Corporate Retreat Home Rentals in Islamorada, Florida Keys

Elevate Your Corporate Retreat Experience

 

Welcome to the ideal destination for corporate retreats in the picturesque setting of Islamorada, Florida Keys. Our exclusive rental homes offer the perfect blend of luxury, comfort, and convenience, tailored to meet the unique needs of your corporate gatherings.

 

Islamorada’s Unmatched Location

 

Nestled in the heart of the Florida Keys, Islamorada is renowned for its stunning blue-green waters, world class fishing, and upscale village charm.  It’s a paradise that provides the perfect backdrop for productive work sessions and memorable team-building activities.

 

Islamorada Unique Getaways:

 

• Rent a private island for a week and host entertaining events, corporate fishing trips and more. Have employees looking forward to the trip all year long.

 

• Rent multiple luxury 4 bedroom villas in the same building and host employees and families, and more! 20+ top tier, luxury bedrooms overlooking the Ocean!

 

• Or choose an oceanfront estate for a month and have groups come and go with cleanings in between. 7 bedrooms with plenty of excursions to choose from.

 

Browse properties below or call us 9-5pm, M-F and tell us about your requirements.  305-664-3333 • Rentals@islandvilla.com

 

COLLECTION OF HOMES FOR CORPORATE EVENTS:

67

Happy Ours $30,000 / monthly

Happy Ours

$30,000 / monthly

Mile Marker 74.5 – Open Bayfront Welcome to Happy Ours – an exquisite six-bedroom, six-bathroom waterfront estate offering over 5,000 square feet of air-conditioned luxury and an additional 4,500 square feet of expansive covered terraces and deck space. Nestled in the prestigious Port Antigua gated…

6 beds 6 baths
Details
77

*NEW* Venetian Moon $22,000 / monthly

*NEW* Venetian Moon

$22,000 / monthly

Mile Marker 86 – Open Bayfront   Welcome to your dream retreat in Islamorada, nestled in the exclusive Venetian Shores neighborhood. This meticulously appointed, custom-built 5-bedroom, 5.5-bath home offers an extraordinary escape for those seeking elegance and relaxation in the Florida Keys.   Step into…

5 beds 5.5 baths
Details
27

Maison Residences – Unit 101 – Beachfront $12,000-$14,000 - Discounted Summer rates available

Maison Residences – Unit 101 – Beachfront

$12,000-$14,000 - Discounted Summer rates available
Introducing Maison Residences 101... Islamorada, also known as “Village of Islands” or the “Fishing Capital of the World,” is a village of six islands located approximately 90 minutes south of Miami. The popular vacation destination boasts a wide range of activities, from the Theater of...
4 beds 4.5 baths
Details
61

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 beachside pool.

The front home sits waterfront with 1 bedroom 1 bath upstairs, and a separate 1 bedroom 1 bath downstairs.  Downstairs is great for entertaining with a pool table, wet bar, poker table and more.

The garden cottage sits back on the property with two bedrooms and one bathroom and is just a walk through the sandy garden away from the ocean front house.

The ocean front paradise is also a ‘Destination/Wedding Location!’

$9,000/week –  Call for Holiday Rates.

The viewing dock is just that, it is too shallow for boats so boats are prohibited. But great for light flats fishing, catch small flats fish or pitch a kayak out. We do have information on nearby marinas for dockage.

Please note, the Pool is heated to 88 degrees and does NOT have a hot tub.   The side pool is a spa with jets.

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Oceanfront Beach Cottages

4 beds 3 baths
Details
46

Tea Table Key Private Island Estate and Wedding Venue $25,000 - $35,000 Weekly, Call for Holiday Wedding and event fees

Tea Table Key Private Island Estate and Wedding Venue

$25,000 - $35,000 Weekly, Call for Holiday Wedding and event fees

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 beachside pool.

The front home sits waterfront with 1 bedroom 1 bath upstairs, and a separate 1 bedroom 1 bath downstairs.  Downstairs is great for entertaining with a pool table, wet bar, poker table and more.

The garden cottage sits back on the property with two bedrooms and one bathroom and is just a walk through the sandy garden away from the ocean front house.

