
Monroe Area Rentals

- From $513 per night (USD)
VRBO
BOOKING SMOKING HOT 2025 DEALS NOW!
- 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 $513 per night (USD)VRBO
- From $266 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 $266 per night (USD)Expedia
- From $1202 per night (USD)
VRBO
Paradise Cove on the Gulf 5 bedroom 3 bath with pool and dockage, kayaks, bikes,
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Vaca-21-484 Paradise Cove on The Gulf is a Florida Keys Paradise for Everyone. This is a modern design home with sleek ...
From $1202 per night (USD)VRBO
- From $619 per night (USD)
Expedia
408 Mariners Club oceanfront | 3 Bed, 3 Bath
- 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 $619 per night (USD)Expedia
- From $962 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 $962 per night (USD)VRBO
- From $690 per night (USD)
Expedia
801 Mariners Club Key Largo | 4 Bed, 4 Bath
- 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 $690 per night (USD)Expedia
- From $210 per night (USD)
VRBO
Lush Gardens-Pool-Jacuzzi-No Contact Check-In
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $210 per night (USD)VRBO
- Click For Pricing
Expedia
FANTASY WEEK
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $628 per night (USD)
VRBO
Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 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 $628 per night (USD)VRBO
- From $151 per night (USD)
Expedia
Petite Pearl! Spacious 1 Bedroom, 1 Bath Pool Condo- RealKeyWest
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Petite Pearl, your hidden gem nestled in the heart of the coveted Meadows district in Key West. A stone's thr ...
From $151 per night (USD)Expedia
- From $1077 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 $1077 per night (USD)VRBO
- From $908 per night (USD)
Expedia
Waterfront home with Cabana Club access, private pool, spa, & 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 $908 per night (USD)Expedia
- From $955 per night (USD)
VRBO
Historic Old Town Key West - Turtle House, Sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
OVERVIEW The Turtle House is a 100+ year old recently completely renovated “Conch” house. The house can be described as ...
From $955 per night (USD)VRBO
- From $231 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 $231 per night (USD)Expedia
- From $667 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 $667 per night (USD)VRBO
- From $410 per night (USD)
Expedia
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $410 per night (USD)Expedia
- From $332 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 $332 per night (USD)VRBO
- From $1677 per night (USD)
Expedia
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 $1677 per night (USD)Expedia
- From $394 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 $394 per night (USD)VRBO
- From $230 per night (USD)
Expedia
Amazing newly remodeled Coastal Condo w Ocean view
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Newly remodeled Condo come be amazed. Come enjoy this new super comfy Condo, loaded with amenities, maybe the nicest in ...
From $230 per night (USD)Expedia
- From $274 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 $274 per night (USD)VRBO
- From $285 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 $285 per night (USD)Expedia
- From $221 per night (USD)
VRBO
Our Happy Place 2 bed 2 bath with Boat slip Open water views of Boot Key Harbor
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $221 per night (USD)VRBO
- From $534 per night (USD)
Expedia
Vaca Cove unit A Shore Thang 4 Bedrooms 3 Baths, Pool, Ocean View with Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
VACA-23-193 Built in 2016, this rental offers beautiful Bonefish Bay views and private boat access. This home features ...
From $534 per night (USD)Expedia
- From $613 per night (USD)
VRBO
Vaca Cove unit D Sunset Pointe 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
VACA-23-232 Vaca Cove is a private oasis comprised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf ac ...
From $613 per night (USD)VRBO
- From $582 per night (USD)
Expedia
Vaca Cove B Sea Forever 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View with
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
VACA-22-360 Built in 2016, this rental offers beautiful Bonefish Bay views and private boat access. This home features ...
From $582 per night (USD)Expedia
- From $228 per night (USD)
VRBO
Paradise Found- Scuba Divers-Boat Owners Welcome-Key Largo-Kampground
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 2 bedroom home in gated community. Newly renovated full size kitchen & bath, large refridgerator with ice make ...
From $228 per night (USD)VRBO
- From $409 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 $409 per night (USD)Expedia
- From $635 per night (USD)
VRBO
Vaca Cove G Life’s a Marathon 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
VACA-22-102 Vaca Cove is a private oasis comprised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf ac ...
From $635 per night (USD)VRBO
- From $319 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 $319 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:
- 2
- 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 $500 per night (USD)
Expedia
Waterfront Home w\/ Private Dock, Outdoor Shower & Home Office - Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Casa Palmera Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $500 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 $340 per night (USD)
Expedia
B307 Moon Bay | 3 Bed, 2.5 Bath
- 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 $340 per night (USD)Expedia
- From $682 per night (USD)
VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 3
- Bathrooms:
- 1
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $682 per night (USD)VRBO
- From $480 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 $480 per night (USD)VRBO
- From $597 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 $597 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 $459 per night (USD)
VRBO
RELAX AWAY- NEW 4BDRM W\/ 40FT DOCK & PRIVATE POOL
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
RELAX AWAY @ SOMBRERO (Marathon Lic # VACA-22-432) - ENJOY OUR NEW 1800 SQ FT HOME, 4/3 WITH COVERED BALCONY & PATIO & S ...
