Summerland Cove Rentals
- From $300 per night (USD)
VRBO
Pool Home on Tranquil Private Cruikshank Island available for MARCH 2024!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private is ...
From $300 per night (USD)VRBO
- From $200 per night (USD)
Expedia
Kelly's Kabin - Adorable Private Summerland Key Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors ...
From $200 per night (USD)Expedia
- From $251 per night (USD)
VRBO
Deep\/Wide\/Flow-Though Canal, 1st Canal From Open Water, No Hwy 1 Road Noise
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Amazing canal front 3 bed 3 bath open concept house located in prestigious community of Summerland Key Cove. It is the ...
From $251 per night (USD)VRBO
- From $599 per night (USD)
Expedia
One of the very few beach houses with a daily, rental license in the Keys.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
This is a newly remodeled four bedrooms elegant house. The property has its own private beach located in the heart of Su ...
From $599 per night (USD)Expedia
- From $219 per night (USD)
VRBO
Summerland Cove Paradise Waterfront Deep Water Canal
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 Bed 2 bath Florida Keys home. In need of a serene getaway with the ocean at arms reach? This 3 bedroom, 2 bathroom hom ...
From $219 per night (USD)VRBO
- From $444 per night (USD)
Expedia
Ocean Front Modern Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands ...
From $444 per night (USD)Expedia
- From $199 per night (USD)
VRBO
Latitude Adjustment | 3 Bed, 2 Bath
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3 bedroom/2 bathroom canalfront home on Summerland Key just a few homes in from open water. Vaulted ceilings, updated an ...
From $199 per night (USD)VRBO
- From $224 per night (USD)
Expedia
Forever Summer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Waterfront house with heated pool. Located on the canal of Summerland Ke ...
From $224 per night (USD)Expedia
- From $112 per night (USD)
VRBO
Summerland Canal-Front Escape w\/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summerland Canal Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $112 per night (USD)VRBO
- From $223 per night (USD)
Expedia
Canalfront house with private pool, WiFi, private washer\/dryer, and central AC
- Bedrooms:
- 4
- Bathrooms:
- 2
- Sleeps:
- 6
Skyway Living Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $223 per night (USD)Expedia
- From $1000 per night (USD)
VRBO
Summerland Breeze - Three house retreat, perfect for multiple families
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Breathtaking property located on desirable Summerland Key right on the ocean. There are three structures on the property ...
From $1000 per night (USD)VRBO
- From $369 per night (USD)
Expedia
Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple Families, Dogs OK!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Welcome to "Anchors Aweigh," your passport to the ultimate oceanfront retreat on the tranquil shores of Summerland Key. ...
From $369 per night (USD)Expedia
- From $152 per night (USD)
VRBO
Tropical Island Sanctuary
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our beautiful tropical island retreat! Enjoy all the the splendor the lower Keys have to offer from our home ...
From $152 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to 'Lake It Easy' – Your Canal Front Oasis on Summerland Key! Indulge in the laid-back Florida Keys lifestyle in ...
From $242 per night (USD)Expedia
- From $399 per night (USD)
VRBO
Emerald Seas - Florida Keys Ocean Front Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal ...
From $399 per night (USD)VRBO
- From $415 per night (USD)
Expedia
Location Location! Beautiful views from every angle. Summerland Cove rare point
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 7
If you’re looking for a coastal experience with a modern peaceful clean stay this home is for you. Stay comfortably in S ...
From $415 per night (USD)Expedia
- From $450 per night (USD)
VRBO
Plane to Sea - Canal Front 2\/2 with Pool & Airplane Hangar
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your dream vacation getaway in the Florida Keys! The stunning 'Plane to Sea' property offers a unique blend o ...
From $450 per night (USD)VRBO
- From $239 per night (USD)
VRBO
LIVING IN BEAUTIFUL PARADISE
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy the view from the large porch overlooking a deep, wide, crystal blue, clear canal with quick boating access to bot ...
From $239 per night (USD)VRBO
- From $395 per night (USD)
VRBO
Open water pool home 25miles from Key West
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Relax by the pool with heater/chiller, jets and sundeck. Over 100' of seawall on deep water. Kayaks on-site. Second flo ...
From $395 per night (USD)VRBO
- From $550 per night (USD)
VRBO
Beach Bliss, Oceanfront with pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Beach Bliss has everything you need for a spectacular vacation. The views inside and outside the home are mesmerizing. T ...
From $550 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this Florida Keys gem, The Blue Pearl. The Blue Pearl is a beautiful, updated waterfront home with pool in a ...
From $575 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Oceanfront house private beach & protected canal dockage for up to 36' boat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
The Key-ver beach house is an oceanfront vacation rental in the world-famous Florida Keys on the southern end of Summerl ...
From $250 per night (USD)VRBO
- From $960 per night (USD)
VRBO
Luxurious, Private, Oceanfront, Gated Home
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Stunning 1 acre oceanfront gated estate with lush landscaping, beach and extreme privacy due to the adjacent wildlife re ...
