Summerland Key Rentals
From $536 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 $536 per night (USD)VRBO
From $1965 per night (USD)VRBO
Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,400 square foot custom built home set ...
From $1965 per night (USD)VRBO
From $1297 per night (USD)VRBO
One of the very few beach houses with a daily, rental license in the Keys.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
"THE POOL MAY BE HEATED FOR AN ADDITIONAL FEE OF $25 PER DAY OF STAY" This is a newly remodeled four bedrooms elegant ho ...
From $1297 per night (USD)VRBO
From $301 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 $301 per night (USD)VRBO
From $701 per night (USD)VRBO
Mariners Cove - The Kraken House
- Bedrooms:
- 3
- 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 $701 per night (USD)VRBO
From $244 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 $244 per night (USD)VRBO
From $263 per night (USD)VRBO
Florida keys Waterfront,Forever Summer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Lo ...
From $263 per night (USD)VRBO
From $304 per night (USD)Expedia
Starfish Cottage - Summer fun. Sleeps 4 -boating fishing and Lobster 🦞 season.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Star Fish Cottage is a one bedroom unit that includes a Queen-sized bed and TV in the bedroom, a full kitchen, bath ...
From $304 per night (USD)Expedia
From $703 per night (USD)VRBO
Waterfront Sunrise & Sunset Full Views! Pool, dock, lift, Industerial Ice Maker
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to Paradise at the End of The Road. This home is so secluded you will think you are on your own private island. ...
From $703 per night (USD)VRBO
From $381 per night (USD)VRBO
Fishermens' dream B.Y.O. boat ocean front with protected canal 600' to bluewater
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is an oceanfront vacation rental in the world-famous Florida Keys on secluded southern end of Summerland Key, mile ...
From $381 per night (USD)VRBO
From $923 per night (USD)VRBO
Summerland Nest - Ocean view with private beach and pool
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. ...
From $923 per night (USD)VRBO
From $653 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 $653 per night (USD)VRBO
From $679 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 $679 per night (USD)VRBO
From $188 per night (USD)Expedia
Ground Level Home With Deepwater Canal And 30' Of Dock Space
- 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 $188 per night (USD)Expedia
From $186 per night (USD)VRBO
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional pol ...
From $186 per night (USD)VRBO
From $355 per night (USD)Expedia
PALM COTTAGE - Sleeps 4 summer fun ..lobster season.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently reno ...
From $355 per night (USD)Expedia
From $1177 per night (USD)VRBO
~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings t ...
From $1177 per night (USD)VRBO
From $332 per night (USD)VRBO
Florida Keys Paradise!
- Bedrooms:
- 3
- 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 $332 per night (USD)VRBO
From $590 per night (USD)VRBO
Ocean Breeze House - Summer fun Sleeps 8 boating, fishing and 🦞 Lobster season.
- 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 $590 per night (USD)VRBO
From $270 per night (USD)Expedia
SEA SHELL COTTAGE, perfect for 2. Summer fun boating, fishing 🎣 and 🦞 Lobster
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink, microwave oven and toaster oven. The main ...
From $270 per night (USD)Expedia
From $325 per night (USD)VRBO
FLAMINGO COTTAGE summer fun. Pool, boating, fishing lobster season.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Flamingo Cottage is a studio unit that includes a Queen-sized bed in the bedroom area, a full kitchen, bathroom with ...
From $325 per night (USD)VRBO
From $736 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 $736 per night (USD)VRBO
From $626 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 $626 per night (USD)VRBO
From $304 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 $304 per night (USD)VRBO
From $396 per night (USD)VRBO
Summerland Airport Hangar Home with Pool, Private Runway and deep wide Canal
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Drive In, Fly In. Boat Out. Live Elevated. Welcome to a truly rare gem nestled between Marathon and Key West—a sol ...
From $396 per night (USD)VRBO
From $611 per night (USD)Expedia
Gorgeous 3 Bedroom 2 Bath Open Water Pool Home on Summerland Key
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gorgeous open water 3 bedroom 2 bath pool home on Summerland Key! This completely remodeled home features an open floor ...
From $611 per night (USD)Expedia
From $673 per night (USD)VRBO
Beautiful 3 Bedroom 3 Bath Open Water Pool Home With Excellent Boating
- 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 $673 per night (USD)VRBO
From $520 per night (USD)Expedia
Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
🏡 Amenities: Dock, Guest Cottage, Pool, Spa, Outdoor Kitchen, Firepit 🌊 Kayaks, and Paddle Boards 📍 30 Minutes to K ...
From $520 per night (USD)Expedia
From $187 per night (USD)VRBO
Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Escape to the laid-back beauty of Summerland Key at this charming canal-front retreat, designed for boating, fishing, an ...
From $187 per night (USD)VRBO
From $315 per night (USD)Expedia
Canalfront house with private pool, WiFi, private washer/dryer, and central AC
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
With three separate living areas and a private heated pool, this charming home is full of comfortable spaces for guests ...
From $315 per night (USD)Expedia