Skip to main content

The 10 Best Cottages in Islamorada, USA

Check out our selection of great cottages in Islamorada

Filter by:


Review Score

Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest Price First Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

Featuring air-conditioned accommodation with a pool with a view, garden view and a patio, Anglers Reef Getaway is set in Islamorada. This beachfront property offers access to a balcony, squash on the squash court, free private parking and free WiFi. The property is non-smoking and is situated 600 metres from Windley Key.

loved the location and the quick responses from the host.

Show more Show less
9
Wonderful
24 reviews

Anglers Reef Paradise is located in Islamorada, 300 metres from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi.

This air-conditioned holiday home has 2 bedrooms and 2.5 bathrooms, a cable flat-screen TV, and a fully equipped kitchen. The holiday home also provides a bathroom with a shower.

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

Show more Show less
9.2
Wonderful
25 reviews
Price from
£190
per night

Boasting air-conditioned accommodation with a balcony, Isla Tamarillo - Waterfront Boutique Resort, Island Paradise, Prime Location is set in Islamorada. The property is around 1 km from Upper Matecumbe Key, 4.3 km from Windley Key and 20 km from Pigeon Key. The accommodation provides a 24-hour front desk and parking on-site.

Show more Show less
Price from
£521
per night

Boasting air-conditioned accommodation with a balcony, Isla Mirabelle - Waterfront Boutique Resort, Island Paradise, Prime Location is set in Islamorada. The property is around 1 km from Upper Matecumbe Key, 4.3 km from Windley Key and 20 km from Pigeon Key. The accommodation provides a 24-hour front desk and parking on-site.

Show more Show less
Price from
£583
per night

Located in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Mamey - Waterfront Boutique Resort, Island Paradise, Prime Location provides air-conditioned accommodation with a balcony and free WiFi. The property is set 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation offers a 24-hour front desk and parking on-site.

Show more Show less
Price from
£374
per night

Set in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Lychee - Waterfront Boutique Resort, Island Paradise, Prime Location offers air-conditioned accommodation with a balcony and free WiFi. The property is located 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation provides a 24-hour front desk and parking on-site.

Show more Show less
Price from
£383
per night

Located in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Lime - Island Paradise, Waterfront Pool, Prime Location provides air-conditioned accommodation with a balcony and free WiFi. The property is situated 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation features a 24-hour front desk and parking on-site.

Show more Show less
Price from
£466
per night

Situated in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Kiwi - Waterfront Boutique Resort, Island Paradise, Prime Location features air-conditioned accommodation with a balcony and free WiFi. The property is located 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation provides a 24-hour front desk and parking on-site.

Show more Show less
Price from
£220
per night

Set in Islamorada, 1 km from Upper Matecumbe Key and 4.3 km from Windley Key, Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location offers air-conditioned accommodation with a balcony and free WiFi. The property is situated 20 km from Pigeon Key, 33 km from John Pennekamp State Park and 47 km from Florida Keys Aquarium Encounters. The accommodation features a 24-hour front desk and parking on-site.

Show more Show less
Price from
£447
per night

Set in Islamorada, less than 1 km from Windley Key and 5 km from Upper Matecumbe Key, Peaceful Palms A2 offers air-conditioned accommodation with a terrace and free WiFi. With sea views, this accommodation features a balcony. The accommodation provides a 24-hour front desk and parking on-site.

Show more Show less
Price from
£271
per night

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.
Search cottages in Islamorada

Most booked cottages in Islamorada this month

Enjoy breakfast in Islamorada!

These cottages in Islamorada have options with FREE cancellation

  • Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location

    Isla Key Guava - Waterfront Boutique Resort, Island Paradise, Prime Location offers accommodations in Islamorada, a 12-minute walk from Upper Matecumbe Key and 2.7 miles from Windley Key.

  • Peaceful Palms A2
    Free cancellation options available

    Peaceful Palms A2 is a recently renovated vacation home in Islamorada, near Windley Key. This vacation home features air-conditioned accommodations with a terrace.

  • West Plaza Del Lago
    Free cancellation options available

    West Plaza Del Lago offers accommodations in Islamorada, a 12-minute walk from Sea Oats Beach and 1.3 miles from Anne's Beach.

