All Florida Keys Vacation Rentals

Futura Yacht club #302 $1,400 weekly, $1,600 Holidays

Futura Yacht club #302

$1,400 weekly, $1,600 Holidays

MM 88.5. 2 bedrooms, 2 baths, sleeps 4. 3rd floor. King in master W/ queen size bed in guest. Heated pool, beautiful sunsets, and lit tennis, basketball, and volleyball courts. Optional deeded dock for boats. #VR-178

2 beds 2 baths
2 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

Blue Heaven Bahamas $5,600 / weekly

Blue Heaven Bahamas

$5,600 / weekly

Truly Heaven

5/5 Stars Stayed Mar 2019

Melanie W. • St Louis

Blue Heaven was a perfect home away from home for our family of 5. The living spaces were so comfortable, well-appointed, and well-supplied. The location – steps from the waves and also a short walk to town and harbor – was ideal. We couldn’t have been happier!

3 beds 3 baths
3 beds 3 baths

Futura Yacht Club #403 $1,400 / Week, $1,600 Holidays

Futura Yacht Club #403

$1,400 / Week, $1,600 Holidays

MM 88.5. 2 bedroom, 2 baths, sleeps 4. 4th Floor. King in master w/ 2 twins in guest. Heated pool, screened Lanai, tennis courts, basketball and volleyball courts. Optional dock for boats up to 33′. Beautiful sunsets. #VR-17

2 beds 2 baths
2 beds 2 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

Sunset Lagoon $5,500 - $7,500 Weekly

Sunset Lagoon

$5,500 - $7,500 Weekly

MM 90.  5 BR. One of the best homes for families, Sunset Lagoon has 5 bedrooms nestled on the Florida Bay in Islamorada, Florida Keys.   Let the kids hang out at the pool while you launch your boat out the convenient dockage to the back country or Atlantic Ocean.

This home is complete with beautiful Sunset views and a game room for the kids.

5 beds 5 baths
5 beds 5 baths

Sea Shore Drive $7,200 / monthly

Sea Shore Drive

$7,200 / monthly

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

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

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

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

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

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

Angler’s Reef Garden Side $2,600 / weekly

Angler’s Reef Garden Side

$2,600 / weekly

MM 85. 2 Bedroom & 2.5 Bath. Located on the quiet side of Angler’s Reef Village. A walk down quaint streets to pool, ocean and beach!

2 beds 2.5 baths
2 beds 2.5 baths

Aguazul $4,500 weekly - $14,000 monthly ~ Call for holiday rates

Aguazul

$4,500 weekly - $14,000 monthly ~ Call for holiday rates

Mile Marker 88. Four bedroom/three baths. Sleeps 8. Ocean front estate with fantastic views, heated pool and deep water dockage. Exclusive Community. Vacation Rental License #VR-014.  

5 beds 4 baths
5 beds 4 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

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

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

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

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

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

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

Sunset Dream $12,000 / monthly

Sunset Dream

$12,000 / monthly

Mile Marker 83 – Bayfront Five bedroom/four bath home located on the Florida Bay.   Sunset Dream has an ideal view for Sunsets, dolphins, and a view of the Florida Bay Keys.  Heated pool gives plenty of fun for the family.   This home is older, but…

5 beds 4 baths
5 beds 4 baths

Unit 301 located within Maison Matecumbe gated community. Mile Marker 81. NEWLY DONE POOL and HOT TUB! 3 bedrooms, 2 baths, sleeps 6, pool, sandy beach. Vacation Rental License #VR-111.  

3 beds 2 baths
3 beds 2 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

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

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

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

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

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 $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

Sandy Point Townie 11,500 Monthly

Sandy Point Townie

11,500 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

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

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

Sandy Point Duplex $12,000 Monthly

Sandy Point Duplex

$12,000 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

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, features 2 bedrooms, 2.5 baths, and a custom pool featuring a private lounging beach.

