image description

Search Your Destination Now!

Key West Rentals

Rental Rates ($USD weekly)

Bedrooms

Guests

Check Rates & Availability:

Update Results Reset Dates

Results: 91 - 120 of 403 Rentals

  • 2 Bedrooms 2 Baths Sleeps 4
    $3,000 - 7,440

    per month (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 4

    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 ...

    Details
  • 2 Bedrooms 2 5 Baths Sleeps 4
    $2,632 - 3,962

    per week (USD)

    By: VRBO

    2 Bedrooms, 2.5 Baths, Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    Foundry - Located in the Truman Annex, one of Key West’s most prestigious and luxurious gated waterfront neighborhoods, ...

    Details
  • October Unit 2br 2ba-beach pool sunset view June Unit 1br 1ba-marina view
    $413

    per week (USD)

    By: VRBO

    October Unit 2br 2ba-beach, pool, sunset view June Unit 1br 1ba-marina view

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    I have 2 Units available for rent. One in June and one in October, they are not equally the same. My October unit is a 2 ...

    Details
  • Villa 4 Bedrooms 3 Baths Sleeps 8
    $800 - 1,450

    per night (USD)

    By: VRBO

    Villa, 4 Bedrooms, 3 Baths, Sleeps 8

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    The Perfect Getaway Wow---it sure is. Walk by on Greene Street a stone's throw from the water and wharf, some time and ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 4
    $378 - 875

    per night (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Jasmine Place is a beautiful and enchanting home conveniently located next door to the Ernest Hemingway Home and Museum ...

    Details
  • A Stylish 2Bd 2 5Ba Caribbean Surprise Right off Duval with Backyard Oasis
    $19,350

    per month (USD)

    By: VRBO

    A Stylish 2Bd/ 2.5Ba Caribbean Surprise Right off Duval with Backyard Oasis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A STYLISH CARIBBEAN SURPRISE RIGHT OFF DUVAL... Private single-family home with peaceful porches totaling two bedrooms, ...

    Details
  • Private 5BR 5 5BA Old Town Estate Home + Private Pool 29 night minimum stay
    $2,723 - 6,230

    per week (USD)

    By: VRBO

    Private 5BR/5.5BA Old Town Estate Home + Private Pool / 29 night minimum stay***

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    10

    THE EXPERIENCE... "Amazing Stay!!! Amazing Location!!! Wow!!! Absolutely Amazing location. Close to everything. Huge sp ...

    Details
  • 2 Bedroom 2 Full Bath with private deck overlooking the shared pool
    $770

    per week (USD)

    By: VRBO

    2 Bedroom, 2 Full Bath with private deck overlooking the shared pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    When choosing your dates, please keep in mind that we rent a minimum of 7 DAYS from SATURDAY to SATURDAY. (One exception ...

    Details
  • 3BR 3BA Old Town Home + Pool Parking near Duval 29 night minimum stay
    $1,547 - 4,781

    per week (USD)

    By: VRBO

    3BR/3BA Old Town Home + Pool & Parking near Duval / 29 night minimum stay***

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    THE EXPERIENCE... "Beautiful Middle of Everything. Lovely to look at, nicely restored and well maintained. Hemingway Ho ...

    Details
  • End unit on waters edge privacy quiet bird preserve see sunset sunrise
    $10,470

    per month (USD)

    By: VRBO

    *** End unit on waters edge, privacy, quiet, bird preserve, see sunset & sunrise

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

    (Please contact owner for stays less than 28 days before you book !!!!. ) Military Vouchers Welcome! In Key West - N ...

    Details
  • ATLANTIC BREEZE Spacious 2 2 w Sleeper Sofa Parking Pool and Beach
    $245

    per night (USD)

    By: VRBO

    "ATLANTIC BREEZE" ~ Spacious 2/2 w/ Sleeper Sofa, Parking, Pool and Beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...