The ocean front paradise is also a ‘Destination/Wedding Location!’

$9,000/week –  Call for Holiday Rates.

The viewing dock is just that, it is too shallow for boats so boats are prohibited. But great for light flats fishing, catch small flats fish or pitch a kayak out. We do have information on nearby marinas for dockage.

Please note, the Pool is heated to 88 degrees and does NOT have a hot tub.   The side pool is a spa with jets.

[vc_video link='https://www.youtube.com/watch?v=o0jYKUSoVlY']

Oceanfront Beach Cottages

6 beds 5 baths
Details
Large private estate ocean front home with beach side pool
32

Green Turtle Beach $13,500 -$15,000, Call for Holiday Rates

Green Turtle Beach

$13,500 -$15,000, Call for Holiday Rates

Mile Marker 81. Ocean front estate with five bedrooms, five & a half baths.   One of the most ultra-luxurious properties in Islamorada, Green Turtle Beach features an immaculately manicured 4 acres of ocean front land.   Catch ocean breezes off the multiple porches and balconies at…

5 beds 5.5 baths
Details
48

Maison Residences – Unit 201 – Oceanfront Price is in Property Description

Maison Residences – Unit 201 – Oceanfront

Price is in Property Description

$8-12,500 WEEKLY FALL SEASON $16,000 WEEKLY RENTAL SEASON Please call for holiday rates   Introducing Maison Residences Unit 201, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — A world-class oceanfront residence, located in the heart of Islamorada in the Florida…

4 beds 4.5 baths
Details
48

Maison Residences – Unit 204 – Oceanfront Price is in Property Description

Maison Residences – Unit 204 – Oceanfront

Price is in Property Description

$8-12,500 WEEKLY FALL SEASON $16,000 WEEKLY RENTAL SEASON Please call for holiday rates   Introducing Maison Residences Unit 204, Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE — A world-class oceanfront residence, located in the heart of Islamorada in the Florida…

4 beds 4.5 baths
Details
80

Maison Residences – 8 Bedrooms – Full Floor steps to beach $18,000-$24,000 Weekly

Maison Residences – 8 Bedrooms – Full Floor steps to beach

$18,000-$24,000 Weekly

Please call for holiday rates   Introducing Maison Residences Full floor for rent – Oceanfront & Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE —   Units 201 and 202 rented together. Full floor… Private steps to pool, beach and Atlantic Ocean! 8…

8 beds 9 baths
Details
florida keys ocean front vacation rental home with pool and beach
56

Ishmael’s Watch $20,000 / Monthly Call for Holiday rates

Ishmael’s Watch

$20,000 / Monthly Call for Holiday rates

Mile Marker 77 – Oceanfront – Lower Matecumbe Key.   Six 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…

6 beds 4 baths
Details
46

Paradise Found- w/ incredible neighborhood beach! $15,000 / Monthly *$11,000 Summer & Fall Special*

Paradise Found- w/ incredible neighborhood beach!

$15,000 / Monthly *$11,000 Summer & Fall Special*

Mile Marker 75 – Bayside 🏖️ Luxurious 4 Bedroom, 4 Bath Vacation Rental Home with Dockage and Beach Access in Islamorada, Florida Keys 🏖️ Nestled in the heart of the enchanting Islamorada, known as the “Village of Islands,” this exquisite 4-bedroom, 4-bath vacation rental home…

4 beds 4 baths
Details

 

 

Activities & Attractions

 

  • World famous fishing
  • Legendary and celebrated sunsets
  • Village festivals
  • Kayak and paddle board excursions
  • Snorkel, eco tours and more!

 

Local Cuisine

 

Treat your team to the local flavors of Islamorada. With fresh seafood and waterfront dining options, your coworkers will always remember the taste of the Keys.

 

Book Your Corporate Retreat Today

 

Transform your next corporate retreat into an unforgettable experience. Browse our selection of luxurious rental homes and contact us to start planning your perfect retreat in Islamorada, Florida Keys. Our team is ready to assist you in creating an event that combines business and pleasure in the most stunning of settings.

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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