Florida Keys Rentals
- 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 $342 per night (USD)
Expedia
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 $342 per night (USD)Expedia
- Click For Pricing
VRBO
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 ...
Click For PricingVRBO
- From $1027 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 $1027 per night (USD)VRBO
- From $770 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 $770 per night (USD)VRBO
- From $513 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 $513 per night (USD)VRBO
- From $268 per night (USD)
VRBO
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 $268 per night (USD)VRBO
- Click For Pricing
Expedia
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 ...
Click For PricingExpedia
- From $178 per night (USD)
VRBO
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 $178 per night (USD)VRBO
- From $212 per night (USD)
Expedia
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 $212 per night (USD)Expedia
- From $486 per night (USD)
VRBO
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 $486 per night (USD)VRBO
- From $155 per night (USD)
Expedia
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 $155 per night (USD)Expedia
- From $589 per night (USD)
VRBO
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 $589 per night (USD)VRBO
- From $409 per night (USD)
Expedia
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 $409 per night (USD)Expedia
- From $390 per night (USD)
VRBO
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 $390 per night (USD)VRBO
- From $435 per night (USD)
Expedia
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 $435 per night (USD)Expedia
- From $162 per night (USD)
VRBO
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 $162 per night (USD)VRBO
- From $242 per night (USD)
Expedia
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 $242 per night (USD)Expedia
- From $356 per night (USD)
VRBO
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 $356 per night (USD)VRBO
- From $235 per night (USD)
Expedia
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 $235 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $288 per night (USD)
Expedia
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 $288 per night (USD)Expedia
- Click For Pricing
VRBO
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 PricingVRBO
- From $399 per night (USD)
Expedia
**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 $399 per night (USD)Expedia
- From $408 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 $408 per night (USD)VRBO
- From $259 per night (USD)
Expedia
~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 $259 per night (USD)Expedia
- 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 $320 per night (USD)
Expedia
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 $320 per night (USD)Expedia
- From $406 per night (USD)
VRBO
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 $406 per night (USD)VRBO
- Click For Pricing
Expedia
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 PricingExpedia
- From $457 per night (USD)
VRBO
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 $457 per night (USD)VRBO
- From $425 per night (USD)
Expedia
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 $425 per night (USD)Expedia
- From $300 per night (USD)
VRBO
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 $300 per night (USD)VRBO
- 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 $254 per night (USD)
VRBO
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 $254 per night (USD)VRBO
- From $356 per night (USD)
Expedia
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 $356 per night (USD)Expedia
- From $295 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 $295 per night (USD)VRBO
- From $357 per night (USD)
Expedia
KEY COLONY BEACH REMODELED! 80FT DOCK. CABANA CLUB INCLUDED. 331
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
KEYS BEST SECRET ISLAND. NO NEED TO BE ELSE WHERE.. BEAUTIFUL ISLAND, HAS EVERYTHING YOU NEED TO RELAX. 5 STAR RESTAUR ...
From $357 per night (USD)Expedia
- From $444 per night (USD)
VRBO
Elegant ~ Stylish ~ Well-Designed 124 Mariners Club Key Largo
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Ahh...you are here! Villa 124 at Mariners Club is a two bedroom, two and one-half bath luxury villa with stunning harbo ...
From $444 per night (USD)VRBO
- From $307 per night (USD)
Expedia
Island Tides ~ Top Floor ~ Ocean view! 4409 Ocean Pointe Suites
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
No zoom lens required for THIS view! A recently renovated, open concept living area decorated with pops of color and ch ...
From $307 per night (USD)Expedia
- From $425 per night (USD)
VRBO
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy waterfront villa with heated pool and quick access to Ocean and Gulf fishing and diving. Laid back Tiki Hut great f ...
From $425 per night (USD)VRBO
- From $352 per night (USD)
Expedia
Marlin House at Mariner's Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in a secluded and quiet lush tropical setting. This is a Two bedroom, two bath 2nd floor condo with gorgeous ma ...
