Florida Keys Rentals
- From $432 per night (USD)
VRBO
Aqua Lodge Houseboat \"Calypso\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
It doesn’t get much more unique than the Aqua Villas at Mangrove Marina. Come experience the adventure of living on the ...
From $432 per night (USD)VRBO
- From $390 per night (USD)
Expedia
Aqua Lodge Houseboat \"Captain's Quarters\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Aqua Villas at Mangrove Marina Resorts “Captain’s Quarters” houseboat, located between Key Largo and Isla ...
From $390 per night (USD)Expedia
- From $180 per night (USD)
VRBO
Private Tropical Oasis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our Green Turtle! My family and I relocated to the beautiful Florida Keys, from Orlando. The property we pur ...
From $180 per night (USD)VRBO
- From $125 per night (USD)
Expedia
Sunsets over the water
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Sunset views over the water has this large 1/1 with 1 assigned parking space. Only a few minutes from the Island of Key ...
From $125 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Anchor's Away: Discover Charm on the Canal, Swift Atlantic Access, Dockage & Above Ground Pool Await
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Anchor's Away - Your Waterfront Haven in Marathon! Escape to Anchor's Away, your charming waterfront sanctua ...
From $225 per night (USD)VRBO
- From $430 per night (USD)
Expedia
Spectacular Water Front Home! Key Largo, Ocean side, Sea Breeze
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Breathtaking concrete home with 2,200SF A/C and 6,900SF lot, freshly remodeled with elegance having large impact windows ...
From $430 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Aqua Lodge Houseboat \"The Grey Lady\"
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This houseboat has 2 Queen beds, 1 Double bed and 1 Twin bed. The houseboat has a flat-screen TV with cable in the livin ...
From $450 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Tarpon Tales | Fantastic boating, pet-friendly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
An angler's dream! Comfy 2 bedroom / 2 bathroom home on a large and lush canalfront property just minutes from the chann ...
From $175 per night (USD)VRBO
- From $163 per night (USD)
VRBO
Casa Playa | Canalfront getaway, 4 beds, 2 baths, on Ramrod Key
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Casa Playa, your spacious 4-bedroom, 2-bathroom retreat nestled in the serene beauty of Ramrod Key. This invi ...
From $163 per night (USD)VRBO
- From $232 per night (USD)
Expedia
Newfound Paradise | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gorgeous open water views from this 3 bedroom, 2 bath pool home on Ramrod Key. Open plan main living area with ample sea ...
From $232 per night (USD)Expedia
- From $277 per night (USD)
VRBO
Casa Verde - Perfection in a monthly rental - private pool - RealKeyWest
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
The moment you walk thru the door you are greeted by soothing tropical colors and high vaulted ceilings. The large mast ...
From $277 per night (USD)VRBO
- Click For Pricing
Expedia
Canalfront home with WiFi, water views, washer\/dryer, central AC & tiki bar
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Brass Bell Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
Click For PricingExpedia
- From $575 per night (USD)
VRBO
Key West Beach House with heated pool, tiki, and dock.♿︎
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to Key West. Located on this beautiful island 13 miles from downtown is this quaint 2-level beach home. With sle ...
From $575 per night (USD)VRBO
- From $436 per night (USD)
Expedia
The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to 'The Blue Pearl' – the ultimate destination for large families or multiple families seeking an expansive and ...
From $436 per night (USD)Expedia
- From $338 per night (USD)
VRBO
Aqua Lodge Houseboat \"Yellow Tail \"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Are you ready to be adventurous , do something unique and fun? Well, it doesn’t get Yellow Tail houseboat, is a 1 bedro ...
From $338 per night (USD)VRBO
- From $338 per night (USD)
Expedia
Aqua Lodge Houseboat \"Tarpon\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
This Aqua Lodge has a master bedroom with a queen-sized bed, equipped with TV and Air Conditioning unit. The cathedral c ...
From $338 per night (USD)Expedia
- From $290 per night (USD)
VRBO
**SEAPORT SENSATION @ OLD TOWN VILLAS** Condo & 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! It is not so ...
From $290 per night (USD)VRBO
- From $354 per night (USD)
Expedia
**COASTAL LOVING @ OLD TOWN** Chic 4BR Home & Pool + LAST KEY SERVICES...
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! If you’re loo ...
