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From $734 per night (USD)
VRBO
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites - CLEANING FEE INCLUDED
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $734 per night (USD)
VRBO
From $750 per night (USD)
Expedia
4-Bed 4.5 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED Non-Waterfront
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $750 per night (USD)
Expedia
From $669 per night (USD)
VRBO
3 Bed 3 Bath Condo @ Bayfront Suites - CLEANING FEE INCLUDED (Non-Waterfront)
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $669 per night (USD)
VRBO
From $679 per night (USD)
Expedia
4-Bed, 3-Bath Waterfront Condo at Bayfront Suites -CLEANING FEE INCLUDED
Bedrooms:
3
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 $740 per night (USD)
VRBO
4-Bed, 4.5 Bath Condo & Bayfront Suites-non waterfront CLEANING FEE INCLUDED
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $740 per night (USD)
VRBO
From $597 per night (USD)
Expedia
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina- CLEANING FEE INCLUDED
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Bayfront Suites offers incredibly spacious, meticulously designed homes for a variety of guests. In this specific proper ...
From $597 per night (USD)
Expedia
From $348 per night (USD)
VRBO
Tavernier Oceanfront Resort Condo-Pool, Dockage, Kayaks, Onsite Restaurant & Bar
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 $348 per night (USD)
VRBO
From $423 per night (USD)
Expedia
Marathon 3BR on 55' Canal Boat Dock w Pool Spa Hot Tub Free pool heat bay side
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Mirage Manor — your private waterfront escape in the beautiful Florida Keys. Perfectly situated on a quiet b ...
From $423 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water ...incredible views. ...
From $324 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Its an enjoyable two bed/bath unit with pleasant view of the marina and 0cean.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your Newly Renovated Oceanfront Vacation Home: In June 2018, the Condo unit had a total renovation including installati ...
From $240 per night (USD)
Expedia
From $214 per night (USD)
VRBO
coral stone 28 day minimum rental
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 $214 per night (USD)
VRBO
From $572 per night (USD)
Expedia
FULL TIME MGR - LUXURY PENTHOUSE - OFFERS KEY LARGO'S BEST PANORAMIC OCEAN VIEWS
Bedrooms:
2
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 $572 per night (USD)
Expedia
From $253 per night (USD)
VRBO
Spring & summer dates available licensed rental vr #25-0235 NO BOATS
Bedrooms:
1
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 $253 per night (USD)
VRBO
From $344 per night (USD)
Expedia
Charming Cabana-Condo in Picturesque Tavernier
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Nestled in the heart of the Florida Keys, in the picturesque city of Tavernier, this charming oceanfront condo ...
From $344 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Waterfront luxury Villa (59) with sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This recently renovated and spacious 3BD, 2.5BA Villa is the perfect blend of comfort and coastal charm. Each bedroom fe ...
From $540 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Harbor House a quaint 2bed/2bath open water single family home with 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 $353 per night (USD)
Expedia
From $303 per night (USD)
VRBO
Paradise found at the Key West Golf Club!
Bedrooms:
1
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 $303 per night (USD)
VRBO
From $522 per night (USD)
Expedia
Summer is here! Don't wait- book your dream stay 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 $522 per night (USD)
Expedia
From $1138 per night (USD)
VRBO
Paradise Cove on the Gulf 5 bedroom 3 bath with pool Ice Machince dockage, kayaks, bikes, paddleboards and more
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Vaca-24-265 Paradise Cove on The Gulf is a Florida Keys Paradise for Everyone. This is a modern design home with sleek ...
From $1138 per night (USD)
VRBO
From $596 per night (USD)
Expedia
5 Seas Retreat 4 bed 2 bath dock, pool, Sandy Beach Dockage For up to a 25 ft boat
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Vaca-25-71 Sandy Beach is a rarity for the Keys. Gorgeous open water sunset views await you at this fully furnished tro ...
From $596 per night (USD)
Expedia
From $781 per night (USD)
VRBO
408 Mariners Club - Stunning 3 bedroom oceanfront retreat
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to Townhouse 408 — a stunning, ocean-view retreat where luxury meets tranquillity. Perfectly positioned overlook ...
