Choose Key West Rentals for Restful and Relaxing Getaways

Planning a trip to Key West, Florida, one of the top spots for honeymoon vacation rentals, means that you’re well on your way to a sunny and tropical getaway from all of the stress of your life at home. Key West condos offer economical and convenient ways to take in all that this beautiful island has to offer, with easy access to both the beach and busy nightlife.

Key West Rentals Offer Easy Beach Access


No matter what you plan on doing during your stay, Key West vacation rentals can be found on the beach if you want to be able to simply wake up in the morning and walk directly out to the ocean. You may also find one of the Key West condo rentals on a private beach area so that you and your family can enjoy your stay away from the crowds.

Find Key West Vacation Rentals near Several Attractions and Activities


You should plan on several activities while staying at one of the Key West rentals, as you’ll have one less thing to worry about before heading out for a day on the town. Snorkeling, chartering a deep-sea fishing boat and even shopping for local novelties are some of the most common activities before retiring to one of the Key West vacation rentals. Consider a Key West rental on the golf course if you like to putt around on the green.

Stay for a Season at Key West Condo Rentals


If you’re planning on staying with a group, Key West condo rentals offer ideal solutions for several bedrooms and accommodations very near each other. Some Key West rentals can also be reserved for long-term stays if you want to get away from chilly winter weather for a season.

This island is known for its relaxed lifestyle, beauty and catering activities to tourists. There’s no doubt that you and your family will feel welcome at any of the Key West vacation rentals, and well-rested upon your return home. You’ll also like the convenient amenities of Key West condo rentals for entertaining your newfound friends you’re sure to meet in this tropical oasis! Search today!

Expand your search for Florida vacation rentals to include Miami vacation rentals and Ft. Lauderdale rentals in South Florida, Destin vacation rentals and Siesta Key rentals on the Gulf Coast, or Orlando vacation home rentals near Disney.
For more info, check out our guide to Key West vacations, including articles like the top Key West beaches.

You have sent
a request for
information to
this owner.
FILTERS
List View
Map View
Cancel Apply Filters
  1.  >
  2.  >
  3.  >
  4.  >
  5.  >
  6.  >

Key West: Condos, Houses & More(793)

sort by HomeAway Sort
Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access
    2 Bedrooms,
  • 1 Bathroom
    • , Sleeps 4
$1,300 - $1,950
per week

Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access

Book it Now!
7 night Minimum Stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
  1. Lower Florida Keys >
  2. Key West Condo
#244472
    (61)
    Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10
      3 Bedrooms,
    • 3 Bathrooms
      • , Sleeps 10
    $695 - $855
    per night

    Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10

    Book it Now!
    2 - 4 night Minimum Stay
    • 3 BR,
    • 3 BA,
    • Sleeps 10
    1. Lower Florida Keys >
    2. Key West Condo
    #367100
      (12)
      Charming Condo in Old Town Key West's Truman Annex
        1 Bedrooms,
      • 1 Bathroom
        • , Sleeps 2
      $1,200 - $1,850
      per week

      Charming Condo in Old Town Key West's Truman Annex

      Book it Now!
      7 night Minimum Stay
      • 1 BR,
      • 1 BA,
      • Sleeps 2
      1. Lower Florida Keys >
      2. Key West Condo
      #290407
        (32)
        Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!
          2 Bedrooms, Sleeps 4
        $1,300 - $1,950
        per week

        Key West Condo in Truman Annex with Whirlpool Tub, 2 Bikes, & Access to Pool!

        Book it Now!
        7 night Minimum Stay
        • 2 BR,
        • Sleeps 4
        1. Lower Florida Keys >
        2. Key West Condo
        #938538
          (18)
          Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West
            3 Bedrooms,
          • 2 Bathrooms
            • , Sleeps 10
          $1,800 - $2,900
          per week

          Oceanfront Acre Heated Private Pool Sandy Area Dock 15 Min Key West

          7 night Minimum Stay
          • 3 BR,
          • 2 BA,
          • Sleeps 10
          1. Lower Florida Keys >
          2. Key West House
          #317093
            (51)
            Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean
              1 Bedrooms,
            • 1 Bathroom
              • , Sleeps 2
            $149 - $189
            per night

