Summerland Key Vacation Rentals in the Lower Florida Keys

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.



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 u.......

8.0 Star Review

3 Bedrooms - Sleeps 10
Summerland Key Vacation Rental
Pets Allowed

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 to Big Pine Key, Bahia Honda National Park, and Marathon Key. The major attractions of Key West are only 35 minutes to the south. Public transportati.......

9.8 Star Review

3 Bedrooms - Sleeps 5
Summerland Key Vacation Rental
Pets Allowed

Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,400 square foot custom built home set on over an acre of tropical landscaping with a sparkling newly resurfaced heated pool on beautiful Summerland Key in the Lower Florida Keys. This house is permitted for daily, weekly or monthly rental. (Daily and weekly rental permits are rare in the Florida Keys!)

Enjoy watching sunrise views over the open water of the Florida Keys. Our Non-Smoking home, Seaclusion.......

10.0 Star Review

3 Bedrooms - Sleeps 10
Summerland Key Vacation Rental

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.



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 t.......

9.2 Star Review

4 Bedrooms - Sleeps 12
Summerland Key Vacation Rental
Pets Allowed

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 relax by the new pool & spa. The house is tastefully furnished for your comfort. Spacious kitchen to cook your lobsters and fish.

Keywords: .......

10.0 Star Review

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental

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 countertops and stainless appliances. Both bathrooms have dual sinks.

Everything is light and bright with lots of windows and doors for the view. .......

10.0 Star Review

2 Bedrooms - Sleeps 4
Summerland Key Vacation Rental
Pets Allowed

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 make all your water accessibility needs easy.

Open floor plan that flows to the outside porch allows for tropical breezes and spacious enterta.......

10.0 Star Review

2 Bedrooms - Sleeps 8
Summerland Key Vacation Rental
Pets Allowed

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 outdoor kitchen and entertainment area, over .5 acres of lush tropical landscaping, outdoor fire pit, private boat dock on canal and lots of room to en.......

9.8 Star Review

5 Bedrooms - Sleeps 10
Summerland Key Vacation Rental
Pets Allowed

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 free-flowing floor plan with granite countertops and stainless appliances. The views from every window will make you feel like you're in paradise at each glance. After a day on the water, d.......

10.0 Star Review

3 Bedrooms - Sleeps 8
Summerland Key Vacation Rental
Pets Allowed

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 vacationers (2 adult and 2 childrens kayaks) as well as use of kayak dock, fish cleaning table, and bait freezer. The kids are sure to be entertained by.......

9.6 Star Review

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental
Pets Allowed

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 paradise! Great base camp for lobstering and fishing! .......

4 Bedrooms - Sleeps 8
Summerland Key Vacation Rental

Quiet, secluded Keys house with a pool. 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. This area has lots wildlife and deer. Come enjoy and relax .......

9.6 Star Review

6 Bedrooms - Sleeps 14
Summerland Key Vacation Rental
Pets Allowed

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 natural history mounts, area-related books and other reading material. Ceiling fans everywhere. Tile and hardwood floors downstairs.

In-ground h.......

10.0 Star Review

4 Bedrooms - Sleeps 8
Summerland Key Vacation Rental

MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. 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 countertops, stainless steel appliances, and an eat in kitchen island, separate dining room.Outdoor chest/bait freezer and.......

9.4 Star Review

4 Bedrooms - Sleeps 8
Summerland Key Vacation Rental
Pets Allowed

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 more. It has a gas BBQ Grill. It's on a large fenced in lot with a nice shady area under Florida Native Gumbo Limbo Trees. Enjoy your own private spa.......

9.4 Star Review

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental

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, this because monkey research was once performed there.

Interestingly, the research was stopped due to 'monkey business,' i.e that the primat.......

10.0 Star Review

4 Bedrooms - Sleeps 9
Summerland Key Vacation Rental

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. The Bent Prop Restaurant is located next to the marina. Canal is great for swimming and paddle boarding. We have 2 paddle boards for your use. 21 miles to.......

9.6 Star Review

2 Bedrooms - Sleeps 4
Summerland Key Vacation Rental

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 fisherman's paradise. Your unforgettable Florida Keys experience awaits at Dickey's Dockside Retreat.

The Space:
Dickey's Dockside Retreat .......

10.0 Star Review

3 Bedrooms - Sleeps 8
Summerland Key Vacation Rental
Pets Allowed

Breathtaking Open Water Views. This spectacular home is in impeccable condition. New Custom Pool. Dock up to a 31' boat. 2 kayaks and 2 bicycles for your use. Beautiful landscaping. Oversized covered porch. Super fast WiFi Cable 75inch TV. Gourmet kitchen. Washer and dryer. Extra refrigerator and freezer in the air conditioned downstairs space. Super Clean. Plenty of parking. 6 person maximum. LOCAL Laws require a 28 Day minimum rental........

10.0 Star Review

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental
Pets Allowed

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 fully equipped with new stainless steel appliances, quartz countertops, with French doors that open to a screened in deck overlooking the water if you pr.......

4 Bedrooms - Sleeps 10
Summerland Key Vacation Rental
Pets Allowed

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 canal frontage featuring a 90' concrete dock, and a private kayak launch.

The main level of the home features a wrap-a-round deck, a spacious livi.......