  • Villa Riolo
    Free cancellation options available

    Villa Riolo is located in Islamorada, just 1.6 miles from Sea Oats Beach and 5.7 miles from Upper Matecumbe Key. Both free Wifi and parking on-site are available at the vacation home free of charge.

  • Sunshine Place
    Free cancellation options available

    Sunshine Place offers accommodations in Islamorada, a 17-minute walk from Windley Key and 2.6 miles from Upper Matecumbe Key.

  • Sandglass 4
    Free cancellation options available

    Sandglass 4 is located in Islamorada, just a few steps from Sea Oats Beach and 1.4 miles from Anne's Beach.

  • Pelican Landing
    Free cancellation options available

    Pelican Landing is located in Islamorada, just a 12-minute walk from Sea Oats Beach and 1.4 miles from Anne's Beach.

  • Palms 417
    Free cancellation options available

    Palms 417 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key. This beachfront property offers access to a terrace.

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

  • Palms 407

    Palms 407 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 404

    Palms 404 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 317

    Palms 317 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 314

    Palms 314 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 313

    Palms 313 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 309

    Palms 309 offers accommodations in Islamorada, 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Palms 301

    Palms 301 is located in Islamorada, just 2.1 miles from Upper Matecumbe Key and 5.2 miles from Windley Key.

  • Ocean Harbour K31

    Ocean Harbour K31 is located in Islamorada, just 2.7 miles from Windley Key and 6 miles from Upper Matecumbe Key.

Cottages That Guests Love in Islamorada

  • Avg. price/night: £195.75
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 1,109 reviews
    The location was great. There were plenty of place to sit in the sun or shade. The bungalow was roomy and clean. Staff were friendly. I loved sitting outside and watching the iguanas.
    Ellen
    Young couple
  • Avg. price/night: £207.24
    7.9
    Scored 7.9
    Good
    Rated good
     · 1,037 reviews
    We stayed in one of the bungalows that had a small front porch overlooking the ocean. Being able to sit out on that porch and watch the sun rise and set over the beautiful ocean view was our favorite part of our stay. The front desk staff was very friendly and helpful. We liked the breakfast too.
    Roseluvsretro
    Family with young children
  • Avg. price/night: £172.55
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 848 reviews
    I always stay at this resort every time I go to the keys. The staff is wonderful, the pool is nice and the bungalow I stayed in was facing the ocean, so relaxing! Thank you!
    Karole
    Solo traveler
  • Avg. price/night: £172.55
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 848 reviews
    We loved the cottage, just s short walk to the beach and heated pool. Beautiful views of the Ocean from the property and in the pool. Paddleboards and Kayaks that are free to use, this is just a wonderful place to getaway.
    John
    Family with young children
  • Avg. price/night: £195.75
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 1,109 reviews
    Cute place, well cared for. Little beach, boat docks, soft sand, grills, bikes, clean pool. We had a bungalow which had plenty of room. The only down side was highway noise at night and no blackout curtains, but not too bad. Overall it was an excellent value.
    Dianne
    Young couple
  • Avg. price/night: £300.98
    9.1
    Scored 9.1
    Wonderful
    Rated wonderful
     · 166 reviews
    Hidden gem. Beach was great. Staff super friendly. It was like an airbnb without the fees. It was a cottage with a separate bedroom and then jitchen and sofa area with a screened in p I rch. I originally did not look at this when it popped up on booking.com., out of my price range. But then booking.com made a huge booking error (and did not compensate us for it). Then I book this. Next time I am looking for an airbnb I will look this one up.
    laurie
    Young couple
  • Avg. price/night: £327.49
    8.5
    Scored 8.5
    Very Good
    Rated very good
     · 1,542 reviews
    Great installation, charming personal. Cozy room and decoration We will come back for sure!
    Ana
    Family with young children
  • 8.0
    Scored 8.0
    Very Good
    Rated very good
     · 1,197 reviews
    The property we originally booked was under repair so they gave us a lovely cottage over looking the docks.
    nicola
    Young couple
  • Avg. price/night: £172.55
    8.7
    Scored 8.7
    Excellent
    Rated excellent
     · 848 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: £195.75
    8.1
    Scored 8.1
    Very Good
    Rated very good
     · 1,109 reviews
    The beds were soft. The bungalow reminded me of a Beach cottage/shore house.
    S.
    Young couple