            Charming, Romantic, Funky, Cozy, Unique, Beautiful, Island Charm, Beach, Ocean

            Book it Now!
            2 - 3 night Minimum Stay
            • 1 BR,
            • 1 BA,
            • Sleeps 2
            1. Lower Florida Keys >
            2. Key West Bungalow
            #972748
              (8)
              Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West
                2 Bedrooms,
              • 2 Bathrooms
                • , Sleeps 6
              $975 - $1,550
              per week

              Ocean Perch , Dock 80'Heated Pool Deep Channel Tennis 15 min Key West

              7 night Minimum Stay
              • 2 BR,
              • 2 BA,
              • Sleeps 6
              1. Lower Florida Keys >
              2. Key West House
              #315267
                (45)
                HGTV Featured Home - Boaters Paradise! Waterfront Key West Home
                  3 Bedrooms,
                • 2 Bathrooms
                  • , Sleeps 6
                $6,409 - $7,196
                per month

                HGTV Featured Home - Boaters Paradise! Waterfront Key West Home

                28 night Minimum Stay
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                1. Lower Florida Keys >
                2. Key West House
                #277391
                  (33)
                  STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN
                    1 Bedrooms,
                  • 1 Bathroom
                    • , Sleeps 4

                  STEPS FROM DUVAL! LUXURIOUS, SLEEPS 2-4, OLD TOWN

                  • 1 BR,
                  • 1 BA,
                  • Sleeps 4
                  1. Lower Florida Keys >
                  2. Key West Condo
                  #966039
                    (17)
                    Private Luxury in Prestigious Casa Marina Neighborhood
                      3 Bedrooms,
                    • 3 Bathrooms, 
                    • 1 Half Bath
                      • , Sleeps 7
                    $3,500 - $8,800
                    per month

                    Private Luxury in Prestigious Casa Marina Neighborhood

                    28 night Minimum Stay
                    • 3 BR,
                    • 3 BA,
                    • 1 HF BA,
                    • Sleeps 7
                    1. Lower Florida Keys >
                    2. Key West House
                    #298674
                      (14)
                      Private Yacht 3 blocks from Duval Street & Sloppy Joe's
                        3 Bedrooms, Sleeps 6
                      $575 - $650
                      per night

                      Private Yacht 3 blocks from Duval Street & Sloppy Joe's

                      2 - 5 night Minimum Stay
                      • 3 BR,
                      • Sleeps 6
                      1. Lower Florida Keys >
                      2. Key West Yacht
                      #390580vb
                        (21)
                        Walk to the beach!
                          1 Bedrooms,
                        • 1 Bathroom
                          • , Sleeps 2
                        $2,146 - $2,884
                        per month

                        Walk to the beach!

                        Book it Now!
                        28 night Minimum Stay
                        • 1 BR,
                        • 1 BA,
                        • Sleeps 2
                        1. Lower Florida Keys >
                        2. Key West Studio
                        #392129
                          (5)
                          'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..
                            3 Bedrooms,
                          • 2 Bathrooms
                            • , Sleeps 8
                          $400 - $750
                          per night

                          'CASA LOUISA @ UPPER DUVAL': Historic Conch Cottage & Pool 1/2 Block off Duval..

                          4 night Minimum Stay
                          • 3 BR,
                          • 2 BA,
                          • Sleeps 8
                          1. Lower Florida Keys >
                          2. Key West Cottage
                          #135603
                            (45)
                            Ocean Suite at the Galleon Resort
                              2 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 8
                            $495 - $695
                            per night

                            Ocean Suite at the Galleon Resort

                            Book it Now!
                            2 - 4 night Minimum Stay
                            • 2 BR,
                            • 2 BA,
                            • Sleeps 8
                            1. Lower Florida Keys >
                            2. Key West Condo
                            #929000
                              (4)
                              Oceanfront Condominium - Key West Oceanfront at the Coral Reef
                                2 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 6
                              $265 - $495
                              per night

                              Oceanfront Condominium - Key West Oceanfront at the Coral Reef

                              4 - 5 night Minimum Stay
                              • 2 BR,
                              • 2 BA,
                              • Sleeps 6
                              1. Lower Florida Keys >
                              2. Key West Condo
                              #154612
                                (34)
                                'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..
                                  2 Bedrooms,
                                • 2 Bathrooms, 
                                • 1 Half Bath
                                  • , Sleeps 6
                                $3,300 - $5,500
                                per week

                                'WINDOWS ON THE GULF @ THE ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo..

