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Summerland Key Rentals

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age 0-16
138 Results

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138 Houses

Blue weekly vacation rental, great view. Heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$397

Gone Fishing

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$214

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$203

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$232

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$416

Mermaid's Tale

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$220

NEW LISTING! Incredible oceanfront home on large lot w/bar, dock & amazing views

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 13

Price per night from

$986

Another Day In Paradise

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$271

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$142

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$452

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 30 minutes

Price per night from

$290

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

$772

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$199

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$286

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$235

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

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 1 hour 1 minutes

Price per night from

$1,271

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$109

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

$162

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$180

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$270

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$334

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$174

Great rentals within 20 miles that match your search

La Brisa

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$186

Isle Of View II

Key West boathouse

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 19 minutes

Price per night from

$231

Mango House

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$104

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

Waterfront Home in The Fabulous Florida Keys!

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$289

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 35 minutes

Price per night from

$346

3/2 Pool Home on Cudjoe Key. Room for 25-28 foot boat.

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$191

Buccaneer Boathouse

Little Torch Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$114

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$156

Palma House

Ramrod Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$152

Tee by the Sea - Luxury 2/2 1/2 with huge pool, parking and 7 Bikes FREE

Key West apartment

2 bedrooms / 3 bathrooms / sleeps 6

“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What I experienced during my stay here is nothing short of Perfect!!! The entire condo was clean and spacious, everything inside the condo worked, the beds and all furniture were clean and comfortable, plenty of towels and linens, the showers, water presure and plumbing were excellent, the pool was clean, relaxing and private, the nights were quiet for sleeping and the gated community within the condo were friendly and fun. The bikes were the best part...10-15 minutes and you were on Duval Street, or the Southernmost Point, or Fort Zachery beach with no hassles what so ever, and I got some good exercise!!! I will definately stay here again!!!

Responds fast! avg. 3 hours 51 minutes

Price per night from

$289

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. 1 hour 22 minutes

Price per night from

$487

Keys Escape

Cudjoe Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$195

Starfish House - Dock your boat at your front door

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 22 minutes

Price per night from

$529

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$117

Viewing 38 of 138
rentals in Summerland Key

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