From $781 per night (USD)
VRBO
From $1080 per night (USD)
Expedia
Egret House @ Tarpon Point
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Indulge in breathtaking ocean vistas from every living level, complemented by an inviting waterfront pool! The ...
From $1080 per night (USD)
Expedia
From $691 per night (USD)
VRBO
801 Mariners Club - Luxury Key Largo Townhouse
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 wit ...
From $691 per night (USD)
VRBO
From $233 per night (USD)
Expedia
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 $233 per night (USD)
Expedia
From $607 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 $607 per night (USD)
VRBO
From $459 per night (USD)
Expedia
*Newly Renovated Single Family Home w/Private Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Perfectly situated in KCB w/ up to 50' dockage on a wide and pristine canal that leads easy access to both the Ocean & t ...
From $459 per night (USD)
Expedia
From $958 per night (USD)
VRBO
Historic Old Town Key West - Turtle House, Sleeps 6
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 $958 per night (USD)
VRBO
$Stunning Ocean View/Sunsets, A true \Gem by the Sea\ great for relaxation & fun$
From $258 per night (USD)
Expedia
Stunning Ocean View/Sunsets, A true \"Gem by the Sea\" great for relaxation & fun
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Beautiful 2 Bedroom, 1 1/2 bathroom Condo with den with a futon, located in Moon Bay located in Key Largo. Property is ...
From $258 per night (USD)
Expedia
From $643 per night (USD)
VRBO
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach, plus Den
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come stay at the Salty Pelican in Angler's Reef! Recently updated 2 bedroom 2 bath plus a den downstairs with a pull out ...
From $643 per night (USD)
VRBO
From $378 per night (USD)
Expedia
CLEAR water views @Tiki haven! Quick ocean access, Pool, HotTub, FUN! FREE ICE!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VIEWS to live for!! Book this 2 bed 2 baths side for the family or RENT the ENTIRE DUPLEX & book the 1 bed 1 bath (Pro ...
From $378 per night (USD)
Expedia
From $255 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 $255 per night (USD)
VRBO
From $228 per night (USD)
Expedia
Amazing newly remodeled Coastal Condo w Ocean view
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
Newly remodeled Condo come be amazed. Come enjoy this new super comfy Condo, loaded with amenities, maybe the nicest in ...
From $228 per night (USD)
Expedia
From $415 per night (USD)
VRBO
Seascape Vacation!!!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Beautiful vacation spot perfect for you and your family.This wonderful one bedroom home filled with colorful patterns ca ...
From $415 per night (USD)
VRBO
From $441 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 $441 per night (USD)
Expedia
From $629 per night (USD)
VRBO
Shore Thang at Vaca Cove 4 Bedrooms 3 Baths, Pool, Ocean View with Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Vaca-23-193 Shore Thang: A Waterfront Paradise with Boating, Fishing & Luxury Living Welcome to Shore Thang, a stunnin ...
From $629 per night (USD)
VRBO
From $385 per night (USD)
Expedia
Sunset Pointe at Vaca Cove4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View with Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Vaca-23-232 Vaca Cove: Your Private Waterfront Oasis in the Florida Keys Welcome to Vaca Cove, a serene retreat locate ...
From $385 per night (USD)
Expedia
From $655 per night (USD)
VRBO
Sea Forever at Vaca Cove 4 Bed 3 Baths, Saltwater Pool, Jacuzzi, Ocean View with Dock
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Vaca-22-360 Built in 2016, this rental offers beautiful Bonefish Bay views and private boat access. This home features ...
From $655 per night (USD)
VRBO
From $241 per night (USD)
Expedia
Paradise Found- Scuba Divers-Boat Owners Welcome-Key Largo-Kampground
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Charming 2 bedroom home in gated community. Newly renovated full size kitchen & bath, large refridgerator with ice make ...
From $241 per night (USD)
Expedia
Click For Pricing
VRBO
Open Water Paradise 2/2 Half Duplex in Key Colony Beach at Marathon, FL
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Welcome to Open Water Paradise in the Keys. Ocean living at its Best! Nestled along Bonefish Bay, Open Water Paradise ...
