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From $219 per night (USD)
VRBO
Comfortable Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Flagler Station Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $219 per night (USD)
VRBO
From $490 per night (USD)
Expedia
Waterfront Home with 33-Ft. Dock and Cabana Club Membership with Beach and Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Ninth Street Cabana Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $490 per night (USD)
Expedia
From $352 per night (USD)
VRBO
Waterfront home with private dock, canal views, large terrace & modern kitchen
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
La Isla Bonita Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $352 per night (USD)
VRBO
From $506 per night (USD)
Expedia
W04 - 209 Sombrero Beach Rd.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Newer built canal front townhouse in the Anglers area of the Sombrero Beach neighborhood. This home features a private h ...
From $506 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Keys Cottage with Beach and Dockage! Bayfront Property!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
"Deckhouse" is the perfect beachy cottage for your Keys vacation! It has a full-size kitchen with granite countertops an ...
From $461 per night (USD)
VRBO
From $184 per night (USD)
Expedia
KCB-access Private Cabana Club, Dock on Canal, PET Friendly, Pickle ball courts
Bedrooms:
1
Bathrooms:
1
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 $184 per night (USD)
Expedia
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VRBO
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
We are moving to a monthly rental model and passing on the savings to you. Here in Key West we believe in One Human Fam ...
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VRBO
From $473 per night (USD)
Expedia
Waterfront Cottage - Beach and Dockage! Open Water Views!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
In a world of chain hotels and paved over paradise, experience the Florida Keys the way they used to be! Sitting on a pr ...
From $473 per night (USD)
Expedia
$\Your own private resort\ - Mockingbird Pointe - Waterfront, pool and dockage$
From $478 per night (USD)
VRBO
\"Your own private resort\" - Mockingbird Pointe - Waterfront, pool and dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Mockingbird Pointe is a quiet secluded 1/2 acre tropical waterfront paradise in the heart of the Florida Keys with priva ...
From $478 per night (USD)
VRBO
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Expedia
Nader's Vacation Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
We have our 3 bedroom 2 bathroom home in Little Torch Key available for anyone looking to take a vacation in the lower ...
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Expedia
From $386 per night (USD)
VRBO
P64 - Spacious 3 bedroom duplex in Key Colony with dockage and Cabana Club...
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Beautiful duplex home in Key Colony Beach. Key Colony Beach is a small, friendly, walkable island with easy access to lo ...
From $386 per night (USD)
VRBO
Click For Pricing
Expedia
Manatee Bay , Pool table, Jacuzzi, Pool, Kayaks, REDUCED RATES AVAIL NOW<br>
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
The Manatee Bay has the best of all worlds. It has a large custom fiberglass pool situated next to a 20 ft+ deep and bea ...
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Expedia
From $284 per night (USD)
VRBO
Waterfront 80' heated pool hottub Gorgeous views 20 mins to Key West & Marathon
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This Lobstering paradise is just 2 houses down from open water on a deep 60 foot wide canal, gorgeous open water views, ...
From $284 per night (USD)
VRBO
From $643 per night (USD)
Expedia
A Taste Of Vitamin Sea 4bed/3bath updated single family with pool, dockage &
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
STR21-000361 Your vacation awaits at A Taste of Vitamin Sea in desirable Key Colony Beach! Vitamin Sea’s canal fronta ...
From $643 per night (USD)
Expedia
From $901 per night (USD)
VRBO
Elegant Home with Beach & Dockage! Spectacular Sunsets!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
This elegant home is located on a beautiful 2.5 acre gated beachfront estate with amazing views of our beautiful island ...
From $901 per night (USD)
VRBO
From $295 per night (USD)
Expedia
MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and professionally decorat ...
From $295 per night (USD)
Expedia
From $2002 per night (USD)
VRBO
~DREAMING ON DUVAL~ Grand 5 bedroom, 4.5 bath home with private pool/parking
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
THE PROPERTY: Dreams do come true in Key West! As you enter the front gate of this luxury property, you arrive in a priv ...
