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Results: 839 Rentals

  • Oceanview Rooftop Retreat  3BR 3BA in Marathon FL
    From $496 per night (USD)

    VRBO

    Oceanview Rooftop Retreat 3BR 3BA in Marathon FL

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Summary: Welcome to Rooftop Bliss – the ultimate family getaway in Marathon, FL! This spacious 3BR/3BA villa is perfect ...

    From $496 per night (USD)

    VRBO

    Details
  • Charming canal-front home with 37-ft dock, kayaks, grill, patio & club access
    From $272 per night (USD)

    Expedia

    Charming canal-front home with 37-ft dock, kayaks, grill, patio & club access

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Gray Pelican House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...

    From $272 per night (USD)

    Expedia

    Details
  • Maison Grand Blue Arenas/MiniGolf/BeachCanal/Game Room
    From $1099 per night (USD)

    VRBO

    Maison Grand Blue Arenas/MiniGolf/BeachCanal/Game Room

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    About this space Luxury Waterfront Oasis w/ Private Pool, Mini Golf, 124’ Dockage, and More! The space Welcome to your ...

    From $1099 per night (USD)

    VRBO

    Details
  • *New* Turtles Pace-Private Beach
    From $387 per night (USD)

    Expedia

    *New* Turtles Pace-Private Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the perfect getaway in this beachfront condo in Key Colony Beach, FL. With direct access to a private beach, yo ...

    From $387 per night (USD)

    Expedia

    Details
  • Lady O's Retreat - Key Colony Beach
    From $488 per night (USD)

    VRBO

    Lady O's Retreat - Key Colony Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Welcome to your perfect tropical getaway! This stunning, completely remodeled half duplex in Key Colony Beach offers a b ...

    From $488 per night (USD)

    VRBO

    Details
  • H's Hideaway - Key Colony Beach
    From $445 per night (USD)

    Expedia

    H's Hideaway - Key Colony Beach

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Updated two-bedroom, two bathroom half duplex on 11th street. Excellent location towards the end of the canal, yielding ...

    From $445 per night (USD)

    Expedia

    Details
  • 4 Ever Big Sky in Key Colony Beach
    From $777 per night (USD)

    VRBO

    4 Ever Big Sky in Key Colony Beach

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    Come check out this brand new private Key Colony Beach rental! Fully equipped with a private pool, large private outdoor ...

    From $777 per night (USD)

    VRBO

    Details
  • 3/2.5  duplex in Key Colony - dock and Cabana Club
    From $269 per night (USD)

    VRBO

    3/2.5 duplex in Key Colony - dock and Cabana Club

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to your spacious sanctuary at Key Colony Beach, where comfort and convenience converge in this lovely 3-bedroom, ...

    From $269 per night (USD)

    VRBO

    Details
  • Hate To Leave It in marathon
    From $386 per night (USD)

    VRBO

    Hate To Leave It in marathon

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Island Time Starts Now Your Florida Keys Escape!Stay in a top-rated, sun-filled home in Marathon's exclusive Bougainvil ...

    From $386 per night (USD)

    VRBO

    Details
  • *New* Blue Paradise-Beach/Pool
    From $361 per night (USD)

    Expedia

    *New* Blue Paradise-Beach/Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Wake up to breathtaking ocean views in this stunning condo nestled in Key Colony Beach. Perfectly positioned just steps ...

    From $361 per night (USD)

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    Details
  • New Listing 20% Discount at Seahorse Landing!
    From $441 per night (USD)

    VRBO

    New Listing 20% Discount at Seahorse Landing!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Luxury Meets Adventure at Seahorse Landing! 40’ of dockage, SUP, & the equipment you’ll need to explore the beautiful b ...

    From $441 per night (USD)

    VRBO

    Details
  • Cabana Club, Kayaks, Pets, Boat Dock, Near Golf!
    From $355 per night (USD)

    Expedia

    Cabana Club, Kayaks, Pets, Boat Dock, Near Golf!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    7

    Welcome to Latitude Adjustment – Your Slice of Paradise in Key Colony Beach! Escape to Latitude Adjustment, a beautifull ...

    From $355 per night (USD)

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    Details
  • Ocean Bliss on Beach Heated Pool & Views Unit 32
    From $201 per night (USD)

    VRBO

    Ocean Bliss on Beach Heated Pool & Views Unit 32

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    About this space Wake up to palm trees and the sound of waves. Lounge by the heated pool, stroll to your private beach, ...

    From $201 per night (USD)

    VRBO

    Details
  • Located in Marathon, FL, in the heart of the Florida Keys. Seaside Escape!
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    Expedia

    Located in Marathon, FL, in the heart of the Florida Keys. Seaside Escape!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Make yourself at home in this 2-bedroom Marathon retreat. This house features 1 king bed and 1 twin bed, perfect for a s ...

