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Summerland Key Vacation Rentals

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38 rentals in Summerland Key.
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Cayo Villa, vacation rental in Summerland Key

Cayo Villa

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Blue Lagoon, vacation rental in Summerland Key

Blue Lagoon

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cove Isles, vacation rental in Summerland Key

Cove Isles

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cruikshank, vacation rental in Summerland Key

Cruikshank

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Casa Turquesa, vacation rental in Summerland Key

Casa Turquesa

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Paradise Palms, vacation rental in Summerland Key

Paradise Palms

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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1 other traveler has booked this property
Big Torch Retreat, vacation rental in Summerland Key

Big Torch Retreat

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Family Friendly House In Paradise, vacation rental in Summerland Key

Family Friendly House In Paradise

5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1 other traveler has booked this property
++++PERFECT KEYS POOL  HOME, MINUTES TO KEY WEST, CONVENIENT TO EVERYTHING++++, vacation rental in Summerland Key

++++PERFECT KEYS POOL HOME, MINUTES TO KEY WEST, CONVENIENT TO EVERYTHING++++

3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Summerland Key

The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Front Access - Sunrise View - Fishing - Snorkeling - Pet Friendly - Unit 1, vacation rental in Summerland Key

Ocean Front Access - Sunrise View - Fishing - Snorkeling - Pet Friendly - Unit 1

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock., vacation rental in Summerland Key

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

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 other travelers have booked this property
Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like, vacation rental in Summerland Key

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

5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Oceanfront House, vacation rental in Summerland Key

Oceanfront House

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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1 other traveler has booked this property
Blue vacation home, water front, boat dock, heated private Pool., vacation rental in Summerland Key

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

4 bedrooms
2 bathrooms
Sleeps 8
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3 other travelers have booked this property
Gone Fishing, vacation rental in Summerland Key

Gone Fishing

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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3/2 on the Water in Paradise Monthly Rental 28 Day min., vacation rental in Summerland Key

3/2 on the Water in Paradise Monthly Rental 28 Day min.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Salty Retreat, vacation rental in Summerland Key

Salty Retreat

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hogfish Hideout, vacation rental in Summerland Key

Hogfish Hideout

3 bedrooms
2 bathrooms
Sleeps 8
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Acreage Multi-Million Dollar  Beachfront Mansion w/ Pool & Billiards, vacation rental in Summerland Key

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

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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New listing! Incredible oceanfront home on large lot w/bar, dock & amazing views, vacation rental in Summerland Key

New listing! Incredible oceanfront home on large lot w/bar, dock & amazing views

4 bedrooms
3 bathrooms
Sleeps 13
Match: Sleeps
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Mariner's Cove In The Florida Keys, vacation rental in Summerland Key

Mariner's Cove In The Florida Keys

5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Canal Front - Recently Renovated And Very Clean Throughout :), vacation rental in Summerland Key

Canal Front - Recently Renovated And Very Clean Throughout :)

3 bedrooms
1 bathroom
Sleeps 6
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Kelly's Kabin private cottage on Summerland Key, vacation rental in Summerland Key

Kelly's Kabin private cottage on Summerland Key

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Oceanfront Sunsets in the Florida Keys, vacation rental in Summerland Key

Oceanfront Sunsets in the Florida Keys

4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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BRAND NEW WATERFRONT 3/2, vacation rental in Summerland Key

BRAND NEW WATERFRONT 3/2

3 bedrooms
2 bathrooms
Sleeps 8
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Mermaid's Tale, vacation rental in Summerland Key

Mermaid's Tale

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Isle Be Back!, vacation rental in Summerland Key

Isle Be Back!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Caribbean Dream, vacation rental in Summerland Key

Caribbean Dream

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Keys Life, vacation rental in Summerland Key

Keys Life

3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!, vacation rental in Summerland Key

Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Pointe, vacation rental in Summerland Key

The Pointe

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Spacious duplex w/ocean views, shared hot tub, furnished deck area, & more!, vacation rental in Summerland Key

Spacious duplex w/ocean views, shared hot tub, furnished deck area, & more!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Charming waterfront home w/ a shared hot tub, balcony, & boat dock!, vacation rental in Summerland Key

Charming waterfront home w/ a shared hot tub, balcony, & boat dock!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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New listing! Canal front home with dock, quick ocean access and a hot tub!, vacation rental in Summerland Key

New listing! Canal front home with dock, quick ocean access and a hot tub!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sailfish Manor, vacation rental in Summerland Key

Sailfish Manor

3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Villa and guest house with private pool, central AC, internet, and washer/dryer, vacation rental in Summerland Key

Villa and guest house with private pool, central AC, internet, and washer/dryer

6 bedrooms
5 bathrooms
Sleeps 16
Match: Sleeps
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Bright, spacious home with private pool, internet, private washer/dryer, & loft!, vacation rental in Summerland Key

Bright, spacious home with private pool, internet, private washer/dryer, & loft!

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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