From $960 per night (USD)VRBO
- From $375 per night (USD)
VRBO
Oceanfront Sunsets in the Florida Keys
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
FOLSOM'S FOLLY... Summerland Key, Florida Interesting architecture with breezy views of the water. All rooms beautiful ...
From $375 per night (USD)VRBO
- From $220 per night (USD)
VRBO
Canal Front (Deep Water) Tropical Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in ...
From $220 per night (USD)VRBO
- From $600 per night (USD)
VRBO
Mariners Cove - The Kraken House
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet C ...
From $600 per night (USD)VRBO
- From $175 per night (USD)
VRBO
Relax at the flying hogfish
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West an ...
From $175 per night (USD)VRBO
- From $420 per night (USD)
VRBO
Spectacular sunsets and open water views at this 3 BR 3 BA
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Spectacular sunsets and open water views at this 3 BR 3 BA home on Summerland Key. Brand new dock for your large boat ...
From $420 per night (USD)VRBO
- From $314 per night (USD)
VRBO
Views Views! Direct Oceanfront, Beautiful Inside!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
View, views, views! Totally beautiful modern home has a very large balcony which provides an opportunity for endless d ...
From $314 per night (USD)VRBO
- From $335 per night (USD)
VRBO
Beautiful Lagoon view on canal pool home Summerland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Home has high vaulted ceiling and 30 feet of sliding glass windows which over looks the canal, lagoon and ocean. On quie ...
From $335 per night (USD)VRBO
- From $430 per night (USD)
VRBO
Solstice Seaside Waterfront House w\/Pool & Spectacular Ocean Views\/Min 28 Nights
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' seawal ...
From $430 per night (USD)VRBO
- Click For Pricing
VRBO
WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,000 square foot custom built home set ...
Click For PricingVRBO
- From $199 per night (USD)
VRBO
THE NEW HIDDEN HAMMOCK RESORT - Green Cottage - Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Green Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $199 per night (USD)VRBO
- From $520 per night (USD)
Expedia
Mad Mahi - Deep Water Canal
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
This Summerland Key home is perfect for the avid fisherman. Deep Water Canal with easy access to both the Gulf and Atl ...
From $520 per night (USD)Expedia
- From $280 per night (USD)
VRBO
Ocean View Splendor on Summerland Key
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy the beautiful waterfront elevated home in the Florida Keys overlooking the Atlantic Ocean. Relax in the screened ...
From $280 per night (USD)VRBO
- From $900 per night (USD)
VRBO
~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 14
Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...
From $900 per night (USD)VRBO
- From $286 per night (USD)
VRBO
Relaxing 2\/2 Get Away in the Lower Keys! by RedAwning
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Spacious Canal Front Home with Fast WiFi, Central AC, & Private Hot Tub Chill at a spacious and recently renovated hom ...
From $286 per night (USD)VRBO
- From $338 per night (USD)
VRBO
Florida Keys Paradise!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for the ultimate vacation experience? Our vacation home has everything you need to relax and have fun. We are lo ...
From $338 per night (USD)VRBO
- From $250 per night (USD)
VRBO
Summerland Cove..MM25 Summerland Key, Fl..Canal front-one street from open water
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House ...
From $250 per night (USD)VRBO
- From $299 per night (USD)
Expedia
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Ocean Breeze is the largest of our 5 cottages at 1500 square feet. It's perfect for your family vacation, sleeping 7 pe ...
From $299 per night (USD)Expedia
- From $150 per night (USD)
VRBO
SEA SHELL COTTAGE UNIT #2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink and microwave oven. Enjoy the communal outdoor ...
From $150 per night (USD)VRBO
- From $305 per night (USD)
Expedia
Large 5 Bedroom Canal Home in Summerland Key, FL with Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to Palm Mansion! This large family home with 5 bedrooms and 3 full baths is located on a wide, deep canal suited ...
From $305 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Super Nice 2 BR Canal Home in Summerland w\/ Great Boating Access & Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Summerland Key House! This amazing 2 bedroom home on Summerland Key is a perfect Keys vacation home! It has e ...
From $250 per night (USD)VRBO
- From $450 per night (USD)
VRBO
Come relax at Sandy Bottom Beach Cottage!!!!!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautiful Summerland Key!! Two houses from the Atlantic Ocean. Enjoy boating, kayaking, swimming in the 28' x 9' swim s ...
From $450 per night (USD)VRBO
- Click For Pricing
VRBO
Waterfront villa with pool, outdoor areas, home gym, & fillet station
- Bedrooms:
- 8
- Bathrooms:
- 6
- Sleeps:
- 14
Tarpon Ranch Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
Click For PricingVRBO
- From $395 per night (USD)
Expedia
PEACEFUL PARADISE DEEP WATER CANAL 5 MINUTES TO OCEAN Fishing and Lobster season
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location Location Location! Welcome to our very special community Summerland Key. Summerland is one of the best fishi ...
From $395 per night (USD)Expedia
- From $155 per night (USD)
VRBO
Boat Dock \/ Private Airstrip
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your Canal Front Oasis on Summerland Key! Dock your boat along the sea wall, offering convenient access to wo ...
