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The best cottages in Islamorada

Check out our selection of great cottages in Islamorada

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Anglers Reef Getaway, hotel in Islamorada

Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

The area and amenities are great.
Scored 9.1
9.1
Rated wonderful
Wonderful
21 reviews
Anglers Reef Paradise, hotel in Islamorada

Just a 6-minute walk from Windley Key and one mile from Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise features accommodations in Islamorada, with pool with a view and a garden.

It was very clean and confortable; and the facilities where great, we enjoyed our time at the beach and used the canoes and paddle board! Great time
Scored 9.3
9.3
Rated wonderful
Wonderful
24 reviews
Fiesta Key RV Resort Waterfront Cottage 33, hotel in Islamorada

Located in Layton in the region of Florida, this family and is 28 miles from Key Largo. The property features views of the sea and is 21 miles from Marathon.

Location is still the same
Scored 8.5
8.5
Rated very good
Very Good
62 reviews
Hideaway with Resort Privileges, hotel in Islamorada

Hideaway with Resort Privileges is located in Key Largo, just 3.2 miles from Pigeon Key and 5.2 miles from John Pennekamp State Park. This beachfront property offers access to a balcony and free Wifi....

Spotlessly clean, great location, and every amenity you can think of. Just perfect!
Scored 9.2
9.2
Rated wonderful
Wonderful
18 reviews
LICENSED MGR - LUXURIOUS OCEANFRONT CONDO W/STUNNING VIEWS - UPSCALE OCEANFRONT RESORT!, hotel in Islamorada

Featuring a garden, LICENSED MGR - LUXURIOUS OCEANFRONT CONDO W/STUNNING VIEWS - UPSCALE OCEANFRONT RESORT! features accommodations in Key Largo.

fantastic view , great location
Scored 9.2
9.2
Rated wonderful
Wonderful
5 reviews
LICENSED Mgr - LUXURY VIP PENTHOUSE SUITE - OFFERS RESORTS BEST PANORAMIC OCEAN VIEWS!, hotel in Islamorada

LICENSED Mgr - LUXURY VIP PENTHOUSE SUITE - OFFERS RESORTS BEST PANORAMIC OCEAN VIEWS! is located in Key Largo, just 3.3 miles from Pigeon Key and 5.5 miles from John Pennekamp State Park.

Amazing views, fully functional kitchen and onsite security. The large pool was extra nice.
Scored 9.4
9.4
Rated wonderful
Wonderful
5 reviews
LICENSED MGR - 3/3.5 MODERN VILLA - KEY LARGO'S PREMIER OCEANFRONT RESORT AND MARINA!, hotel in Islamorada

Providing a garden, LICENSED MGR - 3/3.5 MODERN VILLA - KEY LARGO'S PREMIER OCEANFRONT RESORT AND MARINA! offers accommodations in Key Largo.

Unit was beautiful. 3 stories, comfortable. No complaints about the owners unit. It was good and he is a conscientious owner. Great beds. Overall the villa property was nice.
Scored 8.3
8.3
Rated very good
Very Good
6 reviews
All cottages in Islamorada
Looking for a cottage?
Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.

Most booked cottages in Islamorada this month

Enjoy breakfast in Islamorada!

  • Anglers Reef Getaway
    Scored 9.1
    9.1
    Rated wonderful
    Wonderful
     · 21 reviews

    Offering an outdoor swimming pool and a garden, Anglers Reef Getaway in Islamorada is close to Windley Key and Windley Key Fossil Reef Geological State Park.

    loved the location and the quick responses from the host.

  • Anglers Reef Paradise
    Scored 9.3
    9.3
    Rated wonderful
    Wonderful
     · 24 reviews

    Just a 6-minute walk from Windley Key and one mile from Windley Key Fossil Reef Geological State Park, Anglers Reef Paradise features accommodations in Islamorada, with pool with a view and a garden.

    Location & the grounds & pool were amazing.

