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  1. 1758 Palm Point Home

    1758 Palm Point Home

    Marathon, FL

    Direct and easy gulf access! Beautiful two bedroom, two bath home in Marathon has a fantastic Gulf view and quick, easy access to open water! Very spacious, concrete dock, sundeck on top of home makes for spectacular sunrise and sunset scenes....

    $233 to $310/night

  2. 236 Bonefish at Marathon

    236 Bonefish at Marathon

    Marathon, FL

    Straight shot to the Atlantic Ocean! Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable...

    Pool

    $465 to $621/night

  3. Waterfront Luxury Villa 59

    Waterfront Luxury Villa 59

    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

    $392 to $1175/night

  4. Waterfront Luxury Villa 51

    Waterfront Luxury Villa 51

    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

    $392 to $1175/night

  5. Waterfront Luxury Villa 29

    Waterfront Luxury Villa 29

    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

    $359 to $1175/night

  6. Waterfront Luxury Villa 54

    Waterfront Luxury Villa 54

    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

    $359 to $1175/night

  7. Waterfront Luxury Villa 34

    Waterfront Luxury Villa 34

    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

    $359 to $1175/night

  8. Sombrero Cozy Condo #205

    Sombrero Cozy Condo #205

    Marathon, FL

    Newly Renovated Condo, Canal Front. Walk To Shopping, Restaurants & Golf. 1 Bedroom, 1 Bath, Sleeps 4 Queen bed in bedroom, bring sleeping bags for the kids in the living room! NON SMOKERS ONLY!!!! One of the best unit in the complex, end unit,...

    Pool

    $115 to $143/night

  9. Boot Key Harbor Canal Comfy Condo

    Boot Key Harbor Canal Comfy Condo

    Marathon, FL

    This one bedroom updated condo is centrally located in the beautiful Florida Keys, Marathon, midway between Key Largo and Key West. near historical Crane Point, Seven Mile Bridge and Pigeon Key. Third floor with easy access elevator, awesome...

    $115 to $143/night

  10. 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

  11. Tingler Island mansion

    Tingler Island mansion

    Marathon, FL

    Mediterranean styling, oceanview, pool, dockage, hot tub! Gorgeous, 4 bedroom, 4 full bath home, plus 1/2 bath, located on exclusive Tingler Island and near Sombrero Beach! This 3297 square feet tri- level floor plan provides space and privacy for...

    Pool Hot Tub

    $543 to $931/night

  12. Dori's Casa Condominium

    Dori's Casa Condominium

    Marathon, FL

    2/2 second floor corner condo completely renovated with canal view! This cute condo has a serene beachy feel with canal view. Dockage, pool available with this small complex. Sombrero Beach is only a mile walk, run, job or bike away! Queen bed in...

    Pool

    $233 to $310/night

  13. Sunny Yacht Club Townhome

    Sunny Yacht Club Townhome

    Marathon, FL

    Bonefish Yacht Club Townhome. A 3 bedroom 3 bath town house with lovely views of the canal basin. The first living level has an open living, dining and kitchen area with a bedroom (2 twin beds) and full bath. Second level has the master suite with a...

    Pool

    $171 to $543/night

  14. Fisherman's Delight Townhome

    Fisherman's Delight Townhome

    Key Colony Beach, FL

    Quick Ocean access in Key Colony Beach! This 2100 sq ft bright and spacious property is located just 3 houses back from the canal entrance to Shelter Bay, which provides quick access to the Ocean or Gulf. It also includes membership to the Cabana...

    Pool

    $202 to $310/night

  15. Conch Crib House at Marathon

    Conch Crib House at Marathon

    Marathon, FL

    Looking for a nice clean and updated place in the Keys? This home will NOT disappoint. Superbly renovated, ground level house. The kitchen has been updated with stone tile counters. Bathrooms are marble and tile. Full kitchen with stove and fridge,...

    $187 to $280/night

  16. 15 Coco Plum Beach access

    15 Coco Plum Beach access

    Marathon, FL

    Lovely home on beautiful Coco Plum Beach with 100' of deep water dockage! This 5 bedroom, 4 bath home features high ceilings, all tile floors, granite and stainless kitchen and large screened porch overlooking the waterway. The master bedroom has a...

    Pool Hot Tub

    $621 to $1008/night

  17. 240 MahiMahi at Marathon

    240 MahiMahi at Marathon

    Marathon, FL

    Quick Atlantic access, dockage, pool! Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable...

    Pool

    $465 to $621/night

  18. 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

    $883 to $1656/night

  19. 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

    $1104 to $1767/night

  20. 215 Coastal Feel condo

    215 Coastal Feel condo

    Marathon, FL

    Newly Renovated Condo, Canal Front. Walk To Shopping, Restaurants & Golf. 1 Bedroom, 1 Bath, Sleeps 4 King bed in bedroom, bring sleeping bags for the kids in the living room! This is non smoking property. One of the best unit in the complex,...

    Pool

    $109 to $136/night

  21. Terry's Getaway at Marathon

    Terry's Getaway at Marathon

    Marathon, FL

    Walk to Sombrero Beach! Escape to gorgeous Marathon, Florida Keys for a romantic getaway or a fun family retreat. For families with young children this Keys Vacation home is located just two blocks away from beautiful Sombrero Beach with a...

    $236 to $283/night

  22. 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

    $903 to $1694/night

  23. Oceanview Casa Condo 204

    Oceanview Casa Condo 204

    Key Colony Beach, FL

    Tropical condo with spectacular ocean view! Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/air conditioning and a private patio or balcony. This unit has a great corner view...

    Pool

    $187 to $217/night

  24. 238 Tarpon Home at Marathon

    238 Tarpon Home at Marathon

    Marathon, FL

    Tarpon, dolphin, cobia--name your fishing season! Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most...

    Pool

    $465 to $621/night

  25. Yellowtail for dinner!

    Yellowtail for dinner!

    Marathon, FL

    With quick, easy access to the Gulf and Atlantic Ocean, this home is perfect for fishing, snorkeling, boating and just laying by the pool! This three-bedroom, three-bath home, which sleeps eight, has a 60-foot dock with ample room for your boat. It...

    Pool

    $264 to $543/night

  26. Waterfront Luxury Villa 62

    Waterfront Luxury Villa 62

    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

    $844 to $1808/night

  27. 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

    $883 to $1656/night

  28. 371 Pool for You Home

    371 Pool for You Home

    Key Colony Beach, FL

    Absolutely charming, warm and inviting home. Single family home on lovely 12th Street in Key Colony Beach. Quick access to the ocean or gulf, with 80' of deep water dockage (with step down dock). Bait freezer, fish cleaning table, gas grill, hi...

    Pool

    $326 to $512/night

  29. Waterfront Luxury Villa 60

    Waterfront Luxury Villa 60

    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

    $362 to $1085/night

  30. 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

    $790 to $1242/night