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Cottages, Villas, Apartments in Summerland Key
Holiday Rentals
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Florida (FL)
Florida Keys
Lower Keys
Cottages, Villas, Apartments in Summerland Key
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Internet or Wifi (134)
Air Conditioning (132)
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Kid friendly (134)
Pet friendly (72)
Smoking allowed (5)
Elder access (1)
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Holiday Rental House (136)
Condominium/Apartment (0)
Cabin Holiday Rental (0)
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Waterfront (79)
Boat Available (7)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Boondocks Miniature Golf
Florida Keys Jet Ski Rentals
Summerland Marina Boat Rentals
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136 rentals
in Summerland Key.
Private Secluded Ocean View & Pool Near Key West
29
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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SEA SHELL COTTAGE UNIT #2
9
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
Match:
Sleeps
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FLAMINGO COTTAGE UNIT #1
27
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
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As seen on
Beachside * Torchview Waterfront Retreat
17
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
PALM COTTAGE
26
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel
19
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Deep/Wide/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
13
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
20 ft from your room to a clean canal full of fish and lobsters and crabs.
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 2
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Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
12
Holiday Rental House
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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 House
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2 bedrooms
1 bathroom
Sleeps 4
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Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock
4
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
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Perfect Boating Access to Kemp Channel Cudjoe Key New POOL!
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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As seen on
Blackbeard`s Hideaway | Cozy canalfront cottage is an angler's dream on Cudjoe
1
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Walk to the Pool - Venture Out Unit 333
4
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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As seen on
Beach Bliss, Oceanfront with pool
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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As seen on
Sunshine 23 | Dog-friendly 2 bed/2 bath canalfront boating home on Cudjoe Key
1
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Oceanfront house private beach & protected canal dockage for up to 36' boat
10
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
Holiday Rental House
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2 bedrooms
3 bathrooms
Sleeps 5
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Keys cottage, oceanfront, dock, private, great location, fenced backyard
4
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
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As seen on
Dickey's Dockside Retreat
1
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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As seen on
Waterfront House in the heart of Cudjoe Key.
2
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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As seen on
Beautiful Lagoon view on canal pool home Summerland
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
Match:
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As seen on
Oceanfront Home With Large Private Deck with boat dockage
9
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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As seen on
Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 10
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Sleeps
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Vacation like a local
8
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Sleeps
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November 2024 special rate! Fisherman’s paradise! Ice machine, bait freezer, etc
4
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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As seen on
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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As seen on
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock
3
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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As seen on
Foster`s Folly | Gorgeous canalfront pool home close to open water on Cudjoe Key
1
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Tarpon Canal | Nearly new 3 bed/2 bath home with canal views on Ramrod Key
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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As seen on
Waterfront Captain House with Boat Basin & Ramp!
4
Holiday Rental House
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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
1
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
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Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple
4
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps
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As seen on
Waterfront beach house with boat ramp
10
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
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Stylish & Modern Summerland Key Private Retreat!
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Sleeps
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Bungalows at Sugarloaf Beach - Mi Azucar
1
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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September Special Rate! Book Now at this canal front pool home
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Cudjoe Key 3bdr,2 bath Pool, 20 min from Key West, Ocean Access, Bikes, Canoe
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
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Villa Paradise | 4 bed/2 bath canalfront home on Ramrod Key
1
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 7
Match:
Sleeps
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Solstice Seaside Waterfront House w/Pool & Spectacular Ocean Views/Min 28
9
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
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Florida Keys Paradise!
1
Holiday Rental House
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3 bedrooms
4 bathrooms
Sleeps 6
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Reel Caribbean Getaway
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Sleeps
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Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
7
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Sleeps
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Oasis - Ocean view with pool and hot tub
13
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 12
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Sleeps
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Mariners Cove - The Kraken House
8
Holiday Rental House
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5 bedrooms
5 bathrooms
Sleeps 10
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Sleeps
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Great Location , Great Vibes, Great Pool
4
Holiday Rental House
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6 bedrooms
6 bathrooms
Sleeps 14
Match:
Sleeps
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As seen on
Open Water ~ Pool Home in Summerland Key
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Sleeps
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Open Water Modern Home 2/2
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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As seen on
L' archipel | Canalfront 2 bedroom retreat on Ramrod Key with brand new dock!
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 6
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Showing results 1-50 of 136
Frequently Asked Questions about Summerland Key
Do any holiday rentals in Summerland Key have a pool?
Yes, here are some popular holiday rentals in Summerland Key that have a pool:
Private Secluded Ocean View & Pool Near Key West
SEA SHELL COTTAGE UNIT #2
FLAMINGO COTTAGE UNIT #1
See all holiday rentals with a pool in Summerland Key on Tripadvisor
Do any holiday rentals in Summerland Key have internet access?
Yes, here are some popular holiday rentals in Summerland Key that have internet access:
Private Secluded Ocean View & Pool Near Key West
SEA SHELL COTTAGE UNIT #2
FLAMINGO COTTAGE UNIT #1
See all holiday rentals in Summerland Key on Tripadvisor
What are the best pet friendly rentals in Summerland Key?
The best pet friendly rentals in Summerland Key are:
Private Secluded Ocean View & Pool Near Key West
SEA SHELL COTTAGE UNIT #2
FLAMINGO COTTAGE UNIT #1
See all pet friendly holiday rentals in Summerland Key on Tripadvisor
What are some great rentals in Summerland Key that are kid friendly?
Some of the most popular kid friendly rentals in Summerland Key are:
Private Secluded Ocean View & Pool Near Key West
SEA SHELL COTTAGE UNIT #2
FLAMINGO COTTAGE UNIT #1
See all kid friendly holiday rentals in Summerland Key on Tripadvisor
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