Click For Pricing
VRBO
From $333 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 $333 per night (USD)
Expedia
From $311 per night (USD)
VRBO
B307 Moon Bay - 3 bedroom end unit with gourmet kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This fully renovated bay front end-unit condo in Moon Bay has been reconfigured to allow for each bedroom to have its ow ...
From $311 per night (USD)
VRBO
From $289 per night (USD)
Expedia
**COLORS OF THE KEYS** Villa Near Duval + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! COLORS OF THE ...
From $289 per night (USD)
Expedia
From $400 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 $400 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Renovated 2BR Villa with Spa, Water Views & Private Patio with Private Dip Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
We offer nightly and weekly rentals, you can save money by booking directly from an owner. We would love to host your ...
From $459 per night (USD)
Expedia
From $336 per night (USD)
VRBO
Tranquility on the Top Floor - Ocean Pointe 2404
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Escape to Ocean Pointe 2404, a serene oceanfront condominium in Tavernier, your perfect Florida Keys retreat. ...
From $336 per night (USD)
VRBO
From $554 per night (USD)
Expedia
Hidden Paradise 3bed/3bath single family home with open water views & dockage
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 $554 per night (USD)
Expedia
From $409 per night (USD)
VRBO
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 $409 per night (USD)
VRBO
From $539 per night (USD)
Expedia
124 Mariners Club - Luxury villa with stunning harbor and ocean view
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ahh...you are here! Villa 124 at Mariners Club is a two-bedroom, two-and-a-half-bath luxury villa with stunning harbor ...
From $539 per night (USD)
Expedia
From $498 per night (USD)
VRBO
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 c ...
From $498 per night (USD)
VRBO
From $534 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 $534 per night (USD)
Expedia
From $517 per night (USD)
VRBO
Tropical Escape at Mariner’s Club 2BR Key Largo Condo w/ Pools & Marina
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Mariner’s Club Key Largo, a private oceanfront resort offering the ultimate blend of relaxation and adventure ...
From $517 per night (USD)
VRBO
From $591 per night (USD)
Expedia
OCEANFRONT with Pool & Dock - Approved Dog OK! Gated Estate - A Tropical Oasis!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Mar Azul is a High-end Oceanfront Residence overlooking the tranquil Offshore Flats of Marathon. Enjoy a Secluded, Luxur ...
From $591 per night (USD)
Expedia
From $598 per night (USD)
VRBO
701 Mariners Club Live the Florida Keys dream!
Bedrooms:
3
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 $598 per night (USD)
VRBO
Click For Pricing
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! ...
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Expedia
From $433 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 $433 per night (USD)
VRBO
From $622 per night (USD)
Expedia
September, 2026~399/NT~ BOOK ANY 7 DAYS~POOL/ICE MCHN, SEE VIDEO OF OUR HOME!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
**OUR VACATION RENTAL PROVIDES A WALK AROUND VIDEO TO HELP YOU SEE WHAT YOU ARE BOOKING AND TO HELP WITH PLANNING ON YOU ...
From $622 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Big Pine Key, 3 BR, 2 1/2 Bath, Private Canal, Close to everything, KW
Bedrooms:
2
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 $314 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Bayside is a first floor apartment overlooking the beautiful waters of Florida Bay. Bayside is located on a small resort ...
From $287 per night (USD)
Expedia
From $492 per night (USD)
VRBO
Key West On My Mind, Ocean Views, Renovated Kitchen, Last minute deals
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Stunning 2-Bedroom Ocean-View Oasis at 1800 Atlantic – Key West Welcome to your perfect tropical escape! This beautiful ...
From $492 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Premier Ocean views, expansive balcony, renovated kitchen & bath 2024
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 $527 per night (USD)
Expedia
From $613 per night (USD)
VRBO
NEW! Casa Palma - NO HIDDEN FEES! Golf Cart, 2 King, Pool, Beach, Tennis, Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
No Hidden Fees! Book any of my homes with confidence. Unlike many vacation rentals, I don't add resort, guest, or manage ...
