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Islamorada Holiday Rentals

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Management: Verified owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 3
Min stay:7
Best Location in Complex! This Florida Keys condo rental is Licensed! Relax in this luxurious gated waterfront condominium. Beautiful Water/Ocean View, Heated ...
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  • Weekly
    £909 - £1,333
  • Monthly
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Management: Verified owner
Property: Holiday Rental House
Bedrooms: 3, sleeps 6
Bathrooms: 3
Min stay:28
Welcome to the Bamboo Lodge, if you are looking for the locals island life, this is it! 3/2 Tropical pool home in the heart of Islamorada, Cheeca Resort ...
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  • Weekly
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  • Monthly
    £2,181 - £2,786

The following rentals are within 40 kilometers of Islamorada, Florida Keys, Florida.

Contact Owner
Nightly rate from
£106
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 4
Bathrooms: 2
Luxurious penthouse condominium is located in prestigious Islamorada, Florida. Sitting next to the third largest reef in the world, Islamorada offers ...
  • Nightly
    £106
  • Weekly
    £666
  • Monthly
    £1,817
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 2
This beautiful water front home is located at MM 74.5 Islamorada FL. the fishing capital of the world, So bring your boat . It can be docked behind the house ...
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Management: Verified owner
Property: Holiday Rental House
Bedrooms: 4, sleeps 12
Bathrooms: 3
4 bedrooms 3 baths, (separate 3/2 up and 1/1 down) can be rented together or separately. Private beach for the community within walking distance complete ...
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Management: Professional
Property: Condo/Apartment
Bedrooms: 3, sleeps 6
Bathrooms: 2
28 Night Minimum. Bayfront complex in Islamorada. A private 70 unit community with heated pool, tennis court and sunning beach. This three bedroom, two bath ...
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  • Weekly
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  • Monthly
    £1,524 - £1,688
Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 8
Bathrooms: 2
Min stay:3
Congratulations, you have just discoverd one of the most unique properties in the heart of Key Largo. This OCEAN FRONT condo is located inside Kawama Yacht ...
  • Nightly
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  • Weekly
    £485 - £969
  • Monthly
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Management: Verified Plus owner
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Min stay:3
Your vacation begins the moment you drive through our gatehouse entrance into our beautifully landscaped tropical grounds and enter your spacious 2 bedroom 2 ...
  • Nightly
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  • Weekly
    £485
  • Monthly
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Contact Owner
Nightly rate from
£103
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 2, sleeps 4
Bathrooms: 1
Min stay:2
This is a Beautiful private home in Key Largo Florida, close to everything you need to make this the perfect vacation. If you love diving, we are 5 minutes ...
  • Nightly
    £103
  • Weekly
    £484
  • Monthly
    £1,333
Management: Verified Plus owner
Property: Holiday Rental House
Bedrooms: 4, sleeps 12
Bathrooms: 3
Private beach, water view, dream home, infinity edge pool (pool heater available upon request) Nestled in the vacation destination of the nation rests a ...
  • Nightly
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  • Weekly
    £1,636
  • Monthly
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Villa 13, Key Largo
Contact Manager
Nightly rate from
£151
Management: Professional
Property: Holiday Rental House
Bedrooms: 3, sleeps 8
Bathrooms: 3
Unique two-story villa on gorgeous marina with lovely views from both floors. Ground floor has family room with kitchenette for convient snacking, bed and ...
  • Nightly
    £151 - £167
  • Weekly
    £818 - £999
  • Monthly
    £2,286 - £2,920
Management: Professional
Property: Holiday Rental House
Bedrooms: 2, sleeps 6
Bathrooms: 3
28 Night Minimum. You will experience complete comfort and relaxation in this two story townhouse, situated right off the heated pool and playground. Two ...
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  • Weekly
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  • Monthly
    £1,524 - £1,688
5409 Ocean Pointe, Tavernier
Contact Manager
Nightly rate from
£81
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
From sunrise to sunset you can enjoy the many activities Ocean Pointe has to offer or just relax in your oceanfront condo and surround yourself with our ...
  • Nightly
    £81 - £142
  • Weekly
    £485 - £756
  • Monthly
    £1,408 - £1,823
3305 Ocean Pointe, Tavernier
Contact Manager
Nightly rate from
£81
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
The Upper Keys premier oceanfront resort with something for everyone. Heated, junior olympic size pool, spa, tennis courts, beach area, volley ball and ...
  • Nightly
    £81 - £142
  • Weekly
    £485 - £756
  • Monthly
    £1,408 - £1,823
408 Kawama Tower, Key Largo
Contact Manager
Nightly rate from
£81
Management: Professional
Property: Condo/Apartment
Bedrooms: 2, sleeps 6
Bathrooms: 2
Fabulous oceanfront complex with a plethora of amenities! Enjoy the comfort and convenience of a private residence and be within minutes of world-class ...
  • Nightly
    £81 - £142
  • Weekly
    £485 - £756
  • Monthly
    £1,408 - £1,823
Islamorada Holiday Rental Advice
Posted by muraviou, 22 Mar 2009
... for 3 days.the boat rental is in ... ... to get the boat from his dock everyday,its like a 45 minute drive...do you think he just wants to make it easier for himself? the hotel tells me the have rental boats there all the time? someone please help me ... more
Posted by flowers52, 26 Mar 2009
... the shallow water. when on vacation a 45 minute drive there and back every day is really a lot of your vacation fishing time. there a a lot of boat rentals much closer to where you are staying, bud and marys and lots of others. as they said earlier, ask ... more
Posted by PrincessPalmTree, 12 Jan 2009
... member joining us at our vacation rental in Islamorada and she will be coming down from West Palm Beach. The Greyhound bus schedule appears to be the most straight forward path with one stopover in Miami. My concern is that it is a 2.5 hour layover and my family ... more
Posted by bornwithwheels, 28 Jul 2008
... that great but it's something to do. There is also a movie theater in Key Largo. Hampton might have paddle boats or kayaks they can use to explore the water area near the hotel. I sure others will have suggestions on the fishing / dolphin swim Have a great vacation ... more
Posted by keymom, 28 Jul 2008
... the Tarpon feeding and kayak rentals, too. I think they have jet ski rentals but you need a license for that if you are under a certain age. You may want to call ahead for that. Leave the kids at the Hampton one night and go with your spouse to ... more
Posted by bluewater, 28 Jul 2008
... year. Once you get your rental car - check out Aqua Ranch in Grassy Key - feed and/or swim with the Cobia. Bahia Honda is a good afternoon too. Christmas is a great time of year here in the Keys. It's a VERY busy time too, be prepared to wait ... more
Posted by gabirds, 5 Aug 2006
Beware if you are intending to book a houseboat vacation in Islamorada with the company Houseboat Vacations. Boats are very old, poor condition, one a/c for two bedrooms and lounge (stiffling hot!), hundreds of horseflies even ay sea. If you go, think camping and roughing it. ... more
Posted by ArtKarakos, 15 Jul 2008
Any suggestions on a good Houseboat rental company if we want to take one out in the Islamorada area? Thanks, Art ... more
Posted by MoonlightMile, 10 Jun 2008
check out vrbo (vacation rentals by owner) www.vrbo.com They will have hundreds of listings ... more
Posted by Keysplanner, 20 Jun 2008
Island Villa Rental Properties has always done a great job for me. When you call ask for Karissa. ... more
Professionally managed typically means…
  • Member of the FlipKey Verified Property Manager program
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
Verified Plus property owner typically means…
  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Verified property owner typically means…
  • Verification of owner name and address via valid credit card
  • History of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns