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From $314 per night (USD)
VRBO
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: "Island Time" is a newly renovated 2-bedroom, 2-bath condo in the gated La Brisa community. Located across fro ...
From $314 per night (USD)
VRBO
From $342 per night (USD)
Expedia
Captain's Wheel at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This very popular getaway in the award-winning Truman Annex is a tropically decorated 2 bedroom, 2.5 bath town home feat ...
From $342 per night (USD)
Expedia
From $617 per night (USD)
VRBO
**WALKING ON SUNSHINE** Ocean Condo & Pool + 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! WALKING ON SU ...
From $617 per night (USD)
VRBO
From $297 per night (USD)
Expedia
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Description: Beautiful newer 2 bedroom / 2 bath elevated tropical home near a waterfront common area in Venture Out, an ...
From $297 per night (USD)
Expedia
From $314 per night (USD)
VRBO
A Low Tide at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A Low Tide is a charming first floor end unit in the Shipyard Condominiums in the award winning gated community of the T ...
From $314 per night (USD)
VRBO
From $1743 per night (USD)
Expedia
Southern Palms - Steps to Duval with Private Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Summary: Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, o ...
From $1743 per night (USD)
Expedia
From $408 per night (USD)
VRBO
Beach Vacay Starts Here! Pool, Beach Access, Pet-friendly
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Oceanfront family-friendly property with direct beach access and pool This listing is for a room within a hotel. ✦ You ...
From $408 per night (USD)
VRBO
From $419 per night (USD)
Expedia
Seaside Escape with Luxe Interior and Ocean Views
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Experience ultimate relaxation at Ocean Pointe 2401, a charming oceanfront condo in Tavernier. Perfect for div ...
From $419 per night (USD)
Expedia
From $2257 per night (USD)
VRBO
Barry Beach & Guesthouse
Bedrooms:
5
Bathrooms:
8
Sleeps:
20
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront homes with 200 foot dock for your boat. Two excl ...
From $2257 per night (USD)
VRBO
From $452 per night (USD)
Expedia
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Come stay at the Tipsy Turtle in Angler's Reef! This magnificent home with ocean views from all 4 balconies is located ...
From $452 per night (USD)
Expedia
From $433 per night (USD)
VRBO
PELICAN'S PERCH Summer Rates!!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s Old Town neighborhood ...
From $433 per night (USD)
VRBO
From $484 per night (USD)
Expedia
A Sunset & Harbour View at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Exceptional accommodations, spectacular location and first class amenities await you and your group! This two bedroom, ...
From $484 per night (USD)
Expedia
From $511 per night (USD)
VRBO
Villa 5020 on Duck Key Boat Slip Available - 2BD 2.5BA
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy a nicely renovated Villa on Duck Key. Boat slip available for additional $100 a night. Ask for availability. Th ...
From $511 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Paradise Moon Bay!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
JUST RENOVATED, Paradise at Moon Bay! A spacious 2 Bedroom, 1.5 Bathroom located on the third flood overlooking the bay. ...
From $249 per night (USD)
Expedia
From $566 per night (USD)
VRBO
Key Largo Ocean Shore Villa 2 with pool & boat slip
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This centrally located boater`s paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill do ...
From $566 per night (USD)
VRBO
From $1007 per night (USD)
Expedia
W07 - New Luxury Property! Breathtaking Canal Front Pool Home - Sleeps 14
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
Welcome to paradise! Escape to this luxurious 6 bedroom/6.5 bathroom home designed for VIP guests. Each bedroom i ...
From $1007 per night (USD)
Expedia
From $447 per night (USD)
VRBO
Captains Quarters - Cudjoe Key - Pool- Waterfront w/ Boat Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Captain’s Quarters — Your Waterfront Escape on Beautiful Cudjoe Bay Discover the perfect blend of comfort, l ...
