Fleming Key, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Fleming Key, Florida on RentalSaver.com!

Fleming Key Rentals

From $378 per night (USD)
VRBO
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PICTURE PERFECT PARADISE... This newly renovated retreat is nestled in the highly sought-after neighborhood of The Meado ...
From $378 per night (USD)
VRBO
From $153 per night (USD)
Expedia
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town. A great place for a coup ...
From $153 per night (USD)
Expedia
From $855 per night (USD)
VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $855 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Historic Apartment On The Waterfront
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Newly renovated historic apartment in the heart of Key West. 10 foot ceilings and huge windows allow bright, natural lig ...
From $275 per night (USD)
VRBO
Click For Pricing
VRBO
Fantasy Festival October 20, 2022-October 23, 2022 Studio Downtown Sunset Harbor
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Hyatt Residence Club Key West Sunset Harbor Fantasy Fest 2022 Location......Location, Location, Location....In the hear ...
Click For Pricing
VRBO
$**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE$
From $1141 per night (USD)
Expedia
**CASA SERENDIPITY @ OLD TOWN** Historic 3BR\/2BA Home & Pool + LAST KEY SERVICE
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! Sometimes in ...
From $1141 per night (USD)
Expedia
From $265 per night (USD)
VRBO
PEAK OF DUVAL | 2 Bed, 2 Bath
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...
From $265 per night (USD)
VRBO
$Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking$
From $2064 per night (USD)
Expedia
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)
Expedia
From $296 per night (USD)
VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport wi ...
From $296 per night (USD)
VRBO
$\Tranquility \ At Ann Street Gardens Steps From Duval$
From $534 per night (USD)
Expedia
\"Tranquility \" At Ann Street Gardens Steps From Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $534 per night (USD)
Expedia
$Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen\n$
From $230 per night (USD)
VRBO
Spec. 4-29 &4-30 169.00 lodg. + extras Close to beach plus kitchen\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
ALSO WE'VE GOT YOUR BACK----ASK ABOUT OUR COVID & STORM POLICIES ...
From $230 per night (USD)
VRBO
From $974 per night (USD)
Expedia
The Gideon Lowe House - Old Town Key West
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegance, Sophistication, Perfection! Nothing compares to this extraordinary Old Town Key West residence. It exudes ch ...
From $974 per night (USD)
Expedia
From $1139 per night (USD)
VRBO
Island Chic: Luxury 3-Bedroom Waterfront Home with Private Pool AND Dock!
Bedrooms:
5
Bathrooms:
3
Sleeps:
8
Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay a ...
From $1139 per night (USD)
VRBO
From $524 per night (USD)
Expedia
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $524 per night (USD)
Expedia
From $868 per night (USD)
VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $868 per night (USD)
VRBO
From $142 per night (USD)
Expedia
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $142 per night (USD)
Expedia
From $1378 per night (USD)
VRBO
Eisenhower Retreat: Conch style home in Oldtown with private pool AND dock!
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch H ...
From $1378 per night (USD)
VRBO
From $1314 per night (USD)
Expedia
Bayview Retreat: Spacious Luxury Waterfront Home with Private Pool and Dock!
Bedrooms:
5
Bathrooms:
4
Sleeps:
10
Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boas ...
From $1314 per night (USD)
Expedia
$NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes\n$
From $182 per night (USD)
VRBO
NEWLY Redecorated as of 4-15-25. The current pics. do not reflect the changes\n
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
NEWLY REDECORATED AS OF APRIL 15. 2025 all dark natural wood walls and cabinets gone instead painted off-white color th ...
From $182 per night (USD)
VRBO
From $723 per night (USD)
Expedia
Key West Oasis, Seperate Cottage, Very Private Pool and Back Yard
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Please Note: Key West Oasis is NOT suitable for families with young children, as the 2nd bedroom is not attached to the ...
From $723 per night (USD)
Expedia
From $132 per night (USD)
VRBO
Mango Tree Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $132 per night (USD)
VRBO
From $6452 per night (USD)
VRBO
Family Ready 1 BR Suite | Outdoor Pools | 4 Suites
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $6452 per night (USD)
VRBO
From $4848 per night (USD)
VRBO
Waterfront Room Retreat: Sparkling Pools | Three Spacious Rooms
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $4848 per night (USD)
VRBO
$Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!$
From $235 per night (USD)
VRBO
Cottage in Old Town Key West w\/ Pool, Parking and Privacy. One block from Duval!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Down a hidden lane in the heart of Old Town Key West you will find Loco Court Cottages. The compound is located one blo ...