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    Expedia

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  • Sunset Key Escape Waterfront Pool Home with Dock and Sunset Views
    From $502 per night (USD)

    VRBO

    Sunset Key Escape Waterfront Pool Home with Dock and Sunset Views

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Wake up to sweeping Gulf views and end the day with world class Florida Keys sunsets. This 3 bedroom, 3 bath waterfront ...

    From $502 per night (USD)

    VRBO

    Details
  • Sailfish Point - Luxury Waterfront Pool Home, 80' Dock
    From $819 per night (USD)

    Expedia

    Sailfish Point - Luxury Waterfront Pool Home, 80' Dock

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Sailfish Point This beautiful Key Colony Beach home is the ultimate tropical escape, comfortably sleeping up to 8 guest ...

    From $819 per night (USD)

    Expedia

    Details
  • Sunny Waterfront Key Colony 3BR 2BA Villa w/ Dock
    From $433 per night (USD)

    VRBO

    Sunny Waterfront Key Colony 3BR 2BA Villa w/ Dock

    Bedrooms:
    6
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy this spacious waterfront home in Key Colony Beach w/ a private dock for boats up to 36 ft, ample parking & outdoor ...

    From $433 per night (USD)

    VRBO

    Details
  • Boat Dock, Cabana Club, Paddleboard, Ground Level
    From $256 per night (USD)

    Expedia

    Boat Dock, Cabana Club, Paddleboard, Ground Level

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to Sea Escape – Your Key Colony Beach Retreat Discover the relaxed charm of island living at Sea Escape, a coz ...

    From $256 per night (USD)

    Expedia

    Details
  • Beach Bliss Awaits: Immaculate Condo Just Steps from Your Private Beach Oasis!
    From $295 per night (USD)

    VRBO

    Beach Bliss Awaits: Immaculate Condo Just Steps from Your Private Beach Oasis!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Escape to paradise in our inviting 1st floor condo. Perfectly situated steps from your own private beach and pool. Spac ...

    From $295 per night (USD)

    VRBO

    Details
  • Salty Breezes Condo 2bed 2bath second floor with e
    From $147 per night (USD)

    Expedia

    Salty Breezes Condo 2bed 2bath second floor with e

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    14-night minimum stay per condominium association rules no pets.Escape to Oceanfront Paradise at Casa Clara Condominiums ...

    From $147 per night (USD)

    Expedia

    Details
  • Clara`s Ocean Gem Condo 2bed 2bath third floor wit
    From $164 per night (USD)

    VRBO

    Clara`s Ocean Gem Condo 2bed 2bath third floor wit

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    14-night minimum stay per condominium association rules no pets.This Spacious, Comfortable Condo is fully furnished and ...

    From $164 per night (USD)

    VRBO

    Details
  • New! Splash Into Me! 3 BR in Key Colony w/ dockage
    From $410 per night (USD)

    Expedia

    New! Splash Into Me! 3 BR in Key Colony w/ dockage

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Welcome to this beautifully upgraded 3-bedroom, 2-bath canal-front home, perfectly located in the heart of Key Colony Be ...

    From $410 per night (USD)

    Expedia

    Details
  • Lazy Dayz - Charming 5 Bedroom Home in KCB w/heate
    From $601 per night (USD)

    VRBO

    Lazy Dayz - Charming 5 Bedroom Home in KCB w/heate

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Welcome to your perfect Florida Keys escape! This wonderful 5-bedroom, 4-bathroom home in the prestigious Key Colony Bea ...

    From $601 per night (USD)

    VRBO

    Details
  • Sunshine Getaway in KCB <br>      Luxury Pool Home
    From $505 per night (USD)

    Expedia

    Sunshine Getaway in KCB <br> Luxury Pool Home

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Sunshine Getaway in KCB Brand new to the Rental market, Crisp and Clean Luxury Pool Home, Walk to Sunset Park & Local Di ...

    From $505 per night (USD)

    Expedia

    Details
  • Huge Waterfront 5-bedroom Villa Key Colony Beach pet-friendly private pool, dock
    From $987 per night (USD)

    VRBO

    Huge Waterfront 5-bedroom Villa Key Colony Beach pet-friendly private pool, dock

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Experience Key Colony Beach like a local in this lovely 5-bedroom house. Each bedroom features a king bed, ensuring a co ...

    From $987 per night (USD)

    VRBO

    Details
  • The Turquoise Turtle-Beach/Pool
    From $342 per night (USD)

    Expedia

    The Turquoise Turtle-Beach/Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to your oceanfront escape in Key Colony Beach! This spacious 2BR/2BA condo offers the perfect blend of comfort a ...