From $352 per night (USD)Expedia
- From $500 per night (USD)
VRBO
Oceanfront Luxury 'Mar Azul'
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
High-end Estate overlooking tranquil 'Bonefish Flats' in picturesque Marathon. Designer decorated with contemporary colo ...
From $500 per night (USD)VRBO
- From $266 per night (USD)
Expedia
Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Parrotfish Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $266 per night (USD)Expedia
- Click For Pricing
VRBO
The Hammocks- Marathon Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Beautiful centrally located resort with full amenities. Water sport rentals on site, walking distance to restaurants. Ti ...
Click For PricingVRBO
- From $483 per night (USD)
Expedia
Your own tropical oasis! 701 Mariners Club Key Largo
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
It’s time to live the Florida Keys dream! Claim a corner of paradise all for yourself in this 3-story, 3-bedroom, 3-1/2 ...
From $483 per night (USD)Expedia
- From $1619 per night (USD)
VRBO
Lush Garden Estate in Islamorada FL, W\/ Pool, Dockage, Ocean Front & great views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Villa Rental Properties offers this 3 bedroom home with a one bedroom guest house, rents all as one. Located on t ...
From $1619 per night (USD)VRBO
- Click For Pricing
Expedia
Lovely 1\/1 condo with assigned dock on open canal
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy our peaceful and centrally-located condo; in a quiet neighborhood which encourages walking and biking with a boat ...
Click For PricingExpedia
- From $194 per night (USD)
VRBO
Paradise in Plantation Key\/Deep Water Canal House\/Boat Dock\/MM 89
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise in Plantation Key. If you are looking to relax and learn about “Keys Time” you are looking in the right area! ...
From $194 per night (USD)VRBO
- From $515 per night (USD)
Expedia
Oceanfront Balcony w\/Panoramic View, Beach, Pool, Hot Tub, Tennis & Fishing Pier
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Get that peaceful "Keys-y" feeling... Upon entering our luxuriously remodeled condo, you will be impressed with expansiv ...
From $515 per night (USD)Expedia
- From $267 per night (USD)
VRBO
Beachfront Hideaway in the heart of Key Largo! Your own private beach!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
“Treetops” is a truly unique slice of paradise. Nestled amid the trees, with a peekaboo view of the Gulf of Mexico, and ...
From $267 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Your Best Fishing And Relaxing Experience! (2\/2) Waterfront Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This secluded waterfront home is located on a cul-de-sac quiet street mile marker 25. This home has all the amenities yo ...
From $180 per night (USD)Expedia
- From $199 per night (USD)
VRBO
Escape to Sunset Marina-2bed 2bath condo w\/ ocean views, dock space, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and prim ...
From $199 per night (USD)VRBO
- From $506 per night (USD)
Expedia
WOW~ 349\/NT~APRIL-MAY 2024\/~POOL\/LG ICE MACHINE, DOCK~PRIVATE YARD~BOOK TODAY!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Upon entering the driveway to VRBO's Premiere Partner's home, SUNNY DAZE ESCAPE you will know why we are a premiere priv ...
From $506 per night (USD)Expedia
- From $331 per night (USD)
VRBO
Big Pine Key, 3 BR, 2 1\/2 Bath, Private Canal, Close to everything, KW
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Florida Keys, Big Pine Key, located in Big Pine Key Florida. This home was remodeled in 2018 with new everything includi ...
From $331 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful 3 bed\/3 bath Canal Home with Ocean Access in Key largo - 60 foot Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
This beautiful Key Largo 2 story home has 3 bedrooms, 2 bathrooms upstairs with another full bathroom downstairs. This ...
Click For PricingExpedia
- From $250 per night (USD)
VRBO
Bayside: 1st Floor Apartment in Native Hammock on Florida Bay
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a nat ...
From $250 per night (USD)VRBO
- From $344 per night (USD)
Expedia
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $344 per night (USD)Expedia
- From $174 per night (USD)
VRBO
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
water front home is located on 100 foot wide canal with your own 30 feet of Free dockage. We are pet friendly. Furnished ...
From $174 per night (USD)VRBO
- From $367 per night (USD)
Expedia
Key West Affordable Ocean View Condo. Clean priced well on the Atlantic
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to y ...