From $2002 per night (USD)
VRBO
From $528 per night (USD)
Expedia
Henry's Penthouse on the Ocean in Key West - weekly / nightly rentals
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Spectacular ocean views from this condo located on the top floor with 1350 sq ft of fabulous living space and a 45 ft pr ...
From $528 per night (USD)
Expedia
From $449 per night (USD)
VRBO
**OLD TOWN OASIS @ THE ANNEX** Oceanside 2BR/2BA Condo & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! OLD TOWN OASI ...
From $449 per night (USD)
VRBO
From $707 per night (USD)
Expedia
Waterfront home with dock, pool table & private pool - walk to Sombrero Beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Anchor House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $707 per night (USD)
Expedia
From $532 per night (USD)
VRBO
Luxury 3BR/3BA Cottage with the Best Sunset Views in the Florida Keys!
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Professionally decorated, fully renovated Cottage with 3 Bedrooms & 3 Bathroom Cottage located in the Village at Hawks ...
From $532 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Island Time in Key Largo | Luxurious Condo Oasis | FREE TRAVEL INSURANCE ON WEE
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summary: 🌿Stunning Condo with Garden View Nestled in the tropical paradise of Tavernier, Key Largo, our lovingly mainta ...
From $254 per night (USD)
Expedia
From $340 per night (USD)
VRBO
Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This beautiful newly refreshed vacation rental is all about the view. It is upstairs with an unobstructed view of the Fl ...
From $340 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Canal-front home remodeled for HGTV with private swimming pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
La Pirata Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $409 per night (USD)
Expedia
From $362 per night (USD)
VRBO
Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Partial list of rental amenities at Craig & Cindy's Truman Annex Shipyard Condos include: 2 bedrooms 1 bath {queen and ...
From $362 per night (USD)
VRBO
From $475 per night (USD)
Expedia
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
From $475 per night (USD)
Expedia
From $1113 per night (USD)
VRBO
Waterfront Duck Key Villa
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Come and enjoy Duck Key in the Florida Keys, known as America's Caribbean, a lush shangri-la with tropical vegetation an ...
From $1113 per night (USD)
VRBO
From $248 per night (USD)
Expedia
Vacation like a local
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home. Plenty of room for boat and great ...
From $248 per night (USD)
Expedia
From $542 per night (USD)
VRBO
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
We are proud to announce- Castaway Island has been named for 2024’s KW people’s choice awards as a FINALIST for Best Va ...
From $542 per night (USD)
VRBO
From $242 per night (USD)
Expedia
COCONUT Adorable cottage in Old Town
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
The 'Coconut' as it's so lovingly referred to is the perfect Pied A Terre for your vacation in the Florida Keys. Open l ...
From $242 per night (USD)
Expedia
From $224 per night (USD)
VRBO
Ocean Shores Home Key Largo
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Oceanside single family home in one of Key largo most desirable neighborhoods with waterview and private pool. Large lot ...
From $224 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #11 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $221 per night (USD)
Expedia
$Dog-Friendly Canalfront Home with Dock, Central AC, Fast WiFi, & Washer\/Dryer$
From $480 per night (USD)
VRBO
Dog-Friendly Canalfront Home with Dock, Central AC, Fast WiFi, & Washer\/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Relax Inn Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $480 per night (USD)
VRBO
From $167 per night (USD)
Expedia
Snowbird-Friendly Home with Central AC, High-Speed WiFi, and Washer/Dryer
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
White Palm Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired ...
From $167 per night (USD)
Expedia
From $320 per night (USD)
VRBO
**COASTLINE COMFORT @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! When your vac ...
From $320 per night (USD)
VRBO
From $310 per night (USD)
Expedia
**SET SAIL @ COCONUT MALLORY** Condo + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! SET SAIL cele ...
From $310 per night (USD)
Expedia
Click For Pricing
VRBO
Cozy studio cottage in Old Town Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cute Studio cottage with additional sleeping loft. Nicely landscaped shared pool and outside area. Walking distance to ...
