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Price per night from
$379
Price per night from
$448
Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like
Summerland Key house
- 5 bedrooms
- 5 bathrooms
- sleeps 10
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$766
Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards
Summerland Key house
- 4 bedrooms
- 3 bathrooms
- sleeps 10
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$1,721
Luxury Oceanview Pool Eco-friendly Villa Near Key West
Summerland Key villa
- 4 bedrooms
- 2 bathrooms
- sleeps 12
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$701
Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, Do
Summerland Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
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$172
Price per night from
$384
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Do
Summerland Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 10
Responds fast! avg. 2 hours 34 minutes
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$162
Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapi
Summerland Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
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$296
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock &
Summerland Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 34 minutes
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$180
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$395
Price per night from
$231
Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti
Summerland Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 12
Responds fast! avg. 2 hours 34 minutes
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$174
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Bre
Summerland Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
Responds fast! avg. 2 hours 34 minutes
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$179
Oceanview Cottage: Embrace Island Living with Sandy Toes and Breathtaking Open W
Summerland Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
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$172
The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room fo
Summerland Key house
- 4 bedrooms
- 3 bathrooms
- sleeps 12
Responds fast! avg. 2 hours 34 minutes
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$174
Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple F
Summerland Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 12
Responds fast! avg. 2 hours 34 minutes
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$179
Price per night from
$234
The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock
Summerland Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 6
Responds fast! avg. 2 hours 34 minutes
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$144
Great rentals within 20 miles that match your search
Fisherman's Paradise in the Heart of Big Pine Key
Big Pine Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 6
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$114
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$172
“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!
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$575
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$793
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$623
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$1,950
Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys
Ramrod Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$210
Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)
Cudjoe Key house
- 2 bedrooms
- 2 bathrooms
- sleeps 4
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$229
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$775
Responds fast! avg. 3 hours 38 minutes
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$517
Price per night from
$208
Price per night from
$178
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$141
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$253
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$174
Price per night from
$171
Oceanside, pet friendly, smart home with plenty of paddle equipment
Cudjoe Key house
- 3 bedrooms
- 2 bathrooms
- sleeps 8
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$224
$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
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$259
Price per night from
$184