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  1. HOUSE
    261 11th St Home at Key Colony Beach

    261 11th St Home at Key Colony Beach

    Key Colony Beach, FL

    Relish in emerald canal views at this lovely 4BR/3BA Key Colony Beach home, complete with a spacious waterside deck and sparkling pool. New wood-grain ceramic tiles line every room, with fun mermaid accents greeting you at every turn. Bring your...

    Pool Pets OK
    FREE CANCELLATION

    $364 to $709/night

  2. TOWNHOUSE
    1110 Fleming St Apartment Unit 3

    1110 Fleming St Apartment Unit 3

    Key West, FL

    Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use...

    Pool
    FREE CANCELLATION

    $99 to $160/night

  3. HOUSE
    810 Terry Lane House

    810 Terry Lane House

    Key West, FL

    Affectionately known as the Captain’s Quarters, this two-story custom-built 3BR/3BA is located on a quiet lane in Bahama Village. This lovely neighborhood exudes a charming old Key West vibe. Step out to your back yard for a dip in the private...

    Pool
    FREE CANCELLATION

    $327 to $728/night

  4. TOWNHOUSE
    Waterfront luxury Villa (14) with sunset views and boat slip

    Waterfront luxury Villa (14) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  5. HOUSE
    704 Thomas Street Home

    704 Thomas Street Home

    Key West, FL

    Property Overview  This 4BR/1.5BA tropical retreat is situated in a lush gated community, enveloped by Spanish lime trees, hibiscus, orchids, and a wide variety of beautiful species and exotic palms. In a prime locale, you’ll be within minutes of...

    Pool Hot Tub Pets OK
    FREE CANCELLATION

    $737 to $1,238/night

  6. HOUSE
    Captain's Daughter

    Captain's Daughter

    Key West, FL

    "Captain's Daughter” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropically furnished yard, a prime Old Town location, and a private 43’ boat slip. Through the sliding glass doors of the living...

    Pool Pets OK
    FREE CANCELLATION

    $1,045 to $1,807/night

  7. HOUSE
    Seafarer's Refuge

    Seafarer's Refuge

    Key West, FL

    "Seafarer’s Refuge” is a spacious home with the ability to sleep a large group comfortably, a private pool and tropically furnished yard, a prime Old Town location, and a private 43’ boat slip. All of the typical Key West spots are...

    Pool Pets OK
    FREE CANCELLATION

    $836 to $1,694/night

  8. HOUSE
    Eisenhower Retreat

    Eisenhower Retreat

    Key West, FL

    A reflection of old Key West, Eisenhower's Retreat was designed and built with the architectural feel of an old "Conch House", but with all the amenities of a new luxury home. Situated on the edge of Old Town Key West near everything Key West has to...

    Pool Pets OK
    FREE CANCELLATION

    $836 to $1,694/night

  9. DUPLEX
    99 Sombrero Blvd Duplex Unit B

    99 Sombrero Blvd Duplex Unit B

    Marathon, FL

    Enjoy expansive views of Boot Key Harbor at this waterfront 2BR/2BA (plus loft) duplex in Marathon, with easy access to the ocean and gulf. After a day on the water, dock your boat along the 45-foot seawall. Then gather to watch gorgeous sunsets...

    Pets OK
    FREE CANCELLATION

    $246 to $446/night

  10. HOUSE
    Tropical Oasis

    Tropical Oasis

    Key Largo, FL

    "Tropical Oasis" is an exceptional single family home designed for tropical living - charming interior and extraordinary outdoor living areas. Open concept living area on the middle level of the home offers a formal dining with 8 chairs and 3 bar...

    Pool Pets OK
  11. TOWNHOUSE
    Waterfront luxury Villa (30) with sunset views and boat slip

    Waterfront luxury Villa (30) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  12. TOWNHOUSE
    Waterfront luxury Villa (60) with sunset views and boat slip

    Waterfront luxury Villa (60) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  13. TOWNHOUSE
    Waterfront luxury Villa (43) with sunset views and boat slip

    Waterfront luxury Villa (43) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  14. VILLA
    Waterfront Luxury Villa (62) with sunset views and boat slip

    Waterfront Luxury Villa (62) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $914 to $1,958/night

  15. HOUSE
    Octopus Garden 805

    Octopus Garden 805

    Key West, FL

    Perfectly located and fully remodeled in 2018, Octopus's Garden is steps from Duval Street and the home of Ernest Hemmingway. The homes historical outer appeal gives way to a modern designed interior that is furnished to perfection! This stunning 3...