From $354 per night (USD)Expedia
- From $273 per night (USD)
VRBO
Casa Del Mar in Venture Out Unit 253
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
VO253 Open Water Views 35' Dockage Sparkling Clean 2Bd/1Ba Vacation Home! THIS IS ONE OF THE NICEST UNITS IN ALL OF VENT ...
From $273 per night (USD)VRBO
- From $394 per night (USD)
Expedia
Island Adventure II 4 Bedrooms 4.5 Baths, Pool, Ocean View with Dock & Kayaks
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
VACA-22-74 "Island Adventure" was built-in 2021, with Family, Fun, Luxury, and Water Sports Lovers in Mind. The home is ...
From $394 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Flirty Flamingo Key West
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Flirty Flamingo is luxurious and in a prime Key West location. Built in 1998 and meticulously cared for this spacious 3 ...
From $350 per night (USD)VRBO
- From $183 per night (USD)
VRBO
Runaway Bills | 3 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This stylish Conch Home is tucked away on a quiet lane in Old Town Key West. Surrounded by distinctive neighborhoods thi ...
From $183 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Key Largo large 4\/3 Waterfront home access to the Bay
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Beautiful New Home on the water in the Florida Keys. Mile marker 103. 4 bedrooms all newly furnished, 3 full bathroom, ...
From $250 per night (USD)VRBO
- From $115 per night (USD)
Expedia
NEWLY RENOVATED Key Largo Beach Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Immerse into this private beach-style cottage that has stunning bay views and is a minute's walk from a private beach. T ...
From $115 per night (USD)Expedia
- From $450 per night (USD)
VRBO
KEY LARGO BRAND NEW HOUSE WITH POOL & DOCKAGE
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to paradise! This home is a new listing to VRBO. If you are looking for a large beautiful home with a pool in a ...
From $450 per night (USD)VRBO
- From $231 per night (USD)
Expedia
Canal front getaway w\/ water view & access to the Cabana Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A Wave From it All Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $231 per night (USD)Expedia
- From $622 per night (USD)
VRBO
Waterfront Town Home on a Lagoon, Marina, Tennis, Pickleball, Bikes, Kayaks
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
If your dates are not available or if you are looking for two units, check out my other VRBO Unit #2523121. Enter the n ...
From $622 per night (USD)VRBO
- From $296 per night (USD)
Expedia
Key Largo Treasure at Kawama Yacht Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Two bedrooms, each with their own balconies, one overlooks the pool, the other State Park Hardwood Hammock. There is ple ...
From $296 per night (USD)Expedia
- From $538 per night (USD)
VRBO
Oasis Vacation! 406 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this elegant island townhome in Mariner's Club, Key Largo's premier resort. Updated and upgraded! This is ...
From $538 per night (USD)VRBO
- From $707 per night (USD)
Expedia
Your dreams of paradise are about to come true! 411 Mariners Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spend tranquil days on the sun-kissed balcony with ocean views! Cool down with a plunge in the pool then make plans to ...
From $707 per night (USD)Expedia
- From $233 per night (USD)
VRBO
Paradise for Rent (Condo and Private Boat Slip) monthly discount for sept & oct
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
We are happy to answer all questions! SOME OF OUR DATES ARE LISTED AS CHECK IN AND OUT ON SATURDAY, PLEASE ASK IN CASE ...
From $233 per night (USD)VRBO
- From $406 per night (USD)
Expedia
Henry's Piece of Paradise on the Ocean in Key West - Weekly \/ Nightly
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean vi ...
From $406 per night (USD)Expedia
- From $677 per night (USD)
VRBO
Breathtaking harbor and ocean view! Room for the whole family! 131 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious and gracious, 4 bedroom, 3 bath, top floor, corner villa with a jaw-dropping view of the resort's harbor and th ...
From $677 per night (USD)VRBO
- From $297 per night (USD)
Expedia
Memorial Day Last Minute Discount - Deep Water Canal Home in Boot Key Harbour!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
If you’re looking for larger accommodations, please view our home across the street, VRBO # 2413494! Enjoy total privac ...
