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Paradise House in Islamorada

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vacation rental description

Our house is your house...
   Come relax in our beautiful bayside paradise. The Bayside Cottages is a privately owned hidden jewel harboring three unique cottages and a small guest cottage. Ranging from one to two bedrooms, each residence is self-sufficient with its own well equipped kitchen, television, and all the comforts of home. Our property has been family owned and entertaining guest for over 35 years. Come see the keys through a locals eyes...

    This cozy islamorada cottage known as The Paradise House, is the perfect choice for your next get away.Extra clean with fresh tropical decor.  Sleeps up to two guest;if you need additional space we also have an adorable guest house that sleeps two.You will love the secluded private beach, beautifully landscaped with a fire pit surrounded by adirondack chairs and shady palm trees.  A fishing dock extends out over 120 feet into the pristine waters of the Florida Bay, with plenty of shade and seating including hammock swings and lounge chairs. We even have an outdoor kitchen with a stainless steel grill and your own private tiki hut. Your furry friends are welcome and they will love our large fenced grassy yard with shallow water access for swimming and playing fetch! Dockage and fish cleaning station are available on site along with kayaks, floats, snorkel equipment, lobster gear, fishing poles and  light tackle all free for you to enjoy! Dockage and trailer parking available. Inquire for details. 

This is a shared property with one other one bedroom cottage a two bedroom cottage and a small guest cottage. If your dates requested are already booked you may be interested in one of our other cottages...

We also do weddings!

Call Lori for more information.

Visit our website for more photos of the property and to also view our other cottages available! 

Deposits and cancellations:
The security/damage deposit of $300 is due at the time of booking. The remaining balance is due 30 days prior to your arrival date. Because of our size, cancellations affect us significantly. For any cancellation or change of dates, we must receive 30 days notice prior to your confirmed arrival for a refund of your deposit, less a $50 service charge. If any full, partial cancellation or change of dates is made within 30 days, regardless of the reason, you are financially responsible for the entire reservation, unless we can re-book your cottage. However, you are always welcome to send a friend or family member in your place. We realize that cancellations are often beyond your personal control. For this reason we recommend purchasing travel insurance for peace of mind. The Bayside Cottages will be happy to supply your travel insurance company with any needed documentation regarding our policy and your reservation. 

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property availability

  • dates with deals
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Last modified on 08-21-2014 at 2:30 PM.

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lori singleton

house rental amenities

  • Private Beach with fire pit
  • Outdoor kitchen and tiki hut
  • Kayaks and paddle boat
  • Fishing Dock
  • Fishing poles, tackle and fish cleaning station
  • Snorkle gear
  • Lobstering equipment
  • Coolers
  • Dockage available
  • Flat screen TV  DVD player 

activities and attractions in Islamorada The Florida Keys


Local artistry and shopping

Fishing capital of the world


Kite boarding

Dolphin encounters

Waterfront dining

Day Spas

vacation rental rates

*Three night minimum

The Paradise House 

$250-$300 per night

$1700-$2050 per week

December 15th - April 15th    Nightly $300 Weekly $2050  

April 16th - September 15th   Nightly $275  Weekly $1875

September 16th -December 14th Nightly $250 Weekly $1700

7.5% sales tax not included in rate 

Rates are subject to change at anytime until deposit is received.

Inquire for Holiday Rates.   

One time pet fee of $50 per pet  (dogs only) limit 2 

Cleaning Fee $125 

Three night minimum 

Boat dockage and trailer parking $20 per day 

Refundable Deposit of $300 due up front to reserve. 

Forms of Payment 

Visa, Mastercard or Discover Credit Cards. Check, Cashiers Check or Money Order.

The Refundable Deposit is due at the time of booking to reserve. Total payment is due 30 days prior to arrival date. For any booking made within 30 days of the arrival date the total payment will be due at the time of booking.  

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lori singleton

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  • owner lori singleton

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payment methods

Owner has not provided their accepted payment methods

Prior to paying a reservation deposit, always verify payment instructions by calling the phone number displayed on this listing page. By contacting the owner directly and paying by an approved method - credit card, paypal, check or bank transfer - your reservation payment will be protected up to $1,000.

Learn more in our Security Center
Top things to do in Islamorada
  • Scuba Dive
  • Offshore and Backcountry fishing
  • waterfront dining
  • Sunset cruises
  • Kite Boarding
Top things to do on a budget
  • snorkeling
  • kyaking
  • Fish right off the dock!
Top things to do with a family
  • dolphin encounters
  • fishing
  • eco-tours

lori singleton , owner

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lori singleton

traveler reviews for this islamorada house rental

Better than I imagined!

