We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals near Robbie's of Islamorada

77522 Overseas Hwy, Islamorada, Florida 33036-3813
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    $353 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 69 Rentals in Islamorada
    Ocean-Front Caribbean Home.1 / 21
    (3)Excellent
    1.7 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    2.1 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    107 San Remo Drive1 / 36
    (2)Excellent
    2.2 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    82754 Overseas Highway1 / 58
    (4)Excellent
    1.0 miles from Robbie's of Islamorada
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 7, 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed May 9, 2017
    Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
    See all reviews
    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Children's Pool
    • Washer
    • Waterfront
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 32
    (3)Excellent
    3.9 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 25, 2018
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed February 2, 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    See all reviews
    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This 2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    BEACON REEF 3101 / 21
    (6)Excellent
    0.6 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Terrace
    • Cable/satellite TV
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 25, 2020
    Islamorada really is a sweet spot on the keys. Much nicer than Marathon, tons of high end restaurants, fishing charters everywhere. This complex is spotless, large heated pool...
    Reviewed March 11, 2020
    It is comforting when you first check in to know everything you need is there on the property. More importantly the Keys Holiday Rentals personnel have gone out of there way to...
    See all reviews
    About this property
    <b> Minimum Rental: 28 Days </b> 'Beacon Reef 310' is located in one of the most desirable condominium complexes in the Upper Keys. Convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your own private...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    PALMS 3091 / 25
    (3)Excellent
    0.6 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Patio
    • Parking
    • Internet Access
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 12, 2020
    This was our 2nd year of renting unit #309 at The Palms in Islamorada. The unit was immaculate and well stocked to make our month-long stay relaxing and enjoyable! The Palms...
    Reviewed August 23, 2018
    Last year we spent 3 months in this location, and we enjoyed it so much we increased our stay to 4 months this year. Close to restaurants and marinas.
    See all reviews
    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #309' is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    0.6 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area...
    Reviewed November 5, 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach...
    See all reviews
    About this property
    <b> Minimum Rental: 7 Days </b> Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month....
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Save time - get the best Islamorada rentals sent straight to your email!
    Get the List
    Blue Dolphin  Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool1 / 38
    (3)Excellent
    3.8 miles from Robbie's of Islamorada
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
    other traveler has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2020
    Perfect vacation house on the ocean, close to everything. The spacious house was immaculate when we checked in. The owner was extremely friendly and responsive. It was perfect...
    Reviewed April 28, 2019
    The location, the amenities, the house, and the pool area was perfect. Everything needed to spend a weeks vacation with your family is within this home. I bring my 3 grown...
    See all reviews
    About this property
    Beautiful Gated Oceanfront 1.8 Acre Estate located in Islamorada featuring amazing ocean views. 5 Bedrooms, 4 Baths, Winding Staircase, Expansive Ocean Views, Over 4000 Sq. Ft. of Living Space. Heated Pool, Sandy Back Yard, Gated Entrance Lined With Palm Trees. Enjoy the Ocean Views and...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Patio
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for...
    See all reviews
    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Windy Cove #11 / 19
    (2)Excellent
    0.7 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 18, 2021
    We stayed here for Christmas 2020 and it was so perfect! Right on the water, great location, close to Starbucks and Publix. Very private, we were the only people there all...
    Reviewed July 7, 2019
    We had the best time in Windy Cove #1!!!! This condo was perfect for us. Each bedroom was a nice size and the view was amazing!! Everything was clean and it was very...
    See all reviews
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    LYONS LANDING1 / 25
    (1)Excellent
    2.2 miles from Robbie's of Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Terrace
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 27, 2017
    Every room is comfortable,charming and the property managed to make you feel comfortable and at home..with every amenity..including an ice maker..so nice to have here in The...
    See all reviews
    About this property
    <b> Minimum Rental: 28 Days </b> 'Lyons Landing' is an exceptional VENETIAN SHORES single family home with pool, dock, boat lift and outdoor living area! Everything you need for a spectacular holiday awaits you in this extraordinary home. 3 bedrooms and two baths on the upper level plus a...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    PALMS 3141 / 25
    (2)Excellent
    0.6 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 5, 2018
    Key Holiday Rentals are the best, they are there when you need them and are there to answer any questions you have .
    See all reviews
    About this property
    <b> Minimum Rental: 28 Days </b> This condo offers breathtaking oceanfront views. Imagine watching the sun rise as you lay comfortably in your bed or have your morning beverage on the balcony and enjoy watching the fishing boats leave for their day's adventure. You'll be able to see cruise...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.7 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo features 3 bedrooms and 2 bathrooms, a balcony off the living room, a private balcony off the master bedroom, and the quaintness of only 4 other units in the complex. Enjoy a drink by the pool, soak...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    LITTLE BAY - Cottage1 / 24
    (3)Very good
    0.6 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Internet Access
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 4, 2019
    Loved the house and the key west feel. Beautiful kitchen and living area. Very comfy bed and nice master bath. The only reason I rated it a four was the water area. We really...
