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Monthly Rentals in Islamorada

(70 rentals)
Islamorada Condo
Sleeps 6, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful area of island on ocean

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$97
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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$146
avg per night
Islamorada Townhome
Sleeps 4, 2 bedrooms, 2.5 bathrooms
1 review

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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Featured review

"Great Location"

This condo was very conveniently located. We could snorkel at John Pennekamp and kayak the mangroves of Islamorado. Plenty of close good seafood restaurants in vicinity. Spend the day at Bahia Honda.

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$276
avg per night
Islamorada House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Fisherman's Gem 113 Iroquois Drive Islamorada, FloridaLOCATION: Oceanside Canal home with Boat dock and Boat RampMIMINUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 74This waterfront, ground-level Islamorada home, featuring...

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$191
avg per night
Islamorada Townhome
Sleeps 4, 2 bedrooms, 1.5 bathrooms
2 reviews

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

"Perfect vacation spot!"

Loved everything. We enjoyed the pool, the long pier, and the ocean breeze. Everyday was relaxing. Many great restaurants close by.

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$168
avg per night

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Islamorada House
Sleeps 10, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

PROPERTY NAME: Casa Lisbon 125 Lisbon Court, Islamorada, FloridaLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of Port AntiguaMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 74.5 DETAILS: Casa Lisbon offers a...

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$447
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

PROPERTY NAME: Ocean Harbour K31 87851 Old Highway, Islamorada, FloridaLOCATION: Ocean Front CondoMINIMUM STAY: 28 Days, MILE MARKER: 87.8DETAILS: Gorgeous 3 bedroom ocean front condo with unobstructed ocean views from the screened balcony. Check out the photos! The kitchen was completely...

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$300
avg per night
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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$500
avg per night
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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$215
avg per night
Islamorada Townhome
Sleeps 6, 2 bedrooms, 3 bathrooms
2 reviews

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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Featured review

"Absolutely perfect stay"

We stayed at this location in April-May 2026. It was amazing. My parents stayed with my husband and I and our 10 year old son. The unit was immaculate. It was clean, beautiful and fully equipped for our...

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$174
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founder's Park

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Long-term rental available in the beautiful Venetian Shores community of Islamorada, Florida. This 3-bedroom, 2-bath home sits on a secluded plugged canal by the water. Enjoy a large master bedroom, a spacious open layout, and a generous outdoor deck ideal for entertaining. Additional features include...

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$275
avg per night
Islamorada House
Sleeps 6, 2 bedrooms, 2 bathrooms

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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$190
avg per night
Islamorada Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

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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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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$305
avg per night
Islamorada House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
2 reviews

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

"Incredible rental!"

We had the pleasure of staying in this home, and we cannot say enough good things about it. First and foremost, our host, Giovanna, was exceptional. She made sure we had an incredible stay and was so helpful...

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$1,064
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

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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Featured review

"Amazing stay!!"

We had an amazing stay at this Airbnb in Islamorada, Florida! The property had everything we needed and felt comfortable from the moment we arrived.One of the biggest highlights for us was the boat...

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$167
avg per night
Islamorada House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

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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$799
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 House
Sleeps 5, 2 bedrooms, 2.5 bathrooms

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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$225
avg per night
Islamorada Apartment
Sleeps 4, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

for more photos and info!!Serene and tranquil view of the canal in your backyard. Ample balcony with sitting area to enjoy your morning coffee. Short walking distance to a beautiful private beach “White Marlin Beach” approximately one block or less away. The unit is located on the second...

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$125
avg per night
Islamorada Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 2 miles to Founders Park

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

*Discover Elevated Island Living at Sea Breeze 41 Luxury 3BR/2BA Condo with Private Boat Slip in Exclusive Coral Harbour Club, IslamoradaWelcome to Sea Breeze 41 — your personal slice of tropical paradise in the heart of the Florida Keys. Nestled within the highly coveted Coral Harbour Club,...

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$208
avg per night
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