Search Your Destination Now!

Fleming Key Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Update Results Reset Dates
Filter

Results: 223 Rentals

  • Pelican Landing Dominica Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Dominica Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Pelican Landing Abaco Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Abaco Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • LOST SHAKER OF SALT ~ Relax!
    From $695 per night (USD)

    VRBO

    "LOST SHAKER OF SALT" ~ Relax!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    THE HEART OF OLD TOWN... Charming Old Town home in the heart of Key West.  Located on Southard Street just steps from Du ...

    From $695 per night (USD)

    VRBO

    Details
  • Tropical Jewel
    From $228 per night (USD)

    VRBO

    Tropical Jewel

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    WELCOME TO TROPICAL JEWEL! We are complying with the directives listed on the Monroe County website. Please be awar ...

    From $228 per night (USD)

    VRBO

    Details
  • Galleon Resort Efficiency in Old Town
    From $171 per night (USD)

    VRBO

    Galleon Resort Efficiency in Old Town

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    2

    This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size b ...

    From $171 per night (USD)

    VRBO

    Details
  • Southernmost Bliss
    From $527 per night (USD)

    VRBO

    Southernmost Bliss

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Nestled at th ...

    From $527 per night (USD)

    VRBO

    Details
  • Star of the Seaport
    From $872 per night (USD)

    VRBO

    Star of the Seaport

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! For a truly o ...

    From $872 per night (USD)

    VRBO

    Details
  • SERENITY~ Impeccable!
    From $1145 per night (USD)

    VRBO

    "SERENITY"~ Impeccable!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    LOCAL LIVING.... Spend time relaxing in Paradise in the perfect home. Serenity is a beautifully decorated,  4 bedroom ho ...

    From $1145 per night (USD)

    VRBO

    Details
  • Pelican Landing St.John Penthouse
    From $400 per night (USD)

    VRBO

    Pelican Landing St.John Penthouse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $400 per night (USD)

    VRBO

    Details
  • BOOMERANG BOATHOUSE~ Charm!
    From $1295 per night (USD)

    VRBO

    "BOOMERANG BOATHOUSE"~ Charm!

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    8

    RETURN TO EQUANIMITY... “Boomerang Boathouse” is nestled in the peaceful neighborhood locals refer to as The Meadows.  T ...

    From $1295 per night (USD)

    VRBO

    Details
  • La Casita En Cima
    From $124 per night (USD)

    VRBO

    La Casita En Cima

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This quaint l ...

    From $124 per night (USD)

    VRBO

    Details
  • Pelican Landing Eleuthera Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Eleuthera Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Historic Seaport Charmer
    Click For Pricing

    VRBO

    Historic Seaport Charmer

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Short one block walk to the harbor with great restaurants and bars. Park your car in the City Old Town Garage across the ...

    Click For Pricing

    VRBO

    Details
  • The Lime & The Coconut
    From $872 per night (USD)

    VRBO

    The Lime & The Coconut

    Bedrooms:
    9
    Bathrooms:
    6
    Sleeps:
    16

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! According to ...

    From $872 per night (USD)

    VRBO

    Details
  • Heavenly Zen
    From $472 per night (USD)

    VRBO

    Heavenly Zen

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! In the Histor ...

    From $472 per night (USD)

    VRBO

    Details
  • Bay Villas@Trumbo Point
    From $99 per night (USD)

    VRBO

    Bay Villas@Trumbo Point

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    6

    Bay Villas is a charming 2-story waterfront condo located on Hilton Haven Road, a quiet cul-de-sac on Trumbo Point, whic ...

    From $99 per night (USD)

    VRBO

    Details
  • Pagitt House
    From $506 per night (USD)

    VRBO

    Pagitt House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    WELCOME TO PAGITT HOUSE! We are complying with the directives listed on the Monroe County website. Please be aware ...

