Monroe Area Rentals
- From $1038 per night (USD)
VRBO
Seabreeze Marathon Oceanside with Cabana Club Membership
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Seabreeze Marathon! Don't look any further for your perfect vacation destination. This property is a newly r ...
From $1038 per night (USD)VRBO
- Click For Pricing
Expedia
Sunset views at the Galleon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
You will be back year after year! Unit features full kitchen with Master King, Guest Twin Beds, and Pull out Sleeper Sof ...
Click For PricingExpedia
- From $1252 per night (USD)
VRBO
Upper Bayview North: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1252 per night (USD)VRBO
- From $666 per night (USD)
Expedia
Island life meets luxury at 604 Mariners Club Key Largo
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to "Vacay Vibes", a funky and fun 4 bedroom, completely updated and renovated townhouse with an Instagram photo ...
From $666 per night (USD)Expedia
- From $208 per night (USD)
VRBO
Upscale Townhouse with Golf and Lake Views, Shared Pool, WiFi, and AC - Dogs OK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Tipsy Mermaid Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $208 per night (USD)VRBO
- From $293 per night (USD)
Expedia
~HORSE CONCH~ Amazing location with shared pool and covered balcony!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
THE PROPERTY: Enjoy your stay in the tropics at Horse Conch, part of the highly touted "Queen Conch" complex, which incl ...
From $293 per night (USD)Expedia
- From $459 per night (USD)
VRBO
MAY SPECIAL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our beautiful 4bdrm/ 3 full bath waterfront home. Relax and relish the tropical waters that surround you in p ...
From $459 per night (USD)VRBO
- From $327 per night (USD)
Expedia
Villa Largo Island Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Indulge in endless sun-soaked delights at this stunning property nestled within one of the most sought-after an ...
From $327 per night (USD)Expedia
- From $1327 per night (USD)
VRBO
Upper Bayview South: Waterfront 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1327 per night (USD)VRBO
- From $821 per night (USD)
VRBO
Exquisite Key Colony Beach Retreat- 420\/430 11th Street KCB
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Have you been dreaming of a sun-soaked Florida Keys getaway with ample space for your whole family? Turn those dreams in ...
From $821 per night (USD)VRBO
- From $235 per night (USD)
VRBO
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cottage #13 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. SpaciouQuaint, clean, co ...
From $235 per night (USD)VRBO
- From $764 per night (USD)
Expedia
To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Forget your worries in this spacious and serene space. Relax while sitting and watching TV or listening. . to music in ...
From $764 per night (USD)Expedia
- From $1338 per night (USD)
VRBO
Beach House, Waterfront, Sombrero Beach, Florida Keys Rental, Private Pool, Dock
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
New Listing - Family Reunion Large Vacation Rental 6 bedrooms 5 baths steps to Sombrero Beach. 6 bedrooms (5 King size b ...
From $1338 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Paradise Without A Passport New Home Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Brand New Home, Brand New Furniture, Sunset and Ocean Views, Outdoor communal Fire Pits, Outdoor Kitchen, Grill, Possibl ...
From $450 per night (USD)Expedia
- From $1176 per night (USD)
VRBO
Bayview North One: Waterfront 4 Bedroom 4 Bath Condo at Bayfront Suites
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1176 per night (USD)VRBO
- From $810 per night (USD)
Expedia
Sunset North: Luxury 4 Bedroom 4.5 Bath Condo at Bayfront Suites & Marina
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $810 per night (USD)Expedia
- From $745 per night (USD)
VRBO
Upper Sunset South: Luxury 3 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $745 per night (USD)VRBO
- From $1280 per night (USD)
Expedia
Bayview South: 4 Bedroom 3 Bath Waterfront Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $1280 per night (USD)Expedia
- Click For Pricing
VRBO
Oceanfront BEACH HOUSE with DOCKAGE and BOAT LIFT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a stroll along the dock to watch the rising morning sun, lounge on the dock netting and become entranced by the la ...
Click For PricingVRBO
- From $863 per night (USD)
Expedia
Upper Sunset North: Luxury 4 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $863 per night (USD)Expedia
- From $868 per night (USD)
VRBO
Bayview Middle: Waterfront 3 Bedroom Condo at Bayfront Suites & Marina
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $868 per night (USD)VRBO
- From $489 per night (USD)
Expedia
Hidden Gem-Key West 3/2 wading pool home with parking -RealKeyWest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stroll down Higgs Lane to arrive at your Old Town Key West vacation home. Unpack and unwind at this Gem of a house wh ...