From $613 per night (USD)
VRBO
From $859 per night (USD)
Expedia
Perfect 7-Night Keys Getaway: Pool, Tiki & Dock
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
🐠 Fish Camp – Private Keys Oasis | Pool, Tiki Bar, 5-Bay Dock Welcome to Fish Camp – your private, gated slice of parad ...
From $859 per night (USD)
Expedia
From $573 per night (USD)
VRBO
Casa Papa Del Mar Ocean Front 1800 Atlantic spectacular view and Island charm
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 $573 per night (USD)
VRBO
From $492 per night (USD)
Expedia
Moonlight Paradise Upgraded Family oasis Tropical views expansive balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Moonlight Luxury Beachfront Condo in Key West Your Private Oasis on the Beach Escape to paradise at Moonlig ...
From $492 per night (USD)
Expedia
From $220 per night (USD)
VRBO
Charming 2 Bdrm Oceanfront Oasis Key West Beach access Old Town Bike ride.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious 2-Bedroom Condo with Ocean Views & Island Comforts This beautiful 2-bedroom, 2-bath condo offers a lovely view ...
From $220 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
From $408 per night (USD)
VRBO
~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 $408 per night (USD)
VRBO
From $251 per night (USD)
Expedia
Monthly historic old town rental Key West quaint 1 block to Duval
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Historic 2-Bedroom Cigar Maker’s Cottage – A Key West Gem! Step back in time and experience Old Key West charm in this ...
From $251 per night (USD)
Expedia
From $587 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 $587 per night (USD)
VRBO
From $184 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 $184 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Key West Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Keys to Paradise: A 5-Star Beachside Retreat in Key West Welcome to Keys to Paradise, a luxurious 3-bedroom, 2-bath co ...
From $362 per night (USD)
VRBO
From $362 per night (USD)
Expedia
Casa Coastal East – Morning Sunrises, Evening Vibes, Island Home in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
CONSTRUCTION NOTICE- Balcony Restoration Project – 1800 Atlantic Start Date: May 2025-Estimated Completion: Spring 2026 ...
From $362 per night (USD)
Expedia
From $610 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 $610 per night (USD)
VRBO
From $408 per night (USD)
Expedia
Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Ocean View Condo at 1800 Atlantic – Your Perfect Key West Retreat Experience stunning ocean views and modern comfort in ...
From $408 per night (USD)
Expedia
From $538 per night (USD)
VRBO
Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 Bedroom, 2 Bath Garden View Condo – 1800 Atlantic, Key West Escape to paradise in this beautifully renovated garden-v ...
From $538 per night (USD)
VRBO
From $527 per night (USD)
Expedia
Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Anchor Drop – Oceanfront Escape in Key West Welcome to Anchor Drop, a beautifully renovated two-bedroom condo in the ex ...
From $527 per night (USD)
Expedia
From $469 per night (USD)
VRBO
Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tropical Luxury in Key West – 2-Bedroom, 2-Bath Oasis Welcome to your beautifully decorated two-bedroom, two-bath retre ...
From $469 per night (USD)
VRBO
From $600 per night (USD)
Expedia
NEW! Casa Azul - NO HIDDEN FEES! Golf Cart, 2 Kings, Pool, Beach, Tennis, Kayaks
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
No Hidden Fees! Book any of my homes with confidence. Unlike many vacation rentals, I don't add resort, guest, or manage ...
From $600 per night (USD)
Expedia
From $365 per night (USD)
VRBO
Oceanfront Overlook 2 Bdrm premiere monthly keys style with resort amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Oceanfront Overlook – Your Perfect Island Retreat Welcome to Oceanfront Overlook, a one-of-a-kind unit offering an unpa ...
From $365 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Sea La Vie, Elegant Key West 2BR/2BA | Renovated Condo at 1800 Atlantic
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Beautifully Renovated 2nd Floor Condo with Ocean & Preserve Views – 28-Day Minimum Stay Welcome to your home away from ...
From $267 per night (USD)
Expedia
From $298 per night (USD)
VRBO
Private Tropical Beach White Sand-No Stairs-King Bed-Heated Pool- Superfast WiFi
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step outside your door and onto your private white sandy tropical beach—no stairs, no crowds, just the sound of the wave ...
