Updating...

More filters

Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
High chair
Sea view
Safe
Dishwasher
Children's pool
Clothes dryer
Ceiling Fans
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (unheated)
Shared outdoor pool (heated)
Cribs
Table tennis
Games room
Swing set or jungle gym
Pool or snooker table
Fax machine
Video player
Boat available
Staffed property
Private fishing lake or river
Trampoline
Climbing frame
Bicycles available
Towels provided
Linen provided
Microwave
Freezer
Fridge
Stove
Housekeeping Included

See all

Less

Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible
Secure parking

See all

Less

Beach or lakeside relaxation
City breaks
Walking trips
Tennis in town

Water sports
Horse riding
Fishing
Cycling trips
Waterfront
Golf within 30mins drive

See all

Less

109 houses

Sort by:

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

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$558

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$224

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$485

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$454

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

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$885

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Rental types

All filters match

Price per night from

$153

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$336

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$302

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$234

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$123

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$279

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

Match: Rental types

All filters match

Price per night from

$1,737

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 30 minutes

Match: Rental types

All filters match

Price per night from

$262

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

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$163

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$247

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 37 minutes

Match: Rental types

All filters match

Price per night from

$190

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Match: Rental types

All filters match

Price per night from

$437

New Listing! Summerland Canal-Front Escape w/ Private Pool & Boat Basin

Summerland Key house

2 bedrooms / 1 bathroom / sleeps 6

Match: Rental types

All filters match

Price per night from

$119

New Listing!!! Birds of Paradise - Amazing Sunsets, Open Water Views, Dockage &

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$179

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$271

Sailfish Manor

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 9

Match: Rental types

All filters match

Price per night from

$302

The Pointe

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Match: Rental types

All filters match

Price per night from

$193

Blue Fish Point - Luxurious Private Boating Oasis With Amazing Sunsets, Dog Frie

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 10

Match: Rental types

All filters match

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

Match: Rental types

All filters match

Price per night from

$174

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$200

The Hideaway - Find Us and Get Lost! Newly Decorated Canal Front Home With Docka

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$144

Great rentals within 20 miles that match your search

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$597

Charming House on deep clear canal

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 8

Match: Rental types

All filters match

Price per night from

$159

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

Big Pine Key house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 55 minutes

Match: Rental types

All filters match

Price per night from

$203

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$4,058

Hogfish Retreat

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$182

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Match: Rental types

All filters match

Price per night from

$189

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$133

Big Pine 2/2 ,Water Views

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 1 hour 44 minutes

Match: Rental types

All filters match

Price per night from

$148

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

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$133

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 48 minutes

Match: Rental types

All filters match

Price per night from

$116

Sun Kissed

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$115

Breeze Swept

Big Pine Key house

3 bedrooms / 2 bathrooms / sleeps 6

Match: Rental types

All filters match

Price per night from

$221

Viewing 38 of 109
houses in Summerland Key

Also consider

Little Torch Key 20 properties
Marathon 194 properties
Key Largo 153 properties
Key West 117 properties
Islamorada 77 properties
Lower Keys 46 properties
Key Colony Beach 34 properties
Cudjoe Key 27 properties
Matecumbe Key 24 properties
Stock Island 20 properties
Big Pine Key 18 properties
Duck Key 15 properties
Long Key 11 properties
Ramrod Key 8 properties
Sugarloaf 6 properties
Treasure Island 410 properties
St. Pete Beach 260 properties
Tampa 178 properties
Fort Pierce 117 properties
Naples Park 53 properties
Palm Beach Shores 33 properties
Ruskin 28 properties
Gainesville 28 properties
Stuart 23 properties
Seminole 18 properties
Villano Beach 14 properties
Port Richey 13 properties
Wellington 11 properties
Boca Raton 9 properties
Cedar Key 7 properties
Oneco 7 properties
Riviera Beach 5 properties

COVID-19 Update

Houses Summerland Key

Per night

109 houses

Viewing 38 of 109houses in Summerland Key

Also consider

Viewing 38 of 109
houses in Summerland Key