    From $342 per night (USD)

    Expedia

    Details
  • Welcome to Casita Azul located at 10 Clara Blvd., Key Colony Beach.
    From $195 per night (USD)

    VRBO

    Welcome to Casita Azul located at 10 Clara Blvd., Key Colony Beach.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Super cute and bright 1 bedroom, 1 bath half duplex with a lovely view of the canal from the living room. The home also ...

    From $195 per night (USD)

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    Details
  • *NEW* Penthouse-Beach Front
    From $396 per night (USD)

    Expedia

    *NEW* Penthouse-Beach Front

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Live the island dream in this stunning 2 Bed | 2 Bath Penthouse Condo perfectly situated in the heart of Key Colony Beac ...

    From $396 per night (USD)

    Expedia

    Details
  • Paradise Palms in Marathon
    From $354 per night (USD)

    VRBO

    Paradise Palms in Marathon

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your perfect Florida Keys getaway! This 2-bedroom, 2.5-bath townhouse-style condo offers comfort, convenience ...

    From $354 per night (USD)

    VRBO

    Details
  • Paradise Point - Luxury Oceanfront Estate w/ Pool, Dock, Outdoor Kitchen & Family Amenities
    From $855 per night (USD)

    Expedia

    Paradise Point - Luxury Oceanfront Estate w/ Pool, Dock, Outdoor Kitchen & Family Amenities

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    Paradise Point Paradise Point is the ultimate in luxury waterfront living in the heart of Marathon, Florida Keys. Perfe ...

    From $855 per night (USD)

    Expedia

    Details
  • Luxurious Waterfront 4BR Getaway in Marathon
    From $620 per night (USD)

    VRBO

    Luxurious Waterfront 4BR Getaway in Marathon

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Step into the luxurious 4BR 3Bath waterfront getaway of Ocean Muse in tranquil Marathon, FL! Escape the big‑cit ...

    From $620 per night (USD)

    VRBO

    Details
  • Sip Slidin' Hideaway
    From $573 per night (USD)

    Expedia

    Sip Slidin' Hideaway

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Waterfront Paradise w/ Pool, Grotto Slide & Direct Ocean Access! Slide into vacation mode at this stunningly renovated w ...

    From $573 per night (USD)

    Expedia

    Details
  • Canal-front duplex with Cabana Club membership, private dock, canal views, grill
    From $371 per night (USD)

    VRBO

    Canal-front duplex with Cabana Club membership, private dock, canal views, grill

    Bedrooms:
    6
    Bathrooms:
    4
    Sleeps:
    10

    Palm Breeze Retreat 320 & 330 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simpl ...

    From $371 per night (USD)

    VRBO

    Details
  • Welcome to Castillo Del Mar. A peaceful, salty newly remodeled ocean front home!
    From $470 per night (USD)

    Expedia

    Welcome to Castillo Del Mar. A peaceful, salty newly remodeled ocean front home!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    This Key Colony Beach townhome boasts 2 inviting bedrooms with 2 queen beds and 1 king bed. The property includes 2 bath ...

    From $470 per night (USD)

    Expedia

    Details
  • Salty Sunsets in Marathon
    From $393 per night (USD)

    VRBO

    Salty Sunsets in Marathon

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Salty Sunsets Relax in the Florida KeysThis property was sold in March 2025 and is now under new ownership. The new own ...

    From $393 per night (USD)

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    Details
  • Beach Club Tidal Wave-Beach/Pool
    From $305 per night (USD)

    Expedia

    Beach Club Tidal Wave-Beach/Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to your perfect island getaway! This charming 2-bedroom condo is located just steps from the ocean at Key Colony ...

    From $305 per night (USD)

    Expedia

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  • #1 Island Hideaway 89 - OCEAN FRONT
    From $241 per night (USD)

    VRBO

    #1 Island Hideaway 89 - OCEAN FRONT

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy the BEST VIEW from your living room window, 1st floor balcony and 2nd floor balcony directly overlook the Atlantic ...

    From $241 per night (USD)

    VRBO

    Details
  • A piece of paradise! Adorable 2 bedroom, 2 bathroom canal front half duplex
    From $265 per night (USD)

    Expedia

    A piece of paradise! Adorable 2 bedroom, 2 bathroom canal front half duplex

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A piece of paradise! Adorable 2 bedroom, 2 bathroom canal front duplex with 37.5' of dock space and membership to the Ca ...

    From $265 per night (USD)

    Expedia

    Details
  • The Sea Shanty
    From $442 per night (USD)

    VRBO

    The Sea Shanty

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Experience Marathon like a local in this 4-bedroom house. With 2 king beds, 1 queen bed, and 1 twin bed, this tremendous ...

    From $442 per night (USD)

    VRBO

    Details