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Islamorada Vacation Rentals

(111 rentals)
Islamorada House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Casa Mar 115 Ponce de Leon Blvd, Islamorada, FloridaLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Port AntiguaMINIMUM STAY: 28 DaysMILE MARKER: 74.5 DETAILS:Stunning two-story, 3-bedroom resort-style, professionally decorated home. Inside,...

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$600
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Ocean Harbour K31 87851 Old Highway, Islamorada, FloridaLOCATION: Ocean Front CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months Allowed MILE MARKER: 87.8DETAILS: Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened...

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$300
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
9 reviews

Distance to beach: 0.9 miles to Founders Park

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Oceanfront gated community. Offers pool overlooking the ocean, pier which you can fish off of, clubhouse, sauna, exercise room, and very clean bathrooms by the pool. 2 Bed, 2 Bath. Master bedroom offers queen bed, sitting room, coffee, 50 inch smart tv, storage, master bath separate toilet. 2nd Bedroom...

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Featured review

"Super comfortable condo - amazing location - wonderful host!"

We spent a month in Sharon's condo (January 2025). Upon arrival we had everything we needed for the month! She goes above and beyond stocking the kitchen, cleaning supplies, pantry etc. The bedrooms are...

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$174
avg per night
New
Islamorada House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Hi, nice to meet you!!! If you like to be somewhere surrounded by a magnificent peace and balance, fresh, organized and a very clean home, "you just found it". You will be happy to go out in the boat and come back to a relaxing home to enjoy the rest of the day with family or friends with...

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$336
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

Immerse yourself in the luxury and beauty of Oceanside, a brand-new gated community with 9 beachfront homes nestled in the heart of Islamorada. Our 4 bedroom home invites you to experience modern coastal comfort while its nearly 3000 square feet of indoor space provide ample room for family and friends....

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Featured review

"Beautiful stay"

We had the best time at this house! Giovanna and her husband were wonderful hosts and were on top of everything we needed. The house itself is in a great location close to shops and restaurants. Book the...

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$1,077
avg per night

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Islamorada Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs...

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Featured review

"Unit 205 Beacon Reef"

Love Beacon Reef and the unit was very comfortable and well equipped. Very close to the pool and the staircase from the balcony was convenient

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$183
avg per night
Islamorada House
Sleeps 12, 4 bedrooms, 3 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

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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Featured review

"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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$500
avg per night
Islamorada Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom...

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Featured review

"Beautiful waterfront Condo"

We had a wonderful month in Islamorada at this outstanding waterfront condo with pool and sauna, dock etc. The views were gorgeous from the 3 decks in this corner unit. The area is exciting and near both...

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$177
avg per night
Islamorada House
Sleeps 3, 1 bedroom, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Sunshine Place 84371 Overseas Highway, Islamorada, FLLOCATION: Oceanside HouseMINIMUM STAY: WeeklyMILE MARKER: 84.3DETAILS: "Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing...

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$269
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to White Marlin Beach

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

*******Check us out on VRBO No. 2003434******** Please go to ....**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.As soon as you walk into this home you will...

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$350
avg per night
New
Islamorada House
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Marlin House 156 Venetian Drive, Islamorada, FL 33036LOCATION: Bayside Canal home located in the popular Islamorada neighborhood of White Marlin BeachMINIMUM STAY: 90 days, this is a 3 month minimumMILE MARKER: 74.5DETAILS: You will love this charming and cozy Keys Holiday...

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$216
avg per night
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Islamorada Weather

 | 

7524°  6217°
JANUARY
Ocean 7423°
7624°  6217°
FEBRUARY
Ocean 7423°
7826°  6518°
MARCH
Ocean 7624°
8228°  7021°
APRIL
Ocean 7926°
8529°  7423°
MAY
Ocean 8127°
8731°  7725°
JUNE
Ocean 8329°
8932°  7926°
JULY
Ocean 8530°
8932°  7826°
AUGUST
Ocean 8730°
8731°  7725°
SEPTEMBER
Ocean 8530°
8429°  7423°
OCTOBER
Ocean 8328°
8027°  7021°
NOVEMBER
Ocean 7926°
7624°  6518°
DECEMBER
Ocean 7625°

FAQ

How many vacation rentals are there in/around Islamorada?

There are 111 Islamorada vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Islamorada?

There are vacation rentals available in Islamorada for as low as $87 per night with an average price per night of $431.

Can I rent a house in Islamorada?

Yes, you can find house rentals in Islamorada close to Theater of the Sea, Florida Keys Brewing Company, and History of Diving Musem. Don't forget to stop in to Founder's Park or Alligator Reef.

Do any vacation rentals in Islamorada have a pool?

Yes there are 54 vacation rentals with a pool in Islamorada on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Islamorada vacation rentals on the ocean?

There are 44 oceanfront rentals in Islamorada available on FloridaRentals.com. Use our filters to search and book yours today!