From $459 per night (USD)VRBO
- From $374 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 $374 per night (USD)Expedia
- From $361 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 $361 per night (USD)VRBO
- From $316 per night (USD)
Expedia
Tranquil Top Floor Condo w\/ Ocean Views close to Attractions in the Upper Keys
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Atlantic Ocean greets you in this charming 1 bedroom condo on the top floor of building two, located in Ocean Pointe ...
From $316 per night (USD)Expedia
- From $501 per night (USD)
VRBO
Hidden Paradise: A Serene Waterside Retreat - 3-Bedroom, 3-Bath Single Family
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover comfort and ample space in this three-bedroom waterfront oasis, a perfect single family abode that boasts an ex ...
From $501 per night (USD)VRBO
- From $399 per night (USD)
Expedia
KEY COLONY BEACH Island Paradise! 80FT DOCK. 331
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
KEYS BEST SECRET ISLAND. HAS EVERYTHING YOU NEED TO RELAX. 5 STAR RESTAURANTS, BARS, CAFE’S, MARINA, POST OFFICE, BOUT ...
From $399 per night (USD)Expedia
- From $489 per night (USD)
VRBO
124 Mariners Club Key Largo | 2 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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 $489 per night (USD)VRBO
- From $365 per night (USD)
Expedia
4409 Ocean Pointe Suites | 2 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
No zoom lens required for THIS view! A recently renovated, open concept living area decorated with pops of color and ch ...
From $365 per night (USD)Expedia
- From $488 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 $488 per night (USD)VRBO
- From $761 per night (USD)
Expedia
Marlin House at Mariner's Club
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $761 per night (USD)Expedia
- From $571 per night (USD)
VRBO
OCEANFRONT Private Pool Dock Approved Dog OK! Gated Estate - A Tropical Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Mar Azul is a High-end Oceanfront Residence overlooking the tranquil Offshore Flats of Marathon. Enjoy a Secluded, Luxur ...
From $571 per night (USD)VRBO
- From $516 per night (USD)
Expedia
Amazing waterfront home with private beach, dock, pool, WiFi & outdoor kitchen
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Parrotfish Point Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $516 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 $569 per night (USD)
Expedia
701 Mariners Club Key Largo | 3 Bed, 3.5 Bath
- Bedrooms:
- 4
- Bathrooms:
- 4
- 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 $569 per night (USD)Expedia
- Click For Pricing
VRBO
Lovely 1\/1 condo with assigned dock on open canal
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy our peaceful and centrally-located condo; in a quiet neighborhood which encourages walking and biking with a boat ...
Click For PricingVRBO
- From $257 per night (USD)
Expedia
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 $257 per night (USD)Expedia
- From $1322 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 $1322 per night (USD)VRBO
- From $669 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 $669 per night (USD)Expedia
- From $361 per night (USD)
VRBO
Beachfront Hideaway in the heart of Key Largo! Your own private beach!
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $361 per night (USD)VRBO
- From $579 per night (USD)
Expedia
FISHERMAN'S PARADISE~POOL\/ICE MACHINE, DOCK~ONLY 399\/NT APRIL\/MAY 2025-NO HLDYS
- 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 $579 per night (USD)Expedia
- From $212 per night (USD)
VRBO
Your Best Fishing And Relaxing Experience! 2\/2 Waterfront Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
This secluded waterfront home is on a quiet dead-end street at mile marker 25. It offers all the amenities you need to e ...
From $212 per night (USD)VRBO
- From $375 per night (USD)
Expedia
Big Pine Key, 3 BR, 2 1\/2 Bath, Private Canal, Close to everything, KW
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
**** THE HOUSE IS NOW PAINTED WHITE, HAS A NEW FRESH LOOK**** Florida Keys, Big Pine Key, located in Big Pine Key Florid ...
From $375 per night (USD)Expedia
- From $220 per night (USD)
VRBO
Hidden Paradise-2bed 2bath condo w\/ ocean views, dock space, pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
AGE REQUIREMENT: Everyone must be 25 years or older. Families are welcome as long as children are accompanied with their ...
From $220 per night (USD)VRBO
- From $347 per night (USD)
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 ...
From $347 per night (USD)Expedia
- From $354 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 $354 per night (USD)VRBO
- From $535 per night (USD)
Expedia
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $535 per night (USD)Expedia
- From $543 per night (USD)
VRBO
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $543 per night (USD)VRBO
- From $535 per night (USD)
Expedia
NEW! OCEANSIDE CASA PALMA!VOTED #1! GOLF CART-PICKELBAL\n-KAYAK- BEACH- POOL-FISH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Palma, Live the Lavish Keys Life in the ultimate oceanside vacation rental in Key Largo! With a stellar ...