From $447 per night (USD)
VRBO
From $165 per night (USD)
Expedia
Tranquil Oasis Beach Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly renovated 2 bedroom /2 bath home. Fully furnished for you and your family. Sleeps 4, 2 queen size beds. Just added ...
From $165 per night (USD)
Expedia
From $501 per night (USD)
VRBO
Spectacular Views of Ocean with Pool and Boat Slip.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cozy Ocean Front Retreat with heated pool and boat slip up to 30’. Corner unit with panoramic views. Oversized patio for ...
From $501 per night (USD)
VRBO
From $378 per night (USD)
Expedia
Canal Front home with easy Ocean access
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
You found it!! Bring your boat! Charming cottage located in Venture Out, resort style community located on Cudjoe Key, ...
From $378 per night (USD)
Expedia
From $1086 per night (USD)
VRBO
3-Story spacious conch style home w/ private pool & dock!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
"Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropicall ...
From $1086 per night (USD)
VRBO
From $364 per night (USD)
Expedia
Walk to Sombrero Beach •Waterfront, 50’ Dock, Spa, Kayaks, Bikes, Ideal Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Islandville Florida Keys – Sombrero Beach Stilted Beach House VACA22-191 Relax in this fully renovated Florida Keys ge ...
From $364 per night (USD)
Expedia
From $229 per night (USD)
VRBO
Casa Marina - Key Largo Waterfront Home with Private Pool, Boat Ramp & Dockage!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
For more pictures and recommendations on where to go and what to do in the FL Keys follow @mmjkeysrentals on Instagram. ...
From $229 per night (USD)
VRBO
From $238 per night (USD)
Expedia
WATERFRONT Key Colony Beach Retreat 37’ Dock Cabana Club- Kayak & Bikes- Parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Escape to the Florida Keys and experience waterfront living at its best! Whether you’re planning a boating adventure, a ...
From $238 per night (USD)
Expedia
From $644 per night (USD)
VRBO
DUPLEX IN DUCK KEY Grand 3/2 W/90' Private Dock, Trailer Storage included
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait an ...
From $644 per night (USD)
VRBO
From $260 per night (USD)
Expedia
Beautiful Remodeled Condo 2B 1.5Ba
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Is SUN and FUN listed as keys to your next vacation? Look no further because you will find huge quantities right here in ...
From $260 per night (USD)
Expedia
From $350 per night (USD)
VRBO
Heart of Old Town on QUIET Peacon Lane. Historic Seaport. Duval St. PETS WELCOME
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Single family home. (Not a condo.) We welcome kids, pets, partners, friends. Free off street parking for 2-3 vehicles. ...
From $350 per night (USD)
VRBO
From $505 per night (USD)
Expedia
Thanksgiving week opened-up! Fall Discounts:)
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
DIRECT OCEANFRONT, fully updated, ground floor, single-family Home; 3 Bedrooms, 3 Baths. The home is all new and beautif ...
From $505 per night (USD)
Expedia
From $302 per night (USD)
VRBO
Carriage House at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red b ...
From $302 per night (USD)
VRBO
From $301 per night (USD)
Expedia
Unique Home with loft @ Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Now more than ever it is important it is important to choose a home that is thoroughly cleaned and well maintained. We ...
From $301 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Keys Waterfront Condo: Pool, Beach & Stunning Views!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Escape to paradise in, 2209 Ocean Pointe, a charming oceanfront condo in Tavernier, Florida! Perfect for famil ...
From $344 per night (USD)
VRBO
From $329 per night (USD)
Expedia
Ocean Views + SandyToes at Ocean Pointe Suites
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: Indulge in the serene scenery, at our charming oceanfront condo at Ocean Pointe Suites. Ideal for couples, sol ...
From $329 per night (USD)
Expedia
From $1297 per night (USD)
VRBO
Serenity - 5bed/3bath single family - Large, Luxurious, Open Water View
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Enjoy life at Serenity with unobstructed views of the Vaca Cut from this amazing home! Located on the ocean side, it’s t ...