From $235 per night (USD)
VRBO
From $1928 per night (USD)
VRBO
Tropical Hideaway: Room in Resort - Steps from Key West's Vibrance | 2 Units
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1928 per night (USD)
VRBO
From $827 per night (USD)
Expedia
4-bedroom vacation home in Key West - steps to Duval St & Florida Keys Beaches
Bedrooms:
5
Bathrooms:
6
Sleeps:
10
Escape to the heart of Key West's historic district and immerse yourself in the vibrant island lifestyle. This 4-bedroom ...
From $827 per night (USD)
Expedia
From $952 per night (USD)
VRBO
Bella Grand Premier Estate Key West - 2 Blocks off Duval w Private Pool
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
Inspired by romantic turn-of-the-century architecture, Bella Grand Premier Estate is a unique Old Town Key West estate w ...
From $952 per night (USD)
VRBO
From $4581 per night (USD)
VRBO
Resort Room with Direct Access to Water Adventures | 3 Suites Ideal for Family
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $4581 per night (USD)
VRBO
From $168 per night (USD)
VRBO
Conch Republic Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Summer Discounts!This historic conch home, circa 1890, is your dream vacation spot. The welcoming property has been comp ...
From $168 per night (USD)
VRBO
From $409 per night (USD)
Expedia
Old Town Classic with plenty of charm, porch swing and parking
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Beautiful home with covered porch and swing! Full kitchen, washer/dryer, TV, Internet, A/C, separate patio area with twi ...
From $409 per night (USD)
Expedia
$\A Bird's Eye View\ at The Truman Annex in Key West$
From $393 per night (USD)
VRBO
\"A Bird's Eye View\" at The Truman Annex in Key West
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Stunning, Modern 2 bedroom, 1 bathroom second floor condo in the Truman Annex Shipyard Complex completely renovated. Ful ...
From $393 per night (USD)
VRBO
$Waterfront Penthouse sleeps 16 w\/Pool & Boat Dock$
From $1814 per night (USD)
VRBO
Waterfront Penthouse sleeps 16 w\/Pool & Boat Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Gorgeous completely renovated 2400sqft waterfront Penthouse condo in downtown Key West. Boat slips available on ...
From $1814 per night (USD)
VRBO
$Abaco Key West • 2\/2 End Unit Waterfront + Dockage$
From $642 per night (USD)
VRBO
Abaco Key West • 2\/2 End Unit Waterfront + Dockage
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax & fish! Bring your family & friends to this 1350 sqft Waterfront corner home. Boat slips availabl ...
From $642 per night (USD)
VRBO
$Curaçao 2BR Condo w\/ Pool & Waterfront Dock$
From $514 per night (USD)
Expedia
Curaçao 2BR Condo w\/ Pool & Waterfront Dock
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring family & friends to this 1200 sqft waterfront condo in historic Old Town Key West. On-site ...
From $514 per night (USD)
Expedia
$Downtown Aruba 2BR\/2BA • Pool, Dock, Pet OK$
From $695 per night (USD)
VRBO
Downtown Aruba 2BR\/2BA • Pool, Dock, Pet OK
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with ...
From $695 per night (USD)
VRBO
From $1894 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Parking, Dock
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring your family & friends to this 2200sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1894 per night (USD)
VRBO
From $700 per night (USD)
VRBO
Old Town Eleuthera • 2BR Waterfront Corner Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this fully updated 1350sqft Waterfront corner condo home. Boat sl ...
From $700 per night (USD)
VRBO
$Downtown 4\/4 Waterfront Penthouse Pool, Dock, Pet$
From $1729 per night (USD)
VRBO
Downtown 4\/4 Waterfront Penthouse Pool, Dock, Pet
Bedrooms:
4
Bathrooms:
4
Sleeps:
15
Summary: Bring your family & friends to this 2400sqft waterfront Penthouse condo. Boat slips available on site with com ...
From $1729 per night (USD)
VRBO
From $1771 per night (USD)
VRBO
Downtown Waterfront Penthouse Pool, Dock, Parking
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Summary: Bring your family & friends to this 2000sqft waterfront Penthouse condo. Endless water views from one of the t ...
From $1771 per night (USD)
VRBO
From $405 per night (USD)
Expedia
Sunshine Siesta Cottage~Great Old Town Location, Pool, Private Hot Tub!
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
BOOK NOW! Walk down the secluded brick path of the 4-unit compound, past the tropical foliage to Unit B, adjacent to the ...
From $405 per night (USD)
Expedia
From $518 per night (USD)
VRBO
**MARGARET’S MAGIC COMPOUND @ SOLARIS HILL** Old Town Compound & Pool + LAST KEY
Bedrooms:
5
Bathrooms:
4
Sleeps:
8
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival! Travelers fro ...