    From $506 per night (USD)

    VRBO

    Details
  • The Galleon Resort
    From $59 per night (USD)

    VRBO

    The Galleon Resort

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Studio(lock-out) for rent 5th floor. The Galleon Resort has its own marina, fishing charters on-site, tiki bar that serv ...

    From $59 per night (USD)

    VRBO

    Details
  • Key West Sailing Adventure
    Click For Pricing

    VRBO

    Key West Sailing Adventure

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Hurry pick your last minute summer vacation package with sailing dates filling in fast! NOTE: MAKE SURE TO INSURE YOU ...

    Click For Pricing

    VRBO

    Details
  • Pelican Landing Harbor Island Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Harbor Island Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Villa Olivietta
    From $343 per night (USD)

    VRBO

    Villa Olivietta

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This ultimate ...

    From $343 per night (USD)

    VRBO

    Details
  • CAROLINE ON MY MIND ~ Special!
    From $125 per night (USD)

    VRBO

    "CAROLINE ON MY MIND" ~ Special!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    CLASSIC KEY WEST.... This retreat is an elegant two bedroom, 2 bath condominium one block off of famous Duval Street. Se ...

    From $125 per night (USD)

    VRBO

    Details
  • The Contented Crane
    From $382 per night (USD)

    VRBO

    The Contented Crane

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Traveling to ...

    From $382 per night (USD)

    VRBO

    Details
  • Pineapple Cottage
    From $478 per night (USD)

    VRBO

    Pineapple Cottage

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    WELCOME TO PINEAPPLE COTTAGE! We are complying with the directives listed on the Monroe County website. Please be awa ...

    From $478 per night (USD)

    VRBO

    Details
  • The Ibis & The Crane
    From $763 per night (USD)

    VRBO

    The Ibis & The Crane

    Bedrooms:
    9
    Bathrooms:
    6
    Sleeps:
    16

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Dreaming of a ...

    From $763 per night (USD)

    VRBO

    Details
  • The Artists' Muse
    From $584 per night (USD)

    VRBO

    The Artists' Muse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! For many, the ...

    From $584 per night (USD)

    VRBO

    Details
  • Absolute Key West
    From $329 per night (USD)

    VRBO

    Absolute Key West

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    This Private home is located in the historic Truman Annex of old town Key West, where you can get away from it all while ...

    From $329 per night (USD)

    VRBO

    Details
  • Villa Aqua
    From $50 per night (USD)

    VRBO

    Villa Aqua

    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 $50 per night (USD)

    VRBO

    Details
  • The Commodore's Manor
    From $763 per night (USD)

    VRBO

    The Commodore's Manor

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    14

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! THE COMMODORE ...

    From $763 per night (USD)

    VRBO

    Details
  • Key West Suites Hotel #201
    From $234 per night (USD)

    VRBO

    Key West Suites Hotel #201

    Bedrooms:
    1
    Bathrooms:
    0
    Sleeps:
    6

    Key West Suites Hotel #201 Welcome to your charming private studio apartment right on Duval street! Built in 1919, it u ...

    From $234 per night (USD)

    VRBO

    Details
  • CONCH HEAVEN ~ Easy Breezy!
    From $645 per night (USD)

    VRBO

    "CONCH HEAVEN" ~ Easy Breezy!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    OLD TOWN LOCATION... A beautifully furnished and comfortable home, located a short distance from Duval Street.  Have bik ...

    From $645 per night (USD)

    VRBO

    Details
  • Galleon Resort Waterfront Luxury in Old Town Key West
    From $350 per night (USD)

    VRBO

    Galleon Resort Waterfront Luxury in Old Town Key West

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    This is a large (1245 SF) 1BR/1BA condo on the 6th floor of the Galleon Resort & Marina.....and is a one of a kind. It ...

    From $350 per night (USD)

    VRBO

    Details
  • Eisenhower Retreat
    From $599 per night (USD)

    VRBO

    Eisenhower Retreat

    Bedrooms:
    4.5
    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 $599 per night (USD)

    VRBO

    Details
  • Banyan Court 238
    From $100 per night (USD)

    VRBO

    Banyan Court 238

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    This is a luxury town home, located in the heart of old town and walking distance to all main attractions, including th ...

