Summerland Key Vacation Rentals in the Lower Florida Keys

Summerland Key Private vacation home 8.0

Welcome to 'Lake It Easy' – Your Canal Front Oasis on Summerland Key! Indulge in the laid-back Florida Keys lifestyle in this beautifully updated canal-front home. Dock your boat along the sea wall, offering convenient access to world-class fishing just minutes away. Whether you're cooling off with a dip in your private pool or unwinding on the b.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 10

Vacation Home

Summerland Key Private vacation home 9.8

Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors. There is ample parking for multiple vehicles and your boat. The property is fully licensed for nightly, weekly, or monthly rentals.
Summerland Key is located at mile marker 24, which allows you to enjoy short drives north t.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 5

Vacation Home

Summerland Key Private vacation home 10.0

Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,000 square foot custom built home set on over an acre of tropical landscaping with a sparkling new heated pool on beautiful Summerland Key in the Lower Florida Keys. This house is permitted for weekly or monthly rental.(Weekly rental permits are rare in the Florida K.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 10

Vacation Home

Summerland Key Private vacation home 9.2

Welcome to 'The Blue Pearl' – the ultimate destination for large families or multiple families seeking an expansive and accommodating retreat. With two distinct living areas, this spacious haven offers ample room to gather together or find your own space for relaxation. Step onto the sand and revel in the 125 feet of oceanfront that's all yours. .......read more

4 Bedroom(s)
3 Bath(s) Sleeps 12

Vacation Home

Summerland Key Private vacation home 10.0

Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private island off East Caribbean Drive, Summerland Key Florida only a 20 minute drive to Key West for a night on the town.
Enjoy the gorgeous sunsets in the evening while relaxing on the porch where the tropical breezes flow through or.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Summerland Key Private vacation home 10.0

View, views, views! Totally beautiful modern home has a very large balcony which provides an opportunity for endless dreaming and relaxation as you look at the ocean and the islands directly offshore. There is also a dock for your boat and many palms to ensure you feel like you are in Paradise in the Keys!

The kitchen has granite countert.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 10.0

Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in Summerland Key! Privacy 6' Walls surround the Villa to allow sunbathing delights!

The Custom Canal Front Dock has Fenders, Cleats, and water spigots for all your boat needs. The Dock also has a swim platform and ladder to .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 9.8

Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet Chef's kitchen, formal dining room, breakfast nook, living area, private theater with 70" HD flat screen, oversized washer/dryer, ample outdoor seating, pool chase loungers & umbrellas, hammocks, outdoor gazebo/ wet bar with full o.......read more

5 Bedroom(s)
5 Bath(s) Sleeps 10

Vacation Home

Summerland Key Private vacation home 10.0

NEW POOL completed by JUNE 2024!!!! Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-story, waterfront home. This waterfront Little Torch Key home is situated on a tranquil corner lot in the Mates Beach neighborhood. This home has been stylishly upgraded and features a spacious fre.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 9.6

Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West and minutes from Looe Key. Enjoy the private pool and large sun deck for BBQing or relaxing. Canal access is perfect for kayaking and there is only a 10 minute boat ride to the ocean. A canoe and Four kayaks are provided for va.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Summerland Key Private vacation home

Secluded lower keys oasis on 4 acres. Incredible sunrises and sunsets over the water and jungle. Room for the whole family. Close to boat ramps. Sleeps 8 easily with the possibility for more. 4 bedrooms, 3.5 baths. 20 mins to KW. 30 mins to Marathon. House has undergone a major remodel and will continue to be updated. Come enjoy our tropical paradi.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 9.6

Quiet, secluded Keys house ideal for larger groups of friends and family's. Equal distance to Marathon and Key West. Larger wrap around screen porch. Deep water canal , easy boat ride to golf and ocean access. Watch the stars at night. Bring you toys and boat. Big deep water dock , can bring up to 33 foot boat. You can also fish off the dock. .......read more

6 Bedroom(s)
6 Bath(s) Sleeps 14

Vacation Home

Summerland Key Private vacation home 10.0

FOLSOM'S FOLLY... Summerland Key, Florida

Interesting architecture with breezy views of the water. All rooms beautifully furnished in relaxed Keys style, including the 'Nautical Room', the 'Captain's Room', the 'Fish Room', and a private master suite with private bath, twin sinks, and French doors onto a deck with teak chairs. Interesting n.......read more