From $489 per night (USD)Expedia
- From $276 per night (USD)
VRBO
Island Escape at Ocean Pointe
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated unit with fresh paint, updated cabinets in kitchen and bathroom, new ceiling fans. Updated living room ...
From $276 per night (USD)VRBO
- From $549 per night (USD)
VRBO
This Marathon Canal home has a pool and hot tub! Park your boat in your backyard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Mirage Manor has had lots of happy visitors, but needed a bigger and better pool. Construction is now complete and rent ...
From $549 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. ...
From $250 per night (USD)VRBO
- From $217 per night (USD)
Expedia
Its an enjoyable two bed\/bath unit with pleasant view of the marina and 0cean.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Your Newly Renovated Oceanfront Vacation Home: In June 2018, the Condo unit had a total renovation including installati ...
From $217 per night (USD)Expedia
- From $759 per night (USD)
VRBO
Middle Sunset: 3 Bedroom 3 Bath Luxury Condo at Bayfront Suites & Marina
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $759 per night (USD)VRBO
- Click For Pricing
Expedia
Fantastic Waterfront Location, Beautiful Ocean Views & Near Key West
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is a newly renovated ocean front cottage attached to the main house with private pool and boat docking available. ...
Click For PricingExpedia
- Click For Pricing
VRBO
Condo 2br\/2bath waterfront
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Situated just off the historic Florida Keys Overseas Highway, The Hammocks at Marathon™ lets you and your family experie ...
Click For PricingVRBO
- From $106 per night (USD)
Expedia
coral stone
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our apartment offers all the comforts of home, 120 paces to Duval Street - shopping, restaurants and nightlife. Near Hem ...
From $106 per night (USD)Expedia
- From $272 per night (USD)
VRBO
Dog-friendly oceanfront home with private pool, screened porch & outdoor kitchen
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Blue Water Bungalow Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $272 per night (USD)VRBO
- From $389 per night (USD)
Expedia
Amazing Key Largo Paradise 2\/2 Townhouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to the Keys in this 2bedroom 2 bath townhome overlooking a tranquil lagoon. Swim or Snorkel the Saltwater Lagoon, ...
From $389 per night (USD)Expedia
- From $652 per night (USD)
VRBO
VIP LUXURY PENTHOUSE SUITE! - OFFERS KEY LARGO'S BEST PANORAMIC OCEAN VIEWS!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $652 per night (USD)VRBO
- From $157 per night (USD)
Expedia
Spring & summer dates available licensed rental vr #24-0235 NO BOATS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a legally licensed rental in the Village of Islamorada license # vr 131 The entire condo has been updated ...
From $157 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Enjoy Ocean Views, Pool & Cabana Bar @ Sunkissed Suite
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Relax and amongst the tropical sights and sounds in our ocean front condo located in Ocean Pointe Suites. Ideal for Coup ...
From $225 per night (USD)VRBO
- From $530 per night (USD)
Expedia
Gorgeous Gulf-front home with dock, private pool & gas grill
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Sunset Sanctuary Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $530 per night (USD)Expedia
- From $422 per night (USD)
VRBO
Waterfront luxury Villa (59) 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 $422 per night (USD)VRBO
- From $533 per night (USD)
Expedia
3 Bedroom Oceanfront Townhouse in the fabulous Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This townhouse at Key Colony Point is a beautiful holiday location. Key Colony Point is at the corner of Marathon, so yo ...
From $533 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Bayfront Home with Beach & Open Water Views! Amazing Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Imagine enjoying sunsets and margaritas, only a few yards from the water, with its gentle waves and warm breezes. Loungi ...
From $500 per night (USD)VRBO
- From $260 per night (USD)
Expedia
Harbor House 2bed 2bath Open water views & dockage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Quaint little 2 bedroom 2 bath single family right on Boot Key Harbor! The porch overlooks the harbor where you can sit ...
From $260 per night (USD)Expedia
- From $700 per night (USD)
VRBO
WASTIN AWAY IN MARGARITAVILLE! HYATT RESIDENCE CLUB JEWEL IN HEART OF KEY WEST
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
ONLY AVAILABLE 2/20-2/27: PRIME REAL ESTATE IN THE HEART OF KEY WEST. HYATT RESIDENCE CLUB COVETED RESORT SUNSET HARBOR ...
From $700 per night (USD)VRBO
- From $425 per night (USD)
Expedia
Spotless Fully Renovated Family Home. Free parking WiFi Pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our new fully renovated townhouse hosted by HomeAway Premier Partner Roy Svenningsen. This home is located in ...
