 per night (USD)VRBO
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 $430 per night (USD)VRBO
From $585 per night (USD)Expedia
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 $585 per night (USD)Expedia
From $372 per night (USD)VRBO
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 $372 per night (USD)VRBO
From $122 per night (USD)Expedia
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 ...
From $122 per night (USD)Expedia
From $465 per night (USD)VRBO
🌸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 $465 per night (USD)VRBO
From $659 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 $659 per night (USD)VRBO
From $339 per night (USD)VRBO
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 $339 per night (USD)VRBO
From $617 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 $617 per night (USD)VRBO
From $403 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 $403 per night (USD)VRBO
From $279 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 $279 per night (USD)Expedia
From $404 per night (USD)VRBO
Bohemian Breeze @ Truman Annex
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $404 per night (USD)VRBO
From $2270 per night (USD)Expedia
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 $2270 per night (USD)Expedia
From $512 per night (USD)VRBO
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 $512 per night (USD)VRBO
From $181 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 $181 per night (USD)Expedia
From $358 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 $358 per night (USD)VRBO
From $377 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 $377 per night (USD)Expedia
From $366 per night (USD)VRBO
Cozy condo with free WiFi & fantastic location in central Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Truman @ Duval - Unit C Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $366 per night (USD)VRBO
From $271 per night (USD)Expedia
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)Expedia
From $243 per night (USD)VRBO
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)VRBO
From $410 per night (USD)Expedia
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 $410 per night (USD)Expedia
From $319 per night (USD)VRBO
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 $319 per night (USD)VRBO
From $230 per night (USD)Expedia
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 $230 per night (USD)Expedia
From $807 per night (USD)VRBO
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 $807 per night (USD)VRBO
From $158 per night (USD)Expedia
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)Expedia
From $270 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 $270 per night (USD)VRBO
From $168 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 $168 per night (USD)Expedia
From $325 per night (USD)VRBO
*Paradise Awaits* Sunshine, Boating, Fishing, RELAXING & RESTING! At It's BEST!*
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
My home is perfect for the all around Fishermen,Diving Groups, Family Reunions, Wedding Courts, Diver Certificate Instru ...
From $325 per night (USD)VRBO
From $805 per night (USD)Expedia
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 $805 per night (USD)Expedia