Monthly Rentals in Islamorada

(72 rentals)
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Islamorada House
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
3 reviews

$1400

avg/night

$1,400
avg per night
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Key Amenities

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

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

Featured review

"Best vacation ever"

I can’t express enough how our month in this house was above expectations. It was my retirement party and over the month had friends, family and high school buddies. The house was huge and 5 couples were ...

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 50 yards to White Marlin

$295

avg/night

$295
avg per night
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Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Located across from White Marlin beach This canal home has protected deepwater dockage , on the most sought-after street, on Gulfview Drive in Islamorada. Enjoy sunset and bay views from White Marlin Beach. Gulfview, known as the 'sugar sand beach', offers 3 bedrooms, 2 bathrooms, dining, ...

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Property Type

Islamorada House

Featured review

"Clean and comfortable in a great location"

The home is very comfortable with three bedrooms and a spacious living/dining area. The master bedroom is a bit cozy and lacks a closet, but the two bedrooms that share the Jack-and-Jill bathroom have ...

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Islamorada Townhome
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms

$126

avg/night

$126
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Fully furnished 2 bedroom 1. 1/2 baths with balcony, heated pool, sauna and fitness room. Also a community room with flat screen and full kitchen, pool and ping pong. Beautiful ocean view from pool and community room. Huge ocean front dock for fishing, snorkeling and kayaking. WiFi , restaurants ...

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Property Type

Islamorada Townhome

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Islamorada House
2 BR | 2.5 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2.5 bathrooms

$161

avg/night

$161
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

PROPERTY NAME: Mango House 81212 Old Highway Islamorada, FloridaLocation: Ocean side located on the Old Road by Green Turtle RestaurantMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedMile Marker : 81Details: This home is absolutely beautiful with Keys ...

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Property Type

Islamorada House

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Islamorada House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms

$667

avg/night

$667
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • WiFi

About this property

Seeing is believing. The Captain's Quarters is a direct, oceanfront home on the Atlantic shoreline of Islamorada. For your planned getaway, come enjoy truly private and relaxing oceanfront living in the heart of Islamorada, in a unique home boasting a treasure-trove of Florida Keys history. The ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3.5 bathrooms
2 reviews

$965

avg/night

$965
avg per night
View Details

Key Amenities

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

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and ...

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Property Type

Islamorada House

Featured review

"Bayside Paradise Perfection"

Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt ...

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Islamorada Townhome
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$265

avg/night

$265
avg per night
View Details

Key Amenities

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

About this property

Breathtaking Waterfront 2/2.5 Townhouse In Desirable Futura Yacht Club. Lots of outdoor living space,great for entertaining and enjoying the magnificent unobstructed Bayviews and beautiful sunset! Futuravis a gated community with a large pool tennis courts, boat ramp,beach and boat/trailer storage,parking ...

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Property Type

Islamorada Townhome

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Islamorada House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms

$253

avg/night

$253
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Harbor House 101 San Juan Dr., Islamorada, FLLOCATION: Bayside Canal home located in the Upscale Venetian Shores CommunityMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 86DETAILS: Ready for occupancy this winter! This ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to beach: 0.5 miles to White Marlin Beach

$350

avg/night

$350
avg per night
View Details

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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Property Type

Islamorada House

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Islamorada Townhome
2 BR | 3 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 3 bathrooms
1 review

$175

avg/night

$175
avg per night
View Details

Key Amenities

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

About this property

Enjoy breathtaking sunsets on the private beach while staying in this beautifully remodeled corner unit. The unit was completely gutted in 2021 and features 2 bedrooms plus a built out loft and 3 full bathrooms.The unit has a huge master with a king bed plus a bathroom/walk-in closet and ...

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Property Type

Islamorada Townhome

Featured review

"A perfect place to relax and unwind"

Spending the month of December at this beautiful condo with my family was an unforgettable experience. The condo itself was warm, cozy, and inviting, with all the amenities we could possibly need for a ...

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Islamorada Condo
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms

$97

avg/night

$97
avg per night
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Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful area of island on ocean

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Property Type

Islamorada Condo

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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founders Park

$165

avg/night

$165
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condominium (CHC) . Your spacious 3 Bedroom / 2 Bathroom island getaway exudes luxury tropical vibes and is professionally decorated in Tropical Modern style. A 30' Boat Slip ...

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Property Type

Islamorada Condo

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Islamorada Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$298

avg/night

$298
avg per night
View Details

Key Amenities

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

About this property

We have owned and rented this property for 20 years and have been coming to Seagulls Condominiums for over 40 years. The condo bathrooms and bedrooms have just been updated and the entire building has just finished a major upgrading and painting. If my pics don't import from vrbo 49422, then you ...

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Property Type

Islamorada Condo

Featured review

"Outstanding view and amenities. Will return soon!"

Classic art deco style building which was fully remodeled both inside and out. The owners are very responsible and have been doing this a long time.

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Islamorada Apartment
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$183

avg/night

$183
avg per night
View Details

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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Property Type

Islamorada Apartment

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Islamorada House
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 3 bathrooms
3 reviews

$525

avg/night

$525
avg per night
View Details

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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Property Type

Islamorada House

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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Islamorada House
3 BR | 2.5 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2.5 bathrooms

$667

avg/night

$667
avg per night
View Details

Key Amenities

  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

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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Islamorada Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$131

avg/night

$131
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

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Property Type

Islamorada Condo

Featured review

"Wonderful"

I highly recommend this vacation spot. Not only is the condo very nice the whole property is set up for your every need. The owner and property manager are very nice and accommodating. I was amazed by the ...

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Islamorada House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$183

avg/night

$183
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Villa Riolo 130 Columbus Drive, Islamorada, FLLOCATION: Gated Oceanside House on canalMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.5DETAILS: "Villa Riolo" is an updated single family stilt home and perfect ...

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Property Type

Islamorada House

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Islamorada House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$217

avg/night

$217
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner

About this property

The moment you step inside this calming retreat in exclusive Venetian Shores you feel on vacation with permanently assigned boat slip in private marina just around the corner. All new kitchen, baths, porcelain tile flooring, fully furniture and LOTS more. Three bedrooms, two bath home on a peaceful plugged ...

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Property Type

Islamorada House

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Islamorada Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms
1 review

$140

avg/night

$140
avg per night
View Details

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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Property Type

Islamorada Townhome

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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Islamorada House
5 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3 bathrooms
5 reviews

$667

avg/night

$667
avg per night
View Details

Key Amenities

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

About this property

Deam home in they keys is a 4000 square foot home on water with heated/chilled 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 and three baths. Equipped with four king beds, one ...

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Property Type

Islamorada House

Featured review

"Amazing home and amazing renter️"

This home is a literal dream for individuals wanting to enjoy the beautiful outdoors in Islamorada. The beds were super comfortable, and the kitchen was roomy and had everything we needed. The additional ...

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Islamorada Townhome
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms
3 reviews

Distance to beach: 0.5 miles to Port Antigua Private Beach

Inquire for rates

Inquire for rates

View Details

Key Amenities

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

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

Featured review

"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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Islamorada Vacation Rentals