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VRBO
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Expedia
Sun of a Beach: Luxurious 7-Bedroom Split-Level Home with private pool, hot tub
Bedrooms:
5
Bathrooms:
7
Sleeps:
16
Indulge in the charm of this splendid split-level residence nestled in the heart of the captivating Florida Keys. This d ...
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Expedia
From $254 per night (USD)
VRBO
Work remote, or not at all, in paradise at this cozy, beachy condo!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $254 per night (USD)
VRBO
From $223 per night (USD)
Expedia
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cottage #15 - Quaint, clean, comfortable cottage just 20 miles from Key West. Bring the family. Located on a compound wi ...
From $223 per night (USD)
Expedia
From $600 per night (USD)
VRBO
136 Mariners Club | 3 Bed, 3 Bath
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This spectacular 2600 square foot villa boasts a blissful atmosphere and breathtaking view of the harbor and Atlantic Oc ...
From $600 per night (USD)
VRBO
From $662 per night (USD)
Expedia
Heart of Key West - 2BR Waterfront at the Galleon Resort
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Located in the heart of Old Town Key West. This resort overlooks the Gulf of Mexico with a private marina, private beach ...
From $662 per night (USD)
Expedia
From $289 per night (USD)
VRBO
610 Mariners Club | 1 Bed, 1 Bath
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Sweet studio apartment in coveted Mariners Club on the island of Key Largo. This is a duplex-style, ground floor 1-bedr ...
From $289 per night (USD)
VRBO
From $225 per night (USD)
Expedia
Canal-front Keys escape with amazing view, boat access, firepit, gril, AC, & W/D
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Torchbearer - Lower Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter you ...
From $225 per night (USD)
Expedia
From $370 per night (USD)
VRBO
Waterfront escape with dock, furnished deck & patio, grill & central AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Dockside Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired d ...
From $370 per night (USD)
VRBO
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Expedia
Pristine Waterfront Charmer - Outdoor Living & Dining, Dock, AC - Snowbirds OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Tradewinds Treat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
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Expedia
From $455 per night (USD)
VRBO
Welcome to the Shady Palms - Private Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Step into this beautifully restored and redecorated 1933 Key West home. This first-floor home has Bahama shutters throug ...
From $455 per night (USD)
VRBO
From $841 per night (USD)
Expedia
Ocean view home with private pool, hot tub, Cabana club and 40 ft dock for boats
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Ocean's Edge Retreat is a 3 bedroom / 3 bath home with open water views of the Atlantic Ocean and directly on the canal. ...
From $841 per night (USD)
Expedia
From $918 per night (USD)
VRBO
**ENVY OF THE ISLAND @ OLD TOWN** Pristine Home & Pool + LAST KEY SERVICES...
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! While Old Tow ...
From $918 per night (USD)
VRBO
From $287 per night (USD)
Expedia
Doc`s Holiday 2bed/2bath half duplex with Cabana Club
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This half dupex in Key Colony Beach is situated on the East side of the island, just a short stroll away from the Cabana ...
From $287 per night (USD)
Expedia
From $157 per night (USD)
VRBO
Ground-level getaway with free WiFi, private deck, & shared outdoor pool
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Louisa's Garden Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $157 per night (USD)
VRBO
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Expedia
Oceanfront! Oceanfront! Oceanfront!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
License # 25-0123 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th ...
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Expedia
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VRBO
Stay & Play; Enjoy Scenic Views Ocean Pointe 5312
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Upon entering the home you’ll be greeted by laidback island decor and vast ocean views. The Tommy Bahama Tiki inspired a ...
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VRBO
From $730 per night (USD)
Expedia
Mariners Club 410 - Oceanview 3 levels!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Trip Advisor Award Winner! Oceanview from all three levels! From your living room or master suite enjoy the expansive ...
