Summerland Key Rentals

/ Home
/ Vacation Rentals
/ United States
/ Florida
/ Florida Keys
/ Lower Keys
/ Summerland Key
Book with confidence.

Updating...

age 0-16
84 Results

Relevance

Price: low to high

Price: high to low

Reviews

Why am I receiving these results?

84 Houses

Why am I receiving these results?

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

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$556

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$379

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

Summerland Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Wireless Internet

All filters match

Price per night from

$765

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

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Wireless Internet

All filters match

Price per night from

$1,720

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

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$161

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Wireless Internet

All filters match

Price per night from

$698

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

Match: Wireless Internet

All filters match

Price per night from

$172

The Helms House

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$287

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

Match: Wireless Internet

All filters match

Price per night from

$172

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

Match: Wireless Internet

All filters match

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

Match: Wireless Internet

All filters match

Price per night from

$180

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$396

The Pointe

Summerland Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Wireless Internet

All filters match

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

Match: Wireless Internet

All filters match

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

Match: Wireless Internet

All filters match

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

Match: Wireless Internet

All filters match

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

Match: Wireless Internet

All filters match

Price per night from

$179

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

Match: Wireless Internet

All filters match

Price per night from

$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

Match: Wireless Internet

All filters match

Price per night from

$114

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!

Match: Wireless Internet

All filters match

Price per night from

$573

Fandango

Cudjoe Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

Match: Wireless Internet

All filters match

Price per night from

$622

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Wireless Internet

All filters match

Price per night from

$791

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

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Wireless Internet

All filters match

Price per night from

$308

Starfish House - Dock your boat at your front door

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$573

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Wireless Internet

All filters match

Price per night from

$1,948

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$287

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$458

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Match: Wireless Internet

All filters match

Price per night from

$802

Hogfish Retreat

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$178

Match: Wireless Internet

All filters match

Price per night from

$210

Match: Wireless Internet

All filters match

Price per night from

$228

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

Match: Wireless Internet

All filters match

Price per night from

$774

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

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$573

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

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$476

Florida Keys at it's best

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Wireless Internet

All filters match

Price per night from

$241

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Wireless Internet

All filters match

Price per night from

$253

$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

Match: Wireless Internet

All filters match

Price per night from

$258

Match: Wireless Internet

All filters match

Price per night from

$333

Viewing 38 of 84
rentals in Summerland Key

×

Also consider