From $155 per night (USD)VRBO
- From $258 per night (USD)
Expedia
Waterfront home with boat\/canal access, screened lanai, & renovated interior
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Endless Summerland Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $258 per night (USD)Expedia
- From $625 per night (USD)
VRBO
Open Water ~ Pool Home in Summerland Key
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Prime Oceanfront Tropical Gem & The Ultimate in Luxury Waterfront Living! Florida Keys luxury deep water oceanfront pool ...
From $625 per night (USD)VRBO
- From $714 per night (USD)
Expedia
Newly Renovated Ocean Estate- Relax and enjoy this magnifecent
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Magnificent Ocean Front Estate! Enjoy breathtaking views of the ocean from the large screened in porch. Prepare freshly ...
From $714 per night (USD)Expedia
- From $429 per night (USD)
VRBO
Reel Caribbean Getaway | 4 Bed, 2.5 Bath
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Fantastic deep-water boating from this spacious, gated, 4 bedroom / 2.5 bath home on Summerland Key's Caribbean Drive Ea ...
From $429 per night (USD)VRBO
- Click For Pricing
Expedia
Key house on canal 5-minutes to ocean with 75’ of dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
This rustic home offers open beamed ceilings and peek-a-boo views of the ocean from the top living area. Complete with 7 ...
Click For PricingExpedia
- From $540 per night (USD)
VRBO
Beautiful Oceanfront Villa with Pool and near Key West, Florida
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Make some memories at this unique and family-friendly place. Beautiful, custom designed concrete waterfront pool home wi ...
From $540 per night (USD)VRBO
- From $250 per night (USD)
Expedia
Peaceful ocean front cottage.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This classic keys cottage is tucked among the palm trees on the open water of Niles Channel. Enjoy the breath taking sun ...
From $250 per night (USD)Expedia
- From $177 per night (USD)
VRBO
Recently Renovated Home With Deepwater Canal
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first can ...
From $177 per night (USD)VRBO
- From $189 per night (USD)
Expedia
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
PINK COTTAGE UNIT #3 - Sleeps 4 ACCOMODATIONS: UNIT #3 comes with TV, AC, WIFI & Full Kitchen. full kitchen. Enjoy th ...
From $189 per night (USD)Expedia
- From $550 per night (USD)
VRBO
REEL ESCAPE - 4 Bedroom \/ 2 Bathroom w\/ Pool & Deep Water Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Impeccably designed and maintained canal front home in Summerland Cove with a Pool! This fully fenced and gated para ...
From $550 per night (USD)VRBO
- From $126 per night (USD)
VRBO
Love Shack | 2 Bed, 1 Bath
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
While not directly waterfront, this retreat boasts convenient access to a nearby boat ramp, making it ideal for boating ...
From $126 per night (USD)VRBO
- From $650 per night (USD)
VRBO
Paradise Views: Oceanfront\/Boating
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy one of Florida's most tranquil oceanfront settings. A romantic interlude and tropical adventure where absolutely e ...
From $650 per night (USD)VRBO
- From $270 per night (USD)
Expedia
Summerland Keys Upgraded Waterfront Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful oasis on the water with plenty of room for your boat and trailer! With 50 f ...
From $270 per night (USD)Expedia
- From $300 per night (USD)
VRBO
Summerland Key Oceanfront
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Please check out the new updated photos of all the repairs and updates. The house now has new impact windows and doors, ...
From $300 per night (USD)VRBO
- From $300 per night (USD)
VRBO
Summerland Key House Open Air Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summerland Key House is all about open air living. Cypress plank cathedral ceilings extend through the bedrooms, bathro ...
From $300 per night (USD)VRBO
- From $465 per night (USD)
VRBO
Windswept Beach
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to our newly renovated 3 bedroom, 3 bathroom home with stunning open water views! This modern home is perfect fo ...
From $465 per night (USD)VRBO
- From $500 per night (USD)
VRBO
3 Bedroom 3 Bath Pool Home with Gorgeous Atlantic Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the Prestigious neighborhood of Summerland Key Isles!! This gorgeous 3 bedroom 3 bath property has one of the ...
From $500 per night (USD)VRBO
- From $215 per night (USD)
VRBO
Beautiful 3 bed 2 bath deep water canal front home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bedroom 2 bath canal front home on Summerland Key. This home features deep water dockage, great access to th ...
From $215 per night (USD)VRBO
- From $190 per night (USD)
VRBO
Deep water Boating ~ Bay Views ~ 3 bed 2 bath + outside shower
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Thank you for checking out the Key Lime Cottage! This deceivingly spacious 3 bedroom 2 bath home is tastefully furnish ...
From $190 per night (USD)VRBO
- From $184 per night (USD)
VRBO
FLAMINGO COTTAGE UNIT #1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Flamingo Cottage comes with TV, AC & WIFI. UNIT #1 has full kitchen, and it's own private space. Enjoy the communal ...
From $184 per night (USD)VRBO
- From $233 per night (USD)
VRBO
Summerland Cottage-Relax At Our Little Piece of Paradise!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
** Phone Meeting Required before booking approval!! Host Missy Proctor (561) 667-0160 *** Don't forget to check the VR ...
From $233 per night (USD)VRBO