  • Remodeled Stilt home with Ocean Views home

    Remodeled Stilt home with Ocean Views home is located in Islamorada, just 1.3 miles from Sea Oats Beach and 5.9 miles from Upper Matecumbe Key. This beachfront property offers access to a balcony.

  • Treasure Cove
    Breakfast options

    Treasure Cove is located in Islamorada, just a 1-minute walk from Sea Oats Beach and 1.3 miles from Anne's Beach.

  • Treasure Harbor Hideaway - Upper

    Treasure Harbor Hideaway - Upper is located in Islamorada, just 1.7 miles from Windley Key and 5 miles from Upper Matecumbe Key.

  • Treasure Harbor Hideaway - Lower

    Treasure Harbor Hideaway - Lower is located in Islamorada, just 5 miles from Upper Matecumbe Key and 8.5 miles from Pigeon Key. Guests can go for a swim in the pool with a view.

  • Beautiful 2 bedroom with Boat Slip home

    Beautiful 2 bedroom with Boat Slip home offers accommodations in Islamorada, 1.6 miles from Sea Oats Beach and 5.7 miles from Upper Matecumbe Key.

  • Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal, home

    Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal, home offers accommodations in Islamorada, a 12-minute walk from Sea Oats Beach and 1.4 miles from Anne's...

These cottages in Islamorada have options with FREE cancellation

Traveling by car? These cottages in Islamorada offer free parking!

Cottages That Guests Love in Islamorada

  • Avg. price/night: $150.75
    Scored 8.6
    8.6
    Rated excellent
    Excellent
     · 882 reviews
    We stayed in the bungalow. The location cannot be beat! Beautiful views, and the moment you wake up. We also love having kayaks and paddle boards available at any time. They also did some upgrades on the inside, which were very nice. It is not fancy, but it’s perfect for our needs. We have visited three times and it has become our little piece of paradise.
    Susan
    Group
  • Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 882 reviews
    Self catering. Disappointed with quality of facilities and accommodation for the price paid
    tina
    Young couple
  • Avg. price/night: $461.54
    Scored 9.0
    9.0
    Rated wonderful
    Wonderful
     · 43 reviews
    The place was idyllic. Immaculate in every way. So peaceful, clean and well presented. The lady that greeted us was so very helpful. Thank you.
    David
    Young couple
  • Avg. price/night: $186.41
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 1,376 reviews
    The bungalow (which was a tiny duplex) was directly in front of the driveway, you could literally step out your door and be in the driveway. The private beach was littered with empty bottles and cigarette butts. Sea grass was covering the beach area. No exhaust fans in the bathroom. We didn't like much about the place and left early.
    Timothy
    Young couple
  • Avg. price/night: $186.41
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 1,376 reviews
    The quality of the newly renovated bungalow. Free coffee!
    Keith
    Young couple
  • Avg. price/night: $186.41
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 1,376 reviews
    I have been staying at Breezy Palms since 1987. The bungalow we stayed in appeared to have been recently refurbished and with new beds. Very big improvement over the past conditions.
    M
    Mike
    Group
  • Avg. price/night: $302.79
    Scored 8.5
    8.5
    Rated very good
    Very Good
     · 1,574 reviews
    Great installation, charming personal. Cozy room and decoration We will come back for sure!
    Ana
    Family with young children
  • Avg. price/night: $486
    Scored 8.0
    8.0
    Rated very good
    Very Good
     · 1,018 reviews
    The property we originally booked was under repair so they gave us a lovely cottage over looking the docks.
    nicola
    Young couple
  • Scored 8.7
    8.7
    Rated excellent
    Excellent
     · 882 reviews
    Love the area, cottage/ bungalow. Staff was SO Nice, Daniell at Check in in was beyond helpful, including during the wk. Lev an Chris the bartenders are great an friendly, Chris also took us fishing
    Kelly
    Group
  • Avg. price/night: $186.41
    Scored 8.2
    8.2
    Rated very good
    Very Good
     · 1,376 reviews
    The beds were soft. The bungalow reminded me of a Beach cottage/shore house.
    S.
    Young couple