From $518 per night (USD)
VRBO
From $707 per night (USD)
Expedia
Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House
Bedrooms:
4
Bathrooms:
4
Sleeps:
7
Enjoy all of Key West's exciting activities from the privacy and comfort of your own two-story, historic home in Old Tow ...
From $707 per night (USD)
Expedia
From $147 per night (USD)
VRBO
Campbell Cottage in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location...Location...Location! Campbell Cottage is perfectly located to walk to almost everything Key West has to offer ...
From $147 per night (USD)
VRBO
From $476 per night (USD)
Expedia
The Courtyard in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Vacation ever so comfortably in this well-designed one bedroom, one-full-bath courtyard unit at Campbell Court. You can ...
From $476 per night (USD)
Expedia
From $192 per night (USD)
VRBO
Anchor's Away in Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Need a refresher course in relaxation? Find it behind the brass seahorse knocker on the front door of this three-bedroom ...
From $192 per night (USD)
VRBO
From $470 per night (USD)
Expedia
Coral Condo in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom ...
From $470 per night (USD)
Expedia
From $241 per night (USD)
VRBO
La Hacienda in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most dis ...
From $241 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Campbell Suite in Key West
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Let your rendezvous with paradise begin at the Campbell Courtyard compound in the heart of Old Town Key West. Campbell S ...
From $420 per night (USD)
Expedia
From $105 per night (USD)
VRBO
Bay's Hideaway in Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summer Discounts!Just the mere idea of planning a vacation puts a smile on most faces. If your vacation includes a stay ...
From $105 per night (USD)
VRBO
From $684 per night (USD)
Expedia
Quilted Giraffe in Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes yo ...
From $684 per night (USD)
Expedia
From $235 per night (USD)
VRBO
MONTHLY - 1 block from the Seaport and 2 blocks from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This beautifully decorated property has soaring ceilings with a lovely outdoor dining & bbq area and is walking distance ...
From $235 per night (USD)
VRBO
$Florida | Waterfront 2BR\/2BA w\/ Pool + Dock Access$
From $499 per night (USD)
Expedia
Florida | Waterfront 2BR\/2BA w\/ Pool + Dock Access
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Summary: Time to relax! Bring your family & friends to this 1350 sqft Waterfront condo home. Boat slips available on sit ...
From $499 per night (USD)
Expedia
From $320 per night (USD)
VRBO
Casa Bella Petite le Bleu - Luxury Key West Cottage w Pool - 2 Blocks Off Duval
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
First impressions are everything. And it's love at first sight with the charming 2BR 2BA Casa Bella Petite le Bleu. This ...
From $320 per night (USD)
VRBO
From $240 per night (USD)
Expedia
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Keys Please Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desire ...
From $240 per night (USD)
Expedia
Click For Pricing
VRBO
Single home with pool, center of Old Town
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Beautiful, newly renovated single home of corner lot in the center of old town. 4 blocks from Duval and 4 blocks from se ...
Click For Pricing
VRBO
From $291 per night (USD)
VRBO
Topsail Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Topsail Cottage XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX ...
From $291 per night (USD)
VRBO
$The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars$
From $494 per night (USD)
VRBO
The Jasmine House\nJust a 2 minute walk to Duval and restaurants and bars
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy your tropical vacation, whether work-free or not, in this Old Town home only a couple of minutes from Duval and Wh ...
From $494 per night (USD)
VRBO
Click For Pricing
Expedia
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from Duval St & Seaport!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
City of Key West zoning requires a minimum rental period of 30 days, and no exceptions can be made. Please review additi ...
Click For Pricing
Expedia
From $1002 per night (USD)
VRBO
Designer Octagon House of Key West - w Private Pool - Blocks off Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Standing prominently in the sought-after Key West Historic Seaport Neighborhood, this iconic Designer Octagon House of K ...
From $1002 per night (USD)
VRBO
From $1225 per night (USD)
Expedia
A Palm Tree Haven in Key West
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
This lovely single-family, two-story luxury home is in the prestigious Truman Annex gated community on a very private cu ...
From $1225 per night (USD)
Expedia
From $1804 per night (USD)
VRBO
Harbor House Suite A | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
Welcome to Luxury Harbor House Suites, an exceptional NIGHTLY vacation rental property located in the heart of Key West' ...
From $1804 per night (USD)
VRBO
From $280 per night (USD)
Expedia
UPTOWN FUNK ~ Newly Renovated 3 BR Townhome in Old Town with Parking!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
IMMACULATE UPSCALE DELIGHT… Embrace the island vibes and immerse yourself in the Key West spirit in this enchanting 3 st ...
