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Summerland Key Rentals

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123 Houses

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

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$559

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$232

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$334

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$481

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$161

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$450

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$519

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

$769

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$335

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$314

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$258

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

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$1,728

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$141

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

Reel Paradise

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$287

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 49 minutes

Price per night from

$180

New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 12

Responds fast! avg. 3 hours 49 minutes

Price per night from

$179

The Helms House

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$288

Sailfish Manor

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$314

KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 9

Responds fast! avg. 3 hours 49 minutes

Price per night from

$179

New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 49 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 49 minutes

Price per night from

$180

The Pointe

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$209

BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 13

Responds fast! avg. 3 hours 49 minutes

Price per night from

$174

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 49 minutes

Price per night from

$174

ENDLESS SUMMER COTTAGE - Your Tropical Island Escape, Open Water Views, Amazing

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 3 hours 49 minutes

Price per night from

$179

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$209

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 49 minutes

Price per night from

$144

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!

Price per night from

$576

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms / 4 bathrooms / sleeps 14

Price per night from

$691

Fandango

Cudjoe Key house

5 bedrooms / 3 bathrooms / sleeps 14

Price per night from

$691

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 20

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 3 hours 9 minutes

Price per night from

$2,212

Bay Pointe

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$176

Angelfish Cove

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$159

Bow Channel Manor

Sugarloaf house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$235

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$126

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$129

Viewing 38 of 123
rentals in Summerland Key

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