    From $100 per night (USD)

    VRBO

    Details
  • The Pearl in Paradise
    From $133 per night (USD)

    VRBO

    The Pearl in Paradise

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical d ...

    From $133 per night (USD)

    VRBO

    Details
  • Pelican Landing Antigua Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Antigua Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • SEAPORT SANCTUARY ~ Romantic!
    From $680 per night (USD)

    VRBO

    "SEAPORT SANCTUARY" ~ Romantic!

    Bedrooms:
    1
    Bathrooms:
    1
    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 $680 per night (USD)

    VRBO

    Details
  • Good Vibrations
    From $491 per night (USD)

    VRBO

    Good Vibrations

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    10

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Key West has ...

    From $491 per night (USD)

    VRBO

    Details
  • William Skelton Home
    From $459 per night (USD)

    VRBO

    William Skelton Home

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    The William Skelton "Pink House" is located just steps from Duval Street in the heart of Old Town Key West. At this very ...

    From $459 per night (USD)

    VRBO

    Details
  • Pelican Landing Florida Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Florida Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Studio Blu
    From $134 per night (USD)

    VRBO

    Studio Blu

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Location, location, location! Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in ...

    From $134 per night (USD)

    VRBO

    Details
  • Havana House
    From $204 per night (USD)

    VRBO

    Havana House

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Located on So ...

    From $204 per night (USD)

    VRBO

    Details
  • Pelican Landing Aruba Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Aruba Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • BEACH HOUSE ~ Prestigious!
    From $300 per night (USD)

    VRBO

    "BEACH HOUSE" ~ Prestigious!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    PRESTIGIOUS TROPICAL RETREAT... Indulge in this spectacular two-story home situated in the premier gated community of hi ...

    From $300 per night (USD)

    VRBO

    Details
  • Charming Old Town Cottage
    From $200 per night (USD)

    VRBO

    Charming Old Town Cottage

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    This charming conch home is newly renovated. Classic wood frame with Two bedrooms and Two baths on the first floor as we ...

    From $200 per night (USD)

    VRBO

    Details
  • The Zesty Lime
    From $436 per night (USD)

    VRBO

    The Zesty Lime

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Key West is k ...

    From $436 per night (USD)

    VRBO

    Details
  • Villa Alta
    From $50 per night (USD)

    VRBO

    Villa Alta

    Bedrooms:
    1
    Bathrooms:
    1
    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 wit ...

    From $50 per night (USD)

    VRBO

    Details
  • SEAPORT SUNSETS at Galleon Resort in Old Town (Beach-Pool-BBQ)
    From $480 per night (USD)

    VRBO

    SEAPORT SUNSETS at Galleon Resort in Old Town (Beach-Pool-BBQ)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST HARBOR, SUNSET KE ...

    From $480 per night (USD)

    VRBO

    Details
  • Captain's Daughter
    From $749 per night (USD)

    VRBO

    Captain's Daughter

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    "Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropical ...

    From $749 per night (USD)

    VRBO

    Details
  • Pelican Landing St. Thomas Penthouse
    From $500 per night (USD)

    VRBO

    Pelican Landing St. Thomas Penthouse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $500 per night (USD)

    VRBO

    Details
  • BLUE ROOSTER ~ Paradise!
    From $1445 per night (USD)

    VRBO

    "BLUE ROOSTER" ~ Paradise!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    OLD TOWN PARADISE.... Paradise awaits in a quiet Old Town location.  This four bedroom home is set on a cozy lane that i ...

    From $1445 per night (USD)

    VRBO

    Details
  • Heavenly Hideaway
    From $205 per night (USD)

    VRBO

    Heavenly Hideaway

    Bedrooms:
    2.5
    Bathrooms:
    3
    Sleeps:
    6

    HEAVENLY HIDEAWAY! We are complying with the directives listed on the Monroe County website. Please be aware that info ...

