Pet Friendly Vacation Rentals in Islamorada

(30 rentals)
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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated ...

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Property Type

Islamorada House

"Love this house"

Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient. ...

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2 BR | 2 BA | Sleeps 4 | Quick View

11

Distance to beach: 5 miles to Anne's Beach

$299

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

Two Queen Beds, sleeps 4 + (1 Bedroom / 1 Murphy Bed)/ 2 Bathrooms, Full LaundryDock your boat up to 26 ft. Free boat trailer parking!The "Nest" is located on beautiful Florida Bay (at Mile Marker 82.3) in Islamorada on upper Matecumbe Key . The Villa is a privately owned condo residence ...

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Property Type

Islamorada Condo

"A hidden jewel indeed"

If i could have it for a month, i would be there,,, ,dont need any other place. This place is paradise by the bay,,,beautiful sunsets an accomodations. Ill be back.

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4 BR | 3 BA | Sleeps 8 | Quick View

1

$1286

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

Mile Marker 83 – OceanfrontTwo adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and skiff dock. Relax at the beach or cool down in the beachside pool.The front home ...

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Property Type

Islamorada Cottage

"Osprey Bay January"

Just finished a week at Osprey Bay nice house a little too much up and down with all the steps but spacious Need a larger trash can in the kitchen put it next to the wall near toaster Also new pillows ...

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4 BR | 4.5 BA | Sleeps 8 | Quick View

Distance to beach: 0.5 miles to White Marlin Beach

$692

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Bring your boat and Jet SkisNestled on a canal, less than a 2 minute boat ride to the bay and 10 minutes to the ocean with key access to private White Marlin Beach. New heated pool and hot tub, 70' dock with fish cleaning table, commercial ice machine, double jet ski lift, and two floors facing ...

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Property Type

Islamorada House

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5 BR | 3 BA | Sleeps 12 | Quick View

1

$665

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Beautiful 5 bedroom pool home with 70 foot of dockage at mile marker 74.5 on the bay side. The first floor is a private apartment with two bedrooms, one has a queen and the other two queens. Has a full kitchen, living room, dining area and full bathroom. The second floor has three bedrooms, two with queens ...

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Property Type

Islamorada House

"Summer vacation"

Owner easy to work with, place is nice and clean, is as described. My kids especially enjoyed all of the iguanas that are running around.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool

About this property

$14,000-$16,000 Weekly, Call for holiday rates Maison Residences offers world-class oceanfront residences in the Florida Keys. Unit 102 at Maison Residences is a luxurious property offering sweeping views of the Atlantic Ocean from the kitchen, grand room, master bedroom, and oversized living terraces. ...

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Property Type

Islamorada Condo

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3 BR | 2 BA | Sleeps 8 | Quick View

$425

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,000 Lb boat lift in 2022. New paint inside and out 2022. New furnishings in 2022. White Marlin Beach access and quick boat ride to Channel 2 or 5 bridge or to Robbies Marina. Plenty of ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Just 1 year of guests and the reviews say it ALL!This majestic property is over 2.75 acres of landscaped beauty. There is more white sand on this private lot than any in all of the keys! There are over 100 palm trees with about 60 of them lit up at night, some of the tallest around including the ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Pool
  • Private pool

About this property

A new, private community of 8 upscale homes called Coral Cove is located equidistant between Lorelei's and Chef Michael for easy walking to everything in downtown Islamorada, hence the name.....Heart of Morada! The reviews speak for themselves.Enjoy your private dunk pool or sit around it having drinks ...

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Property Type

Islamorada House

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6 BR | 4 BA | Sleeps 12 | Quick View

3

Distance to beach: 0.5 miles to Port Antigua Private Beach

$440

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Rentals by owner

About this property

This recently renovated property enjoys 6 bedrooms, 4 bathrooms and separate kitchens, living rooms and laundry facilities. It shares an ocean facing veranda with 2 dual gas grills and multiple seating and lounging areas. It has ample offstreet parking for vehicles and trailers. The Admiral on the Cove ...

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Property Type

Islamorada Townhome

"A Spectacular Spot"

We enjoyed our stay at this beautifully furnished and well stocked house. George and Bonnie responded quickly to any questions that we had. The separate living areas allowed us to enjoy family and friends ...

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3 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 2 miles to Anne's Beach State Park

$390

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly

About this property

This updated Port Antigua home with 85 ft. of concrete dock is ready for a new family to enjoy. The open floor plan and vaulted ceilings make this house feel so welcoming! French doors with side lights let in the natural light and open to the lanai where you can enjoy your morning coffee or a cocktail ...

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Property Type

Islamorada House

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4 BR | 4 BA | Sleeps 10 | Quick View

3

Distance to beach: 2 miles to Founders Park

$652

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool
  • Rentals by owner

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock and custom elevator. Beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal with direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one of several patios ...

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Property Type

Islamorada House

"You found it"

If you’re looking for a well kept beautiful home, right on the water positioned right between the Gulf and Atlantic, great pool and hot tub YOU FOUND IT. Communication is great and owner is so helpful. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

MINIMUM RENTAL 1 MONTH: Delightful vacation home located in the popular Islamorada neighborhood of Port Antigua. You will love this charming and cozy home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open into the sunroom extending the living area ...