From $1297 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Cook your Catch in a Gourmet Kitchen- Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $586 per night (USD)
Expedia
From $381 per night (USD)
VRBO
300/NIGHT~ICE MACHINE~POOL~ CLOSE TO OPEN GULF WATER~FAMILY FRIENDLY HOME,
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gulf Winds Hideaway – Your Private Slice of Paradise! Welcome to Gulf Winds Hideaway, a beautifully designed waterfront ...
From $381 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Waterfront Townhouse in Kawama
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy our recently remodeled 2 bed 2 bath waterfront town home with an open floor plan and relaxing views of the salt wa ...
From $420 per night (USD)
Expedia
From $257 per night (USD)
VRBO
Marlin Blue at the Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Trum ...
From $257 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Cool Breeze @ the Key West Golf Club in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club- This community is located on Stock Island which is five miles from Duval Street a ...
From $367 per night (USD)
Expedia
From $206 per night (USD)
VRBO
Tropical Breezes at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $206 per night (USD)
VRBO
From $211 per night (USD)
Expedia
ISLAND TIME at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the ...
From $211 per night (USD)
Expedia
From $453 per night (USD)
VRBO
waterfront cottage near key west, sleeps 6
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your d ...
From $453 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Oceanfront Home With Large Private Deck with boat dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy boating, swimming or just the ocean view in the greatest of privacy. Dinner and entertainment in Key West is a sho ...
From $481 per night (USD)
Expedia
$\Pelican's Perch\ - Gulf Front Condo, Fabulous Views, Heated Pool, Dock, Fishing$
From $332 per night (USD)
VRBO
\"Pelican's Perch\" - Gulf Front Condo, Fabulous Views, Heated Pool, Dock, Fishing
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Pelican's Perch is an upscale, luxury townhouse condo less than 16 yards from the water of the Gulf of Mexico. The cond ...
From $332 per night (USD)
VRBO
From $372 per night (USD)
Expedia
Lower Keys paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Two bedroom 1 bathroom house . New on market, new furniture, new appliances, new painting. Have a breakfast with view o ...
From $372 per night (USD)
Expedia
From $315 per night (USD)
VRBO
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to Paradise! Discover the retreat that is Ocean Pointe, a premier resort nestled in Tavernier, Fl ...
From $315 per night (USD)
VRBO
From $797 per night (USD)
Expedia
**LAYOVER in PARADISE** New Home / Pool + 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 home design ...
From $797 per night (USD)
Expedia
From $294 per night (USD)
VRBO
1 Island Time Escape at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
1 ISLAND TIME ESCAPE at the Truman Annex This Foundry townhome is a Bostonian style 3 level home located in Old Town K ...
From $294 per night (USD)
VRBO
From $573 per night (USD)
Expedia
🌸Home(#5) “AFTER DUNE🍹DELIGHT”(-approximately 50 ft from Private beach entrance)🌸
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
🌸Home(#5) “AFTER DUNE🍹DELIGHT”(-approximately 50 ft from Private beach entrance)🌸 Totally Private😉- Turn-Key and ful ...
From $573 per night (USD)
Expedia
From $290 per night (USD)
VRBO
A License to Chill at the Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The historic Foundry, known as building #101, features three story townhomes, located in the award-winning residential n ...
From $290 per night (USD)
VRBO
From $186 per night (USD)
Expedia
Key largo waterfront jewel
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterfront corner lot location with dock. 3 Bedrooms 2 bathrooms, completely renovated, central A/C, bonus enclosed pati ...
From $186 per night (USD)
Expedia
From $655 per night (USD)
VRBO
315 Mariners Club - 3 bedroom condo with unobstructed ocean views
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Enjoy luxurious Keys living with unobstructed panoramic views of the Atlantic Ocean from your private terrace with a 43 ...