From $425 per night (USD)Expedia
- From $560 per night (USD)
VRBO
~Serene Lily~ Luxurious 2 bed, 2.5 bath home in the upscale Truman Annex
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
WEEKLY RENTAL: This property has a 7 night minimum stay. THE PROPERTY: Located where the Gulf meets the Atlantic, this ...
From $560 per night (USD)VRBO
- From $166 per night (USD)
Expedia
Paradise found at the Key West Golf Club!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
We selected the best of everything to create paradise in Key West. Enjoy tropical breezes as you sip your morning coffee ...
From $166 per night (USD)Expedia
- From $538 per night (USD)
VRBO
NEW YEAR - NEW CRAZY LOW DEALS ON FANTASTIC HOME
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
City of Key West Business License # 28224 We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memo ...
From $538 per night (USD)VRBO
- From $230 per night (USD)
Expedia
STUNNING! Brand New and Unobstructed Bay View with Cabana Club Membership!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
2/2 HALF DUPLEX IN KEY COLONY BEACH ON SADOWSKI CAUSEWAY. COMES WITH CABANA CLUB MEMBERSHIP AS WELL. ENJOY THE POOL, BEA ...
From $230 per night (USD)Expedia
- From $583 per night (USD)
VRBO
Casa Blanca By the Gulf 5 bedroom 3 bath with pool and dockage, kayaks, bikes,
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Vaca-21-484 Casa Blanca By The Gulf is a Florida Keys Paradise for Everyone. This is a modern design home with sleek li ...
From $583 per night (USD)VRBO
- Click For Pricing
Expedia
5 Seas Retreat 4 bedroom 2 bath home with pool and Sandy Beach, and dockage too
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Sandy Beach a Rarety for the Keys. Gorgeous open water sunset views await you at this fully furnished tropical waterfron ...
Click For PricingExpedia
- From $554 per night (USD)
VRBO
Take in the oceanview from 408 Mariners Club oceanfront patio!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Sleeps 6 in beds, maximum occupancy 8 ~ Welcome to this spacious, oceanfront 3-bedroom, 3-bath townhouse ideally located ...
From $554 per night (USD)VRBO
- From $887 per night (USD)
Expedia
Egret House @ Tarpon Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Indulge in breathtaking ocean vistas from every living level, complemented by an inviting waterfront pool! The ...
From $887 per night (USD)Expedia
- From $635 per night (USD)
VRBO
Luxury Key Largo Townhouse unit 801 Mariners Club Key Largo
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This newly renovated townhouse is a refined yet Keysey Key Largo vacation rental (Unit 801) is a 2 story townhouse with ...
From $635 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This 3 bedroom home is located one block from where Tennessee Williams home was located. The home has a true historic fl ...
From $190 per night (USD)VRBO
- Click For Pricing
VRBO
FANTASY WEEK
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Set along the Atlantic Ocean, Hyatt Windward Pointe Resort blends the laid-back Key West style with a modern, upscale re ...
Click For PricingVRBO
- From $570 per night (USD)
Expedia
Casa Cove Beautiful Tropical Decorated 3 KING SUITES Sleeps 8 Pool 2 mi 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 $570 per night (USD)Expedia
- From $179 per night (USD)
VRBO
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $179 per night (USD)VRBO
- From $391 per night (USD)
Expedia
*Newly Renovated Single Family Home w\/Private Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Perfectly situated in KCB w/ up to 50' dockage on a wide and pristine canal that leads easy access to both the Ocean & t ...
From $391 per night (USD)Expedia
- From $850 per night (USD)
VRBO
Old Town Key West - Historic & Charming - 2 Blks From Duval
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $850 per night (USD)VRBO
- From $214 per night (USD)
Expedia
Stunning Ocean View\/Sunsets, A true \"Gem by the Sea\" great for relaxation & fun
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 2 Bedroom, 1 1/2 bathroom Condo with den with a futon, located in Moon Bay located in Key Largo. Property is ...
From $214 per night (USD)Expedia
- From $580 per night (USD)
VRBO
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay at the Salty Pelican in Angler's Reef! This magnificent home with amazing direct ocean views from the master b ...
From $580 per night (USD)VRBO
- From $356 per night (USD)
Expedia
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VIEWS to live for!! Book this 2 bed 2 baths side for the family or TAKE the entire Duplex & book the 1 bed 1 bath (Pro ...
From $356 per night (USD)Expedia
- From $317 per night (USD)
VRBO
Seaport Walkabout- the best location in town
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Open to annual rental at lower rate Two hundred yards from Schooner Wharf and the seaport and steps from Pepe’s in the ...
