Sandy Point Townie $10,000 - $11,000 Monthly

Sandy Point Townie

$10,000 - $11,000 Monthly

Mile Marker 75 – Bayfront From toes in the sand to beverage in hand, this beachfront vacation rental boasts views of the beautiful blue waters of Florida Bay and is just steps away from the waters edge. After a day of sunshine, relax and enjoy…

3 beds 2.5 baths
3 beds 2.5 baths

Mango House $6,000 Monthly

Mango House

$6,000 Monthly

Mile Marker 81 – Heart of Islamorada A magical, modern, Island-style Villa with the ideal location!  This newly renovated Villa, in Green Turtle Beach Neighborhood, features 2 bedrooms, 2.5 baths, and a custom pool featuring a private sandy area around pool.

2 beds 2.5 baths
2 beds 2.5 baths

Sandy Point Duplex $10,000 - $11,000 Monthly

Sandy Point Duplex

$10,000 - $11,000 Monthly

Mile Marker 75 – Bayfront  This waterfront duplex is situated in an upscale community, complete with private beach. The home sits up on stilts and faces Northwest looking over the beautiful waters of Florida Bay. Watch amazing sunsets, relax under the tiki hut with your…

3 beds 3 baths
3 beds 3 baths

Gulfview $12,000 / monthly

Gulfview

$12,000 / monthly

Mile Marker 74 – Bayfront Newly listed for Rentals – This 3 bedroom home is located right on the beach on a quiet road in Lower Matecumbe Key.   An extremely desirable location, this well kept home features one of the best beaches in Islamorada, dockage…

5 beds 4 baths
5 beds 4 baths

Nautica $20,000 / monthly

Nautica

$20,000 / monthly

Mile Marker 83 – Bayfront Four bedroom/four bath clean home located directly on the Florida Bay.  Featuring fantastic sunset views, Nautica Sleeps 8-10 and has a heated pool and good dockage.   Monthly rental only.

4 beds 4 baths
4 beds 4 baths

Virga Limbo $17,000 / monthly

Virga Limbo

$17,000 / monthly

MM 76. Five bedrooms/four baths. Charming bay front home. Hammocks, outdoor bar, and dockage all with views of uninhabited islands that dot the Keys. Sorry, no pets.  

5 beds 4 baths
5 beds 4 baths

Peace of Paradise $20,000 / monthly

Peace of Paradise

$20,000 / monthly

MM 75. Four bedrooms/three and a half baths. Gorgeous house over 3 floors, with heated/cooled pool in quiet, private side street in Lower Matecumbe Key. Directly on the Atlantic with open 180-degree panoramic view. Upscale interior design, fully furnished. Glass elevator. Gorgeous views from every…

4 beds 3.5 baths
4 beds 3.5 baths

Seaside Breezes $14,000/ monthly

Seaside Breezes

$14,000/ monthly

Mile Marker 94. Three bedrooms/two baths.   Ocean front in South Key Largo– this private gated home has dockage and beautiful sunrises.   Enjoy the Atlantic Ocean how a local sees it…  Sleeps 6.  

3 beds 2 baths
3 beds 2 baths

Ocean Terrace $4,500 weekly - $15,000 monthly

Ocean Terrace

$4,500 weekly - $15,000 monthly

Mile Marker 81.5, 3 bedrooms, 3 baths with den, sleeps 6-8, Jacuzzi/splash pool and sandy beach. Vacation Rental License #VR-047.  

3 beds 3 baths
3 beds 3 baths

Little Bay $2,500 weekly/unit

Little Bay

$2,500 weekly/unit

Mile Marker 82 – Bayfront Duplex (up and downstairs). Each unit has 2 bedrooms, 1.5 bath, sleeps 6, basin, dockage, snorkeling. Vacation Rental License #VR-084, & 85.    

2 beds 1.5 baths
2 beds 1.5 baths

Oasis At Tavernier $18,000 - $20,000 Monthly ~ Call for Holiday Rates

Oasis At Tavernier

$18,000 - $20,000 Monthly ~ Call for Holiday Rates

$18,000 – $20,000 monthly~ Call for holiday rates   Mile Marker 92.   This luxurious 6 bedroom estate is located in Tavernier, in the Upper Florida Keys. Conveniently located a short distance from the Atlantic Ocean, deep water dockage makes Oasis in Tavernier perfect for…

6 beds 7 baths
6 beds 7 baths

Little Bay Cottage $2,500 weekly

Little Bay Cottage

$2,500 weekly

Mile Marker 82 – Bayside One bedroom/two bath with Florida room. Newly remodeled. Vacation Rental License #VR-086.  

1 bed 2 baths
1 bed 2 baths

Treehouse $5,000 / monthly

Treehouse

$5,000 / monthly

Mile Marker 96, 1 bedroom, 1 bath, sleeps 4, dock, beach, and sunsets.  