From $655 per night (USD)
VRBO
$\Private Pool\ Waterfront Home across from Golf Course KCB$
From $555 per night (USD)
VRBO
\"Private Pool\" Waterfront Home across from Golf Course KCB
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Casa Aquamarina II, A Peaceful Paradise Retreat! This beautiful 2 Bedroom, 2 Bath Plus spacious 2nd story loft, is the ...
From $555 per night (USD)
VRBO
From $236 per night (USD)
VRBO
2/2 Ocean, Canal, Dock- Fall Getaway @ Casita Mar!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Renting 7 nights+ stays & monthly, too! Saturdays check in/check out applies to summer stays. If specific dates request ...
From $236 per night (USD)
VRBO
From $886 per night (USD)
Expedia
DOLPHIN WATCH at the Truman Annex in Key West
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
VERY LUXURIOUS water front home located in the heart of downtown Key West within walking distance to all downtown attrac ...
From $886 per night (USD)
Expedia
From $846 per night (USD)
VRBO
Key Largo Luxury Townhome | Pools & Marina
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
Key Largo Luxury Townhome at Mariners Club Welcome to your Key Largo getaway at Mariners Club, a beautiful gated oceanf ...
From $846 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Amberjack at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Recently refurbished throughout in a fun, tropical theme, Amberjack is situated on Southard Street in the exclusive gate ...
From $336 per night (USD)
Expedia
From $1000 per night (USD)
VRBO
Catch of the Day at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
View passing ships and sunsets from your own first floor, large deck with plenty of seating for a large family in the Tr ...
From $1000 per night (USD)
VRBO
From $205 per night (USD)
Expedia
SOUTHARD COMFORT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
LOCATION, LOCATION, LOCATION! Southard Comfort is on Southard Street in the TRUMAN ANNEX, which is one of the most beau ...
From $205 per night (USD)
Expedia
From $1029 per night (USD)
VRBO
Mariner's Club 606 • Spacious 4/4 • Pools, Marina & Pickleball
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Welcome to Sea La Vie — Unit 606, where comfort meets coastal style in the heart of Mariner’s Club, one of Key Largo’s ...
From $1029 per night (USD)
VRBO
From $374 per night (USD)
Expedia
Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Key Largo condo, relax in this calm, stylish space. Spacious, fully renovated waterfront 2 bedroom / 2 bath condo with t ...
From $374 per night (USD)
Expedia
From $944 per night (USD)
VRBO
4BR 5BA pool+hot tub closed to Gulf/Atl, kayaks, bikes, deep canal, near beach.
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Perla Blanca – Luxury Waterfront Retreat in Marathon Saturday-to-Saturday Reservations Only Welcome to Perla Blanca, an ...
From $944 per night (USD)
VRBO
From $246 per night (USD)
Expedia
Island Getaway at Ocean Point
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: Come enjoy a fantastic vacation with us at Ocean Pointe Suites! The Space: Prepare for an extraordinary island ...
From $246 per night (USD)
Expedia
From $483 per night (USD)
VRBO
Gorgeous Ocean View in Paradise - Three Bedroom Condo - Minutes from Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the oce ...
From $483 per night (USD)
VRBO
From $754 per night (USD)
Expedia
Luxury Waterfront at Galion Resort in Old Town
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This condo is a 2BR/2BA Penthouse Loft on the 5th floor overlooking the marina. On the first floor is a full sized, ful ...
From $754 per night (USD)
Expedia
From $446 per night (USD)
VRBO
**DOCKSIDE DAYDREAMS @ COCONUT MALLORY** Villa + 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! DOCKSIDE DAYD ...
From $446 per night (USD)
VRBO
From $198 per night (USD)
Expedia
Waterfront paradise in Key Largo with resort style amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Two story townhouse with two bedrooms and two and a half bathrooms overlooking canal. Master features King bed, second b ...
From $198 per night (USD)
Expedia
From $431 per night (USD)
VRBO
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
***NEVER RENTED BEFORE!! Be one of the first to stay in our newly renovated home! With a 35' Seawall for docking your ...