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Property Type

Islamorada House

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6 BR | 6 BA | Sleeps 18 | Quick View

Distance to beach: 5 miles to Founder's Park

$1286

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

MINIMUM RENTAL: 7 NIGHTS This is a lush tropical setting in a gated compound located directly on Florida Bay. Protected dockage in the "Little Bay" will keep your 30' boat (or smaller) safe. There’s a “sunning” area with lounge chairs on the peninsula so you can capture ...

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Property Type

Islamorada Estate

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...

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Property Type

Islamorada House

"A Dream Vacation Home!"

My family and I rented this home during the month of August. This perfect home has everything you need plus more! The home is newly built and maintained extremely well. Its location in Venetian Shores is ...

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5 BR | 3 BA | Sleeps 12 | Quick View

$400

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

MINIMUM STAY: 28 DAYS ONE OF A KIND!!! Magnificent two story townhouse with 5 bedrooms and 3 baths located on Lower Matecumbe in Islamorada. Sandglass is a four-unit condo complex located on Lower Matecumbe in Islamorada. This unit offers 180 degree ocean views and is situated on a large lagoon which ...

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Property Type

Islamorada Condo

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4 BR | 3 BA | Sleeps 8 | Quick View

1

Distance to beach: 5 miles to Founder's

$643

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

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 the bedding is: King, Queen/Queen in Tarpon and Queen, Twin/Twin in Bonefish. ...

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Property Type

Islamorada House

"Awesome"

We stayed for a month at Blue Water Retreat and had an awesome time with family and friends. The ocean views were magnificent. The pool was a big hit with the kids. We even had our dog with us. Hope to ...

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$399

avg/night

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009 and 2022. Relax by the splash pool or sunbathe on the roof top and enjoy the spectacular views. There are blue water ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 28 Days "My Paradise" is an oceanfront beach house with protected dockage and located in the Fishing Capital of the World - Islamorada. Realize your dreams - a beach home located on a swimmable beach and a place to dock your boat. This home is indeed a rare find in The ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly

About this property

Minimum Rental: 28 nightsPelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. The main floor offers 3 bedrooms and an open concept with ample seating for the entire family. The large balcony overlooks a canal where pelicans are usually seen diving into ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days 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. Each unit sleeps ...

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Property Type

Islamorada House

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2 BR | 2 BA | Sleeps 6 | Quick View

Distance to beach: 5 miles to Founders

$429

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days 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 unit sleeps up ...

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Property Type

Islamorada Apartment

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

About this property

Minimum Rental: 7 Days"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 people ...

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Property Type

Islamorada House

"Great time!"

We had a wonderful time at Sunshine Place. The accommodations were far above our expectations. I know this is crazy but you have clean comfortable white sheets, great pillows and a comfortable bed! The ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

MINIMUM STAY: 28 NIGHTS Lyons Landing is an exceptional single family home with pool, dock, boat lift and outdoor living area located in the prestigious neighborhood of Venetian Shores in Islamorada. Everything you need for a spectacular vacation awaits you in this extraordinary home. 3 bedrooms ...

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Property Type

Islamorada House

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool
  • Rentals by owner

About this property

Great house! Great location!HOUSE ON CANAL… 34 foot concrete dock with fish cleaning stand, water and electricity. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. We are also ...

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Property Type

Islamorada House

"Very clean and comfortable home. Exceptional"

My two friends and I agree that in the last 13 years since we have been coming down to Islamorada for our annual fishing trip, this is one of the best places we have stayed in. Instructions were clear, ...

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$1167

avg/night

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Key Amenities

  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool

About this property

Traditional coastal cottage styling built in 2017 and the Pool was added in 2020. Large backyard beach and only steps to the turquoise waters of the Atlantic Ocean. Kayak, paddle board, or kite ski from your backyard! Plenty of parking out front and private gated access; fencing around the perimeter. ...

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Property Type

Islamorada House

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2 BR | 1 BA | Sleeps 4 | Quick View

1

$250

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

Paradise Beautiful and breathtaking ocean views in Lower Matecumbe Key in Islamorada. Private Beach Access to the beautiful White Marlin Beach2/1 Master Bedroom - King size bed Second bedroom - full size bedInflatable full size bed available One full bath with bath tub Living room with ...

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Property Type

Islamorada Apartment

"Wow! What a fantastic place."

Well we definitely will return. Completely MORE than we expected. Very nice and the perfect amount of room for a small family or couples. Great hosts and very responsive. We could not have been any luckier.

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Oceanfront Estate on 3.5 PRIVATE Acres in the Heart Of Islamorada. Features include: Private Boat Basin with 100 of feet of dockage for any size boat, private boat ramp and fishing pier. HUGE salt pool and hot tub, 3rd floor private master suite w/ office, master bathroom and private balcony. This huge ...

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Property Type

Islamorada House

"WOW is all we can say!!! Amazing rental."

We have been renting in the Keys for 22 years, this one topped them all. The grounds are SO secluded and private, makes you feel like your staying in the Jungle. Peacocks, exotic birds, and cool lizards ...

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Rentals by owner

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove ...

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Property Type

Islamorada Cottage

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5 BR | 3 BA | Sleeps 12 | Quick View

4

$1022

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large bedrooms ...

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Property Type

Islamorada House

"Amazing Family Vacation! Beautiful and affordable home in amazing location."

This was our first family trip to the FL keys and we had the most amazing time! Bridget was so helpful, especially since we booked prior to covid and decided to take our planned trip. She answered all my ...

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Islamorada Vacation Rentals