Little Torch Key Rentals with Pools

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46 cottages in Little Torch Key with pools

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Match: Swimming pool

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Price per night from

$802

Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$359

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 24 minutes

Match: Swimming pool

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Price per night from

$402

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Swimming pool

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Price per night from

$308

Great rentals within 20 miles that match your search

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

Match: Swimming pool

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Price per night from

$574

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Swimming pool

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Price per night from

$792

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Swimming pool

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Price per night from

$622

East Sister Rock Island

Marathon Shores house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$2,212

Villa Sombrero, Marathon

Marathon house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$655

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$476

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$574

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$556

Match: Swimming pool

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Price per night from

$333

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$253

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$258

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$379

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$660

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

Match: Swimming pool

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Price per night from

$320

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$286

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Price per night from

$1,319

The Helms House

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$287

3Bd/2Ba POOL on Canal, Dock, Kayaks, Bikes, Fishing Poles, Sombrero Beach 2.3mi

Marathon Shores apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$574

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$434

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 12

Match: Swimming pool

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Price per night from

$700

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$410

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$516

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$1,720

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

Match: Swimming pool

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Price per night from

$545

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$5,727

Beautiful Beachfront Home w/Heated Pool+45' Dock

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

“Beautiful Home and Beautiful Beach Across the Street” My family had a fabulous relaxing vacation. The house and amenities were great. We had a beautiful front porch to watch the morning sunrise and beautiful views of Sombrero Beach. The guys enjoyed fishing everyday while the ladies enjoyed the beach. The beach opens at sunrise and closes at sunset. We had great weather and can't wait to return!

Match: Swimming pool

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Price per night from

$802

Match: Swimming pool

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Price per night from

$820

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Swimming pool

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Price per night from

$1,141

Spacious Top Floor Condo w/ Water View!!

Marathon apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$373

Boutique Resort w/Pool- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$641

Attn:Couples, 3 Kings - Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$581

Boaters’ Paradise - Marlin Bay Resort & Marina

Marathon house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Swimming pool

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Price per night from

$2,191

Home w/Gourmet Kitchen- Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Swimming pool

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Price per night from

$640

Terrace & Roof Top Deck-Marlin Bay Resort & Marina

Marathon house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Swimming pool

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Price per night from

$581

Viewing 38 of 46
rentals in Little Torch Key

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