From $367 per night (USD)Expedia
- Click For Pricing
VRBO
Free Island Sprint has been transformed- Wonderful Renovation done in Fall 21
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lovely 3rd floor interior courtyard view monthly rental. Enjoy the serenity of this bright and airy unit. This unit offe ...
Click For PricingVRBO
- From $443 per night (USD)
Expedia
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA PALMA! PICKLEBALL-KAYAKS- BEACH- POOL
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Palma, Live the Lavish Keys Life in the ultimate vacation rental in Key Largo! With a stellar reputation ...
From $443 per night (USD)Expedia
- From $750 per night (USD)
VRBO
Fish Camp, Fun, Keysy Oasis, with Tiki, pool, dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A funky and fun fisherman's private paradise that we call FISH CAMP, this property has everything needed for a large fam ...
From $750 per night (USD)VRBO
- From $509 per night (USD)
Expedia
Casa Papa Del Mar formerly Ocean Extravaganza - Totally Renovated in 2022.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and ...
From $509 per night (USD)Expedia
- From $365 per night (USD)
VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from ...
From $365 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2 bedroom 2 bath unit, with a lovely view of the Atlantic Ocean. This unit is an extra large floor plan with a ...
From $175 per night (USD)Expedia
- From $156 per night (USD)
VRBO
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
From $156 per night (USD)VRBO
- From $245 per night (USD)
Expedia
~POINCIANA GARDEN~ Casual 1st floor duplex 2 blocks from Duval Street!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
THE PROPERTY: Located on a teeny tiny quiet lane, this comfortably furnished first-floor duplex home comes with Key West ...
From $245 per night (USD)Expedia
- From $395 per night (USD)
VRBO
Key West Beachfront Luxury 2\/2 Condo A212
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 4 ...
From $395 per night (USD)VRBO
- From $135 per night (USD)
Expedia
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fabulous top floor ocean-view penthouse condo. Available during the Spring/Summer Season. Enjoy the Ocean-breeze's from ...
From $135 per night (USD)Expedia
- From $275 per night (USD)
VRBO
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
3 bedroom, 2 bath in private Beachside Resort, yet close to Old Town Key West, just steps to the beach, just a bike ride ...
From $275 per night (USD)VRBO
- From $185 per night (USD)
Expedia
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Coastal East – C231 After a recent remodel of the kitchen and bath, this unit underwent a total makeover with its n ...
From $185 per night (USD)Expedia
- From $509 per night (USD)
VRBO
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon. 2 Bedroom 2 bath suite, some re ...
From $509 per night (USD)VRBO
- From $496 per night (USD)
Expedia
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the ...
From $496 per night (USD)Expedia
- Click For Pricing
Expedia
~ HARRY TRUMAN SUITE ~ Walk to Duval Street from this beautiful property!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
THE PROPERTY: The Harry Truman Suite is on the first floor, in the front of the building. The suites that comprise the T ...
Click For PricingExpedia
- From $403 per night (USD)
Expedia
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
2 Bedroom Garden-View Condo at 1800 Atlantic Key West with king in the Master bedroom, queen in the guest bedroom and a ...
From $403 per night (USD)Expedia
- From $138 per night (USD)
VRBO
Best Downtown Location Monthly Rental Open Nov 2023- Jan 2024
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar ...
From $138 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an e ...
From $175 per night (USD)Expedia
- From $475 per night (USD)
VRBO
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Anchor Drop 307 is an ocean view totally renovated top of the line unit. We have a brand new King mattress in the mast ...
From $475 per night (USD)VRBO
- From $418 per night (USD)
Expedia
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located overlooking the tropical courtyard and garden area. Nicely decorated two bedroom two bath unit. Newly renovated ...
From $418 per night (USD)Expedia
- From $129 per night (USD)
VRBO
Joan's Caribbean Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Just a few minutes from Key West, enjoy the peace and tranquility of this 2 story home, located in the Key West Golf Clu ...
