Monroe Area Rentals
From $338 per night (USD)VRBO
Family Condo in Tavernier Close to Fishing, Dive\/Snorkel Boats, Eco Tours
- 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 $338 per night (USD)VRBO
From $816 per night (USD)VRBO
Bayfront Home with Beach & Open Water Views! Amazing Sunsets!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Best kept secret in the Florida Keys!!! Our many repeat customers and great reviews attest to our gorgeous beachfront pr ...
From $816 per night (USD)VRBO
From $388 per night (USD)VRBO
Harbor House 2bed 2bath Open water views & dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $388 per night (USD)VRBO
From $629 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 $629 per night (USD)Expedia
From $676 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 $676 per night (USD)VRBO
From $485 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 $485 per night (USD)Expedia
From $291 per night (USD)VRBO
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 $291 per night (USD)VRBO
From $190 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 $190 per night (USD)Expedia
From $669 per night (USD)VRBO
Fantastic Fall Special - Act Fast, Open Nights Won't Last
- 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 $669 per night (USD)VRBO
From $1134 per night (USD)Expedia
Casa Blanca By the Gulf 5 bedroom 3 bath with pool and dockage, kayaks, bikes,
- Bedrooms:
- 3
- Bathrooms:
- 6
- 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 $1134 per night (USD)Expedia
From $661 per night (USD)VRBO
5 Seas Retreat 4 bed 2 bath dock, pool, Sandy Beach Dockage For up to a 25 ft
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Sandy Beach a Rarety for the Keys. Gorgeous open water sunset views await you at this fully furnished tropical waterfron ...
From $661 per night (USD)VRBO
From $686 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 $686 per night (USD)Expedia
From $1102 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 $1102 per night (USD)VRBO
From $756 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 $756 per night (USD)Expedia
From $240 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 $240 per night (USD)VRBO
Click For PricingExpedia
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 $962 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 $962 per night (USD)VRBO
From $664 per night (USD)Expedia
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 $664 per night (USD)Expedia
From $761 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 $761 per night (USD)VRBO
From $306 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 $306 per night (USD)Expedia
From $857 per night (USD)VRBO
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 $857 per night (USD)VRBO
From $1042 per night (USD)Expedia
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 $1042 per night (USD)Expedia
From $220 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 $220 per night (USD)VRBO
From $570 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 $570 per night (USD)Expedia
From $532 per night (USD)VRBO
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 $532 per night (USD)VRBO
From $387 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 $387 per night (USD)VRBO
From $2029 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 $2029 per night (USD)VRBO
From $224 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 $224 per night (USD)Expedia
From $402 per night (USD)VRBO
South Point Sunset - Florida Keys waterfront
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Home is currently listed for sale so guests will be given 24hr notice for showing. Nicely appoin ...
From $402 per night (USD)VRBO
From $349 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 $349 per night (USD)Expedia
From $247 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 $247 per night (USD)VRBO
From $267 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 $267 per night (USD)Expedia
From $240 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 $240 per night (USD)VRBO
From $443 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 $443 per night (USD)Expedia
From $395 per night (USD)VRBO
Vaca Cove unit D Sunset Pointe 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
VACA-23-232 Vaca Cove is a private oasis comprised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf ac ...
From $395 per night (USD)VRBO
From $425 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 $425 per night (USD)Expedia
From $245 per night (USD)VRBO
Paradise Found- Scuba Divers Welcome- Best Fishing Glamping-Key Largo-Kampground
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Private house newly renovated kitchen & bath in Key Largo Kampground. The house is fully stocked with everything you nee ...
From $245 per night (USD)VRBO
From $303 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 $303 per night (USD)Expedia
From $354 per night (USD)VRBO
Vaca Cove G Beach Daze 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View with
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
VACA-22-102 Vaca Cove is a private oasis comprised of 7 stilted homes facing Shelter Bay, with direct Ocean and Gulf ac ...
From $354 per night (USD)VRBO
From $429 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 $429 per night (USD)Expedia
Click For PricingVRBO
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 $341 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 $341 per night (USD)Expedia
Click For PricingVRBO
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 $405 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 $405 per night (USD)Expedia
From $1025 per night (USD)VRBO
**COLORS OF THE KEYS @ THE FOUNDRY** Villa Near Duval & Beach + LAST KEY SERVICE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! COLORS OF THE ...
