Discounts and Specials on Homes in the Florida Keys

Still Searching For Your Florida Keys Rental Home?

You're in luck! We have many special rental properties available. Some of these vacation rentals were previously booked but the guests had to cancel giving you the rate opportunity to book a Florida Keys vacation last minute!

Not sure what you're looking for? Keep Searching: Oceanfront Rentals in the Florida Keys, Homes With Private Pools, Pet Friendly Vacation Rentals, Homes With Boat Docks, Homes With Hot Tubs, Homes That Offer Short Stays

Keep an eye on this page for last-minute availability, discounts or special offers from homeowners. These specials make a trip to the Florida Keys that much more rewarding!

Contact our Vacation Specialists at 305.296.9292 and we will help you reserve that much-needed vacation!

5 properties available

Experience the essence of island living at Sea Pointe & Canal-Side Charisma, where both halves of this stunning waterfront duplex are exclusively yours. Perfect for families or groups of friends, this tropical retreat offers the best of Key Colony Beach with spacious accommodations, private amenities, and access to resort-style perks. Nestled a

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Save up to 10% off any new 2026 reservation at KC99

7-night minimum

KC99 - Sea Pointe & Canal-side Charisma 3

KC99 - Sea Pointe & Canal-side Charisma 4

KC99 - Sea Pointe & Canal-side Charisma 5

KC99 - Sea Pointe & Canal-side Charisma 6

KC99 - Sea Pointe & Canal-side Charisma 7

KC99 - Sea Pointe & Canal-side Charisma 8

KC99 - Sea Pointe & Canal-side Charisma 9

KC99 - Sea Pointe & Canal-side Charisma 10

KC99 - Sea Pointe & Canal-side Charisma 5 (2) 2

Canalfront

- Key Colony Beach

4 bedrooms

4 baths

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Welcome to your Key Largo tropical escape — where island breezes, crystalline waters, and the classic Florida Keys lifestyle set the tone for an unforgettable stay. This dog-friendly home is perfect for families, couples, and adventure lovers looking to slow down, unwind, and live the Keys life to the fullest. Step outside to your spacious de

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Fall and Holiday Monthly Specials on The Beach House

Fall & Holiday Monthly Specials: Make Key Largo your home for the season. We’re offering special monthly pricing for October, November, and December at this cozy 2BR/1BA home on Mangrove Ave. With a 28‑night minimum stay, guests enjoy exceptional value and a peaceful neighborhood setting during the best months of the year.

October 28-Night Minimum Stay Special - $3,080

November 28-Night Minimum Stay Special - $3,360

December 28-Night Minimum Special - $3,640

28-night minimum

KL105FLR - The Beach House

Dry Lot

- Key Largo

2 bedrooms

1 bath

Dog Friendly

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Escape the crowds and settle into island living at this comfortable three-bedroom home in Big Pine Key, perfect for extended stays, snowbirds, remote workers, and families looking to experience the Florida Keys at a relaxed pace.After a day of exploring, unwind in your private hot tub beneath the stars, grill dinner on the patio, or enjoy a quiet e

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Book January thru March at Octopus Palms for a Great Rate!

Spend 3 months in the Keys! Book BP13FLR - Octopus Palms for 3 months (January 1- March 31st) for only $22,585.90!

28-night minimum

BP13FLR - Octopus Palms

Dry Lot

- Big Pine Key

3 bedrooms

1 bath

Dog Friendly

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Dolphin Paradise: Dog-Friendly home in Key Largo with a private heated pool that sits on a waterfront lot with a private dock and amazing views!Dolphin Paradise is your perfect escape in the heart of Key Largo, where laid-back island living meets comfort and style. This spacious 5-bedroom, dog-friendly home sits on a beautiful waterfront lot, offer

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Special Monthly Rate at Dolphin Paradise

Monthly Special Rate
Experience elevated waterfront living at 701 Garden State Ln, a spacious 5‑bedroom, 4‑bathroom home with 2 additional half baths, offering the perfect blend of comfort and luxury. This dog‑friendly retreat features a private pool, expansive outdoor living areas, and direct waterfront access, making it ideal for extended stays in the Florida Keys.

For a limited time, the property is offering a 28‑night minimum monthly special, giving guests exceptional value on long‑term stays. Whether you’re seeking a seasonal escape, a remote‑work haven, or a family retreat, this home delivers privacy, space, and resort‑style amenities in one of Key Largo’s most desirable neighborhoods.

October 28-Night Minimum Stay Special - $8,400

December 28-Night Minimum Stay Special - $9,100

28-night minimum

KL106FLR Dolphin Paradise 5 (1) 1

Canalfront

- Key Largo

5 bedrooms

4 baths

2 half baths

Dog Friendly

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Feel the stress melt away as you step into this coastal Key Largo condo, where breezy tropical charm and peaceful surroundings set the tone for your stay. Wake up to lush greenery and the unique island landscape from your private balcony, coffee in hand, as the day begins at your own relaxed pace.Inside, the open, light‑filled layout features coast