From $730 per night (USD)
Expedia
From $426 per night (USD)
VRBO
SOUTHERNMOST SWIM AND SOCIAL CLUB
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Look no further! You've found your home away from home. Where your family and friends can share their own piece of para ...
From $426 per night (USD)
VRBO
From $203 per night (USD)
Expedia
Enjoy a Fun in the Sun getaway 3 Bedroom House, Tiki Hut, Boat Ramp, & Dockage!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Come relax in Florida Keys Paradise while you enjoy the comforts of a clean 3 bedroom house (not a mobile home). Central ...
From $203 per night (USD)
Expedia
From $623 per night (USD)
VRBO
Treasure Cove- 2BDR/2.5BA | 2 Bed, 2.5 Bath
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
~~7 day minimum~~Experience the famous island city of Key West and stay at the Treasure Cove Townhouse in the private P ...
From $623 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Penthouse view - Futura Yacht Club #604
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6) Enjoy penthouse views of the fabulous blue waters of the Atlantic and Flo ...
From $249 per night (USD)
Expedia
From $268 per night (USD)
VRBO
Quiet Lane in the Heart of Old Town, Sleeps 4 + 🐶🐾
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Unbeatable location just 1 block from the iconic Green Parrot Bar and 2 blocks from world famous Duval Street. Blue Heav ...
From $268 per night (USD)
VRBO
From $306 per night (USD)
Expedia
Luxury cottage in the heart of paradise
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
WELCOME ABOARD TO ONE OF LARGER COTTAGES ON THE CAMPGROUND. Comfortable and spacious cottage in the center of KEY LARG ...
From $306 per night (USD)
Expedia
From $258 per night (USD)
VRBO
OCEANFRONT COMMUNITY, LUXURY,BEACH,POOLS, TOP AMENITIES & VALUE in FLORIDA KEYS
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Everything you need to Stay, Love, and Relax..... "Escape to paradise at Kawama Tower 406, a modern, spacious, and luxu ...
From $258 per night (USD)
VRBO
$Blue Home - Receive 500 dollars \ntowards a BOAT RENTAL!$
From $537 per night (USD)
Expedia
Blue Home - Receive 500 dollars \ntowards a BOAT RENTAL!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Receive a $500 boat rental gift certificate from Nothing Better Boat Rentals, LLC. when you book a full week at one o ...
From $537 per night (USD)
Expedia
From $271 per night (USD)
VRBO
One of the Best Private Beaches in US! Great Location fun activities-Fast Wifi!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience Paradise at One of the Best Private Beaches! Let me assist you in finding the best and most affordable fligh ...
From $271 per night (USD)
VRBO
From $489 per night (USD)
Expedia
Waterfront luxury Villa (54) with sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
From $489 per night (USD)
Expedia
Click For Pricing
VRBO
Waterfront luxury Villa (43) with spectacular sunset views and boat slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse y ...
Click For Pricing
VRBO
From $784 per night (USD)
Expedia
ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
WELCOME TO ISLAND TIME! Key West Island Time is a rare find in old town Key West. It is a total of 5 bedrooms and three ...
From $784 per night (USD)
Expedia
From $687 per night (USD)
VRBO
Beautiful Waterfront Gulf of America Great location.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This property is like having your own private resort. On the Gulf of Mexico. Million-dollar waterfront views & sunsets. ...
From $687 per night (USD)
VRBO
Click For Pricing
Expedia
A great place to relax, fish, or even work from. 2/2 , 66 ft
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
2 Master suites with great screened in porch overlooking Bayside canal. 66 dock, fully furnished. Large family room with ...
Click For Pricing
Expedia
$White Home - Receive 500 dollars \ntowards a BOAT RENTAL!$
From $577 per night (USD)
VRBO
White Home - Receive 500 dollars \ntowards a BOAT RENTAL!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Receive a $500 boat rental gift certificate from Nothing Better Boat Rentals, LLC. when you book a full week at one o ...