From $280 per night (USD)
Expedia
From $506 per night (USD)
VRBO
Ann Street Tranquility: A cozy and peaceful cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Stre ...
From $506 per night (USD)
VRBO
From $275 per night (USD)
VRBO
Old Town cottage
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
The newly remodeled home is located in the middle of Old Town down a private lane just a block from Duval Street. One of ...
From $275 per night (USD)
VRBO
From $2892 per night (USD)
VRBO
Your Private Key West Escape | 3 Family Ready Room, Near Duval Street Nightlife
Bedrooms:
3
Bathrooms:
3
Sleeps:
12
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $2892 per night (USD)
VRBO
$Idyllic Key West Room w\/ Poolside Bar & Watersports | 2 Family Rooms$
From $3192 per night (USD)
VRBO
Idyllic Key West Room w\/ Poolside Bar & Watersports | 2 Family Rooms
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3192 per night (USD)
VRBO
From $3017 per night (USD)
VRBO
Key West Room Retreat | Two Family Ready Suites Perfect For Long Stays
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3017 per night (USD)
VRBO
$Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony$
From $931 per night (USD)
VRBO
Perfect Location to Key West Action! Pool and Garden View Room w\/ Balcony
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $931 per night (USD)
VRBO
$Tropical Escape! 2 Spacious Rooms w\/ Balcony$
From $1822 per night (USD)
VRBO
Tropical Escape! 2 Spacious Rooms w\/ Balcony
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1822 per night (USD)
VRBO
$Relaxing Room w\/ Balcony & Breathtaking View$
From $986 per night (USD)
VRBO
Relaxing Room w\/ Balcony & Breathtaking View
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $986 per night (USD)
VRBO
$Spacious Suite w\/ Terrace & Scenic Harbor View$
From $1479 per night (USD)
VRBO
Spacious Suite w\/ Terrace & Scenic Harbor View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1479 per night (USD)
VRBO
From $1396 per night (USD)
VRBO
Best Spot Near Duval Street Nightlife! Suite ScenicHarbor View and Terrace
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1396 per night (USD)
VRBO
From $1760 per night (USD)
VRBO
Your Waterfront Hideaway in the Heart of Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1760 per night (USD)
VRBO
$Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area$
From $1509 per night (USD)
VRBO
Breathtaking Waterfront Retreat | Spacious 1BR Suite w\/ Living Area
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1509 per night (USD)
VRBO
$Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools$
From $1666 per night (USD)
VRBO
Chic Waterfront Room | 1BR Suite w\/ Balcony | Outdoor Pools
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1666 per night (USD)
VRBO
$Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite$
From $1595 per night (USD)
VRBO
Harbor front Hideaway w\/ Pools & Seaside Dining | 1BR Spacious Suite
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1595 per night (USD)
VRBO
From $6102 per night (USD)
VRBO
4 Family Ready Suites | Spacious and Near Duval Street Nightlife
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $6102 per night (USD)
VRBO
From $759 per night (USD)
Expedia
Best Location -Hyatt Sunset Harbor- water view-Jan 26 to Feb 2. Seven nights
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
LISTING is ONLY available January 26 to Feb 2. Best location in town. Only 1.5 blocks to Duvall Street but quiet. Key We ...
From $759 per night (USD)
Expedia
From $641 per night (USD)
VRBO
Deluxe Key West Ocean Front Condo Week - April 22 - 29, 2025
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Deluxe Ocean Front Condo in Key West Florida with a spectacular 3rd Floor balcony view of the Marina and Ocean. One Full ...
From $641 per night (USD)
VRBO
From $894 per night (USD)
VRBO
SEAPORT SUMMIT at Galleon Resort-Beach-Pool-King Suite-BBQ-near Mallory Square
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
GALLEON RESORT LUXURY WATERFRONT PENTHOUSE with LOFT + GREAT VIEWS OF THE MARINA, OCEAN & HISTORIC SEAPORT 5th FLOOR M ...