From $297 per night (USD)Expedia
- From $377 per night (USD)
VRBO
Waterfront luxury Villa (29) with sunset views and boat slip
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $377 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Pool Home on Tranquil Private Cruikshank Island available for MARCH 2024!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...
From $300 per night (USD)VRBO
- From $397 per night (USD)
VRBO
A Cut Above 3bed\/2bath updated half duplex with private pool & cabana club
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
A Cut Above is an updated 3bed/2bath beautifully decorated half duplex in desirable Key Colony Beach. Enjoy the tropical ...
From $397 per night (USD)VRBO
- From $450 per night (USD)
Expedia
Sunset South: First Floor 2 Bedroom 1 Bath Condo at Bayfront Suites & Marina
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $450 per night (USD)Expedia
- From $966 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 $966 per night (USD)VRBO
- From $560 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 $560 per night (USD)Expedia
- From $700 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 $700 per night (USD)VRBO
- From $184 per night (USD)
Expedia
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 $184 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $299 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 $299 per night (USD)Expedia
- From $456 per night (USD)
VRBO
Fathers Day 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 $456 per night (USD)VRBO
- From $213 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 $213 per night (USD)Expedia
- From $979 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 $979 per night (USD)VRBO
- From $254 per night (USD)
Expedia
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 $254 per night (USD)Expedia
- From $950 per night (USD)
VRBO
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 $950 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 $1300 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 $1300 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 $898 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 $898 per night (USD)VRBO
- From $679 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 $679 per night (USD)Expedia
- From $743 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 $743 per night (USD)VRBO
- From $912 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 $912 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 $813 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 $813 per night (USD)Expedia
- From $756 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 $756 per night (USD)VRBO
- From $249 per night (USD)
Expedia
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 $249 per night (USD)Expedia
- From $495 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 $495 per night (USD)VRBO
- From $180 per night (USD)
Expedia
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 $180 per night (USD)Expedia
- From $225 per night (USD)
VRBO
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 $225 per night (USD)VRBO
- From $715 per night (USD)
Expedia
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 $715 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $103 per night (USD)
VRBO
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 $103 per night (USD)VRBO
- From $298 per night (USD)
Expedia
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 $298 per night (USD)Expedia
- From $390 per night (USD)
VRBO
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 $390 per night (USD)VRBO
- From $627 per night (USD)
Expedia
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 $627 per night (USD)Expedia
- From $695 per night (USD)
VRBO
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 $695 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 $233 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 $233 per night (USD)VRBO
- From $520 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 $520 per night (USD)VRBO
- From $275 per night (USD)
VRBO
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 $275 per night (USD)VRBO
- From $700 per night (USD)
Expedia
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)Expedia
- From $425 per night (USD)
VRBO
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)VRBO
- From $361 per night (USD)
Expedia
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 $361 per night (USD)Expedia
- From $483 per night (USD)
VRBO
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 $483 per night (USD)VRBO
- From $158 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 $158 per night (USD)Expedia
- From $450 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 $450 per night (USD)VRBO
- From $221 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 $221 per night (USD)Expedia
- From $548 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 $548 per night (USD)VRBO
- From $704 per night (USD)
Expedia
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 $704 per night (USD)Expedia
- 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 $566 per night (USD)
Expedia
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 $566 per night (USD)Expedia
- From $770 per night (USD)
VRBO
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 $770 per night (USD)VRBO
- From $635 per night (USD)
Expedia
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)Expedia
- From $176 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 $176 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $520 per night (USD)
VRBO
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 $520 per night (USD)VRBO
- From $157 per night (USD)
Expedia
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 $157 per night (USD)Expedia
- From $484 per night (USD)
VRBO
*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 $484 per night (USD)VRBO
- From $786 per night (USD)
Expedia
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 $786 per night (USD)Expedia
- From $201 per night (USD)
VRBO
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 $201 per night (USD)VRBO
- From $556 per night (USD)
Expedia
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 $556 per night (USD)Expedia
- From $283 per night (USD)
VRBO
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 $283 per night (USD)VRBO
- From $289 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 $289 per night (USD)VRBO
- From $624 per night (USD)
VRBO
Waterfront home with Cabana Club access, private pool, hot tub, & 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 $624 per night (USD)VRBO
- From $1645 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 $1645 per night (USD)VRBO