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Florida Keys Rentals

From $670 per night (USD)
VRBO
Elegant waterfront home with private pools, hot tub, & dock - walk to beach
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Key Quest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $670 per night (USD)
VRBO
$New listing 3bd/2bt Sleeps 8 \Sunset Paradise Villa\ on canal Big Pine Key$
From $235 per night (USD)
Expedia
New listing 3bd/2bt Sleeps 8 \"Sunset Paradise Villa\" on canal Big Pine Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
*Bridge restriction***BIMINI TOPS or Fold down T-tops boats ONLY DUE TO WATSON ST BRIDGE. Sunset Paradise Villa is a ...
From $235 per night (USD)
Expedia
From $565 per night (USD)
VRBO
LUXURY VIP SUITE - INDOOR PICKLEBALL - STUNNING OCEAN VIEWS - OCEANFRONT RESORT!
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 $565 per night (USD)
VRBO
From $338 per night (USD)
Expedia
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
If you want to experience the true meaning of a Key Largo Island vacation, then look no further than our spacious townho ...
From $338 per night (USD)
Expedia
From $514 per night (USD)
VRBO
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!
Bedrooms:
4
Bathrooms:
3
Sleeps:
8
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $514 per night (USD)
VRBO
From $566 per night (USD)
Expedia
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Ree ...
From $566 per night (USD)
Expedia
From $456 per night (USD)
VRBO
LICENSED MGER - MODERN 2/2 OCEANFRONT SUITE! OCEAN & MARINA VIEWS! 2 KING BEDS!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
You have just discovered one of the most unique properties in the heart of Key Largo. This oceanfront condo is located i ...
From $456 per night (USD)
VRBO
From $645 per night (USD)
Expedia
808 Mariners Club | 4 Bed, 3.5 Bath
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Designer upgrades make this luxury, two-story townhouse with over 2600 sq of living space the perfect home-away-from-hom ...
From $645 per night (USD)
Expedia
From $292 per night (USD)
VRBO
Relax in the Keys
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Completely remodeled 1st floor - 90’ TV, recliner, full size bathroom, kitchen 2nd floor, 2 bedrooms, 2 bathrooms, kit ...
From $292 per night (USD)
VRBO
From $353 per night (USD)
Expedia
Palm Villa - Sleeps 6, Boat Slip Available
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Villa has a CALIFORNIA KING BED in the Master Bedroom & a Queen Bed in the guest room plus Queen Sleeper Sofa in Li ...
From $353 per night (USD)
Expedia
From $395 per night (USD)
VRBO
Cozy Coastal Villa. Newly renovated private home w/ HEATED pool.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This newly renovated, 3/2 pet-friendly Key Largo vacation home is spaciously laid out over two levels with chic island-i ...
From $395 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Sun, Sea & Sky at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Located in the desirable Truman Annex community, this beautifully maintained second-story Shipyard condo offers the perf ...
From $420 per night (USD)
Expedia
From $171 per night (USD)
VRBO
A little slice of Heaven
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Comfortable mobile home, located on the canal with 53 ft of dock space, with 20, 000 lbs lift, so bring your boat, full ...
From $171 per night (USD)
VRBO
From $437 per night (USD)
Expedia
ANGLER'S RETREAT at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A stay in Anglers Retreat is more then just a rental, but will be part of your Key West vacation experience. In addition ...
From $437 per night (USD)
Expedia
From $344 per night (USD)
VRBO
Beautiful, 2100 sq ft 3/2 w/ocean views & easy ocean & gulf access.
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This is your home away from home. Beautiful 3 story home with spacious master bedroom and bathroom located on top floor ...
From $344 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a la ...
From $459 per night (USD)
Expedia
From $82 per night (USD)
VRBO
Private Home, in the most beautiful, Florida Keys
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
The property is fenced with plenty of car parking. You will book a Family HOME, Our HOUSE is NOT a Trailer or Trailer Pa ...
From $82 per night (USD)
VRBO
From $267 per night (USD)
Expedia
Key Largo-Islamorada area-1 BR, 1 Bath -Privately Owned Condo -Fab Reviews!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
You've found it! No need to look any further. Come on down and explore the beautiful Florida Keys! Picture this... en ...
From $267 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Keys Deal w/Cafe & Pool Bar! Up to 20% Off Beachfront 1BD Sleeps 4.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
New Island Grill Pool Bar & Marina Cafe now open. Deluxe, upgraded 1-bedroom 1 full bath (sleeps four with sofabed) loca ...
