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Wireless Internet
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Pets allowed
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Beach or lakeside relaxation
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80 houses

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Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$378

Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$447

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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Price per night from

$764

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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Price per night from

$172

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$383

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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Price per night from

$168

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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Price per night from

$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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Price per night from

$180

salty slumber get away

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$395

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$230

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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Price per night from

$174

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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Price per night from

$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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Price per night from

$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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Price per night from

$179

Keys Life

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$233

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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Price per night from

$144

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$699

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$161

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$317

Cove Isles

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$197

Casa Turquesa

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$287

Villa Cayo

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$413

Big Torch Retreat

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$163

Family Friendly House In Paradise

Summerland Key house

5 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$516

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

Summerland Key house

4 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$556

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,718

Reel Paradise

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$285

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$286

Into the Mystic

Summerland Key house

6 bedrooms
6 bathrooms

sleeps 12

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Price per night from

$465

Great rentals within 20 miles that match your search

Coconuts on the Water

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

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Price per night from

$206

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

Cudjoe Key house

4 bedrooms
4 bathrooms

sleeps 8

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Price per night from

$517

Waterfront Captain House with Boat Basin and Ramp!

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$743

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$328

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!

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Price per night from

$573

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

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Price per night from

$790

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$621

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. 2 hours 26 minutes

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Price per night from

$544

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

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Price per night from

$516

Viewing 38 of 80
rentals in Summerland Key

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Houses Summerland Key

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Viewing 38 of 80rentals in Summerland Key

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Viewing 38 of 80
rentals in Summerland Key