From $317 per night (USD)VRBO
- From $633 per night (USD)
Expedia
Waterfront home with Cabana Club access, and private pool, hot tub and dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Casa de Rosa Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $633 per night (USD)Expedia
- From $1691 per night (USD)
VRBO
Ultra Luxurious 4 Bedroom ocean front Rental home in Islamorada, Florida Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 202, Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world-c ...
From $1691 per night (USD)VRBO
- From $180 per night (USD)
VRBO
Tiki Time- Canal home with Boat Lift, Key Largo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We think this home is aptly named, with a beautiful Tiki where you can relax waterside, a refreshing drink in hand, and ...
From $180 per night (USD)VRBO
- From $145 per night (USD)
VRBO
The Sylvia Gwynn, Key West Southernmost Point monthly vacation rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Just 1 block from the action of Duval Street lies our newest space located at 1307 Whitehead Street. The Sylvia Gwynn is ...
From $145 per night (USD)VRBO
- From $299 per night (USD)
Expedia
South Point Sunset - Florida Keys waterfront 3\/3 House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Nicely appointed 3/3 waterfront house with heated Inground pool and small beach. Watch dolphins from the living room in ...
From $299 per night (USD)Expedia
- From $1188 per night (USD)
VRBO
Your Home Away From Home! 4 Comfortable Units, Free Parking, Pool and Hot Tub
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
Designed to embrace the ambiance of the Florida Keys with décor that elicits a calm feeling with serene blues, crisp whi ...
From $1188 per night (USD)VRBO
- From $891 per night (USD)
VRBO
Vacation Day Is Always A Great Idea! 3 Convenient Units, Pets Allowed, Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Designed to embrace the ambiance of the Florida Keys with décor that elicits a calm feeling with serene blues, crisp whi ...
From $891 per night (USD)VRBO
- From $593 per night (USD)
VRBO
Perfect Beach Destination! 2 Spacious Units, Pool, Parking, Free Bike Rentals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Designed to embrace the ambiance of the Florida Keys with décor that elicits a calm feeling with serene blues, crisp whi ...
From $593 per night (USD)VRBO
- From $255 per night (USD)
Expedia
Amazing newly remodeled Coastal Condo w Ocean view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Newly remodeled Condo come be amazed. Come enjoy this new super comfy Condo, loaded with amenities, maybe the nicest in ...
From $255 per night (USD)Expedia
- From $165 per night (USD)
VRBO
Blue Chill Vacation!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This tropical vacation home offers two bedrooms, one bathroom and is located in a gated community just 19 miles form Key ...
From $165 per night (USD)VRBO
- From $186 per night (USD)
Expedia
Seascape Vacation!!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful vacation spot on Cudjoe Key perfect for you and your family. This wonderful one bedroom home filled with color ...
From $186 per night (USD)Expedia
- From $226 per night (USD)
VRBO
Seas The Day in Cudjoe Key
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A cozy and small mobile home with Marina access and a boat ramp. With almost perfect weather you experience in the Keys ...
From $226 per night (USD)VRBO
- From $505 per night (USD)
Expedia
Family-size townhouse with private apartment! 705 Mariners Club Key Largo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This is your perfect start to an unforgettable vacation! 705 Mariners Club is a 3-bedroom, 3-story townhouse reflecting ...
From $505 per night (USD)Expedia
- From $170 per night (USD)
VRBO
Our Happy Place 2 bed 2 bath with Boat slip Open water views of Boot Key Harbor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our Happy Place with Sunsets and Open water views of Boot Key Harbor. This condo is a 2 bedroom 2 bath with elevator ac ...
From $170 per night (USD)VRBO
- From $447 per night (USD)
Expedia
Vaca Cove E Endless Summer 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
VACA-23-22 Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf ac ...
From $447 per night (USD)Expedia
- From $283 per night (USD)
VRBO
Vaca Cove unit A Shore Thang 4 Bedrooms 3 Baths, Pool, Ocean View with Dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
VACA-23-193 Built in 2016, this rental offers beautiful Bonefish Bay views and private boat access. This home features ...
From $283 per night (USD)VRBO
- From $446 per night (USD)
Expedia
Vaca Cove unit D Sunset Pointe 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
VACA-23-232 Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf ...
From $446 per night (USD)Expedia
- From $353 per night (USD)
VRBO
Vaca Cove B Sea Forever 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View with
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
VACA-22-360 Built in 2016, this rental offers beautiful Bonefish Bay views and private boat access. This home features ...
From $353 per night (USD)VRBO
- From $165 per night (USD)
Expedia
Paradise Found- Scuba Divers Welcome- Key Largo-Kampground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Private house newly renovated kitchen & bath in Key Largo Kampground. The house is fully stocked with everything you nee ...
