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Summerland Key Holiday Rentals

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64 rentals in Summerland Key.
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Kelly's Kabin private cottage on Summerland Key, holiday rental in Summerland Key
Kelly's Kabin private cottage on Summerland Key, holiday rental in Summerland Key
Kelly's Kabin private cottage on Summerland Key, holiday rental in Summerland Key

Kelly's Kabin private cottage on Summerland Key

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
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++++PERFECT KEYS POOL  HOME, MINUTES TO KEY WEST, CONVENIENT TO EVERYTHING++++, holiday rental in Summerland Key
++++PERFECT KEYS POOL  HOME, MINUTES TO KEY WEST, CONVENIENT TO EVERYTHING++++, holiday rental in Summerland Key
++++PERFECT KEYS POOL  HOME, MINUTES TO KEY WEST, CONVENIENT TO EVERYTHING++++, holiday rental in Summerland Key

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise, holiday rental in Summerland Key
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise, holiday rental in Summerland Key
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise, holiday rental in Summerland Key

Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, holiday rental in Summerland Key
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, holiday rental in Summerland Key
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, holiday rental in Summerland Key

The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanfront Sunsets in the Florida Keys, holiday rental in Summerland Key
Oceanfront Sunsets in the Florida Keys, holiday rental in Summerland Key
Oceanfront Sunsets in the Florida Keys, holiday rental in Summerland Key

Oceanfront Sunsets in the Florida Keys

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Open Ocean View Summerland Key, holiday rental in Summerland Key
Open Ocean View Summerland Key, holiday rental in Summerland Key
Open Ocean View Summerland Key, holiday rental in Summerland Key

Open Ocean View Summerland Key

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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LIVING IN BEAUTIFUL PARADISE, holiday rental in Summerland Key
LIVING IN BEAUTIFUL PARADISE, holiday rental in Summerland Key
LIVING IN BEAUTIFUL PARADISE, holiday rental in Summerland Key

LIVING IN BEAUTIFUL PARADISE

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Canal Front With Lots Of Parking Space, holiday rental in Summerland Key
Canal Front With Lots Of Parking Space, holiday rental in Summerland Key
Canal Front With Lots Of Parking Space, holiday rental in Summerland Key

Canal Front With Lots Of Parking Space

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Acreage Multi-Million Dollar  Beach Mansion w/ Pool & Billiards, holiday rental in Summerland Key
Acreage Multi-Million Dollar  Beach Mansion w/ Pool & Billiards, holiday rental in Summerland Key
Acreage Multi-Million Dollar  Beach Mansion w/ Pool & Billiards, holiday rental in Summerland Key

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Pool Home on Tranquil Private Cruikshank Island **February is Open 2021**, holiday rental in Summerland Key
Pool Home on Tranquil Private Cruikshank Island **February is Open 2021**, holiday rental in Summerland Key
Pool Home on Tranquil Private Cruikshank Island **February is Open 2021**, holiday rental in Summerland Key

Pool Home on Tranquil Private Cruikshank Island **February is Open 2021**

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

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming and Private, holiday rental in Summerland Key
Charming and Private, holiday rental in Summerland Key
Charming and Private, holiday rental in Summerland Key

Charming and Private

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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New Listing!!! The Hideaway - Find Us and Get Lost! Newly Decorated Canal Front, holiday rental in Summerland Key
New Listing!!! The Hideaway - Find Us and Get Lost! Newly Decorated Canal Front, holiday rental in Summerland Key
New Listing!!! The Hideaway - Find Us and Get Lost! Newly Decorated Canal Front, holiday rental in Summerland Key

New Listing!!! The Hideaway - Find Us and Get Lost! Newly Decorated Canal Front

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue Pearl of Summerland Key, holiday rental in Summerland Key
Blue Pearl of Summerland Key, holiday rental in Summerland Key
Blue Pearl of Summerland Key, holiday rental in Summerland Key

Blue Pearl of Summerland Key

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Blue vacation home, water front, boat dock, heated private Pool., holiday rental in Summerland Key
Blue vacation home, water front, boat dock, heated private Pool., holiday rental in Summerland Key
Blue vacation home, water front, boat dock, heated private Pool., holiday rental in Summerland Key

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Blackbeard`s Hideaway, holiday rental in Summerland Key
Blackbeard`s Hideaway, holiday rental in Summerland Key
Blackbeard`s Hideaway, holiday rental in Summerland Key

Blackbeard`s Hideaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 Bedroom/3 Bath Waterfront 28 day rental, holiday rental in Summerland Key
2 Bedroom/3 Bath Waterfront 28 day rental, holiday rental in Summerland Key
2 Bedroom/3 Bath Waterfront 28 day rental, holiday rental in Summerland Key

2 Bedroom/3 Bath Waterfront 28 day rental

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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2 bedroom accommodation in Summerland Key, holiday rental in Summerland Key
2 bedroom accommodation in Summerland Key, holiday rental in Summerland Key
2 bedroom accommodation in Summerland Key, holiday rental in Summerland Key

2 bedroom accommodation in Summerland Key

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, holiday rental in Summerland Key
THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, holiday rental in Summerland Key
THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, holiday rental in Summerland Key

THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Salty Retreat, holiday rental in Summerland Key
Salty Retreat, holiday rental in Summerland Key
Salty Retreat, holiday rental in Summerland Key

Salty Retreat

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hogfish Hideout, holiday rental in Summerland Key
Hogfish Hideout, holiday rental in Summerland Key
Hogfish Hideout, holiday rental in Summerland Key

Hogfish Hideout

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai, holiday rental in Summerland Key
KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai, holiday rental in Summerland Key
KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai, holiday rental in Summerland Key

KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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The Blue Pearl - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, holiday rental in Summerland Key
The Blue Pearl - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, holiday rental in Summerland Key
The Blue Pearl - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, holiday rental in Summerland Key

The Blue Pearl - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa, holiday rental in Summerland Key
New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa, holiday rental in Summerland Key
New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa, holiday rental in Summerland Key

New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Villa Cayo, holiday rental in Summerland Key
Villa Cayo, holiday rental in Summerland Key
Villa Cayo, holiday rental in Summerland Key

Villa Cayo

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage, holiday rental in Summerland Key
THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage, holiday rental in Summerland Key
THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage, holiday rental in Summerland Key

THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blue Lagoon, holiday rental in Summerland Key
Blue Lagoon, holiday rental in Summerland Key
Blue Lagoon, holiday rental in Summerland Key

Blue Lagoon

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront, two-story house w/private outdoor pool, poolside grill, boat access, holiday rental in Summerland Key
Waterfront, two-story house w/private outdoor pool, poolside grill, boat access, holiday rental in Summerland Key
Waterfront, two-story house w/private outdoor pool, poolside grill, boat access, holiday rental in Summerland Key

Waterfront, two-story house w/private outdoor pool, poolside grill, boat access

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Casa Turquesa, holiday rental in Summerland Key
Casa Turquesa, holiday rental in Summerland Key
Casa Turquesa, holiday rental in Summerland Key

Casa Turquesa

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sailfish Manor, holiday rental in Summerland Key
Sailfish Manor, holiday rental in Summerland Key
Sailfish Manor, holiday rental in Summerland Key

Sailfish Manor

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like, holiday rental in Summerland Key
Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like, holiday rental in Summerland Key
Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like, holiday rental in Summerland Key

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

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, holiday rental in Summerland Key
New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, holiday rental in Summerland Key
New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, holiday rental in Summerland Key

New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock., holiday rental in Summerland Key
30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock., holiday rental in Summerland Key
30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock., holiday rental in Summerland Key

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Keys Life, holiday rental in Summerland Key
Keys Life, holiday rental in Summerland Key
Keys Life, holiday rental in Summerland Key

Keys Life

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Cruikshank, holiday rental in Summerland Key
Cruikshank, holiday rental in Summerland Key
Cruikshank, holiday rental in Summerland Key

Cruikshank

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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The Pointe, holiday rental in Summerland Key
The Pointe, holiday rental in Summerland Key
The Pointe, holiday rental in Summerland Key

The Pointe

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do, holiday rental in Summerland Key
BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do, holiday rental in Summerland Key
BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do, holiday rental in Summerland Key

BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O, holiday rental in Summerland Key
BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O, holiday rental in Summerland Key
BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O, holiday rental in Summerland Key

BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Helms House, holiday rental in Summerland Key
The Helms House, holiday rental in Summerland Key
The Helms House, holiday rental in Summerland Key

The Helms House

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lower Keys Waterfront Getaway, holiday rental in Summerland Key
Lower Keys Waterfront Getaway, holiday rental in Summerland Key
Lower Keys Waterfront Getaway, holiday rental in Summerland Key

Lower Keys Waterfront Getaway

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Florida Keys Waterfront House w/Pool & Spectacular Ocean Views/Minimum 28 Nights, holiday rental in Summerland Key
Florida Keys Waterfront House w/Pool & Spectacular Ocean Views/Minimum 28 Nights, holiday rental in Summerland Key
Florida Keys Waterfront House w/Pool & Spectacular Ocean Views/Minimum 28 Nights, holiday rental in Summerland Key

Florida Keys Waterfront House w/Pool & Spectacular Ocean Views/Minimum 28 Nights

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Paradise in the Keys, holiday rental in Summerland Key
Paradise in the Keys, holiday rental in Summerland Key
Paradise in the Keys, holiday rental in Summerland Key

Paradise in the Keys

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Reel Paradise, holiday rental in Summerland Key
Reel Paradise, holiday rental in Summerland Key
Reel Paradise, holiday rental in Summerland Key

Reel Paradise

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cove Isles, holiday rental in Summerland Key
Cove Isles, holiday rental in Summerland Key
Cove Isles, holiday rental in Summerland Key

Cove Isles

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Big Torch Retreat, holiday rental in Summerland Key
Big Torch Retreat, holiday rental in Summerland Key
Big Torch Retreat, holiday rental in Summerland Key

Big Torch Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mariner's Cove In The Florida Keys, holiday rental in Summerland Key
Mariner's Cove In The Florida Keys, holiday rental in Summerland Key
Mariner's Cove In The Florida Keys, holiday rental in Summerland Key

Mariner's Cove In The Florida Keys

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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3 bedroom accommodation in Summerland Key, holiday rental in Summerland Key
3 bedroom accommodation in Summerland Key, holiday rental in Summerland Key
3 bedroom accommodation in Summerland Key, holiday rental in Summerland Key

3 bedroom accommodation in Summerland Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, holiday rental in Summerland Key
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, holiday rental in Summerland Key
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, holiday rental in Summerland Key

Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P, holiday rental in Summerland Key
THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P, holiday rental in Summerland Key
THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P, holiday rental in Summerland Key

THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Family Friendly House In Paradise, holiday rental in Summerland Key
Family Friendly House In Paradise, holiday rental in Summerland Key
Family Friendly House In Paradise, holiday rental in Summerland Key

Family Friendly House In Paradise

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Frequently Asked Questions about Summerland Key


Yes, here are some popular holiday rentals in Summerland Key that have internet access:\n\nSee all holiday rentals in Summerland Key on Tripadvisor