From $129 per night (USD)VRBO
- From $483 per night (USD)
Expedia
NEW! FREE GOLF CART! VOTED #1 RENTAL! CASA AZUL! PICKLEBALL-KAYAKS- BEACH- POOLS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Azul, where The Salt Life Meets Luxury! This licensed and legal vacation rental has received hundreds of ...
From $483 per night (USD)Expedia
- From $149 per night (USD)
VRBO
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen wit ...
From $149 per night (USD)VRBO
- Click For Pricing
Expedia
Ocean Serenity East Endless Ocean Views expansive balcony by Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This is a unique unit with an amazing view of the Atlantic ocean. Your home away from home, all the conveniences you wou ...
Click For PricingExpedia
- From $150 per night (USD)
VRBO
Crystal blue seas, Island Breezes, Morning Sunrises & Key West Island days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Lovely 2nd floor unit. Beautifully renovated, This unit has luxurious finishes. Both bedrooms and the living room open o ...
From $150 per night (USD)VRBO
- From $1116 per night (USD)
Expedia
~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
THE PROPERTY: Come enjoy the Key West cottage lifestyle where you can people watch from your front porch or take a dip ...
From $1116 per night (USD)Expedia
- From $269 per night (USD)
VRBO
No Stairs-Private Tropical Beach-steps from condo-Hi-Speed WIFI-It's Loaded!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ask me about Covid-19 my cancellation policy. Our White Sandy Tropical Private is Beautiful and Private! I also own 3 o ...
From $269 per night (USD)VRBO
- From $175 per night (USD)
Expedia
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a lovely 3rd floor partial ocean-view unit. You will love the spacious 50 ft private balcony that runs the lengt ...
From $175 per night (USD)Expedia
- From $312 per night (USD)
VRBO
NEW!! Thirsty Mermaid - Large 4\/3 Pool Home - RealKeyWest
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Thirsty Mermaid is located in the Casa Marina area just minutes from the Atlantic Ocean. This beautiful property has 2 f ...
From $312 per night (USD)VRBO
- From $349 per night (USD)
Expedia
Duck Key Darling: Remodeled 2-Bedroom, 2-Bath Townhouse with Exclusive Cabana
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Experience the epitome of luxury at Duck Key Darling, a splendid 2-bedroom, 2-bath Townhouse Villa nestled within Hawks ...
From $349 per night (USD)Expedia
- From $165 per night (USD)
VRBO
Couples paradise-king bed\/AC\/kayaks for your use\/fishing\/snorkeling\/diving
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Comforting king size bed with an extra room for storage or office, and perfect outdoor living space make for a great cou ...
From $165 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w\/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $200 per night (USD)Expedia
- From $209 per night (USD)
VRBO
Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...
From $209 per night (USD)VRBO
- From $191 per night (USD)
Expedia
Breezy Half-Duplex with 35 Ft. Dock. - Cabana Club Access with Pool and Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Breezy Palms Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $191 per night (USD)Expedia
- From $216 per night (USD)
VRBO
Dog-friendly waterfront home with dock, pool, gas grill, & beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Ninth Street Getaway Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $216 per night (USD)VRBO
- From $211 per night (USD)
Expedia
Gulf Pointe Paradise
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Gulf Pointe Paradise is a tranquil townhouse featuring a balcony with sweeping Gulf of Mexico views. Dockage is availabl ...
From $211 per night (USD)Expedia
- From $476 per night (USD)
VRBO
Oceanfront Duplex with Beautiful Beach & Dock for Boat Access - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The Zane Grey Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $476 per night (USD)VRBO
- From $187 per night (USD)
Expedia
Waterfront home with 24-foot dock, shared pool, & beach access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Key Lime on Fifth Street Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $187 per night (USD)Expedia
- From $186 per night (USD)
VRBO
Waterfront Home with 35-Foot Dock, Bay Views, WiFi, and Shared Pool and Beach
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Tropical Charm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $186 per night (USD)VRBO
- From $269 per night (USD)
Expedia
Breezy waterfront home with pool, 35-foot dock & cabana club access
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Captain's Haven Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $269 per night (USD)Expedia