From $431 per night (USD)
VRBO
From $479 per night (USD)
Expedia
Pet & Family Friendly, Sleeps 8 - Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $479 per night (USD)
Expedia
From $479 per night (USD)
VRBO
Weekly Resort Activities & Family Fun - Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $479 per night (USD)
VRBO
From $593 per night (USD)
Expedia
Cleanest in the Keys w/Roof Top Deck - Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $593 per night (USD)
Expedia
From $729 per night (USD)
VRBO
Sunnyside Up - Shared Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
9
Summary: Sunnyside Up is a charming Conch-style home on United Street, just steps from Key West’s "Old Town." With an o ...
From $729 per night (USD)
VRBO
From $586 per night (USD)
Expedia
Cozy Cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot do ...
From $586 per night (USD)
Expedia
From $1125 per night (USD)
VRBO
Luxury 5BR/7BA Waterfront Oasis | Private Pool, Dock & 5 Master Suites
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Step into the ideal island retreat at Super Grouper House – a 5-bedroom, 7-bath luxury vacation home in Marathon, Florid ...
From $1125 per night (USD)
VRBO
From $833 per night (USD)
Expedia
Modern Island Luxury | 4 En-Suite Masters, 6 BA, Pool, Dock & Outdoor Oasis
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Step into Snapper House and feel the stress melt away—an upscale, custom-built sanctuary designed for dream vacations on ...
From $833 per night (USD)
Expedia
From $265 per night (USD)
VRBO
Atlantic Escape Luxury Oceanview Key West Condo resort style amenities
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Atlantic Paradise Escape | Luxury Oceanfront Condo in Key West Monthly Rental | Unit MC322 | 2BR, 2BA | Direct Ocean Vi ...
From $265 per night (USD)
VRBO
From $496 per night (USD)
Expedia
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage INCL
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait an ...
From $496 per night (USD)
Expedia
From $607 per night (USD)
VRBO
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Wonderful, oceanfront, two bedroom, two bath, bungalow home is just ten feet from the open water views. Located on the ...
From $607 per night (USD)
VRBO
From $391 per night (USD)
Expedia
Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private 3 bdrm, 2 bath, home in exclusive Cudjoe Gardens @ MM20 on Cudjoe Key. This is a very comfortable home in a nic ...
From $391 per night (USD)
Expedia
From $586 per night (USD)
VRBO
Kayaks, Paddle Boards, Bikes & Fishing- Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $586 per night (USD)
VRBO
From $496 per night (USD)
Expedia
DUPLEX IN DUCK KEY, 2 Bedroom/2 Bath, W/Private 90' Dock, Trailer Storage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Unit in Duck Key next to the biggest resort in the Florida Keys! Located near stores, restaurants, delicatessen, bait a ...
From $496 per night (USD)
Expedia
From $267 per night (USD)
VRBO
WATERFRONT!! Home w/ 37.5-ft dock, Cabana Club Membership!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great scre ...
From $267 per night (USD)
VRBO
From $454 per night (USD)
Expedia
Beach Condo in Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Beautiful Ocean Beach and Pool view from deck. Relax in paradise where everything is steps away! Suntan on the white sa ...
From $454 per night (USD)
Expedia
From $586 per night (USD)
VRBO
Gated Boutique Resort with Pool- Marlin Bay
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Marlin Bay Resort & Marina is a hidden gem located in the heart of The Keys! It is a newly launched boutique resort fea ...
From $586 per night (USD)
VRBO
From $482 per night (USD)
Expedia
Paradise on the Ocean at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
This waterfront two bedroom condo is located in the Truman Annex, Key West's premier residential community. Enjoy endles ...
From $482 per night (USD)
Expedia
From $402 per night (USD)
VRBO
A SUNRISE COTTAGE at The Truman Annex in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This charming 2 story 2 bedroom with loft, two bath cottage in the Shipyard Condominiums is located just off the pool an ...