Review submitted: September 20, 2012   Date of arrival: September 10, 2012

After months of research for accomodations in Islamorada, I found your cottage which seemed to have met all the criteria we were looking for. The anticipation to actually see the cottage in person was making me so nervous. You just never know if you've made a good decision until you see it for yourself. I can tell you that I was not the least bit disappointed at all. The grounds were so nice and relaxing. My fiancee and I actually did more snorkeling off the dock than anywhere else. We started every morning drinking our coffee on the edge of the dock and ended almost every evening watching the boats go by and/or the beautiful sunset. The cottage itself was very charming and I can only hope that if we come back down that way, we can rent it again.

Recommended for: age 55+, pet-friendly, sight seeing, romantic getaway

Helpful votes: 3 / 3


Wow, amazing and beautiful

Review submitted: October 16, 2011   Date of arrival: October 8, 2011

Lori, Your piece of Paradise is amazing. We had been lookinf forward to this vacation for 8 months and I was really nervous about booking a cottage site unseen but when we arrived there I was overjoyed. Your property was even better than I had imagined. The grounds are breathtaking along with the view of the bay. The Paradise Cottage that we rented was very clean, beautifly decorated, and very well stocked with everything I needed to cook with. We had breakfast every morning in the Tikki Hut as well as grilling our dinner in the outside kitchen and eating on the dock. We all enjoyed the Kayak's and the paddle boat. It was also nice that we were able to bring our two little Shih Tzu's and not worry about them getting out of your fenced in property. Little Kobe and Gyzmo enjoyed the vacation as much as we did. Gyzmo had so much fun chasing the lizzards. It was so nice of you to let Ashlyn (our 19 year old granddaughter) use the Oar House with the large bath. She was thrilled to have her very own accomadations. Ashlyn enjoyed the Chair Hammocks on the dock where she spent a lot of her time. Thank you again for such a wonderful vacation. We will see you again next year.

Mike, Rita< Ashlyn, Kobe and Gyzmo

Recommended for: adventure seekers, age 55+, families with young children, people with disabilities, families with teenagers, girls getaway, pet-friendly, sight seeing, romantic getaway

Helpful votes: 4 / 4


This place has it all!

Review submitted: October 6, 2011   Date of arrival: September 28, 2011

We (Me, my husband John, our friends Ronnie and Nikki and our lab Jett)stayed in the sparkling clean Paradise House. It slept all 4 adults and the dog very comfortably. We took full advantage of the fully stocked kitchen inside to save money and cooked all our meals here as well as the outdoor kitchen. We pretty much set up camp the whole time on their dock. It has plenty of seating, places to catch some rays or relax in the shade, easy access for swimming and snorkeling, a dining table for al fresco lunches or sunset cocktails and all the fish and lobster you can eat right off the dock. We felt very comfortable allowing our dog Jett to roam the property freely as the property is completly fenced in. We just had to keep our eye on him near the dock since he loves to swim. The other couple that checked in after us were so cool. They had a dog too about Jett's age and they played the whole time. Laurie and Cory hadn't even been there an hour when Cory dove in and grabbed 3 lobsters right off the dock and gave them to us. They went out again for about an hour the next day and brought back their limit, amazing! My highlight of our 4 night stay was Saturday night, when we all (the 4 of us, Laurie and Cory, and the owners Lori and Bobby) loaded the grill with steaks, lobsters, and hogfish and had dinner under the Tiki Hut. The Tiki Hut has seating for 6 and has a ceiling fan, plenty of lighting and surround sound speakers that you hook your iPod up to. After dinner we hung out by the campfire and roasted marshmallows. I think I drank too many Rum Runners, but it was a night I'll remember for awhile. This property is the biggest bang for your buck out there. We are already working out the details for when we can visit again. To Lori and Bobby: Thank you so much for having us. You both are so kind and down to earth. Your little piece of paradise is so well kept and beautifully designed and all the hard work that goes into it did not go unnoticed. Look no further for a truly affordable Florida Keys experience without sacrificing the luxury. It's really like having an entire resort all to yourselves.

Recommended for: adventure seekers, pet-friendly, romantic getaway

Owners response: Sivan,John,Ronnie,Nikki and Jett,

Thank you so much! You described this place perfectly! We are so happy that you enjoyed your time here and cannot wait to see you again. It was so nice meeting all of you and sharing our little piece of heaven with you. Looking forward to having you as our guest again in the "Conch House"

All the Best,

Helpful votes: 2 / 2


Reviews are the subjective opinions of travelers and not of, Inc.

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lori singleton

Islamorada vacation rental

This vacation rental has been listed since 11/1/2010.

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