4 Bedroom(s)
6 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 9.4

MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Waterfront house with heated pool. Located on the canal of Summerland Key, has a 60 ft dock. Short access to Atlantic and Golf side. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Open kitchen concept with quartz counter.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Summerland Key Mobile home 9.4

LITTLE TORCH TROPICAL OASIS

This Beautiful Oasis is a recently renovated Manufactured Home on the corner of 2 Crystal Clear Swimming Canals. The backyard has a Sun Deck with custom Swim Ladder. Please note this is not a boating canal but you can swim, float or snorkel in your own back yard. This home has all the amenities you may need and .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Summerland Key Private vacation home 10.0

This luxurious cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands, the most prominent of which is Looe Key reef, a popular diving/snorkeling area.

There is an island, located a few miles out directly in front of the home, was formerly called Monkey Island, a name still used by the locals.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 9

Vacation Home

Summerland Key Private vacation home 9.6

The Crab House 28 day rental offers 2 spacious bedrooms 3 bathrooms (1 full bath in garage to use after coming in from boating or diving), on beautiful clear canal. Home offers 60 ft of bulkhead for docking your boat, deep canal, neighborhood marina just 5 blocks away to launch your boat. Marina also sells fuel, bait and fishing supplies. Canal .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4

Vacation Home

Summerland Key Private vacation home 10.0

Summary:
Escape to Dickey's Dockside Retreat. This waterfront paradise in the Florida Keys offers a private dock, perfect for launching your adventures. Immerse yourself in the coastal charm of this vacation rental, where comfort meets adventure. Explore the crystal-clear waters, reel in your catch of the day, and create lasting memories in this.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 10.0

Breathtaking Open Water Views. This canal home is in impeccable condition. Concrete dock with fish cleaning station. Dock your 31' or smaller boat at the dock. 2 kayaks with paddles for your use. Beautiful landscaping. Oversized covered porch. Super fast WiFi Cable TV. Modern kitchen. Washer and dryer. Ample parking. 6 person maximum. LOCAL Law.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Summerland Key Private vacation home

This newly renovated vacation home on a canal in Cudjoe Key is a stunning retreat that offers the perfect blend of comfort, relaxation and adventure.

The living room is furnished with plush sofas and chairs, a large flat-screen TV, making it the perfect spot to unwind after a long day of boating or exploring Key West. The kitchen is ful.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 10

Vacation Home

Summerland Key Private vacation home 10.0

Vista de Sirenas translates to ‘Mermaid Views’ is a piece of paradise with an unobstructed sunset view over open water year round! 3,200 sq ft living space on oversized fenced corner lot at the very end of a private road offering picture perfect sunsets! Boasting 323' of water frontage, this property includes 175' of open water and 148' of cana.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 10

Vacation Home

Summerland Key Private vacation home 9.8

Introducing Casa Rosada, a delightful canal front haven nestled within the enchanting Cudjoe Gardens on Cudjoe Key. Offering an invitation to tropical relaxation, this charming abode provides a tranquil escape from the everyday. Dock your boat along the seawall and embark on fantastic fishing escapades in the pristine waters of the Atlantic or the .......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Summerland Key Private vacation home

Hello ! My name is Debra and I run our VRBO account for our family. We love our salty slice of paradise and I look forward to sharing it with you!

Our oceanside 3/2 home features a large lot, 200ft of concrete dockage, fish cleaning station, & plenty of parking for boats, cars & trailers. You will have a full kitchen, living & dining room, T.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Summerland Key Private vacation home

Welcome to L’archipel, a charming, newly remodeled monthly rental that offers an ideal retreat for those seeking a relaxing getaway in the Florida Keys. Nestled on a serene canal, this property is a haven for water enthusiasts and nature lovers alike. With 2 bedrooms, 1 1/2 baths, and a host of modern amenities, this home promises a comfortable a.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6

Vacation Home

Summerland Key Private vacation home 9.8

Impeccably designed and maintained canal front home in Summerland Cove with a Pool!

This fully fenced and gated paradise retreat has 4 bedrooms and 2 baths with almost 1,900 sq. ft. of indoor living space.

