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Summerland Key Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
134 rentals in Summerland Key.
Private Secluded Ocean View & Pool Near Key West, holiday rental in Summerland Key
Private Secluded Ocean View & Pool Near Key West, holiday rental in Summerland Key
Private Secluded Ocean View & Pool Near Key West, holiday rental in Summerland Key

Private Secluded Ocean View & Pool Near Key West

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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SEA SHELL COTTAGE UNIT #2, holiday rental in Summerland Key
SEA SHELL COTTAGE UNIT #2, holiday rental in Summerland Key
SEA SHELL COTTAGE UNIT #2, holiday rental in Summerland Key

SEA SHELL COTTAGE UNIT #2

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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FLAMINGO COTTAGE UNIT #1, holiday rental in Summerland Key
FLAMINGO COTTAGE UNIT #1, holiday rental in Summerland Key
FLAMINGO COTTAGE UNIT #1, holiday rental in Summerland Key

FLAMINGO COTTAGE UNIT #1

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Beachside * Torchview Waterfront Retreat, holiday rental in Summerland Key
Beachside * Torchview Waterfront Retreat, holiday rental in Summerland Key
Beachside * Torchview Waterfront Retreat, holiday rental in Summerland Key

Beachside * Torchview Waterfront Retreat

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

PALM COTTAGE

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel, holiday rental in Summerland Key
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel, holiday rental in Summerland Key
Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel, holiday rental in Summerland Key

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Holiday Rental House
3 bedrooms
2 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 8
Match: Sleeps
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20 ft from your room to a clean canal full of fish and lobsters and crabs., holiday rental in Summerland Key
20 ft from your room to a clean canal full of fish and lobsters and crabs., holiday rental in Summerland Key
20 ft from your room to a clean canal full of fish and lobsters and crabs., holiday rental in Summerland Key

20 ft from your room to a clean canal full of fish and lobsters and crabs.

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry, holiday rental in Summerland Key
Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry, holiday rental in Summerland Key
Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry, holiday rental in Summerland Key

Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Love Shack | Charming 2 bed/1 bath cottage on Summerland Key, holiday rental in Summerland Key
Love Shack | Charming 2 bed/1 bath cottage on Summerland Key, holiday rental in Summerland Key
Love Shack | Charming 2 bed/1 bath cottage on Summerland Key, holiday rental in Summerland Key

Love Shack | Charming 2 bed/1 bath cottage on Summerland Key

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock, holiday rental in Summerland Key
Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock, holiday rental in Summerland Key
Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock, holiday rental in Summerland Key

Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!, holiday rental in Summerland Key
Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!, holiday rental in Summerland Key
Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!, holiday rental in Summerland Key

Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe, holiday rental in Summerland Key
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe, holiday rental in Summerland Key
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe, holiday rental in Summerland Key

Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Walk to the Pool - Venture Out Unit 333, holiday rental in Summerland Key
Walk to the Pool - Venture Out Unit 333, holiday rental in Summerland Key
Walk to the Pool - Venture Out Unit 333, holiday rental in Summerland Key

Walk to the Pool - Venture Out Unit 333

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Bliss, Oceanfront with pool, holiday rental in Summerland Key
Beach Bliss, Oceanfront with pool, holiday rental in Summerland Key
Beach Bliss, Oceanfront with pool, holiday rental in Summerland Key

Beach Bliss, Oceanfront with pool

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key, holiday rental in Summerland Key
Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key, holiday rental in Summerland Key
Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key, holiday rental in Summerland Key

Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Oceanfront house private beach & protected canal dockage for up to 36' boat, holiday rental in Summerland Key
Oceanfront house private beach & protected canal dockage for up to 36' boat, holiday rental in Summerland Key
Oceanfront house private beach & protected canal dockage for up to 36' boat, holiday rental in Summerland Key

Oceanfront house private beach & protected canal dockage for up to 36' boat

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water, holiday rental in Summerland Key
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water, holiday rental in Summerland Key
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water, holiday rental in Summerland Key

Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Keys cottage, oceanfront, dock, private, great location, fenced backyard, holiday rental in Summerland Key
Keys cottage, oceanfront, dock, private, great location, fenced backyard, holiday rental in Summerland Key
Keys cottage, oceanfront, dock, private, great location, fenced backyard, holiday rental in Summerland Key

Keys cottage, oceanfront, dock, private, great location, fenced backyard

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Dickey's Dockside Retreat, holiday rental in Summerland Key
Dickey's Dockside Retreat, holiday rental in Summerland Key
Dickey's Dockside Retreat, holiday rental in Summerland Key

Dickey's Dockside Retreat

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Lagoon view on canal pool home Summerland, holiday rental in Summerland Key
Beautiful Lagoon view on canal pool home Summerland, holiday rental in Summerland Key
Beautiful Lagoon view on canal pool home Summerland, holiday rental in Summerland Key

Beautiful Lagoon view on canal pool home Summerland

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront House in the heart of Cudjoe Key., holiday rental in Summerland Key
Waterfront House in the heart of Cudjoe Key., holiday rental in Summerland Key
Waterfront House in the heart of Cudjoe Key., holiday rental in Summerland Key

Waterfront House in the heart of Cudjoe Key.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Oceanfront Home With Large Private Deck with boat dockage, holiday rental in Summerland Key
Oceanfront Home With Large Private Deck with boat dockage, holiday rental in Summerland Key
Oceanfront Home With Large Private Deck with boat dockage, holiday rental in Summerland Key

Oceanfront Home With Large Private Deck with boat dockage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, holiday rental in Summerland Key
Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, holiday rental in Summerland Key
Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, holiday rental in Summerland Key

Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront, holiday rental in Summerland Key
Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront, holiday rental in Summerland Key
Beautiful  POOL3/2 Sleeps 8. ALL ROOMS Waterfront, holiday rental in Summerland Key

Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Vacation like a local, holiday rental in Summerland Key
Vacation like a local, holiday rental in Summerland Key
Vacation like a local, holiday rental in Summerland Key

Vacation like a local

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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November 2024 special rate! Fisherman’s paradise! Ice machine, bait freezer, etc, holiday rental in Summerland Key
November 2024 special rate! Fisherman’s paradise! Ice machine, bait freezer, etc, holiday rental in Summerland Key
November 2024 special rate! Fisherman’s paradise! Ice machine, bait freezer, etc, holiday rental in Summerland Key

November 2024 special rate! Fisherman’s paradise! Ice machine, bait freezer, etc

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key, holiday rental in Summerland Key
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key, holiday rental in Summerland Key
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key, holiday rental in Summerland Key

Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock, holiday rental in Summerland Key
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock, holiday rental in Summerland Key
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock, holiday rental in Summerland Key

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key, holiday rental in Summerland Key
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key, holiday rental in Summerland Key
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key, holiday rental in Summerland Key

Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Tarpon Canal | Nearly new 3 bed/2 bath home with canal views on Ramrod Key, holiday rental in Summerland Key
Tarpon Canal | Nearly new 3 bed/2 bath home with canal views on Ramrod Key, holiday rental in Summerland Key
Tarpon Canal | Nearly new 3 bed/2 bath home with canal views on Ramrod Key, holiday rental in Summerland Key

Tarpon Canal | Nearly new 3 bed/2 bath home with canal views on Ramrod Key

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Captain House with Boat Basin & Ramp!, holiday rental in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!, holiday rental in Summerland Key
Waterfront Captain House with Boat Basin & Ramp!, holiday rental in Summerland Key

Waterfront Captain House with Boat Basin & Ramp!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, holiday rental in Summerland Key
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, holiday rental in Summerland Key
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, holiday rental in Summerland Key

Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple, holiday rental in Summerland Key
Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple, holiday rental in Summerland Key
Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple, holiday rental in Summerland Key

Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Waterfront beach house with boat ramp, holiday rental in Summerland Key
Waterfront beach house with boat ramp, holiday rental in Summerland Key
Waterfront beach house with boat ramp, holiday rental in Summerland Key

Waterfront beach house with boat ramp

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stylish & Modern Summerland Key Private Retreat!, holiday rental in Summerland Key
Stylish & Modern Summerland Key Private Retreat!, holiday rental in Summerland Key
Stylish & Modern Summerland Key Private Retreat!, holiday rental in Summerland Key

Stylish & Modern Summerland Key Private Retreat!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bungalows at Sugarloaf Beach - Mi Azucar, holiday rental in Summerland Key
Bungalows at Sugarloaf Beach - Mi Azucar, holiday rental in Summerland Key
Bungalows at Sugarloaf Beach - Mi Azucar, holiday rental in Summerland Key

Bungalows at Sugarloaf Beach - Mi Azucar

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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September Special Rate! Book Now at this canal front pool home, holiday rental in Summerland Key
September Special Rate! Book Now at this canal front pool home, holiday rental in Summerland Key
September Special Rate! Book Now at this canal front pool home, holiday rental in Summerland Key

September Special Rate! Book Now at this canal front pool home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe, holiday rental in Summerland Key
Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe, holiday rental in Summerland Key
Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe, holiday rental in Summerland Key

Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key, holiday rental in Summerland Key
Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key, holiday rental in Summerland Key
Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key, holiday rental in Summerland Key

Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28, holiday rental in Summerland Key
Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28, holiday rental in Summerland Key
Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28, holiday rental in Summerland Key

Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28

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

Florida Keys Paradise!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Reel Caribbean Getaway, holiday rental in Summerland Key
Reel Caribbean Getaway, holiday rental in Summerland Key
Reel Caribbean Getaway, holiday rental in Summerland Key

Reel Caribbean Getaway

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa, holiday rental in Summerland Key
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa, holiday rental in Summerland Key
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa, holiday rental in Summerland Key

Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oasis - Ocean view with pool and hot tub, holiday rental in Summerland Key
Oasis - Ocean view with pool and hot tub, holiday rental in Summerland Key
Oasis - Ocean view with pool and hot tub, holiday rental in Summerland Key

Oasis - Ocean view with pool and hot tub

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Mariners Cove - The Kraken House, holiday rental in Summerland Key
Mariners Cove - The Kraken House, holiday rental in Summerland Key
Mariners Cove - The Kraken House, holiday rental in Summerland Key

Mariners Cove - The Kraken House

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Great Location , Great Vibes, Great Pool, holiday rental in Summerland Key
Great Location , Great Vibes, Great Pool, holiday rental in Summerland Key
Great Location , Great Vibes, Great Pool, holiday rental in Summerland Key

Great Location , Great Vibes, Great Pool

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 14
Match: Sleeps
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Ocean Front Modern Home, holiday rental in Summerland Key
Ocean Front Modern Home, holiday rental in Summerland Key
Ocean Front Modern Home, holiday rental in Summerland Key

Ocean Front Modern Home

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Relax at the flying hogfish, holiday rental in Summerland Key
Relax at the flying hogfish, holiday rental in Summerland Key
Relax at the flying hogfish, holiday rental in Summerland Key

Relax at the flying hogfish

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, holiday rental in Summerland Key
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, holiday rental in Summerland Key
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill, holiday rental in Summerland Key

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Showing results 1-50 of 134
Frequently Asked Questions about Summerland Key