From $268 per night (USD)
VRBO
From $408 per night (USD)
Expedia
P13 - 3 Bedroom Home with Private Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
A premier home in a premier location! This 3 bedroom, 2 bathroom home is one of a kind. An all ground level home boastin ...
From $408 per night (USD)
Expedia
From $447 per night (USD)
VRBO
GREEN BAMBOO at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Welcome to Paradise! This 2 bedroom townhouse, featuring one bedroom with a king and the second bedroom features twin be ...
From $447 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Key Largo Sunset - Bayside open water - Tropical inspired 3 bed/2 bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
This three bedroom, two bathroom bayside retreat provides ideal coastal living with stunning views of the Florida Bay. T ...
From $287 per night (USD)
Expedia
From $621 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 bed 2 bath condo located in the gated La Brisa Condominium complex. Situa ...
From $621 per night (USD)
VRBO
From $607 per night (USD)
Expedia
CAPTAINS 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 $607 per night (USD)
Expedia
From $608 per night (USD)
VRBO
**WALKING ON SUNSHINE @ THE BEACH** Ocean Condo & Large Pool + LAST KEY SERVICES
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
CONSTRUCTION NOTICE - 25% off!!! - 25% off any stay through summer 2026 due to construction at the complex! 25% discount ...
From $608 per night (USD)
VRBO
From $248 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 $248 per night (USD)
Expedia
From $343 per night (USD)
VRBO
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private community with 2 beaches, boat ramp, heated swimming pool, beach volleyball, children's area with playground, la ...
From $343 per night (USD)
VRBO
From $447 per night (USD)
Expedia
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 $447 per night (USD)
Expedia
From $410 per night (USD)
VRBO
Waterfront Dream Condo with Panoramic Views, Near Vaca Cut
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Turn off of Route 1, leave behind all the hubbub of life, while holding on to the infectious laid back, slower-paced atm ...
From $410 per night (USD)
VRBO
Click For Pricing
Expedia
Private luxury retreat all included.
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
All included in this large home has a huge master bedroom with 2 walking closets, opens to large wrap around balcony ove ...
Click For Pricing
Expedia
From $3668 per night (USD)
VRBO
Steps from Duval with Private Pool – Southern Palms
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Summary: Welcome to Southern Palms, the ultimate home base for your Key West adventure! Perfect for couples, friends, or ...
From $3668 per night (USD)
VRBO
From $380 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 $380 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Pristine Top Floor Oceanfront Condo 5 min from Top Local Attractions
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Indulge in the peaceful scenery at our impeccably designed oceanfront property, recently renovated, and situated at Ocea ...
From $409 per night (USD)
VRBO
From $1800 per night (USD)
Expedia
Waterfront Beach Houses with Dock & Heated Pool!
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 exclu ...
From $1800 per night (USD)
Expedia
From $291 per night (USD)
VRBO
3/3 DirectBayAccess CanalHome w/Lift Dock Fenced Pet-Friendly HotTub Grill WIFI
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Immaculately kept Remodeled 2 Story Home in Tavernier with attention to details to make you feel home away from home. Pr ...
From $291 per night (USD)
VRBO
From $396 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 $396 per night (USD)
Expedia
From $505 per night (USD)
VRBO
PELICAN'S PERCH at The Truman Annex in Key West
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 $505 per night (USD)
VRBO
From $802 per night (USD)
Expedia
A SUNSET AND A 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 $802 per night (USD)
Expedia
From $475 per night (USD)
VRBO
ANNIE'S HIDEAWAY at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
This charming one bedroom, one bath 2nd floor property features an Olympic queen in the master bedroom and a large cover ...
From $475 per night (USD)
VRBO
From $580 per night (USD)
Expedia
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. Largest boat that can fit ...
From $580 per night (USD)
Expedia
From $277 per night (USD)
VRBO
Paradise Moon Bay!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
JUST RENOVATED, Paradise at Moon Bay! A spacious 2 Bedroom, 1.5 Bathroom located on the third flood overlooking the bay. ...
From $277 per night (USD)
VRBO
From $245 per night (USD)
Expedia
Canal Front Gem W/ Private Dock, PS4, Free WiFi, & Expansive Balcony W/ Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Saratoga Sunshine Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $245 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Second Floor Condo with Shared Pool, Shared Dock, Central AC, WiFi, and W/D
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gold Starfish Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $333 per night (USD)
VRBO
From $481 per night (USD)
Expedia
Key Largo Ocean Shore Villa 2 with pool & boat slip
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
This centrally located boater`s paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill do ...