    Reviewed January 29, 2016
    Stayed in the cottage, 5 of us in total. Gorgeous cottage inside and out, set on a fabulous site with beautiful trees, shrubs, birds, green grass, stone paths, lots of parking...
    See all reviews
    About this property
    <b> Minimum Rental: 7 Days </b> 'Little Bay's Cottage' is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    SUNSHINE PLACE1 / 23
    (17)Excellent
    0.6 miles from Robbie's of Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Internet Access
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    We really enjoyed Sunshine Place; it was perfect for two people! We took our 18 foot fishing boat, which sat at the small dock all week when we weren't out fishing. A very...
    Reviewed December 15, 2020
    We just finished booking our third time at Sunshine Place for 2021. It has the most beautiful view for a sunrise you will ever see. The kitchen has everything you need to cook...
    See all reviews
    About this property
    <b> Minimum Rental: 7 Days </b> 'Sunshine Place' is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    FLAMINGO COTTAGE1 / 22
    (1)Excellent
    2.9 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Cable/satellite TV
    • Terrace
    • Grill
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 11, 2020
    The flamingo cottage was as advertised. Comfortable surroundings, beautiful pool, private sunbathing areas and beautiful ocean view.
    See all reviews
    About this property
    <b>MINIMUM STAY: 28 DAYS </b>'Flamingo Cottage' is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.0 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    List your property for free!
    List your vacation rental where Tripadvisor travelers can find it.
    Add a Listing
    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    0.6 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Grill
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 7 Days </b> Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Oceanfront Anglers Reef Islamorada Florida Keys1 / 2
    (3)Very good
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Ocean Views
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 24, 2018
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Reviewed August 24, 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
    See all reviews
    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    BEACON REEF 2221 / 25
    (2)Excellent
    0.5 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Hot Tub
    • Parking
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2018
    We have so much enjoyed staying in this condo, Beacon Reef 222. The condo is very comfortable with a great kitchen and living area. The master bedroom is amazing with a large...
    Reviewed July 13, 2017
    Great location! The pool, tiki bar and dock are all top notch. The ocean views are amazing. All equals the perfect family vacation.
    See all reviews
    About this property
    <b> Minimum Rental: 28 Days </b> 'Beacon Reef 222' is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.2 miles from Robbie's of Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Balcony
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Irish Ayes' - Elegant tropical waterfront home with pool, Jacuzzi, dock and custom elevator. Plan your Keys getaway to this absolutely beautiful, spacious, tropical waterfront home located in the prestigious Venetian Shores subdivision of Islamorada. Enjoy unforgettable sunsets while relaxing on...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    Mile Marker 87 - Mina Bay - Oceanfront 'Million Dollar View'1 / 38
    (2)Excellent
    3.4 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 12, 2017
    We spent part of the holidays at Mina Bay! The views are stunning! Not to mention you can hear the sound of the waves from the second bedroom - very relaxing! The unit is...
    Reviewed January 24, 2017
    Beautiful spacious oceanfront condo fully detailed and furnished in a gated community in Islamorada. The location is perfect and the beach is on the doorstep. Perfect for two or...
    See all reviews
    About this property
    Mina Bay - vacation rental with 'the million dollar view'! Truly BAYFRONT on the sandy beach and feet from the pier and dock. Sparkling water's and brilliant sunsets complete this 2 Bd 1.5 Ba plus loft Unit I-1 townhouse. 28 DAY MIMIMUM RENTAL for all guests.  Accommodates a family of 8 perfectly...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Conch & Lobster Homes1 / 49
    (1)Excellent
    1.0 miles from Robbie's of Islamorada
    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 10, 2020
    This place is amazing! Our friend Jen lived in this area for many years and invited us to come for vaca. We love it!!!! We were here during Tropical Storm Eta but we...
    See all reviews
    About this property
    Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
    2.8 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Parking
    • Cable/satellite TV
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and spacious home with three bedrooms, two and half baths, huge new kitchen, new bathrooms, and screened in porches facing East and West. There are great views from every room!!! Tastefully furnished with all linens, comfortable memory foam mattresses, all new appliances, and completely...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    PALMS 4171 / 24
    (1)Excellent
    0.7 miles from Robbie's of Islamorada
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Grill
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #417' has great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants. Watch the sun rise over the ocean as fishing boats leave on their daily...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    3.4 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Terrace
    • Washer
    • Balcony
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87 Our Islamorada beach modern decorated townhome is waiting for you. It’s a two story unit and third level loft; 2 Bedroom/2 Bath - sleeps 8. Next door is Founders Park & Plantation Yacht Harbor. A private gated community with 24hr...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    1.3 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Angler's Reef is a beautiful oceanfront gated community located in Islamorada. This modern updated 2 bedroom, 2.5 bath unit is nicely appointed with granite countertops, stainless appliances, wood floors, dining room seating for four and tasteful decor and furnishings. The unit offers ground floor...
