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Summerland Key Vacation Rentals

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116 rentals in Summerland Key.
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Kelly’s Kabin - Adorable Private Summerland Key Cottage, vacation rental in Summerland Key
Kelly’s Kabin - Adorable Private Summerland Key Cottage, vacation rental in Summerland Key
Kelly’s Kabin - Adorable Private Summerland Key Cottage, vacation rental in Summerland Key

Kelly’s Kabin - Adorable Private Summerland Key Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise, vacation rental in Summerland Key
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise, vacation rental in Summerland Key
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise, vacation rental in Summerland Key

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ocean Front Modern Home, vacation rental in Summerland Key
Ocean Front Modern Home, vacation rental in Summerland Key
Ocean Front Modern Home, vacation rental in Summerland Key

Ocean Front Modern Home

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Oceanfront Sunsets in the Florida Keys, vacation rental in Summerland Key
Oceanfront Sunsets in the Florida Keys, vacation rental in Summerland Key
Oceanfront Sunsets in the Florida Keys, vacation rental in Summerland Key

Oceanfront Sunsets in the Florida Keys

Rental Home
4 bedrooms
6 bathrooms
Sleeps 8
Match: Sleeps
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Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Summerland Key
Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Summerland Key
Banana Cabana, Canal Front Home Sugarloaf Key Mm 17, vacation rental in Summerland Key

Banana Cabana, Canal Front Home Sugarloaf Key Mm 17

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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LIVING IN BEAUTIFUL PARADISE, vacation rental in Summerland Key
LIVING IN BEAUTIFUL PARADISE, vacation rental in Summerland Key
LIVING IN BEAUTIFUL PARADISE, vacation rental in Summerland Key

LIVING IN BEAUTIFUL PARADISE

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Acreage Beach House w/ Pool & Billiards, vacation rental in Summerland Key
Acreage Beach House w/ Pool & Billiards, vacation rental in Summerland Key
Acreage Beach House w/ Pool & Billiards, vacation rental in Summerland Key

Acreage Beach House w/ Pool & Billiards

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Canal Front  With Easy Access To Atlantic Or Gulf, vacation rental in Summerland Key
Canal Front  With Easy Access To Atlantic Or Gulf, vacation rental in Summerland Key
Canal Front  With Easy Access To Atlantic Or Gulf, vacation rental in Summerland Key

Canal Front With Easy Access To Atlantic Or Gulf

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pool Home on Tranquil Private Cruikshank Island, vacation rental in Summerland Key
Pool Home on Tranquil Private Cruikshank Island, vacation rental in Summerland Key
Pool Home on Tranquil Private Cruikshank Island, vacation rental in Summerland Key

Pool Home on Tranquil Private Cruikshank Island

Rental Home
3 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, vacation rental in Summerland Key
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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming and Private, vacation rental in Summerland Key
Charming and Private, vacation rental in Summerland Key
Charming and Private, vacation rental in Summerland Key

Charming and Private

Rental Home
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cudjoe Gardens Estate With Ocean View & Pool, vacation rental in Summerland Key
Cudjoe Gardens Estate With Ocean View & Pool, vacation rental in Summerland Key
Cudjoe Gardens Estate With Ocean View & Pool, vacation rental in Summerland Key

Cudjoe Gardens Estate With Ocean View & Pool

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Blue Pearl of Summerland Key, vacation rental in Summerland Key
Blue Pearl of Summerland Key, vacation rental in Summerland Key
Blue Pearl of Summerland Key, vacation rental in Summerland Key

Blue Pearl of Summerland Key

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage, vacation rental in Summerland Key
THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage, vacation rental in Summerland Key
THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage, vacation rental in Summerland Key

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

Rental Home
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, vacation rental in Summerland Key
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, vacation rental in Summerland Key
Extensive Keys House w/ Bikes, Private Pool, Free WiFi, & In-Home Washer/Dryers, vacation rental in Summerland Key

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

Rental Home
8 bedrooms
7 bathrooms
Sleeps 20
Match: Sleeps
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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., vacation rental in Summerland Key
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.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Blackbeard`s Hideaway, vacation rental in Summerland Key
Blackbeard`s Hideaway, vacation rental in Summerland Key
Blackbeard`s Hideaway, vacation rental in Summerland Key

Blackbeard`s Hideaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Reel Caribbean Getaway, vacation rental in Summerland Key
Reel Caribbean Getaway, vacation rental in Summerland Key
Reel Caribbean Getaway, vacation rental in Summerland Key

Reel Caribbean Getaway

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2 Bedroom/3 Bath Waterfront 28 day rental, vacation rental in Summerland Key
2 Bedroom/3 Bath Waterfront 28 day rental, vacation rental in Summerland Key
2 Bedroom/3 Bath Waterfront 28 day rental, vacation rental in Summerland Key

2 Bedroom/3 Bath Waterfront 28 day rental

Rental Home
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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2 bedroom accommodation in Summerland Key, vacation rental in Summerland Key
2 bedroom accommodation in Summerland Key, vacation rental in Summerland Key
2 bedroom accommodation in Summerland Key, vacation rental in Summerland Key

2 bedroom accommodation in Summerland Key

Rental Home
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, vacation rental in Summerland Key
THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, vacation rental in Summerland Key
THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, vacation rental in Summerland Key

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai, vacation rental in Summerland Key
KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai, vacation rental in Summerland Key
KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Your Boat & Ai, vacation rental in Summerland Key