From $481 per night (USD)
Expedia
From $704 per night (USD)
VRBO
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 $704 per night (USD)
VRBO
From $112 per night (USD)
Expedia
Canal-front home with WiFi, parking, and easy access to open water
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Burgundy Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $112 per night (USD)
Expedia
From $457 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 $457 per night (USD)
VRBO
From $170 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 $170 per night (USD)
Expedia
From $588 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 $588 per night (USD)
VRBO
From $280 per night (USD)
Expedia
Waterfront Cottage: 60-ft. dock, Fish Station, free WiFI, 3 TVs & washer/dryer
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Hook Line & Sunset Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $280 per night (USD)
Expedia
Click For Pricing
VRBO
Coastal Beach Home in the heart of Key Largo.
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Beautifully inspired coastal home is located in heart of Key Largo on the oceanside. Offering pristine open Atlantic vi ...
Click For Pricing
VRBO
From $258 per night (USD)
Expedia
Waterfront Home
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 $258 per night (USD)
Expedia
From $1522 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 $1522 per night (USD)
VRBO
From $367 per night (USD)
Expedia
Walk to Sombrero Beach, Waterfront, 50’ Dock, Spa, Kayaks, Bikes, Ideal Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax in this FULLY UPDATED, Florida Keys gem in Sombrero Beach, 50' private dock with wide & deep channel to ocean (no ...
From $367 per night (USD)
Expedia
From $165 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 $165 per night (USD)
VRBO
From $299 per night (USD)
Expedia
4YR New- 2bed 2bath, 37ft Dock, Cabana Club, Kayak & Bikes- UPDATED
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Duplex, 2 Bedrooms 2 baths w/Cabana Club Access and Private 37.5 ft Dock on 100 ft wide Canal with fish cleaning station ...
From $299 per night (USD)
Expedia
From $525 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 $525 per night (USD)
VRBO
From $253 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 $253 per night (USD)
Expedia
From $523 per night (USD)
VRBO
Waterfront with a pool & private beach access.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterfront with pool. Private beach access within a mile. All amenities needed to enjoy a fun and relaxing vacation. A f ...
From $523 per night (USD)
VRBO
From $517 per night (USD)
Expedia
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 $517 per night (USD)
Expedia
From $674 per night (USD)
VRBO
Fall... Beautiful weather, discounts, flexible cancellation!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
<p>DIRECT OCEANFRONT, fully updated, ground floor, single-family Home; 3 Bedrooms, 3 Baths. The home is all new and beau ...
From $674 per night (USD)
VRBO
From $473 per night (USD)
Expedia
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 br ...
From $473 per night (USD)
Expedia
From $324 per night (USD)
VRBO
Bunk Room at the Grand Maloney
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Grand Maloney Hotel is a new boutique hotel located in the heart of downtown Key West. Our signature red br ...
From $324 per night (USD)
VRBO
From $276 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 $276 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Relax by Keys Waters [Ocean Pointe Suites 2209]
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to our charming 2-bedroom condo in the heart of Tavernier, where the Florida Keys' natural beauty and vibrant cul ...
From $283 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Old Town Key West classic with private saltwater pool & enclosed patio- by shops
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Petronia Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $314 per night (USD)
Expedia
From $333 per night (USD)
VRBO
Escape The Rat Race and Relish In Tranquility
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Kick your shoes off and chill! The turquoise colors of the Atlantic Ocean greet you in this 2 bedroom, 2 bathroom Ocean ...
From $333 per night (USD)
VRBO
From $1355 per night (USD)
Expedia
Serenity in Marathon, FL
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Large, Luxurious, Open Water ViewEnjoy life at Serenity with unobstructed views of the Vaca Cut from this amazing home! ...
From $1355 per night (USD)
Expedia
From $732 per night (USD)
VRBO
Gated w/Bayside Marina- Marlin Bay Resort & Marina
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 $732 per night (USD)
VRBO
From $378 per night (USD)
Expedia
GREAT FAMILY VACATION HOME~Canal-Private Pool~ Dock, Bait Freezer & ICE MACH~
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Gulf Winds Hideaway – Your Private Slice of Paradise! Welcome to Gulf Winds Hideaway, a beautifully designed waterfront ...
From $378 per night (USD)
Expedia
From $390 per night (USD)
VRBO
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 $390 per night (USD)
VRBO
From $491 per night (USD)
Expedia
MARLIN BLUE in the Truman Annex
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 $491 per night (USD)
Expedia
From $444 per night (USD)
VRBO
COOL BREEZE @ the Key West Golf Club
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Cool Breeze at the Key West Golf Club-*****PLEASE NOTE THIS IS A MINIMUM MONTHLY RENTAL ONLY.***** This community is loc ...
