Islamorada, Florida

47 properties available

PROPERTY NAME: The Palms #41779901 Overseas Highway, Islamorada, FLLOCATION: Oceanside Condominium MINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 79.9DETAILS: The Palms of Islamorada is a condo complex consisting of 84 units and is located directly on the Atlantic Ocean. The complex features s

Updated Unit with Beautiful Florida Bay Sunsets

Updated Unit with Beautiful Florida Bay Sunsets 2

Updated Unit with Beautiful Florida Bay Sunsets 3

Updated Unit with Beautiful Florida Bay Sunsets 4

Updated Unit with Beautiful Florida Bay Sunsets 5

Updated Unit with Beautiful Florida Bay Sunsets 6

Updated Unit with Beautiful Florida Bay Sunsets (394083)

PROPERTY NAME: Little Bay Lower Duplex82246 Overseas Highway, Islamorada, FloridaLOCATION: Duplex located directly on the Florida BayMINIMUM STAY: Weekly or MonthlyMILE MARKER: 82.2DETAILS: - Located on a one-acre lush tropical setting in a gated compound directly on Florida Bay- One of 3 separate units for rent by the week or month, each sleepin

Gated Estate Duplex on the Bay with dockage

Gated Estate Duplex on the Bay with dockage 2

Gated Estate Duplex on the Bay with dockage 3

Gated Estate Duplex on the Bay with dockage 4

Gated Estate Duplex on the Bay with dockage 6

Gated Estate Duplex on the Bay with dockage (551732)

This waterfront, ground-level Islamorada home, featuring lavish amenities and gorgeous views, is destined to be the highlight of your next coastal escape. A lush outdoor space invites you to unwind on the dock, grill up the catch of the day, and grab a kayak for a sunset rowing session. Conveniently located, you’ll find Robbie’s of Islamorada, Long

Gemstone Isle (591497)

Swim right up to the edge of luxury at this ultra-private waterfront mansion. Located on one of the most prestigious streets in the Villages of Islamorada, this family-friendly property sits on a sizeable deep-water lagoon with protected boat dockage. Enjoy immaculate indoor/outdoor entertaining space, including wraparound screened balconies with a

Waterfront Wonder (264995)

PROPERTY NAME: Beacon Reef #30683201 Old Highway, Islamorada, FloridaLOCATION: Ocean Side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: Enjoy a relaxing stay here in the Keys at this immaculate and charming two bedroom and two bath condo. While the owners attend to their other

Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean.

Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. 2

Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. 3

Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. 4

Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. 5

Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. 6

Gorgeous 2 bedroom condo with panoramic views of the Atlantic Ocean. (348000)

PROPERTY NAME: Beacon Reef #40683201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Ree

Beautiful unit in one of the most prestigious Condo Complex in Islamorada

Beautiful unit in one of the most prestigious Condo Complex in Islamorada 2

Beautiful unit in one of the most prestigious Condo Complex in Islamorada 3

Beautiful unit in one of the most prestigious Condo Complex in Islamorada 4

Beautiful unit in one of the most prestigious Condo Complex in Islamorada 5

Beautiful unit in one of the most prestigious Condo Complex in Islamorada 6

Beautiful unit in one of the most prestigious Condo Complex in Islamorada (348011)

PROPERTY NAME: Little Bay Compound82246 Overseas Highway, Islamorada, FloridaLOCATION: Cottage and Two Story Duplex Located Directly on the Florida BayMINIMUM STAY: Weekly or MonthlyMILE MARKER: 82.2DETAILS: - Special pricing for renting all three units- Located on a one-acre lush tropical setting in a gated compound directly on Florida Bay- One o

Entire Compound on Gated Bayfront Property

Entire Compound on Gated Bayfront Property 2

Entire Compound on Gated Bayfront Property 3

Entire Compound on Gated Bayfront Property 4

Entire Compound on Gated Bayfront Property 6

Entire Compound on Gated Bayfront Property (551730)

PROPERTY NAME: Pelican Landing60 West Plaza Del Lago, Islamorada, FLLOCATION: Bayside Private Home in the neighborhood of Port AntiguaMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 74.5DETAILS: Pelican Landing is located in the prestigious neighborhood of Port Antigua on a deep and wide canal. T

Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal.

Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal. 2

Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal. 3

Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal. 4

Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal. 5

Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal. 6

Beautiful house located in the prestigious neighborhood of Port Antigua on a deep, wide canal. (348033)

PROPERTY NAME: Blue Water Retreat137 Ocean Lane, Islamorada, FloridaLOCATION: Oceanside Canal home located in Lower Matecumbe, IslamoradaMINIMUM: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.3DETAILS: This home has it all - ocean side Lower Matecumbe location, remodeled in 2009 and 2022. Relax by the sp

Remodeled Stilt home with Ocean Views (348030)

PROPERTY NAME: Beacon Reef #22283201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: Extraordinary oceanfront condo with panoramic views of the Atlantic Ocean. Relax on your balcony or use the spiral stairs to access the sand

Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex

Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex 2

Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex 3

Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex 4

Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex 5

Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex 6

Direct Oceanfront with private staircase to beach prestigious Islamorada CondoComplex (348001)

This deluxe Keys retreat is your ticket to paradise. This gated, canal-front property comes fully equipped for luxury coastal living, with private features including a boat dock, a sparkling in-ground pool, and surrounding deck furnished for outdoor comfort with multiple seating areas, a gas grill, and a shady palapa hut. Bonus items include an ice

Treasure Harbor Hideaway (295046)

PROPERTY NAME: Beacon Reef #30783201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: This like-new 2 bedroom/2 bath condo has fabulous ocean views and was totally remodeled/updated very recently. You'll love the sparkling new