1 bed 1 bath
1 bed 1 bath

Ishmael’s Watch $18,000-$20,000 / monthly

Ishmael’s Watch

$18,000-$20,000 / monthly

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.   Seven bedroom/ four bath luxurious oceanfront premier rental estate on Lower Matecumbe Key in Islamorada. Enjoy a walk around the lush, native garden or take a dip in the oceanfront pool. Catch palm tree shade…

7 beds 4 baths
7 beds 4 baths

Grey Heron Cottage $6,500 Weekly ~ Call for holiday rates

Grey Heron Cottage

$6,500 Weekly ~ Call for holiday rates

Mile Marker 89 – Oceanfront   Grey Heron Cottage Estate (named after original owner) is located on the famous Millionaire’s Row. You’ll love the fantastic sun rises, ocean views, dockage and brand new pool that this property features!   After entering the gated grounds, a…

3 beds 2.5 baths
3 beds 2.5 baths

Villa Paraiso $16,000 / monthly

Villa Paraiso

$16,000 / monthly

The extravagant Villa Paraiso boasts 6.5 bedrooms, with an 88’ dock, two Jacuzzis, veranda, and canal and bay views.  Located Bayside at mm 90, the large, custom built, villa would be perfect for large families or groups.    A large 10 person heated 16’x7′ swim spa…

7 beds 4.5 baths
7 beds 4.5 baths

Sea Shore Drive $7,200 / monthly

Sea Shore Drive

$7,200 / monthly

Mile Marker 80.5. 3 BR – 2BA Large master & bath. Walk to Morada Way festivals and restaurants. Fantastic location! W/ access to neighborhood beach.  

3 beds 2 baths
3 beds 2 baths

The Cove North $3,000 / monthly

The Cove North

$3,000 / monthly

Mile Marker 81 – Heart of Islamorada 1 BR – 1BA Villa on Old Hwy. Short bike ride to Morada Way festivals and restaurants. Fantastic location! Large walk in shower. This is for the North side of the duplex.

1 bed 1 bath
1 bed 1 bath

The Cove South $3,000 / monthly

The Cove South

$3,000 / monthly

Mile Marker 81 – Heart of Islamorada   BR – 1BA Villa on Old Hwy.   This fantastic location is just a short bike ride to Morada Way festivals, the Art Walk, Full Moon Party and restaurants.   Grab breakfast and Coffee at Midway Cafe, lunch at…

1 bed 1 bath
1 bed 1 bath

Tatenda Ishe Cottage $3,500 / monthly

Tatenda Ishe Cottage

$3,500 / monthly

Mile Marker 81.   Cute and cozy two bedroom home located off the main streets, in the heart of Islamorada.  A full porch wraps around the front and back yard, for relaxing and entertaining in the Florida Keys weather.   Natural sunlight fills the main living space as you enter into the quaint cottage. The fully equipped kitchen is open to the dining and the newly renovated bathroom is conveniently located in the middle of the home. Multiple cozy sitting areas lead  you into the tv room, furnished with a flat screen tv and a large leather sofa. The back bedroom features french doors that extend out into a courtyard where you will find a covered sitting area and native landscaping.  The guest bedroom features two twins. Enjoy being a short distance from all the charming restaurants, marinas, shops, and galleries that makes Islamorada the perfect vacation destination.

2 beds 2 baths
2 beds 2 baths

Maison Matecumbe #304 $3,300 / weekly - $9,900 monthly

Maison Matecumbe #304

$3,300 / weekly - $9,900 monthly

Unit 304 located within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 3 baths, 2 stories sleeps 6, pool, sandy beach. New stainless steel appliances. Vacation Rental License #VR-021

3 beds 3 baths
3 beds 3 baths

Seagrape Cottage $7,500 / Month

Seagrape Cottage

$7,500 / Month

MM 81 – Heart of Islamorada 2 bedroom & 2 bath, set in the heart of Islamorada, near restaurants and shopping, great location for walking/biking to cultural areas! Newly renovated and now with a newly installed POOL!  

2 beds 2 baths
2 beds 2 baths

Latitudes $16,000 / Monthly

Latitudes

$16,000 / Monthly

Mile Marker 75 – Bayside Large, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in Islamorada, Florida Keys. This gorgeous home overlooks the pool and canal and is just minutes away from the FAMOUS Port Antigua Neighborhood beach, one of the…

4 beds 2.5 baths
4 beds 2.5 baths

Holly’s Hideout $9,000 / Month

Holly’s Hideout

$9,000 / Month

Mile Marker 91 – Ocean Side Situated on a clean, clear canal with deep water access to either the bay or ocean via Tavernier Creek! Enjoy your island time in this bright and breezy hideaway … Two bedrooms/Two baths upstairs along with open living, dining…

4 beds 3 baths
4 beds 3 baths

Seas the Day $8,000 / Month *SPECIAL* $10,000 July

Seas the Day

$8,000 / Month *SPECIAL* $10,000 July

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. Two private bedroom suits on second floor in addition to the two…

4 beds 4 baths
4 beds 4 baths

Located in Venetian shores, this lower level 2 bedroom unit is complete with pool and dockage.   Dockage has great access to Ocean via Snake Creek where you’ll find the blue green water and the fishing that made Islamorada famous.  The upstairs will not be occupied during…

2 beds 2 baths
2 beds 2 baths

Little Biscuit $7,500 / monthly

Little Biscuit

$7,500 / monthly

MM 74. Three bedrooms/1 bath. Canal front home with beach access.

3 beds 1 bath
3 beds 1 bath

Barefoot Elegance $27,500 / monthly

Barefoot Elegance

$27,500 / monthly

Mile Marker 75, 5 bedrooms, 4 baths, sleeps 10, luxurious, heated pool, deep water dockage. Boathouse with slip.  

5 beds 4 baths
5 beds 4 baths

Oceanista $6,500 / monthly

Oceanista

$6,500 / monthly

Mile Marker 75. Very Private – Two Bedrooms / Two Baths. Sleeps 6. Private waterfront lagoon to accommodate deep water boaters. Oceanfront ‘Walking Beach’ just steps away!   Virtual Tour

2 beds 2 baths
2 beds 2 baths