From $298 per night (USD)
VRBO
From $213 per night (USD)
Expedia
2 Bdrm Monthly ocean view, expansive porch ,renovated unit Key West Fabulous
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Spacious 3rd-Floor Condo with Partial Ocean View & 50-Foot Balcony – Key West Paradise Escape to your island retreat in ...
From $213 per night (USD)
Expedia
From $242 per night (USD)
VRBO
Couples paradise-king bed/AC/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 $242 per night (USD)
VRBO
From $343 per night (USD)
Expedia
Old Town! Spacious Condo in Historic Home w/Pool!
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into ...
From $343 per night (USD)
Expedia
From $308 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 $308 per night (USD)
VRBO
From $275 per night (USD)
Expedia
Gulf Pointe Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: This Gulf-side townhome offers stunning sunsets and radiant Florida Keys sunshine, with an inviting pool just ...
From $275 per night (USD)
Expedia
From $588 per night (USD)
VRBO
Oceanfront Paradise w new 365' Dock Huge Tiki and Firepit. Dogs OK
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Direct Oceanfront Home with plenty of outdoor living space. Huge Tiki Hut with, 50" TV, refrigerator, fire pit area, an ...
From $588 per night (USD)
VRBO
From $1297 per night (USD)
Expedia
One of the very few beach houses with a daily, rental license in the Keys.
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
"THE POOL MAY BE HEATED FOR AN ADDITIONAL FEE OF $25 PER DAY OF STAY" This is a newly remodeled four bedrooms elegant ho ...
From $1297 per night (USD)
Expedia
From $514 per night (USD)
VRBO
**VILLA CUBANA @ OLD TOWN** Cottage Near Duval + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! This colorful ...
From $514 per night (USD)
VRBO
From $759 per night (USD)
Expedia
**MAISON TROPICALE @ OLD TOWN** Historic Home + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Imagine a tra ...
From $759 per night (USD)
Expedia
From $810 per night (USD)
VRBO
W10 - 4 Bedroom Sombrero Isle Beauty on Crystal Lagoon!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This spacious 4-bedroom, 3-bath home is a half a mile from the picturesque Sombrero Beach. Located on Sombrero Is ...
From $810 per night (USD)
VRBO
From $524 per night (USD)
Expedia
**BRISA FRESCA @ THE ANNEX** Airy Home + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! A trip to Key ...
From $524 per night (USD)
Expedia
From $1036 per night (USD)
VRBO
**VILLA OLIVIETTA @ SOLARES HILL** Home & Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! This ultimate ...
From $1036 per night (USD)
VRBO
From $495 per night (USD)
Expedia
**SMOOTH SAILING** Ocean Condo / Pool & Tennis + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Formerly La B ...
From $495 per night (USD)
Expedia
From $345 per night (USD)
VRBO
**VILLA BAHAMA @ THE ANNEX** Villa Near Beach + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! VILLA BAHAMA ...
From $345 per night (USD)
VRBO
From $790 per night (USD)
Expedia
**THE CONTENTED CRANE @ OLD TOWN** Home & Pool + Last Key White Glove Service...
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Traveling to ...
From $790 per night (USD)
Expedia
From $1896 per night (USD)
VRBO
**THE ROYAL COMPOUND @ THE ANNEX** Pool + Last Key White Glove Service...
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Located in th ...
From $1896 per night (USD)
VRBO
From $1783 per night (USD)
Expedia
**SOUTHERNMOST HOSPITALITY VII** 7BR & Pool + Last Key White Glove Service...
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SOUTHERNMOST ...
From $1783 per night (USD)
Expedia
From $352 per night (USD)
VRBO
**GULFSIDE VISTAS @ THE ANNEX** Condo & Pool + Last Key White Glove Service...
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! GULFSIDE VIST ...
From $352 per night (USD)
VRBO
From $2027 per night (USD)
Expedia
**STAR OF THE SEAPORT @ OLD TOWN** Pool + Last Key White Glove Service......
Bedrooms:
5
Bathrooms:
5
Sleeps:
12
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! For a truly o ...
From $2027 per night (USD)
Expedia

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