From $577 per night (USD)
VRBO
From $306 per night (USD)
Expedia
TROPICAL PROPERTIES VACATION RENTAL - KEY WEST
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
****This property requires a minimum stay of 28 nights in the same calendar month**** ***Brand New Pool with waterfall, ...
From $306 per night (USD)
Expedia
$Yellow Home - Receive 500 dollars \ntowards a BOAT RENTAL!$
From $495 per night (USD)
VRBO
Yellow Home - Receive 500 dollars \ntowards a BOAT RENTAL!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Receive a $500 boat rental gift certificate from Nothing Better Boat Rentals, LLC. when you book a full week at one o ...
From $495 per night (USD)
VRBO
From $271 per night (USD)
Expedia
Tropical Jewel: Historic Seaport Oldtown - 2BR/2BA - Pool - RealKeyWest
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
WELCOME TO TROPICAL JEWEL! Near all the action of the historic seaport and Duval Street, you can get out into the cit ...
From $271 per night (USD)
Expedia
From $481 per night (USD)
VRBO
Waterfront luxury Villa (34) with sunset views and boat slip
Bedrooms:
2
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 $481 per night (USD)
VRBO
From $249 per night (USD)
Expedia
Huge Oct savings! Sea-Esta! condo, Beach, Pool, Key Colony Beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Sea-Esta is located on the Atlantic Ocean with a private white sandy beach. If the ocean isn’t calling you, Sea-Esta by ...
From $249 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Lazy Tortuga 2bed/2bath updated half duplex with Cabana Club & dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Lazy Tortuga is a ground level luxurious half duplex! This property features 2 bedrooms and 2 bathrooms. The master bedr ...
From $283 per night (USD)
VRBO
From $461 per night (USD)
Expedia
MAJESTIC PARADISE II Luxury living in Truman Annex. Downtown, pool, 2 blks
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Featured in The Key West Citizen Home of the Week. Perfect location, and newly renovated with fresh paint, new kitchen w ...
From $461 per night (USD)
Expedia
From $229 per night (USD)
VRBO
COZY FAMILY HOME-POOL-HOTTUB -5 minute drive to sombrero beach-private property
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This beautiful home has 2 bedroom and 2 bath, a large Living/Dining and Kitchen area for entertaining. The Dining area ...
From $229 per night (USD)
VRBO
From $424 per night (USD)
Expedia
2 story condo with panoramic bay views and balconies!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a 1,350sqft 2 bedrooms/3 bath condo with amazing unobstructed Gulf Bay views. Right next to vaca cut, sunrise an ...
From $424 per night (USD)
Expedia
From $486 per night (USD)
VRBO
BRAND NEW! KEYS BEACH RETREAT! CAPTIVATING WATERVIEW VILLA! WIFI! FREE GOLF CART
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
2 POOLS, FAST FREE WIFI, SALTWATER SWIMMING LAGOON, 2 KIDS AND 2 JUNIOR KAYAKS, FREE DOUBLE GOLF CART, 2 FREE BICYCLES, ...
From $486 per night (USD)
VRBO
From $1471 per night (USD)
Expedia
Pirate Point, Luxe 5BR Escape w/ Pool, Tiki, & Dock Minutes from the Beach
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
Welcome to Pirate Point – your private slice of paradise. Tucked away at the end of a peaceful canal street on lush, lan ...
From $1471 per night (USD)
Expedia
From $308 per night (USD)
VRBO
Sirena Key Cottage in Venture Out
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
VO365 Sirena Key Cottage 35' Seawall It's a wonderful time to enjoy Paradise! Quick ocean side access to gulf a ...
From $308 per night (USD)
VRBO
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Expedia
Another Day in Paradise Best Waterfront and Poolside Views.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Our Moon Bay Luxury Condominium unit # B403, 4th floor, is located directly on the scenic Blackwater Sound near Florida ...
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Expedia
From $860 per night (USD)
VRBO
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Hidden amongs ...