From $894 per night (USD)
VRBO
$Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View$
From $1022 per night (USD)
VRBO
Waterfront Resort w\/ Outdoor Pools | Spacious Room w\/ Scenic View
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1022 per night (USD)
VRBO
$Scenic Old Town Key West Retreat w\/ Pool Access$
From $911 per night (USD)
VRBO
Scenic Old Town Key West Retreat w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $911 per night (USD)
VRBO
$Waterfront Stay in Duval St. Room w\/ Pool Access$
From $922 per night (USD)
VRBO
Waterfront Stay in Duval St. Room w\/ Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $922 per night (USD)
VRBO
$Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms$
From $3857 per night (USD)
VRBO
Escape to Key West w\/ Exclusive Waterfront Stay & Pool Access | 4 Family Rooms
Bedrooms:
4
Bathrooms:
4
Sleeps:
16
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $3857 per night (USD)
VRBO
From $919 per night (USD)
VRBO
Tropical Getaway! Refreshing Pools: 2 Blocks Away from Duval Street
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $919 per night (USD)
VRBO
From $973 per night (USD)
VRBO
Romantic Key West Getaway | Scenic Pool View Room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $973 per night (USD)
VRBO
From $1258 per night (USD)
VRBO
Harbor Oasis Room: Tranquil Seaport & Water Fun
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1258 per night (USD)
VRBO
From $1188 per night (USD)
VRBO
Perfect Key West Escape! Scenic Harbor View Room Ideal for Romantic Stay
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1188 per night (USD)
VRBO
$Relaxing Room w\/ Water View | Pool Access$
From $1081 per night (USD)
VRBO
Relaxing Room w\/ Water View | Pool Access
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Unwind in Key West's vibrant heart, where every step brings you closer to adventure. Just moments from Duval Street, the ...
From $1081 per night (USD)
VRBO
$Luxury 4BDR\/4BA Penthouse | 4 Bed, 4 Bath$
From $1992 per night (USD)
Expedia
Luxury 4BDR\/4BA Penthouse | 4 Bed, 4 Bath
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Welcome to the Luxury Harbor House Suites! We proudly offer you a newly renovated 2,400SF, 4BDR/4BA Penthouse in the Cit ...
From $1992 per night (USD)
Expedia
$Priced to book! 2 Bdr\/2Ba Walking distance to Duval St., Mallory Square, Trolley$
Click For Pricing
VRBO
Priced to book! 2 Bdr\/2Ba Walking distance to Duval St., Mallory Square, Trolley
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Great location in Key West. The Galleon is Walking distance to shopping, bars, dining, trolley, marina, Duval st., Mallo ...
Click For Pricing
VRBO
From $183 per night (USD)
Expedia
Quaint Pool Cottage in Old Town Key West Great value
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Perfectly situated in Old Town Key West. This quaint pool cottage is perfect for a couple with occasional visitors. beau ...
From $183 per night (USD)
Expedia
From $705 per night (USD)
VRBO
FERNWOOD ~ Dreamy, Lush Estate with Incredible Outdoor Space with Pool & Spa!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
THERE'S NO PLACE LIKE YOUR ISLAND HOME... Located in the highly sought-after area of The Meadows and beneath peaceful sw ...
From $705 per night (USD)
VRBO
From $2782 per night (USD)
Expedia
Old Town Caribbean Estate Key West - Great for Groups - Private Pool - Sleeps 21
Bedrooms:
8
Bathrooms:
10
Sleeps:
21
The Old Town Caribbean Estate is a masterful combination of a classic Key West Victorian home with an exotic Caribbean-s ...
From $2782 per night (USD)
Expedia
From $534 per night (USD)
VRBO
DOWNTOWN KEY WEST 2BED OCEANFRONT!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
This is a great OCEANFRONT unit with large balcony to watch sunsets. Hyatt Sunset Harbor is perfectly located in downtow ...
From $534 per night (USD)
VRBO
$Three Condos w\/ Entertainment, Private Parking & Beach Nearby - Great for Groups$
From $1286 per night (USD)
Expedia
Three Condos w\/ Entertainment, Private Parking & Beach Nearby - Great for Groups
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Three Flowers Guesthouse Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ente ...
From $1286 per night (USD)
Expedia
From $1557 per night (USD)
VRBO
Conch House in Key West
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Quintessential Grand Key West Estate! The James J. Curtis House c. 1874 was acquired by the Navy in 1903 and the home b ...
From $1557 per night (USD)
VRBO
From $135 per night (USD)
Expedia
Cubana Casita in Key West
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Cubana Casita is an easy-access ground floor condo with one bedroom and 1 baths. This special home's 'from the ground up ...
From $135 per night (USD)
Expedia
From $178 per night (USD)
VRBO
The Sea Glass Cottage in Historic Key West
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spend time in beautiful Key West and live like a local in a true Conch Home! The Sea Glass Cottage is perfect for group ...
From $178 per night (USD)
VRBO
Click For Pricing
Expedia
The Sandy Beach House in Historic Key West
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Spend time in Key West and live like a local in a true Conch Home! The Sandy Beach Cottage, a fully-renovated first floo ...
Click For Pricing
Expedia

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