    From $205 per night (USD)

    VRBO

    Details
  • Key West Suites Hotel #205
    Click For Pricing

    VRBO

    Key West Suites Hotel #205

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Key West Suites Hotel Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used t ...

    Click For Pricing

    VRBO

    Details
  • ISLAND TIME ~ Conch Charm!
    From $550 per night (USD)

    VRBO

    "ISLAND TIME" ~ Conch Charm!

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    EASE INTO ISLAND TIME... Award-winning, fully-renovated 1924 traditional conch style home. Relax and watch the world pas ...

    From $550 per night (USD)

    VRBO

    Details
  • Darling of Duval
    From $409 per night (USD)

    VRBO

    Darling of Duval

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Don't miss an ...

    From $409 per night (USD)

    VRBO

    Details
  • Seafarer's Refuge
    From $599 per night (USD)

    VRBO

    Seafarer's Refuge

    Bedrooms:
    4.5
    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 $599 per night (USD)

    VRBO

    Details
  • Maison Tropicale
    From $683 per night (USD)

    VRBO

    Maison Tropicale

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Imagine a tra ...

    From $683 per night (USD)

    VRBO

    Details
  • CAPTAIN'S QUARTERS ~ A Gem!
    From $495 per night (USD)

    VRBO

    "CAPTAIN'S QUARTERS" ~ A Gem!

    Bedrooms:
    3.5
    Bathrooms:
    4
    Sleeps:
    10

    HISTORIC OLD-WORLD CHARM WITH MODERN AMENITIES AND A LAGOON-STYLE POOL.... Once you step through the threshold of this O ...

    From $495 per night (USD)

    VRBO

    Details
  • Island Chic
    From $524 per night (USD)

    VRBO

    Island Chic

    Bedrooms:
    4.5
    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 $524 per night (USD)

    VRBO

    Details
  • Galleon Resort
    From $393 per night (USD)

    VRBO

    Galleon Resort

    Bedrooms:
    2
    Bathrooms:
    2
    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 $393 per night (USD)

    VRBO

    Details
  • Bayview House Apt 1
    From $90 per night (USD)

    VRBO

    Bayview House Apt 1

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Monthly rental STUDIO with POOL just AVAILABLE. Same amenities. Save money if planing to come for over 14 days! Find it ...

    From $90 per night (USD)

    VRBO

    Details
  • **True Love Key West**
    Click For Pricing

    VRBO

    **True Love Key West**

    Bedrooms:
    6
    Bathrooms:
    3
    Sleeps:
    8

    **28-NIGHT MINIMUM PER CITY OF KEY WEST ORDINANCES** Fall in love with Key West while staying in our newly remodeled, g ...

    Click For Pricing

    VRBO

    Details
  • ORCHID ESCAPE~ Historic!
    From $500 per night (USD)

    VRBO

    "ORCHID ESCAPE"~ Historic!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    CLASSIC OLD KEY WEST HOME... This home is boasting a rare combination of location and character. A mix of historic detai ...

    From $500 per night (USD)

    VRBO

    Details
  • Key West Sailing Adventure
    From $215 per night (USD)

    VRBO

    Key West Sailing Adventure

    Bedrooms:
    2.5
    Bathrooms:
    2
    Sleeps:
    4

    Hurry book last minute summer vacation dates that just opened up now! This 37 foot boat is available Key West! This is ...

    From $215 per night (USD)

    VRBO

    Details
  • SEAPORT PANORAMA at Galleon Resort, Key West, FL (Beach-Pool-BBQ)
    Click For Pricing

    VRBO

    SEAPORT PANORAMA at Galleon Resort, Key West, FL (Beach-Pool-BBQ)

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    GALLEON RESORT LUXURY OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING 180 DEGREE FRONT & CORNER BALCONY V ...