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Salty Retreat, vacation rental in Summerland Key
Salty Retreat, vacation rental in Summerland Key
Salty Retreat, vacation rental in Summerland Key

Salty Retreat

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Casa Turquesa, vacation rental in Summerland Key
Casa Turquesa, vacation rental in Summerland Key
Casa Turquesa, vacation rental in Summerland Key

Casa Turquesa

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hogfish Hideout, vacation rental in Summerland Key
Hogfish Hideout, vacation rental in Summerland Key
Hogfish Hideout, vacation rental in Summerland Key

Hogfish Hideout

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront, two-story house w/private outdoor pool, poolside grill, boat access, vacation rental in Summerland Key
Waterfront, two-story house w/private outdoor pool, poolside grill, boat access, vacation rental in Summerland Key
Waterfront, two-story house w/private outdoor pool, poolside grill, boat access, vacation rental in Summerland Key

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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TARPON RANCH -  Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock, vacation rental in Summerland Key
TARPON RANCH -  Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock, vacation rental in Summerland Key
TARPON RANCH -  Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock, vacation rental in Summerland Key

TARPON RANCH - Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock

Rental Home
6 bedrooms
8 bathrooms
Sleeps 14
Match: Sleeps
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New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa, vacation rental in Summerland Key
New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa, vacation rental in Summerland Key
New Listing!!! ANCHORS AWEIGH- Charming Oceanfront Home, Perfect for Multiple Fa, vacation rental in Summerland Key

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Blue Lagoon, vacation rental in Summerland Key
Blue Lagoon, vacation rental in Summerland Key
Blue Lagoon, vacation rental in Summerland Key

Blue Lagoon

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, vacation rental in Summerland Key
THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, vacation rental in Summerland Key
THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The, vacation rental in Summerland Key

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Villa Cayo, vacation rental in Summerland Key
Villa Cayo, vacation rental in Summerland Key
Villa Cayo, vacation rental in Summerland Key

Villa Cayo

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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The Helms House, vacation rental in Summerland Key
The Helms House, vacation rental in Summerland Key
The Helms House, vacation rental in Summerland Key

The Helms House

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Keys Life, vacation rental in Summerland Key
Keys Life, vacation rental in Summerland Key
Keys Life, vacation rental in Summerland Key

Keys Life

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cruikshank, vacation rental in Summerland Key
Cruikshank, vacation rental in Summerland Key
Cruikshank, vacation rental in Summerland Key

Cruikshank

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Sailfish Manor, vacation rental in Summerland Key
Sailfish Manor, vacation rental in Summerland Key
Sailfish Manor, vacation rental in Summerland Key

Sailfish Manor

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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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, vacation rental in Summerland Key
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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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The Pointe, vacation rental in Summerland Key
The Pointe, vacation rental in Summerland Key
The Pointe, vacation rental in Summerland Key

The Pointe

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Paradise in the Keys, vacation rental in Summerland Key
Paradise in the Keys, vacation rental in Summerland Key
Paradise in the Keys, vacation rental in Summerland Key

Paradise in the Keys

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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O, vacation rental in Summerland Key
BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O, vacation rental in Summerland Key
BAYVIEW COTTAGE - Put Your Toes In The Sand & Live Your Island Life, Beautiful O, vacation rental in Summerland Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
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., vacation rental in Summerland Key
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.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cove Isles, vacation rental in Summerland Key
Cove Isles, vacation rental in Summerland Key
Cove Isles, vacation rental in Summerland Key

Cove Isles

Rental Home
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Reel Paradise, vacation rental in Summerland Key
Reel Paradise, vacation rental in Summerland Key
Reel Paradise, vacation rental in Summerland Key

Reel Paradise

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, vacation rental in Summerland Key
New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, vacation rental in Summerland Key
New Listing! CASA ROSADA - Charming Canal Front Home, Pool, Tiki, Dockage & Quic, vacation rental in Summerland Key

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lower Keys Waterfront Getaway, vacation rental in Summerland Key
Lower Keys Waterfront Getaway, vacation rental in Summerland Key
Lower Keys Waterfront Getaway, vacation rental in Summerland Key

Lower Keys Waterfront Getaway

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Summerland Nest - Oceanfront with pool, vacation rental in Summerland Key
Summerland Nest - Oceanfront with pool, vacation rental in Summerland Key
Summerland Nest - Oceanfront with pool, vacation rental in Summerland Key

Summerland Nest - Oceanfront with pool

Rental Home
7 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do, vacation rental in Summerland Key
BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do, vacation rental in Summerland Key
BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do, vacation rental in Summerland Key

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 13
Match: Sleeps
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Sunny Lei is a home with lots of amenities and great location., vacation rental in Summerland Key
Sunny Lei is a home with lots of amenities and great location., vacation rental in Summerland Key
Sunny Lei is a home with lots of amenities and great location., vacation rental in Summerland Key

Sunny Lei is a home with lots of amenities and great location.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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TARPON RANCH -  Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock, vacation rental in Summerland Key
TARPON RANCH -  Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock, vacation rental in Summerland Key
TARPON RANCH -  Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock, vacation rental in Summerland Key

TARPON RANCH - Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dock

Rental Home
7 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P, vacation rental in Summerland Key
THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P, vacation rental in Summerland Key
THE SALTY SAILFISH - Live the Keys Life, Beautiful Canal Front Home, Dockage & P, vacation rental in Summerland Key

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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