    View all property information
    Location Information
    Matecumbe Key, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    3.4 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful two story townhome in a private, gated community with all of the amenities you'd expect while on vacation. Inside: Newly renovated and remodeled unit. Fully equipped kitchen and stainless appliances, large storage cabinets with pull outs. Granite counters etc. Living room area with 60...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    PALMS 3011 / 24
    (1)Very good
    0.7 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2018
    Condo was as advertised. Great location. The pool was very nice and the view from the "beach" area was amazing...but not a beach, concrete. The complex is larger than...
    See all reviews
    About this property
    <b> Minimum Rental: 28 Days </b> 'The Palms #301' is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.3 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Secure Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This beautiful oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    3.8 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Parking
    • Patio
    • Hot Tub
    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>MINIMUM STAY: 1 Month </b> Spectacular oceanfront views are yours from both the master bedroom and the balcony of this beautifully appointed condo. Alligator Reef Lighthouse is easily visible from your master suite or the balcony and you'll be able to watch cruise ships as they pass by...
    View all property information
    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.8 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b>NEW LISTING</b> Minimum Rental 1 month. This is an exceptional 2 bedroom and 2 bath condo located in one of the most popular Islamorada condo complexes - The Palms of Islamorada. The balcony is large enough to dine or recline and offers fabulous open water views. While sipping coffee in...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.6 miles from Robbie's of Islamorada
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Parking
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 7 Nights Saturday to Saturday The Martin Family Fish Camp is located on a private peninsula and offers two houses named Bonefish and Tarpon. Each home offers two private bedrooms. Between the two homes there is sleeping for 10 in beds plus an additional 2 on the sleeper sofa...
    View all property information
    Location Information
    Matecumbe Key, Florida Keys
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    0.5 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Grill
    • Patio
    • Parking
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    <b> Minimum Rental: 1 Month </b> Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other property 'up north' you can relish all the delightful amenities of their condo. This unit is beautifully appointed...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.5 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS NEW TO RENTAL MARKET 'Beacon Reef 301' is a fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo has...
    View all property information
    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.5 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Parking
    • Balcony
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS This exquisite condo has been TOTALLY remodeled and updated from top to bottom. This is a 5th floor unit with ocean views from the balcony and master bedroom suite. The furnishings are all brand new. There are three TV's - one to suit everyone's preference. Dine in...
    View all property information
    Location Information
    Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    3.9 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
    View all property information
    Location Information
    Tavernier, Key Largo
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    3.5 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2.3 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Washer
    • Balcony
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 bedroom / 2 bath / light and airy - large balcony backing up to a quiet nature preserve. Perfect home for a getaway! Centrally located in gorgeous Islamorada. Two bedroom / two bath. Gorgeous private homeowners beach and private dock, close to the best restaurants, and sightseeing. Our home...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Islamorada, Most Popular Florida Key1 / 26
    (2)Excellent
    3.4 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable1 / 50
    (30)Excellent
    3.4 miles from Robbie's of Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Internet Access
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Mitchell's Keys Villa - Private, Secluded House on the Bay1 / 24
    (49)Excellent
    1.2 miles from Robbie's of Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Parking
    • Patio
    • Internet Access
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Islamorada Keys Home In Anglers Reef With Ocean View, Dock,  Pool & Beach1 / 35
    (119)Excellent
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Patio
    • Parking
    • Cable/satellite TV
    • Washer
    • Balcony
    • Air Conditioning
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Welcome to Paradise 'Sandbar Bungalow Villa' * Anglers Reef1 / 37
    (96)Excellent
    1.4 miles from Robbie's of Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Beautiful Water Front in Angler's Reef with View of Sand Bar with Boat Slip1 / 25
    (104)Excellent
    1.3 miles from Robbie's of Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Parking
    • Internet Access
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Mitchell's Bayview Villa - Islamorada House on the Bay1 / 26
    (21)Excellent
    1.2 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    vrbo logo
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.2 miles from Robbie's of Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units. The Upper Duplex is a 1,500 sq ft unit with 2 bedrooms, 2 full...
    View all property information
    Location Information
    Islamorada, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1
    List your property
    Owner log in
    © 2021 TripAdvisor LLC All rights reserved.

    This is the version of our website addressed to speakers of English in the United States. If you are a resident of another country or region, please select the appropriate version of Tripadvisor for your country or region in the drop-down menu.