    Click For Pricing

    VRBO

    Details
  • Pelican Landing Flamingo Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Flamingo Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Cigar Makers Tropical Cottage
    From $500 per night (USD)

    VRBO

    Cigar Makers Tropical Cottage

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Your tropical oasis in Historic Old Town Key West awaits for your monthly rental! 1890 Cigar Maker's Tropical Cottage re ...

    From $500 per night (USD)

    VRBO

    Details
  • Puerta Coralina
    From $273 per night (USD)

    VRBO

    Puerta Coralina

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! This precious ...

    From $273 per night (USD)

    VRBO

    Details
  • Bayview Retreat
    From $599 per night (USD)

    VRBO

    Bayview Retreat

    Bedrooms:
    5.5
    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 $599 per night (USD)

    VRBO

    Details
  • THE SEASHELL ~ Spectacular!
    From $1195 per night (USD)

    VRBO

    "THE SEASHELL" ~ Spectacular!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    CLASSIC KEY WEST.... When only the best will do! The Seashell is the classic Old Town Key West home. Perfect setting for ...

    From $1195 per night (USD)

    VRBO

    Details
  • Villa Vista
    From $50 per night (USD)

    VRBO

    Villa Vista

    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 $50 per night (USD)

    VRBO

    Details
  • Pelican Landing Bonaire Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Bonaire Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • SOUTHERNMOST BELLE ~ Grand!
    From $714 per night (USD)

    VRBO

    "SOUTHERNMOST BELLE" ~ Grand!

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    LUXURY IN OLD TOWN... Grand home in the Historic Seaport area of Old Town Key West. Tucked behind a canopy of palms this ...

    From $714 per night (USD)

    VRBO

    Details
  • Southern Star
    From $218 per night (USD)

    VRBO

    Southern Star

    Bedrooms:
    4.5
    Bathrooms:
    4
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! SOUTHERN STAR ...

    From $218 per night (USD)

    VRBO

    Details
  • Pelican Landing Andros Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Andros Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Pelican Landing Bermuda Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Bermuda Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Tranquility
    From $155 per night (USD)

    VRBO

    Tranquility

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    WELCOME TO TRANQUILITY! We are complying with the directives listed on the Monroe County website. Please be aware tha ...

    From $155 per night (USD)

    VRBO

    Details
  • Pelican Landing Curacao Retreat
    From $300 per night (USD)

    VRBO

    Pelican Landing Curacao Retreat

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $300 per night (USD)

    VRBO

    Details
  • Casa Oliviana
    From $487 per night (USD)

    VRBO

    Casa Oliviana

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    12

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Finally, a la ...

    From $487 per night (USD)

    VRBO

    Details
  • Heart of the Harbor
    From $189 per night (USD)

    VRBO

    Heart of the Harbor

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Embrace the b ...

    From $189 per night (USD)

    VRBO

    Details
  • The Toasted Coconut
    From $436 per night (USD)

    VRBO

    The Toasted Coconut

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Throughout Ke ...

    From $436 per night (USD)

    VRBO

    Details
  • Americana Tropicale
    From $545 per night (USD)

    VRBO

    Americana Tropicale

    Bedrooms:
    5.5
    Bathrooms:
    4
    Sleeps:
    10

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals booked after July 15, 2020 are 100% Refundable until 21 days prior to y ...

    From $545 per night (USD)

    VRBO

    Details
  • Conch Cottage
    From $251 per night (USD)

    VRBO

    Conch Cottage

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    WELCOME TO CONCH COTTAGE! We are complying with the directives listed on the Monroe County website. Please be aware th ...

    From $251 per night (USD)

    VRBO

    Details
  • The Admiral's Estate
    From $531 per night (USD)

    VRBO

    The Admiral's Estate

    Bedrooms:
    6.5
    Bathrooms:
    5
    Sleeps:
    8

    Liksom många av höjdpunkterna i Key West, "The Admiral's Estate" firar en rik historia på ön medan omfamna en modern ö r ...

