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 allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible

See all

Less

Beach or lakeside relaxation
City breaks
Tennis in town
Water sports

Horse riding
Fishing
Waterfront
Golf within 30mins drive

See all

Less

127 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

$554

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$316

Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Rental types

All filters match

Price per night from

$378

Cove Isles

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Rental types

All filters match

Price per night from

$197

Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Rental types

All filters match

Price per night from

$446

Family Friendly House In Paradise

Summerland Key house

5 bedrooms
3 bathrooms

sleeps 8

Match: Rental types

All filters match

Price per night from

$514

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

$761

Villa Cayo

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$412

Casa Turquesa

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$286

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

Match: Rental types

All filters match

Price per night from

$1,712

Big Torch Retreat

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$163

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

$160

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: Rental types

All filters match

Price per night from

$172

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: Rental types

All filters match

Price per night from

$172

Reel Paradise

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$284

Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Bre

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

Match: Rental types

All filters match

Price per night from

$179

Into the Mystic

Summerland Key house

6 bedrooms
6 bathrooms

sleeps 12

Match: Rental types

All filters match

Price per night from

$464

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: Rental types

All filters match

Price per night from

$172

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: Rental types

All filters match

Price per night from

$179

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$285

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

Match: Rental types

All filters match

Price per night from

$382

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: Rental types

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: Rental types

All filters match

Price per night from

$180

salty slumber get away

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$395

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Rental types

All filters match

Price per night from

$230

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: Rental types

All filters match

Price per night from

$174

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: 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

$233

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: Rental types

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: Rental types

All filters match

Price per night from

$113

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

Match: Rental types

All filters match

Price per night from

$619

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms
1 bathroom

sleeps 4

Match: Rental types

All filters match

Price per night from

$140

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms
2 bathrooms

sleeps 10

Match: Rental types

All filters match

Price per night from

$235

Lafitte Landing

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Rental types

All filters match

Price per night from

$143

St. Croix

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Rental types

All filters match

Price per night from

$120

Breeze Swept

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$266

Manatee Bay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$150

Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

Match: Rental types

All filters match

Price per night from

$256

Viewing 38 of 127
houses in Summerland Key

Also consider

Little Torch Key 23 properties
Key West 117 properties
Key Largo 91 properties
Marathon 88 properties
Islamorada 58 properties
Lower Keys 53 properties
Stock Island 27 properties
Cudjoe Key 25 properties
Big Pine Key 23 properties
Matecumbe Key 16 properties
Key Colony Beach 11 properties
Sugarloaf Key 10 properties
Ramrod Key 7 properties
Sugarloaf 6 properties
Florida Panhandle 2,877 properties
New Smyrna Beach 266 properties
North Bay Village 85 properties
West Palm Beach 35 properties
Belleair Beach 20 properties
Tarpon Springs 20 properties
Gulfport 17 properties
Hudson 15 properties
Pelican Bay 13 properties
Miami Gardens 14 properties
Delray Beach 10 properties
Whitney Beach 10 properties
South Venice 10 properties
Virginia Gardens 9 properties
Lehigh Acres 8 properties
Old Town 7 properties
Ormond-by-the-Sea 5 properties
Bokeelia 5 properties

Houses Summerland Key

Per night

127 houses

Viewing 38 of 127houses in Summerland Key

Also consider

Viewing 38 of 127
houses in Summerland Key