On the main level you'll find a well-appointed kitchen with granite counters, stainless appliances, an island, and dining .......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 8.4

Beautiful Ocean/Canal Views 21' Dockage
2Bd/2Ba with Double Porches, Large Landscaped Yard!
Island Breeze is a fabulous location for this 2Bd/2Ba stilt home in the desirable Venture Out Community on Cudjoe Key. Features a 21' Concrete Seawall with breathtaking views of the Atlantic Ocean and located on a 60' wide canal. Situated on an over.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4

Vacation Home

Summerland Key Cottage 9.8

The Green Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently renovated. The kitchen, bathroom tile and furniture are new.

ACCOMODATIONS:

Each unit comes with TV, AC & WIFI. UNIT #1 has full kitchen and UNIT #2 has efficiency kitchen with refrigerator and microwave oven. Enjoy .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Summerland Key Private vacation home 10.0

Newly renovated 2 bedroom, 2.5 bath canal front home with pool in quite, safe neighborhood 25 miles from Key West. House is perfect for couples with 2 king size beds and blackout shades, fully equipped kitchen, front porch with large table, pool, canal front with space for boat, office with computer, wifi, recently renovated. 25 mile drive to Key .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 5

Vacation Home

Summerland Key Private vacation home

Welcome to Paradise at the End of The Road. This home is so secluded you will think you are on your own private island. We feature water views from every room and window, even the laundry room. Completely redone following hurricane Irma, everything is new, updated and designed for relaxation, luxury, and the ultimate fishing experience.

In.......read more

5 Bedroom(s)
5 Bath(s) Sleeps 8

Vacation Home

Summerland Key Private vacation home 10.0

Lower Keys Living at its very best. This This Modern 1,700 sq ft Old Florida Keys Waterfront House is located on Lower Sugarloaf Shores at Mile Marker 17, a half mile off of US 1 in an extremely quiet neighborhood and is available for 28+ day rentals. It is a three bedroom, three baths elevated house. All of the bedrooms are located on the second .......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6

Vacation Home

Summerland Key Mobile home

Only 10 minutes to bahia honda beach, rated top ten every year. 35 min to key west. 3 hrs to miami, a great sight seeing attraction with the 7 mile bridge, and many more. 25 minutes to marathon. 5 or 6 restaurants in the local area. .......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Summerland Key Cottage 9.4

OUR FULLY RENOVATED LARGEST OF FIVE COTTAGES APPROXIMATELY 1500 SQUARE FEET IS NOW AVAILABLE FOR YOUR FAMILY VACATIONS. THIS SPECIOUS COTTAGE SLEEPS SEVEN COMFORTABLY. WITH THE SCREENED-IN PORCH FOR OUTDOOR DINNING TO THE POOL TABLE IN THE BRIGHT AND AIRY GAME ROOM. JUST STEPS AWAY TO THE INDOOR POOL AND TWO BARBECUE AREAS PERFECT FOR EVENING G.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home

Summerland Key Cottage 9.6

Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink and microwave oven. Enjoy the communal outdoor pool and covered patio that has a gas grill and picnic area.

ACTIVITIES:

Fishing adventures, bird watching, water sports or some down time relaxing in nature and the beauty of the most desired key in Florida. We�.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 2

Vacation Home

Summerland Key Private vacation home 9.8

The Flamingo Cottage comes with TV, AC & WIFI. UNIT #1 has full kitchen, and it's own private space. Enjoy the communal outdoor pool and covered patio that has a gas grill and picnic area.

Fishing adventures, bird watching, water sports or some down time relaxing in nature and the beauty of the most desired key in Florida. We’re twenty-f.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4

Vacation Home

Summerland Key Private vacation home 9.4

Fabulous resort-style living & incredible open water views over Niles Channel at this 7 BR 5 BA home on Summerland Key. Just under an acre boasting a sandy beach w/pretty palms, large custom pool, & deep water dockage w/quick access to ocean, gulf & back country. The open Great Room boasts granite kitchen, wood floors & gorgeous water views. 2 BR G.......read more

7 Bedroom(s)
5 Bath(s) Sleeps 12

Vacation Home

Summerland Key Private vacation home 9.0

Beautiful new home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' dock seawall will accommodate boats with up to 40 in length and 5' draft. Direct Ocean access to great offshore/backcountry fishing and reef diving/snorkeling that are literally minutes away. Property features spectacular ocean vie.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 8

Vacation Home