    Pool
    FREE CANCELLATION

    $1,130 to $2,034/night

  16. TOWNHOUSE
    Island Chic Key West House

    Island Chic Key West House

    Key West, FL

    Traditional meets modern in an elegant way, right in the middle of one of Key West’s most historical districts. A stay at this Island Chic property is filled with luxury and personalized touches. A home designed by a local and prestigious...

    Pool Pets OK
    FREE CANCELLATION

    $627 to $1,129/night

  17. TOWNHOUSE
    Bayview Retreat

    Bayview Retreat

    Key West, FL

    Enjoy casual elegance with a view of famous Garrison Bight and centrally located on the edge of Old Town. This home boasts a large two car garage with stairs leading up to the main floor consisting of a sprawling kitchen appointed with all the tools...

    Pool Pets OK
    FREE CANCELLATION

    $836 to $1,694/night

  18. TOWNHOUSE
    Waterfront luxury Villa (42) with sunset views and boat slip

    Waterfront luxury Villa (42) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  19. TOWNHOUSE
    Waterfront luxury Villa (15) with sunset views and boat slip

    Waterfront luxury Villa (15) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  20. HOUSE
    960 W 75th St Home at Marathon

    960 W 75th St Home at Marathon

    Marathon, FL

    Escape to the Florida Keys at this newly remodeled 3BR/2BA vacation home, set along the canal in the island community of Marathon. A water lover’s dream, the home is complete with kayaks, a boat slip, a bait freezer, and a fish cleaning station....

    Pool Pets OK
    FREE CANCELLATION

    $190 to $741/night

  21. HOUSE
    58039 Morton Home

    58039 Morton Home

    Marathon, FL

    Offering an unbeatable location directly on the Gulf of Mexico, this updated 4BR/4BA Marathon home comes with dreamy gulf views, and some of the best sunset views in the Florida Keys! Admire the stunning coastal views from a beautifully landscaped...

    Pool
    FREE CANCELLATION

    $380 to $899/night

  22. CONDOMINIUM
    Moon Bay A410

    Moon Bay A410

    Key Largo, FL

    "Moon Bay #A410" is a 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and...

    Pool

    $183 to $205/night

  23. TOWNHOUSE
    Waterfront luxury Villa (51) with sunset views and boat slip

    Waterfront luxury Villa (51) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  24. TOWNHOUSE
    Waterfront luxury Villa (29) with sunset views and boat slip

    Waterfront luxury Villa (29) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  25. TOWNHOUSE
    Waterfront luxury Villa (59) with sunset views and boat slip

    Waterfront luxury Villa (59) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  26. TOWNHOUSE
    Waterfront luxury Villa (38) with sunset views and boat slip

    Waterfront luxury Villa (38) with sunset views and boat ...

    Marathon, FL

    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located...

    Pool
    FREE CANCELLATION

    $359 to $1,566/night

  27. HOUSE
    12400 Overseas Hwy Home Unit 8

    12400 Overseas Hwy Home Unit 8

    Marathon, FL

    Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. Dock your boat nearby at one of the many spots available for rent, then stroll back to the house to rest and recharge. You’ll feel on top of the world as you gaze...

    Pool
    FREE CANCELLATION

    $151 to $439/night

  28. VILLA
    5030 Sunset Village Dr Villa

    5030 Sunset Village Dr Villa

    Marathon, FL

    Property Overview Escape to this 2BR/1.5BA waterfront Duck Key villa boasting breathtaking aquamarine ocean and sunset views from a private patio and balcony. Your two-story end unit features nautical-inspired design elements paired with lots of...

    FREE CANCELLATION

    $127 to $491/night

  29. HOUSE
    1270 75th St Ocean W Home

    1270 75th St Ocean W Home

    Marathon, FL

    Property Overview  Boasting stunning floor-to-ceiling water views in every room, this newly remodeled 3BR/2.5BA home promises a delightful oceanfront stay in the Florida Keys. A large patio provides ample seating and covered al fresco dining, while...

    Pool Pets OK
    FREE CANCELLATION

    $320 to $979/night

  30. VILLA
    12400 Overseas Hwy Villa #7

    12400 Overseas Hwy Villa #7

    Marathon, FL

    Take in ocean views from the expansive rooftop deck of this 3BR/3BA Marathon home for eight. Your spacious master suite includes a new king bed and private deck. Spend time enjoying the sublime Florida weather on your covered patio and two-story...

    Pool Pets OK
    FREE CANCELLATION

    $151 to $553/night