                                7 night Minimum Stay
                                • 2 BR,
                                • 2 BA,
                                • 1 HF BA,
                                • Sleeps 6
                                1. Lower Florida Keys >
                                2. Key West Condo
                                #390177
                                  (13)
                                  'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...
                                    2 Bedrooms,
                                  • 2 Bathrooms, 
                                  • 1 Half Bath
                                    • , Sleeps 6
                                  $1,950 - $3,500
                                  per week

                                  'VILLA BAHAMA @ THE FOUNDRY': Luxury 2BR/2.5BA Townhome in Truman Annex...

                                  7 night Minimum Stay
                                  • 2 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 6
                                  1. Lower Florida Keys >
                                  2. Key West Villa
                                  #390213
                                    (12)
                                    'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...
                                      2 Bedrooms,
                                    • 2 Bathrooms, 
                                    • 1 Half Bath
                                      • , Sleeps 5
                                    $2,950 - $5,000
                                    per week

                                    'GULFSIDE VISTAS @ TRUMAN ANNEX': Lavish Oceanfront 2BR/2.5BA Penthouse Condo...

                                    7 night Minimum Stay
                                    • 2 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 5
                                    1. Lower Florida Keys >
                                    2. Key West Condo
                                    #904145
                                      (19)
                                      Full Month Discounts Now Available in Truman Annex, Key West
                                        2 Bedrooms,
                                      • 2 Bathrooms, 
                                      • 1 Half Bath
                                        • , Sleeps 5
                                      $1,750 - $2,751
                                      per week

                                      Full Month Discounts Now Available in Truman Annex, Key West

                                      7 night Minimum Stay
                                      • 2 BR,
                                      • 2 BA,
                                      • 1 HF BA,
                                      • Sleeps 5
                                      1. Lower Florida Keys >
                                      2. Key West Condo
                                      #982960
                                        (12)
                                        'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...
                                          2 Bedrooms,
                                        • 2 Bathrooms
                                          • , Sleeps 6
                                        $2,100 - $3,800
                                        per week

                                        'OLD TOWN OASIS @ TRUMAN ANNEX': Luxurious 2BR/2BA Condo + Oceanside Pool...

                                        7 night Minimum Stay
                                        • 2 BR,
                                        • 2 BA,
                                        • Sleeps 6
                                        1. Lower Florida Keys >
                                        2. Key West Condo
                                        #390175
                                          (23)
                                          Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon
                                            2 Bedrooms,
                                          • 2 Bathrooms
                                            • , Sleeps 4
                                          $320 - $375
                                          per night

                                          Key West Boat & Breakfast, Reef Sailing Trips, ASA sailing coming soon

                                          2 - 3 night Minimum Stay
                                          • 2 BR,
                                          • 2 BA,
                                          • Sleeps 4
                                          1. Lower Florida Keys >
                                          2. Key West Yacht
                                          #229193
                                            (19)
                                            Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach
                                              2 Bedrooms,
                                            • 2 Bathrooms
                                              • , Sleeps 6
                                            $520 - $525
                                            per night

                                            Salida del Sol - Waterfront Key West Resort Style Home w/Pool & Beach

                                            Book it Now!
                                            3 night Minimum Stay
                                            • 2 BR,
                                            • 2 BA,
                                            • Sleeps 6
                                            1. Lower Florida Keys >
                                            2. Key West House
                                            #3498085
                                              2 Reviews
                                              Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes
                                                1 Bedrooms,
                                              • 1 Bathroom
                                                • , Sleeps 4
                                              $185 - $328
                                              per night

                                              Luxury Spacious Townhouse overlooking Pool w/ water view & 2 Bikes

                                              3 - 5 night Minimum Stay
                                              • 1 BR,
                                              • 1 BA,
                                              • Sleeps 4
                                              1. Lower Florida Keys >
                                              2. Key West Townhome
                                              #3472045
                                                (8)
                                                Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!
                                                  2 Bedrooms,
                                                • 1 Bathroom
                                                  • , Sleeps 6
                                                $1,195 - $1,895
                                                per week

                                                Tiki Beach Too, Charming Townhome, Old Town, Pool Access, great porch!