    Details
  • You are steps from Duval Street Hemingway House and Blue Heaven Restaurant
    $3,090 - 8,490

    per month (USD)

    By: VRBO

    You are steps from Duval Street, Hemingway House and Blue Heaven Restaurant

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Key West is PARADISE once again! Our neighborhood, Duval Street and all 165 miles from Miami to Key West on US 1 are cle ...

    Details
  • 2-Story Private Home with Private Pool 4 Bedrooms 4 5 Baths Sleeps 8-10
    $545 - 2,845

    per night (USD)

    By: VRBO

    2-Story Private Home with Private Pool, 4 Bedrooms, 4.5 Baths (Sleeps 8-10)

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    THE EXPERIENCE... "Smack dab in the heart of KW. Top notch accommodations. Service exceptional, as well. From the commu ...

    Details
  • 3-Story 4BR 4BA Home in Old Town + Private Saltwater Pool Available Monthly
    $2,177 - 4,676

    per week (USD)

    By: VRBO

    3-Story 4BR/4BA Home in Old Town + Private Saltwater Pool. Available Monthly

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    12

    THE EXPERIENCE... "Dream Living at Bailey's Mango Mansion. The property was everything and more per Last Key Realty's d ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 8
    $300 - 550

    per night (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 2 Bedrooms 1 Bath Sleeps 4
    $1,498 - 2,450

    per week (USD)

    By: VRBO

    2 Bedrooms, 1 Bath, Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    Completely renovated, 7 night minimum rental. This condo has everything you want and more. Paradise is definitely found ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 4
    $1,750 - 2,800

    per week (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 4

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 2 Bedrooms 2 5 Baths Sleeps 6
    $300 - 400

    per night (USD)

    By: VRBO

    2 Bedrooms, 2.5 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Downtown Duval St. 2 bedroom 2 1/2 bath condo, located in the heart of Old Town. Walking distance to many of the main at ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 6
    $1,498 - 2,450

    per week (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 2 Bedrooms 1 Bath Sleeps 5
    $1,498 - 2,450

    per week (USD)

    By: VRBO

    2 Bedrooms, 1 Bath, Sleeps 5

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    5

    7 night minimum stay condo upstairs unit with 2 bedrooms and 1 Bathroom upstairs spacious unit with 1 queen, 2 twins and ...

    Details
  • 3 Bedrooms 2 Baths Sleeps 8
    $4,500 - 8,580

    per month (USD)

    By: VRBO

    3 Bedrooms, 2 Baths, Sleeps 8

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    8

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

    Details
  • 2 Bedrooms 2 Baths Sleeps 8
    $300 - 500

    per night (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 2B Truman Annex Townhouse with En Suite Baths and wonderful deck w gas grill
    $29,850

    per month (USD)

    By: VRBO

    2B Truman Annex Townhouse with En Suite Baths and wonderful deck w gas grill!

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    4

    SURROUNDED BY HISTORY AND BEAUTY... Nestled in Truman Annex along President’s Walk you will find The Nautilus; a sophist ...

    Details
  • 2 Bedrooms 2 5 Baths Sleeps 6
    $300 - 400

    per night (USD)

    By: VRBO

    2 Bedrooms, 2.5 Baths, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Downtown Duval St. 2 bedroom 2 1/2 bath condo, located in the heart of Old Town. Walking distance to many of the main at ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 8
    $300 - 500

    per night (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 8
    $300 - 550

    per night (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 8
    $300 - 550

    per night (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 2 Bedrooms 2 Baths Sleeps 8
    $300 - 500

    per night (USD)

    By: VRBO

    2 Bedrooms, 2 Baths, Sleeps 8

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 3 Bedrooms 3 Baths Sleeps 10
    $400 - 600

    per night (USD)

    By: VRBO

    3 Bedrooms, 3 Baths, Sleeps 10

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
  • 3 Bedrooms 4 Baths Sleeps 10
    $400 - 600

    per night (USD)

    By: VRBO

    3 Bedrooms, 4 Baths, Sleeps 10

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is ...

    Details
We have 403 Key West Rentals
Help us find the best rentals for you...
# of Guests:
Travel Dates:
I don't have specific dates
Continue