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Wireless Internet
Air conditioning
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Children under 5
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Beach or lakeside relaxation
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105 Houses

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

Summerland Key house

4 bedrooms
2 bathrooms

sleeps 8

Match: Children under 5

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Price per night from

$554

Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Children under 5

All filters match

Price per night from

$378

Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Children under 5

All filters match

Price per night from

$446

Family Friendly House In Paradise

Summerland Key house

5 bedrooms
3 bathrooms

sleeps 8

Match: Children under 5

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: Children under 5

All filters match

Price per night from

$761

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

Match: Children under 5

All filters match

Price per night from

$1,712

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

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Children under 5

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Price per night from

$160

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

Match: Children under 5

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Price per night from

$695

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: Children under 5

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: Children under 5

All filters match

Price per night from

$172

Reel Paradise

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Children under 5

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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: Children under 5

All filters match

Price per night from

$179

Into the Mystic

Summerland Key house

6 bedrooms
6 bathrooms

sleeps 12

Match: Children under 5

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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: Children under 5

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: Children under 5

All filters match

Price per night from

$179

The Helms House

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Children under 5

All filters match

Price per night from

$285

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

Match: Children under 5

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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: Children under 5

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: Children under 5

All filters match

Price per night from

$180

salty slumber get away

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 6

Match: Children under 5

All filters match

Price per night from

$394

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Children under 5

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: Children under 5

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: Children under 5

All filters match

Price per night from

$174

Keys Life

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Children under 5

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: Children under 5

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: Children under 5

All filters match

Price per night from

$113

Family Retreat-Ocean front home with private pool

Cudjoe Key house

6 bedrooms
4 bathrooms

sleeps 14

Match: Children under 5

All filters match

Price per night from

$788

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

Match: Children under 5

All filters match

Price per night from

$619

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom
1 bathroom

sleeps 4

Match: Children under 5

All filters match

Price per night from

$172

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

Match: Children under 5

All filters match

Price per night from

$1,939

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

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Children under 5

All filters match

Price per night from

$286

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

2 bedrooms
1 bathroom

sleeps 6

Match: Children under 5

All filters match

Price per night from

$456

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

8 bedrooms
5 bathrooms

sleeps 20

Match: Children under 5

All filters match

Price per night from

$798

Hogfish Retreat

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Children under 5

All filters match

Price per night from

$177

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Children under 5

All filters match

Price per night from

$571

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

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 7

Match: Children under 5

All filters match

Price per night from

$306

Starfish House - Dock your boat at your front door

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Children under 5

All filters match

Price per night from

$571

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Children under 5

All filters match

Price per night from

$474

Viewing 38 of 105
rentals in Summerland Key

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Summerland Key Rentals

Per night

105 Houses

Viewing 38 of 105rentals in Summerland Key

Also consider

Viewing 38 of 105
rentals in Summerland Key