                                                Book it Now!
                                                7 night Minimum Stay
                                                • 2 BR,
                                                • 1 BA,
                                                • Sleeps 6
                                                1. Lower Florida Keys >
                                                2. Key West Townhome
                                                #3539485
                                                  'POOLSIDE RETREAT @ THE POOL': Poolside 2BR/2.5BA Villa with 2 Master Suites...
                                                    3 Bedrooms,
                                                  • 2 Bathrooms, 
                                                  • 1 Half Bath
                                                    • , Sleeps 6
                                                  $3,000 - $5,750
                                                  per month

                                                  'POOLSIDE RETREAT @ THE POOL': Poolside 2BR/2.5BA Villa with 2 Master Suites...

                                                  28 night Minimum Stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 6
                                                  1. Lower Florida Keys >
                                                  2. Key West Villa
                                                  #390207
                                                    (3)
                                                    'SOUTHERNMOST COMFORT @ CASA EAST': Stunning 4BR/4.5BA Home w/ Cottage & Pool...
                                                      4 Bedrooms,
                                                    • 4 Bathrooms, 
                                                    • 1 Half Bath
                                                      • , Sleeps 8
                                                    $9,000 - $17,000
                                                    per month

                                                    'SOUTHERNMOST COMFORT @ CASA EAST': Stunning 4BR/4.5BA Home w/ Cottage & Pool...

                                                    28 night Minimum Stay
                                                    • 4 BR,
                                                    • 4 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 8
                                                    1. Lower Florida Keys >
                                                    2. Key West House
                                                    #990995
                                                      (10)
                                                      'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master Suites...
                                                        2 Bedrooms,
                                                      • 3 Bathrooms
                                                        • , Sleeps 6
                                                      $350 - $700
                                                      per night

                                                      'PUERTA CORALINA @ SOLARES HILL': Charming 2BR/3BA Cottage, 2 Master Suites...

                                                      4 night Minimum Stay
                                                      • 2 BR,
                                                      • 3 BA,
                                                      • Sleeps 6
                                                      1. Lower Florida Keys >
                                                      2. Key West House
                                                      #904144
                                                        (22)
                                                        'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old Town...
                                                          3 Bedrooms,
                                                        • 2 Bathrooms
                                                          • , Sleeps 6
                                                        $5,500 - $14,000
                                                        per month

                                                        'FLAMINGO DREAMS @ SOLARES HILL': Pristine 3BR/2BA Conch Home in Old Town...

                                                        28 night Minimum Stay
                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 6
                                                        1. Lower Florida Keys >
                                                        2. Key West House
                                                        #390211
                                                          (3)
                                                          'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...
                                                            7 Bedrooms,
                                                          • 7 Bathrooms
                                                            • , Sleeps 12
                                                          $9,500 - $12,900
                                                          per week

                                                          'CONCH CASA GRANDE @ THE ANNEX': Enormous 7BR/7BA in Truman Annex...

                                                          7 night Minimum Stay
                                                          • 7 BR,
                                                          • 7 BA,
                                                          • Sleeps 12
                                                          1. Lower Florida Keys >
                                                          2. Key West House
                                                          #390171
                                                            (12)
                                                            'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...
                                                              3 Bedrooms,
                                                            • 3 Bathrooms
                                                              • , Sleeps 6
                                                            $5,500 - $14,000
                                                            per month

                                                            'HIDDEN TREASURE @ CASA EAST': Luxurious 3BR 3BA Villa & Huge Pool near Beach...

                                                            28 night Minimum Stay
                                                            • 3 BR,
                                                            • 3 BA,
                                                            • Sleeps 6
                                                            1. Lower Florida Keys >
                                                            2. Key West House
                                                            #390210
                                                              (7)
                                                              • 1 - 30 of 793
                                                              Advertisement