From $165 per night (USD)Expedia
- From $244 per night (USD)
VRBO
Open Water Paradise 2\/2 Half Duplex in Key Colony Beach at Marathon, FL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Open Water Paradise in the Keys. Ocean living at its Best! Nestled along Bonefish Bay, Open Water Paradise ...
From $244 per night (USD)VRBO
- From $320 per night (USD)
Expedia
Vaca Cove G Beach Daze 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View with
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
VACA-22-102 Vaca Cove is a private oasis compromised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf ...
From $320 per night (USD)Expedia
- From $301 per night (USD)
VRBO
BEAUTIFULLY DESIGNED OCEANFRONT CONDO
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated and is beautiful ...
From $301 per night (USD)VRBO
- Click For Pricing
Expedia
Relaxing getaway with SO much to do! Right on the ocean. You NEED to get away.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful location close to the beach, fishing, all kinds of water sports, or just relaxing because you're on ISLAND TI ...
Click For PricingExpedia
- From $316 per night (USD)
VRBO
Waterfront Home w\/ Private Dock, Outdoor Shower & Home Office - Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Casa Palmera Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $316 per night (USD)VRBO
- Click For Pricing
Expedia
Pirates Pleasure Fishing and Snorkeling.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Mobile home on boating canal, access to the contents for flats fishing and the Atlantic for deep sea fishing. Property ...
Click For PricingExpedia
- Click For Pricing
Expedia
Paradise in the Keys - 2\/2 Open Water with a pool. House is open to a 6 month
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautifully appointed 2 Bed 2 Bath, open water home with pool, located on Ramrod Key. Recently renovated top to bottom a ...
Click For PricingExpedia
- From $345 per night (USD)
VRBO
Mermaid`s Rest - Sunset views! B307 Moon Bay
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
7-night minimum stay requirement. This fully renovated bay front end-unit condo in Moon Bay has been reconfigured to a ...
From $345 per night (USD)VRBO
- From $531 per night (USD)
VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $531 per night (USD)VRBO
- From $412 per night (USD)
VRBO
The Key West Bougain Villa, a Monthly Vacation Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Bougain Villa is found on Whitehead Street. Reserve a stay in this home located in the heart of historic Old Town Ke ...
From $412 per night (USD)VRBO
- From $229 per night (USD)
VRBO
~FISH CAMP!~ Family friendly, canal front, monthly rental.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local ...
From $229 per night (USD)VRBO
- From $463 per night (USD)
Expedia
Waterfront luxury Villa (51) 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 $463 per night (USD)Expedia
- Click For Pricing
VRBO
Beautiful 2\/2 Florida keys home rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with privat ...
Click For PricingVRBO
- From $606 per night (USD)
Expedia
La Casita
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, fully furnished 2BD/2BA single family home is located in the prestigious Casa Marina neighborhood. Speci ...
From $606 per night (USD)Expedia
- From $505 per night (USD)
VRBO
RELAX AWAY- NEW 4BDRM W\/ 40FT DOCK & PRIVATE POOL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
RELAX AWAY @ SOMBRERO - ENJOY OUR NEW 1800 SQ FT HOME, 4/3 WITH COVERED BALCONY & PATIO & SPACIOUS POOL PERFECT FOR YOUR ...
From $505 per night (USD)VRBO
- From $350 per night (USD)
Expedia
Villages at Hawks Cay Villa with Spa
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
In response to COVID-19, our villa will be disinfected and sanitized professionally prior to all check-ins. We offer ni ...
From $350 per night (USD)Expedia
- From $141 per night (USD)
VRBO
Beautiful home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy all that Islamorada has to offer! Live the Keys life in this beautiful deep water canal front home. Lo ...
From $141 per night (USD)VRBO
- From $251 per night (USD)
Expedia
Tranquil Top Floor Suite w\/ Lovely Views close to Attractions in the Upper Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Calm coastal décor greets you in this one bedroom one bathroom Oceanfront Condo. The comforting living room features a f ...
From $251 per night (USD)Expedia
- From $414 per night (USD)
VRBO
Hidden Paradise: A Serene Waterside Retreat - 3-Bedroom, 3-Bath Single Family
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Discover comfort and ample space in this three-bedroom waterfront oasis, a perfect single family abode that boasts an ex ...
From $414 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Family Friendly House In Paradise
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
3 Bedroom / 2 Bath Upstairs 1 King Bed, 2 Queen Spacious office with open water views 2 Bedroom/ 1 Bath Down 1 King, 2 t ...
From $300 per night (USD)VRBO