From $1025 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 $407 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 $407 per night (USD)VRBO
From $756 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 $756 per night (USD)Expedia
Click For PricingVRBO
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 $370 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 $370 per night (USD)Expedia
From $466 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 $466 per night (USD)VRBO
From $689 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 $689 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 $292 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 $292 per night (USD)Expedia
From $516 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 $516 per night (USD)VRBO
From $430 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 $430 per night (USD)Expedia
From $569 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 $569 per night (USD)VRBO
From $487 per night (USD)Expedia
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 $487 per night (USD)Expedia
From $391 per night (USD)VRBO
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 $391 per night (USD)VRBO
From $502 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 $502 per night (USD)Expedia
From $555 per night (USD)VRBO
OCEANFRONT Private Pool Dock Approved Pet 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 $555 per night (USD)VRBO
From $368 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 $368 per night (USD)Expedia
Click For PricingVRBO
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 $586 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 $586 per night (USD)Expedia
Click For PricingVRBO
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 $195 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 $195 per night (USD)Expedia
From $1863 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 $1863 per night (USD)VRBO
From $549 per night (USD)Expedia
15% OFF~ \"BOOK ANY DAY\" SUMMER\/FALL 2024\/~POOL\/LG ICE MACHINE, DOCK~BOOK NOW~
- 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 $549 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
**** THE HOUSE IS NOW PAINTED WHITE, HAS A NEW FRESH LOOK**** Florida Keys, Big Pine Key, located in Big Pine Key Florid ...
From $331 per night (USD)VRBO
From $238 per night (USD)Expedia
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 $238 per night (USD)Expedia
From $530 per night (USD)VRBO
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 $530 per night (USD)VRBO
From $452 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 $452 per night (USD)VRBO
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 located on a cul-de-sac quiet street mile marker 25. This home has all the amenities yo ...
From $212 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 $305 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 $305 per night (USD)VRBO
From $663 per night (USD)Expedia
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has ...
From $663 per night (USD)Expedia
From $265 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 $265 per night (USD)VRBO
From $771 per night (USD)Expedia
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to y ...
From $771 per night (USD)Expedia
From $180 per night (USD)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 ...
From $180 per night (USD)VRBO
From $601 per night (USD)Expedia
NEW! GOLF CART! VOTED #1! OCEANSIDE CASA PALMA! PICKELB-KAYAKS- 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 $601 per night (USD)Expedia
From $771 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 $771 per night (USD)VRBO
From $1168 per night (USD)Expedia
Casa Papa Del Mar on the Atlantic Spectacular views close to Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Casa Papa Del Mar Two Bedroom Premiere Ocean View With a complete 2023 renovation, the décor is inspired by the life and ...
From $1168 per night (USD)Expedia
From $511 per night (USD)VRBO
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Moonlight" is a freshly renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from ...
From $511 per night (USD)VRBO
From $226 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 $226 per night (USD)Expedia
From $214 per night (USD)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 ...
From $214 per night (USD)VRBO
From $655 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 $655 per night (USD)Expedia
From $640 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 $640 per night (USD)VRBO
From $175 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 $175 per night (USD)Expedia
From $329 per night (USD)VRBO
Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Keys to Paradise: A 5-Star Beachside Retreat This beautiful 3-bedroom, 2-bath condo is located in a private beachside r ...
From $329 per night (USD)VRBO
From $214 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 $214 per night (USD)Expedia
From $1202 per night (USD)VRBO
Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Grand Vista - 2 bedroom suite - Totally renovated in 2022 - pictures coming soon. 2 Bedroom 2 bath suite, some re ...
From $1202 per night (USD)VRBO
From $714 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 Completely renovated, this unit features an entirely custom tiled unit. Full ...
From $714 per night (USD)Expedia
From $689 per night (USD)VRBO
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
2 Bedroom, 2 Bath Garden View Condo at 1800 Atlantic, Key West This beautifully renovated condo features a king bed in ...
From $689 per night (USD)VRBO
From $215 per night (USD)Expedia
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 $215 per night (USD)Expedia
From $200 per night (USD)VRBO
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 $200 per night (USD)VRBO
From $547 per night (USD)Expedia
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 $547 per night (USD)Expedia
From $668 per night (USD)VRBO
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautifully decorated two-bedroom, two-bath unit overlooks a tropical courtyard and garden area. The bathrooms have ...
From $668 per night (USD)VRBO
From $313 per night (USD)Expedia
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 $313 per night (USD)Expedia
From $620 per night (USD)VRBO
NEW! GOLF CART! VOTED #1 OCEANSIDE CASA AZUL! PICKLEBA-KAYAKS- 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 $620 per night (USD)VRBO
From $329 per night (USD)Expedia
Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated, this 2-bedroom, 2-bath penthouse offers stunning views of the Atlantic Ocean and Smathers Beach. ...
From $329 per night (USD)Expedia