Monthly Rentals in Islamorada

(68 rentals)
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Islamorada House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
17 reviews

$475

avg/night

$475
avg per night
View Details

Key Amenities

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

About this property

This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...

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Property Type

Islamorada House

Featured review

"Great Pool Rental!"

This was a great house! Our whole family enjoyed the stay very much. It was quiet and the layout of the home is perfect for multiple families to stay. The pool area was very nice and the dock is a perfect ...

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

$100

avg/night

$100
avg per night
View Details

Key Amenities

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

About this property

DECEMBER 2024 ONLY SALE NOW GOING ON! Just over $100 a night! Much less than a motel room. The weather is beautiful, and you can now stay in Islamorada for only chump change! 2025 is fully booked till May 12! We have an unusual time 4/1-18 that we NEVER have done before. Contact me for particulars. ...

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Property Type

Islamorada Condo

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Islamorada House
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
1 review

Distance to beach: 5 miles to Founders Park

$97

avg/night

$97
avg per night
View Details

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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Property Type

Islamorada House

Featured review

"Wonderful stay in the Keys!"

The screened in area and the outdoor space make this rental perfect! We kayaked on the canal, and walked around the neighborhood daily. We watched boats and manatees from the screened in porch. Lee (the ...

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Islamorada Townhome | On the beach
2 BR | 3 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 3 bathrooms

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

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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

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 House | On the beach
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 | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

$1380

avg/night

$1,380
avg per night
View Details

Key Amenities

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

About this property

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, ...

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Property Type

Islamorada House

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

$1013

avg/night

$1,013
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 Townhome
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms

$126

avg/night

$126
avg per night
View Details

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 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
2 reviews

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Located at Mile Maker 87 Bayside. This gated condo complex offers a large heated pool, club house, Jacuzzi, two tennis court, large Bayside beach. This townhouse (sleeps 8) has just been totally renovated with beautiful tropical furniture, all new kitchen, small garden patio with hammock, living room ...

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Property Type

Islamorada House

Featured review

"Great vacation"

We have never stayed in the Florida Keys before so this was a new adventure that we will definitely do again. The weather was a perfect 80 degrees. Nothing but chill time. We would start the day in the ...

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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 | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1406

avg/night

$1,406
avg per night
View Details

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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Property Type

Islamorada House

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

$978

avg/night

$978
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 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
View Details

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

Distance to beach: 2 miles to Founders Park

$207

avg/night

$207
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 Apartment | On the beach
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 | On the beach
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
3 reviews

$1400

avg/night

$1,400
avg per night
View Details

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

$97

avg/night

$97
avg per night
View Details

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 Vacation Rentals