    From $531 per night (USD)

    VRBO

    Details
  • Coastal Cabana
    From $550 per night (USD)

    VRBO

    Coastal Cabana

    Bedrooms:
    3.5
    Bathrooms:
    3
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Located only ...

    From $550 per night (USD)

    VRBO

    Details
  • TwoSim Suite
    From $45 per night (USD)

    VRBO

    TwoSim Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key ...

    From $45 per night (USD)

    VRBO

    Details
  • Pelican Landing St. Kitts Penthouse
    From $400 per night (USD)

    VRBO

    Pelican Landing St. Kitts Penthouse

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    Our beautiful waterfront condos have a range of room types to suite your every need. Whether you want a suite for two or ...

    From $400 per night (USD)

    VRBO

    Details
  • Island Time
    From $338 per night (USD)

    VRBO

    Island Time

    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 $338 per night (USD)

    VRBO

    Details
  • 617 Duval
    Click For Pricing

    VRBO

    617 Duval

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This Elegant & Spacious Apartment is located directly in the center of the Famous Duval Street. Enjoy Dining, Shopping, ...

    Click For Pricing

    VRBO

    Details
  • STRIPES ~ Treetop Condo!
    From $545 per night (USD)

    VRBO

    "STRIPES" ~ Treetop Condo!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key W ...

    From $545 per night (USD)

    VRBO

    Details
  • Casa Victoria
    From $763 per night (USD)

    VRBO

    Casa Victoria

    Bedrooms:
    6.5
    Bathrooms:
    5
    Sleeps:
    12

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! CASA VICTORIA ...

    From $763 per night (USD)

    VRBO

    Details
  • SEAHORSE COVE~ Luxury Oasis!
    From $995 per night (USD)

    VRBO

    "SEAHORSE COVE"~ Luxury Oasis!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...

    From $995 per night (USD)

    VRBO

    Details
  • The Galleon Resort
    From $59 per night (USD)

    VRBO

    The Galleon Resort

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This October condo is a 2BR, 2BA sunset/pool view sleeps 6. Condo has a full modern kitchen with granite/stainless, di ...

    From $59 per night (USD)

    VRBO

    Details
  • Casa Serendipity
    From $322 per night (USD)

    VRBO

    Casa Serendipity

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Sometimes in ...

    From $322 per night (USD)

    VRBO

    Details
  • STARS AND STRIPES ~ Majestic!
    From $600 per night (USD)

    VRBO

    "STARS AND STRIPES" ~ Majestic!

    Bedrooms:
    4
    Bathrooms:
    8
    Sleeps:
    20

    ABUNDANCE IN OLD TOWN... Majestic home in the Historic Seaport area of Old Town Key West. This is THE house to bring eve ...

    From $600 per night (USD)

    VRBO

    Details
  • Banyan Court 214
    From $117 per night (USD)

    VRBO

    Banyan Court 214

    Bedrooms:
    3.5
    Bathrooms:
    2
    Sleeps:
    4

    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps ...

    From $117 per night (USD)

    VRBO

    Details
  • The Palms
    From $150 per night (USD)

    VRBO

    The Palms

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key We ...

    From $150 per night (USD)

    VRBO

    Details
  • The Smiling Ibis
    From $382 per night (USD)

    VRBO

    The Smiling Ibis

    Bedrooms:
    4.5
    Bathrooms:
    3
    Sleeps:
    8

    FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 21 days prior to your arrival! Traveling to ...

    From $382 per night (USD)

    VRBO

    Details
  • Villa Porta
    From $50 per night (USD)

    VRBO

    Villa Porta

    Bedrooms:
    1
    Bathrooms:
    1
    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 $50 per night (USD)

    VRBO

    Details
  • Paradise on Pine
    From $240 per night (USD)

    VRBO

    Paradise on Pine

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Paradise on Pine är en perfekt bild som ligger högt ovanför denna vackra envägsgata med en inbjudande veranda perfekt fö ...

    From $240 per night (USD)

    VRBO

    Details