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Monthly Rentals in Islamorada

(74 rentals)
Islamorada House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Mile marker 77. Deep Water ocean side canal with direct access to the Atlantic Ocean and a straight shot to Alligator Light House. Sunny Patio and splash Pool. 4 Bedrooms/4 Baths. Sleeps 8. There is no cable package with this home so please bring your passwords for live streaming from the smart TVs.The...

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$373
avg per night
Islamorada Villa
Sleeps 14, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

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

About this property

️5 bedroom 4 bathrooms (One bathroom by pool) ️Canal home in Venetian Shores with access to bay and ocean ️100 foot of dockage on 100 foot wide deep canal. Ask about bringing your own boat ️Location of canal is off Snake Creek near MM86 ️ Beautiful large pool with hot tub in tropical setting ️...

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$673
avg per night
Islamorada House
Sleeps 2, 1 bedroom, 1 bathroom
2 reviews

Distance to beach: 5 miles to Founders Park

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Half Duplex HomeAre you seeking a beautiful hideaway close to all the amenities? This delightful 1 bedroom half duplex vacation home has deep water dockage for your boat in the back yard with the view of a beautiful lagoon. This lagoon has schools of tarpon to test your angling skills, and manatees...

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Featured review

"Perfect spot."

My wife and I stayed at this 1 bedroom 1bath duplex on the water. It was perfect for the 2 of us. Clean. Owner was very attentive.

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$87
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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$196
avg per night
Islamorada House
Sleeps 5, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

PROPERTY NAME: The Bungalow House 32 Park Rd Islamorada, FloridaLocation: Bayside Very close to the Publix Shopping CenterMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedMile Marker : 82Details: This home is absolutely beautiful with your own pool and...

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$253
avg per night

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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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$1,101
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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$170
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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$286
avg per night
Islamorada House
Sleeps 10, 5 bedrooms, 7.5 bathrooms

Distance to beach: 4 miles to Founders

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Rare Summer Openings! Your Private Resort Awaits in IslamoradaIf you’ve been dreaming of an island escape with all the luxury of a high-end resort but none of the crowds, this is your chance.Your Own Private Resort in the Florida KeysFrom the moment you arrive, this estate feels more...

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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 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
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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$202
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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$184
avg per night
Islamorada House
Sleeps 8, 3 bedrooms, 3.5 bathrooms
2 reviews

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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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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$978
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

Ocean side pool home with private dock. Beautifully decorated with 2 bedrooms and 2 bathrooms on the main level. Master bedroom has a queen size bed and a full bath. The second bedroom has twin beds. Downstairs is a suite with sleeping accommodations for 4 people and full bathroom. Linens and towels...

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$329
avg per night
Islamorada House
Sleeps 10, 4 bedrooms, 3 bathrooms

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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$667
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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$600
avg per night
New
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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$239
avg per night
Islamorada Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

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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$183
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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$802
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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$318
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 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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$283
avg per night
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
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