From $535 per night (USD)Expedia
- From $1649 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 $1649 per night (USD)VRBO
- From $701 per night (USD)
Expedia
Casa Papa Del Mar Ocean Front 1800 Atlantic spectacular view and Island charm
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $701 per night (USD)Expedia
- From $496 per night (USD)
VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $496 per night (USD)VRBO
- From $229 per night (USD)
Expedia
Ocean Front Key West Oasis Island Tones Charming Historical Downtown area
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $229 per night (USD)Expedia
- Click For Pricing
VRBO
Key West Paradise, Conch Hideaway, Island Vibrations, Balmy Ocean Breezes KWF
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This property features an extra large floor plan from the popular B building at 1800 Atlantic. Enjoy the flow through br ...
Click For PricingVRBO
- From $430 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 $430 per night (USD)Expedia
- From $172 per night (USD)
VRBO
Best Downtown Location Monthly Rental open March 7th 2025 Great deal
- 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 $172 per night (USD)VRBO
- From $571 per night (USD)
Expedia
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 $571 per night (USD)Expedia
- From $167 per night (USD)
VRBO
Vibrant Island retreat, Expansive private balcony, Enjoy the Coastal Breezes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $167 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $315 per night (USD)Expedia
- From $212 per night (USD)
VRBO
Casa Coastal East, Morning sunrises, Evening night time vibes An Island home.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $212 per night (USD)VRBO
- From $667 per night (USD)
Expedia
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $667 per night (USD)Expedia
- From $633 per night (USD)
VRBO
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $633 per night (USD)VRBO
- From $566 per night (USD)
Expedia
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $566 per night (USD)Expedia
- From $196 per night (USD)
VRBO
Carolina to Keys Ocean view dream Monthly pricing Best pool on the Island
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $196 per night (USD)VRBO
- From $638 per night (USD)
Expedia
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $638 per night (USD)Expedia
- From $551 per night (USD)
VRBO
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $551 per night (USD)VRBO
- From $577 per night (USD)
Expedia
NEW! OCEANSIDE CASA AZUL!VOTED #1! GOLF CART-PICKELBALL-KAYAK- BEACH- POOLS-FISH
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Casa Azul, where The Salt Life Meets Luxury! This oceanside licensed and legal vacation rental has received h ...
From $577 per night (USD)Expedia
- Click For Pricing
VRBO
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This beautifully renovated 2-bedroom, 2-bath penthouse offers stunning views of the Atlantic Ocean and Smathers Beach. T ...
Click For PricingVRBO
- From $242 per night (USD)
Expedia
Oceanfront Overlook in open for March of 2025 - Key West's Finest
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Oceanfront Overlook is a unique unit with an amazing view of the Atlantic Ocean, your perfect home away from home, equip ...
From $242 per night (USD)Expedia
- From $212 per night (USD)
VRBO
Sea La Vie, Island Breezes, Morning Sunrises & Key West Island days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $212 per night (USD)VRBO
- From $1603 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 $1603 per night (USD)Expedia
- From $313 per night (USD)
VRBO
Private Beach steps from condo-no stairs-king size bed-fast wifi-it's loaded.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our White Sandy Tropical Private is Beautiful and Private! I also own 3 other listings at the same location and all of t ...
From $313 per night (USD)VRBO
- From $196 per night (USD)
Expedia
Island Style, Morning Sunrises, Salty Ocean Breezes & Downtown Key West days.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
CONSTRUCTION NOTICE - There will be concrete restoration project happening at 1800 Atlantic Starting in May 2025 through ...
From $196 per night (USD)Expedia
- From $409 per night (USD)
VRBO
Thirsty Mermaid - Large 4\/3 Pool Home
- 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 $409 per night (USD)VRBO
- From $457 per night (USD)
Expedia
Duck Key Darling: 2-Bedroom, 2-Bath Townhouse with Exclusive Cabana Club Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience the epitome of luxury at Duck Key Darling, a splendid 2-bedroom, 2-bath Townhouse Villa nestled within Hawks ...
From $457 per night (USD)Expedia
- From $221 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 $221 per night (USD)VRBO
- From $222 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w\/Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $222 per night (USD)Expedia
- From $319 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 $319 per night (USD)VRBO
- From $414 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 $414 per night (USD)Expedia
- From $317 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 $317 per night (USD)VRBO
- From $337 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 $337 per night (USD)Expedia
- From $861 per night (USD)
VRBO
Oceanfront Duplex with Beautiful Beach & Dock for Boat Access - Dogs OK
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
The Zane Grey Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $861 per night (USD)VRBO
- From $277 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 $277 per night (USD)Expedia