10.0 Star Review

4 Bedrooms - Sleeps 10
Summerland Key Vacation Rental
Pets Allowed

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below.



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.......

9.8 Star Review

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental

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, TV, wifi, screened porch, tiki hut & plenty of outdoor space to fish, play, kayak, and Florida Keys sunsets. Quick boat access to both Atlantic & Gulf........

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental

Summary:

Canalfront 2 bedroom retreat on Ramrod Key with brand new dock!



The Space:

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 and enjoyable stay.



As .......

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental

Experience the Ultimate Florida Keys Escape at Reel Escape — Your Spacious 4-Bedroom Summerland Key Retreat

Nestled in the serene beauty of Summerland Key, just a quick 5-minute drive from pristine Florida Keys beaches, Reel Escape offers everything you need for the perfect vacation — whether you crave relaxation, family fun, or thrilling outdoor adventure.

Luxurious Comfort and Space for Family & Friends

This expansive home comfortably sleeps up to 7 guests with four ge.......

9.8 Star Review

4 Bedrooms - Sleeps 8
Summerland Key Vacation Rental
Pets Allowed

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 oversized lot with a patio surrounded by tropical gardens creating lots of privacy between neighbors, it's like living on an Island away from it all! Cov.......

8.4 Star Review

2 Bedrooms - Sleeps 4
Summerland Key Vacation Rental

The Palm Cottage is a standalone unit which is next to the pool and near the outdoor shower. It has been recently renovated. The main room includes a Queen sized bed, TV, table with 4 chairs, a full kitchen, full bath with a walk-in shower. The front room has a trundle bed with two twin mattress and a TV. There is a laundry room on the property for our guests to use that is free of charge.

It can comfortably sleep 3 people. Just outside the front door is an outdoor table and chairs.......

9.8 Star Review

1 Bedrooms - Sleeps 4
Summerland Key Vacation Rental
Pets Allowed

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 West and Marathon in different directions. Close to Looe Key Reef and Tarpon Belly Island. Fish cleaning table on seawall. Shed available for storage .......

10.0 Star Review

2 Bedrooms - Sleeps 5
Summerland Key Vacation Rental

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.

Industrial Ice Maker is located downstairs to keep all of your coolers filled!

The property is gated with ample parking for cars and boat traile.......

5 Bedrooms - Sleeps 8
Summerland Key Vacation Rental

28 consecutive day minimum rental. 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 floor with two full bathrooms. Each bedroom has a queen size bed, closet, dresser, nightstand and TV. The bathroo.......

10.0 Star Review

3 Bedrooms - Sleeps 6
Summerland Key Vacation Rental
Pets Allowed

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. .......

1 Bedrooms - Sleeps 2
Summerland Key Vacation Rental
Pets Allowed

Ocean Breeze is the largest of our 5 cottages at 1500 square feet. It's perfect for your family vacation, sleeping 7 people comfortably, with two full bedrooms (one with a queen bed and the other with two queen beds) and a pull-out sofa as well as two full bathrooms. It comes complete with a full kitchen, large living room with fireplace and dining room as well as a screened-in front porch for outdoor dining. The rear of the house has a game room with a full size pool table and an outdoor pa.......

9.4 Star Review

2 Bedrooms - Sleeps 8
Summerland Key Vacation Rental
Pets Allowed

The Sea Shell Cottage UNIT #2 has efficiency kitchen with refrigerator, sink, microwave oven and toaster oven. The main room has a Queen-sized bed, full bathroom with a walk-in shower, table with 2 chairs and a TV. It comfortably sleeps 2 people. The unit is air conditioned and WiFi service is available throughout the resort. Enjoy the communal outdoor pool and covered patio that has a gas grill, griddle and picnic area. There is a laundry room with washers/dryers for our guests to use fre.......

9.6 Star Review

1 Bedrooms - Sleeps 2
Summerland Key Vacation Rental
Pets Allowed

The Flamingo Cottage is a studio unit that includes a Queen-sized bed in the bedroom area, a full kitchen, bathroom with a walk-in shower, living area with a sofa, TV, table with 4 chairs and some outdoor space in front of the unit with a table and two chairs. It can comfortably sleep 3 adults or 2 adults and 2 small children. The unit is air conditioned and WiFi service is available throughout the resort. Enjoy the communal outdoor pool and covered patio that has a gas grill, griddle and pi.......

9.8 Star Review

1 Bedrooms - Sleeps 4
Summerland Key Vacation Rental
Pets Allowed

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.

Your property manager lives nearby and is available if you have any requests during your stay

Very secluded quite neighborhood

You will.......

9.4 Star Review

7 Bedrooms - Sleeps 14
Summerland Key Vacation Rental

Beautiful home on the oceanside of Summerland Key on a protected deep water canal one lot in from the ocean. 45' seawall will accommodate boats up to 40' in length and 5' in draft. Direct Ocean access to great offshore/backcountry fishing and reef diving/snorkeling that are literally minutes away. The property features spectacular ocean views, a private in-ground heated pool with a paver lounging area, a Tiki Hut, cable TV, a washer and dryer, a gas barbecue grill, and more!

Open conc.......

9.0 Star Review

4 Bedrooms - Sleeps 8
Summerland Key Vacation Rental