2 beds 2.5 baths
2 beds 2.5 baths

Key Lime Villas $3,600 - $4,200 / weekly

Key Lime Villas

$3,600 - $4,200 / weekly

3 Bedrooms & 3.5 bathrooms Villas 1-3 $3,300 – $3,850 Weekly depending on dates Mile Marker 81.6 — Bayside Villas   Key Lime Villas, aptly named for the famous Key’s citrus fruit, are a set of three brand new villas located in the heart of…

3 beds 3.5 baths
3 beds 3.5 baths

Leila’s Beach House $4,750 / weekly

Leila’s Beach House

$4,750 / weekly

Miles Marker 81 – Oceanfront   Cozy, stylish house located in the heart of Islamorada.  3 Bedrooms and 2 baths located right on the ocean with a heated pool, private beach and more!  Enjoy the large master bedroom with master bath and shower.  Located at…

3 beds 2 baths
3 beds 2 baths

Villa Thenardier $12,500 / Weekly

Villa Thenardier

$12,500 / Weekly

Mile Marker 89 — Millionaire’s Row. Four Bedroom/ Six Bath Ultra-Luxurious, Oceanfront estate with more than 6,000 square feet under air and 5500 square feet of covered terraces and deck. Featuring a gourmand’s kitchen, home theatre, gym, tennis, pool, Jacuzzi, outdoor kitchen and more! Located…

Green Turtle Beach $10,500 -$12,500 In season and holidays

Green Turtle Beach

$10,500 -$12,500 In season and holidays

Mile Marker 81. Ocean front estate located on 4 acres, five bedroom/five 1/2 baths. Sleeps 10. Sandy beach and heated pool with jacuzzi. 24 hour caretaker overseas the property. #VR-082   In Season and Holiday Rate: $12,500 Weekly Off Season: $10,500 Weekly Add optional 1…

5 beds 5.5 baths
5 beds 5.5 baths

Conch Villas $3,600 - $4,200 Weekly

Conch Villas

$3,600 - $4,200 Weekly

3 Bedrooms & 3.5 bathrooms Villas 4-6 $3,600 – $4,200 Weekly depending on dates Mile Marker 81.6 — Bayside Villas Conch Villas, aptly named for the famous large snails that inspired the Keys to be called the ‘Conch Republic,’ are a set of three brand…

3 beds 3.5 baths
3 beds 3.5 baths

Bayview Villas $4,600 - $5,600 weekly

Bayview Villas

$4,600 - $5,600 weekly

3 Bedrooms & 3.5 bathrooms Villas 7-9 $3,960 – $7,000 Weekly depending on dates   Mile Marker 81.6 — Bayside Villas   Bayview Villas are named because they are… bayside! The closest villas to the pool, water and dockage, these villas are a set of…

3 beds 3.5 baths
3 beds 3.5 baths

The Beach House $7,000 Weekly - Call for holiday rates

The Beach House

$7,000 Weekly - Call for holiday rates

Mile Marker 80 – Oceanfront   Indulge in the island lifestyle at this beautiful private estate located in the heart of Islamorada. The gated property is lush in tropical landscaping that boost an oceanfront pool, boat dockage, brand NEW tennis court and sand volleyball net….

4 beds 4 baths
4 beds 4 baths

Osprey Bay $5,700-$6,500 Weekly, $22,000 Monthly

Osprey Bay

$5,700-$6,500 Weekly, $22,000 Monthly

Mile Marker 82.7 – Bayfront 5 bedrooms, 3 baths, sleeps 10-12, dockage, pool, spa, and beautiful sunsets. Located in heart of Islamorada. VR-171  

5 beds 3 baths
5 beds 3 baths

Sea Ranch $9,000 weekly ~ Call for holiday rates

Sea Ranch

$9,000 weekly ~ Call for holiday rates

Mile Marker 83 – Oceanfront Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada! This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the…

4 beds 4 baths
4 beds 4 baths

Reservation Procedure

A 30% security deposit is required along with the rental agreement and application within 24 hours to insure your booking.  The security deposit is payable by credit card.  A $75.00 reservation fee, cleaning fee and 12.5% sales and county tax are additional to the rental amount.  The balance due is payable by check or wire transfer within 90 days prior to check in  Cancellations will be refunded in full 90 days prior to check in.  The 30% security deposit will be refunded within 30 days after your departure if the property is found in satisfactory condition.  

 

Please be advised that during the event of a hurricane, your deposit is fully refundable without penalty. You may also use your deposit toward a future rental at a different date.

 

Status of properties and prices are subject to change. If owner changes status of property, a substitution will be made or refund given. Check-in is 4 PM. Check-out is 10 AM.

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