From $402 per night (USD)
VRBO
From $610 per night (USD)
Expedia
Largo Getaway • 3 King Suites + In-Laws Quarters, Pickleball
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
TAKE A VIRTUAL TOUR OF THE ENTIRE UNIT BEFORE BOOKING http:www.youtube.com/@Keylargotravels This property is managed b ...
From $610 per night (USD)
Expedia
From $720 per night (USD)
VRBO
Beautiful Home on the Atlantic Ocean waters
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
“Luxury spacious home with subtle marine decor; high end accommodations. Exceptional location nearby the best convenienc ...
From $720 per night (USD)
VRBO
From $271 per night (USD)
Expedia
P38 - Charming 1 bedroom, waterfront duplex with private hot tub. Cabana Club membership included!
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
This cute and cozy, all ground level 1 bedroom, 1 bath unit is perfect for the couple who loves comfort, quiet and the b ...
From $271 per night (USD)
Expedia
From $315 per night (USD)
VRBO
P37 - Charming 2 bedrooms duplex with Private Pool and Deep water dockage. Cabana Club Membership Included!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Key Colony Delight! This 2 bedroom, 2 bath all ground level duplex in Key Colony Beach is absolutely delightful! Offerin ...
From $315 per night (USD)
VRBO
From $813 per night (USD)
Expedia
Fisherman Paradise, Dock, Pool , Ice Machine, Jacuzzi.
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Spacious 2,800 sf House with four bedrooms with their own end-suite baths. Full house for you and your family to enjoy, ...
From $813 per night (USD)
Expedia
From $394 per night (USD)
VRBO
Cocktails & Dreams: Modern 2nd Floor Condo, Steps from Duval St, Seaport, Waterpark, Beach & Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
***This unit holds a City of Key West Transient License and will be permitted to continue offering weekly rentals beyond ...
From $394 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Almost Paradise at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The c ...
From $220 per night (USD)
Expedia
From $2598 per night (USD)
VRBO
Private Heated Pool & Near Duval - The Curry House
Bedrooms:
9
Bathrooms:
9
Sleeps:
18
Summary: "Curry House" provides three stories full of historic charm that take you back in time. Best of all, when you ...
From $2598 per night (USD)
VRBO
From $351 per night (USD)
Expedia
Curry House Room 1 - Near Duval, Pool & Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summary: "Curry House" provides three stories full of historic conch house charm that take you back in time. This guest ...
From $351 per night (USD)
Expedia
From $327 per night (USD)
VRBO
Sunrise Breeze on the Marina [Ocean Pointe 5302]
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Breeze located on the 3rd floor of the 5th bldg, a premier location at Ocean Pointe. Our sp ...
From $327 per night (USD)
VRBO
From $1621 per night (USD)
Expedia
4BR Key Largo Stay – Pool, Parking + Beach Club
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Endless Summer #42 (4Bed / 4.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of pea ...
From $1621 per night (USD)
Expedia
From $1621 per night (USD)
VRBO
4BR Key Largo Villa w/ Beach & Marriott Perks
Bedrooms:
4
Bathrooms:
4
Sleeps:
9
Gull's Nest #36 Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace and luxury. Ocean ...
From $1621 per night (USD)
VRBO
From $1283 per night (USD)
Expedia
Luxury Villa by the Ocean | Pool & Resort
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Tranquility #19 (3 Bed / 2.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace ...
From $1283 per night (USD)
Expedia
From $1283 per night (USD)
VRBO
Key Largo 3BR Villa | Pool, Kayaks & Resort Perks
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Hideaway #23 (3 Bed / 2.5 Bath) Indulge in a tranquil, carefully crafted vacation rental designed as a haven of peace an ...
From $1283 per night (USD)
VRBO
From $487 per night (USD)
Expedia
Super Comfy and modern with the extras!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
2 bedroom, 2 bathroom large house with game room, tall ceilings, lots of entertaining space and great dock. Comfy couch, ...
From $487 per night (USD)
Expedia

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