From $444 per night (USD)
VRBO
From $435 per night (USD)
Expedia
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 $435 per night (USD)
Expedia
From $517 per night (USD)
VRBO
MANATEE at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
'Manatee' is a beautiful two bedroom, one bath, 1st floor condominium located within the prestigious gated community of ...
From $517 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Looking for the Best Location for Next Getaway? Amazing Room w/ FREE Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is p ...
From $235 per night (USD)
VRBO
From $705 per night (USD)
VRBO
Keys Vacation Starts Here! Three Amazing Units, Free Breakfast, Outdoor Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is p ...
From $705 per night (USD)
VRBO
From $705 per night (USD)
VRBO
Comfort & Convenience! 3 Great Units Near Florida Keys Aquarium Encounters
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is p ...
From $705 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Sunny home w/ firepit, private pool, private gas grill, & tiki bar
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Conch Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $168 per night (USD)
VRBO
From $455 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 $455 per night (USD)
Expedia
From $313 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 $313 per night (USD)
VRBO
From $470 per night (USD)
VRBO
Family & Friends Getaway! 2 Convenient Units, Free Breakfast, Outdoor Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is p ...
From $470 per night (USD)
VRBO
From $235 per night (USD)
VRBO
Relax and Unwind! Relaxing Room, Outdoor Pool w/ Fantastic View, Free Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to our family-friendly property! An unforgettable tropical vacation awaits you in the Middle Keys. Our room is p ...
From $235 per night (USD)
VRBO
Click For Pricing
Expedia
Classic Key West condo w/ private parking, covered porches, & shared pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Cool Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
Click For Pricing
Expedia
From $283 per night (USD)
VRBO
Water Front Sunset View Home
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Stunning sunsets all year around! 180 degrees of open water views. Imagine yourself being able to enjoy your glass of wi ...
From $283 per night (USD)
VRBO
From $222 per night (USD)
Expedia
Beautiful centrally located home in the Florida keys<br>
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Centrally located in the Florida keys close to Islamorada where there are great restaraunts and shops.Park your boat in ...
From $222 per night (USD)
Expedia
$\Pelican's Perch\ - Gulf Front Condo, Fabulous Views, Heated Pool, Dock, Fishing$
From $346 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 $346 per night (USD)
VRBO
From $291 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 $291 per night (USD)
Expedia
From $275 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 $275 per night (USD)
VRBO
From $640 per night (USD)
Expedia
**LAYOVER in PARADISE @ CASA MARINA** New Home / Pool + LAST KEY SERVICES…
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 $640 per night (USD)
Expedia
From $701 per night (USD)
VRBO
Aah PARADISE at the Truman Annex in Old Town Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
AAH PARADISE This Foundry townhome is a Bostonian style 3 level home located in Old Town Key West. This home has been re ...
From $701 per night (USD)
VRBO
From $566 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 $566 per night (USD)
Expedia
From $439 per night (USD)
VRBO
STARFISH - SUNNY TOWNHOME in QUIET TRUMAN ANNEX TWO BLOCKS FROM DUVAL ST.
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Note: In 2026, bookings will require a minimum stay of 28 days, starting on the first of the month. I can adjust the dat ...
From $439 per night (USD)
VRBO
From $593 per night (USD)
Expedia
A LICENSE TO CHILL in the Truman Annex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The historic Foundry, known as building #11, features three story townhomes, located in the award-winning residential ne ...
From $593 per night (USD)
Expedia
From $212 per night (USD)
VRBO
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 $212 per night (USD)
VRBO
From $629 per night (USD)
Expedia
315 Mariners Club Key Largo | 3 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beachfront Oasis Enjoy luxurious oceanfront living with unobstructed panoramic views of the Atlantic Ocean from your pr ...
From $629 per night (USD)
Expedia
$\Private Pool\ Waterfront Home across from Golf Course KCB$
From $498 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 $498 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Casita Mar 2/2 Canal, Direct Ocean Book a Fall Getaway!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Renting 7 nights+ stays & monthly, too! Saturdays check in/check out only applies to holidays, summer & winter stays. S ...
From $249 per night (USD)
Expedia
Click For Pricing
VRBO
BEAUTIFUL SUNSETS IN THE MARATHON KEYS
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Please visit Marathon Key Beach Club website for more detailed pictures of units. Located on the Gulf of Mexico, this p ...
Click For Pricing
VRBO
From $306 per night (USD)
Expedia
Quaint Island Escape Condo w/Spacious Balcony Deck in Beautiful Truman Annex
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This lovely Island Escape Condo is a upper level condo located in the prestigious Truman Annex. Not just another rental ...
From $306 per night (USD)
Expedia

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