Summerland Key Rentals

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75 Houses

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

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$553

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$331

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$513

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$761

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

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,710

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

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$160

Luxury Oceanview Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$707

Oceanside 24 - Lovely Canal Front Home On Summerland Key, Dog Friendly, Close to

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 42 minutes

Price per night from

$102

Key Blessing - Experience The Keys Life, Charming 3 Bedroom Canal Front Home, Do

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 42 minutes

Price per night from

$172

Kiki’s Casa - Beautifully Updated Canal Front Home, Pool & Dockage, Quick Access

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 3 hours 42 minutes

Price per night from

$179

Tarpon Ranch - Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock

Summerland Key house

6 bedrooms / 8 bathrooms / sleeps 14

Responds fast! avg. 3 hours 42 minutes

Price per night from

$180

Casa Rosada - Cudjoe Gardens Canal Front Home, Pool, Tiki, Deep Dockage & Quick

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 42 minutes

Price per night from

$296

The Salty Sailfish - Live the Keys Life, Beautiful Canal Front Home, Dockage & P

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 42 minutes

Price per night from

$180

Blue Fish Point - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 42 minutes

Price per night from

$174

Bayview Cottage - Put Your Toes In The Sand & Live Your Island Life, Beautiful O

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 42 minutes

Price per night from

$180

The Blue Pearl - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 42 minutes

Price per night from

$174

Anchors Aweigh - Charming Oceanfront Home, Perfect for Multiple Families, Pool,

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 42 minutes

Price per night from

$179

The Hideaway - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 42 minutes

Price per night from

$144

Great rentals within 20 miles that match your search

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 3 hours 59 minutes

Price per night from

$684

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Responds fast! avg. 3 hours 59 minutes

Price per night from

$684

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$129

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$113

Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$145

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms / 4 bathrooms / sleeps 7

Responds fast! avg. 3 hours 59 minutes

Price per night from

$684

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

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 59 minutes

Price per night from

$570

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

Little Torch Key house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 59 minutes

Price per night from

$245

Starfish House - Dock your boat at your front door

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 59 minutes

Price per night from

$521

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

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$473

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

8 bedrooms / 5 bathrooms / sleeps 20

Price per night from

$744

Hogfish Retreat

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$177

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 26 minutes

Price per night from

$251

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 48 minutes

Price per night from

$485

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$217

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!

Responds fast! avg. 3 hours 59 minutes

Price per night from

$570

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$171

Tranquility in Paradise - Cudjoe

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$217

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

5 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$382

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$223

Viewing 38 of 75
rentals in Summerland Key

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