From $860 per night (USD)
VRBO
From $425 per night (USD)
Expedia
Villa 5087 on Duck Key BOAT SLIP available
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Enjoy the nicest Fully Renovated Villa on Duck Key. Boat slip available for additional $100 a night. Largest boat that ...
From $425 per night (USD)
Expedia
From $272 per night (USD)
VRBO
Kelly's Kabin - Adorable Private Summerland Key Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $272 per night (USD)
VRBO
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Expedia
Key Colony Beach 3/3 Townhouse - Ocean View
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Unit is in mint condition, located in prime Key Colony Beach surrounded by spectacular ocean views. All furnishings are ...
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Expedia
From $388 per night (USD)
VRBO
Paradise in Beautiful Key Largo!! Amazing Views!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Your dream vacation awaits you at Kawama Yacht Club! A unique gated townhome community located in the heart of Key Larg ...
From $388 per night (USD)
VRBO
From $359 per night (USD)
Expedia
P20 - 551 8th St in Key Colony Beach
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Welcome to the heart of the Florida Keys! Located in the very desirable Key Colony Beach, this 3 bedroom, 3 bath home is ...
From $359 per night (USD)
Expedia
From $248 per night (USD)
VRBO
Sugar Cane - Florida Keys tropical retreat. Newly renovated!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
We have just completely renovated this condo at Ocean Pointe and it's Insta-worthy. Every detail has been designed and c ...
From $248 per night (USD)
VRBO
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Expedia
Absolutely Perfect! Reel Vacation Villa w/Pool, Dock, Close to Beach w/Extras!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
This stunning home on the Intracoastal Waterway is loaded with amenities including a private pool and patio with boat do ...
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Expedia
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VRBO
Cozy 2 Bedroom home in Summerland Key
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Our home is located in a quiet and cozy area 5 minutes away from the famous Ramrod Swim Hole; a local treasure. It is al ...
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VRBO
From $562 per night (USD)
Expedia
ADMIRAL'S PARADISE in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Newly renovated town home located on a charming lane in the Truman Annex. The generous open floor plan features 10 foot ...
From $562 per night (USD)
Expedia
From $358 per night (USD)
VRBO
Charming Half Duplex
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Charming Half Duplex offering 2 bedrooms 2 bathrooms. The home is on a quiet street in a residential neighborhood on a c ...
From $358 per night (USD)
VRBO
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Expedia
Balcony - Sky Suites Retreat, on Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Summary: This elegant, elevated 2nd story loft with vaulted ceilings has been designed for your next dream Key West geta ...
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Expedia
From $393 per night (USD)
VRBO
Bright & Cheery Pool Front Home w/ Optional Boat Slip at Anglers Reef Islamorada
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths w ...
From $393 per night (USD)
VRBO
From $506 per night (USD)
Expedia
LAST MINUTE SUMMER DEALS!!! Waterfront Keys Cottage and Outdoor Living!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sea Salt Cottage is a spacious 3 bedroom 2 bath open concept home on a wide canal with direct access to the ocean. Gues ...
From $506 per night (USD)
Expedia
From $330 per night (USD)
VRBO
Modern-Coastal Spacious Suite [Ocean Pointe 3301]
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Come enjoy this 2 bedroom, 2 bath spacious end suite overlooking the Atlantic Ocean at Ocean Pointe Suites; an ideal des ...
From $330 per night (USD)
VRBO
Click For Pricing
Expedia
Amazing Water Front Pool House & Dock in a very exclusive area!
Bedrooms:
3
Bathrooms:
4
Sleeps:
17
Spectacular home! find the perfect Vacation Rental, two homes in one, with two private entrances , escape to the Flori ...
Click For Pricing
Expedia
From $232 per night (USD)
VRBO
Amazing Ocean view condo
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly Renovated Beach Décor unit! Breathtaking views of the Atlantic ocean and protected Florida Keys mangroves. Heated ...
From $232 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Balcony, Pool, & Pet Friendly - Tortuga Suite
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Welcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 ...
From $394 per night (USD)
Expedia

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