Summerland Key Vacation Rentals in the Lower Florida Keys

Summerland Key Private vacation home

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

Prime Oceanfront Tropical Gem & The Ultimate in Luxury Waterfront Living! Florida Keys luxury deep water oceanfront pool home in prestigious Summerland Cove on Summerland Key, only 30 minutes to Key West. This Spacious 2766 SF 4BR/3.5BA with magnificent open water views will captivate you throughout this 2-story elevated residence. The open entert.......read more

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

Vacation Home

Summerland Key Private vacation home 5.0

A tropical paradise with over 1/3 of an acre of lush landscaping for an unprecedented amount of space and privacy in the Florida Keys. This charming stilted home is beautifully updated, and decorated in a whimsical Keys style.
The open plan kitchen, living, and dining area is a fantastic place to relax after a day on the water or sightseeing in .......read more

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

Vacation Home

Summerland Key Private vacation home 4.9

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 4.7

*Please contact me first before making a online reservation request to confirm if the dates you are interested in are available*

I am only able to rent by the month due to local ordinances.
Check in is on the first on the month and check out is last day of the month.
Pricing:
High Season Jan 1st to March 31st $5,500/month
Mid S.......read more

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

Vacation Home

Summerland Key Private vacation home 4.9

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

Spectacular sunsets and open water views at this 3 BR 3 BA home on Summerland Key. Brand new dock for your large boat with quick access to the open ocean, gulf & back country. This home is like new, built in 2015, it has 1800 square feet and 10 foot ceilings
The fully furnished kitchen has a refrigerator, electric stove, dishwasher, blen.......read more

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

Vacation Home

Summerland Key Private vacation home 5.0

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 5.0

Beautiful property and landscaping, 3/2 with pool sleeps 8-10, large 12,000 sq ft lot with 80' dock, The place to be is downstairs entertaining the family with a large pool and living area with grills to cook up those special fish recipes. There's a large outdoor shower for two, along with outdoor bathroom, no need to go upstairs. relax by the .......read more

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

Vacation Home

Summerland Key Private vacation home 5.0

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

January DEAL! Call me for details! 

Beautifully appointed 2 Bed 2 Bath, open water home with pool, located on Ramrod Key. Recently renovated top to bottom and an exact fit for all your needs during your keys vacation. Sleeps 6 comfortably and Bose surround system- not to mention pool nirvana with heater and chiller (available for extra char.......read more

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

Vacation Home

Summerland Key Private vacation home 4.9

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 4.8

We survived Irma and have been back up and running for two years. Please check out the new updated photos of all the repairs and updates. The house now has new impact windows and doors, new paint in and out, new decking and screens, new tile throughout, the pool has just been resurfaced and upgraded, and new rails and balconies have been installed.......read more

3 Bedroom(s)
3 Bath(s)

Vacation Home

Summerland Key Private vacation home

Villa Paradise is the perfect home base for your Florida Keys adventure. Just four canals in from the ocean on Ramrod Key, you're also just 27 miles up the Overseas Highway from the fun of downtown Key West. This 4 bedroom, 2 bathroom home has 25 feet of available dockage and is equipped with everything you need for your time in the Lower Keys. Th.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 7

Vacation Home

Summerland Key Private vacation home 5.0

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 4.8

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

Welcome to The Black Marlin a contemporary home with a coastal flare. A new construction canal front home located in beautiful Sugarloaf Key, just a few miles to downtown Key West.

With 3 bedroom, 2.5 bathrooms this open concept home flows seamlessly throughout the entire property.

The home is full of natural light with oversized win.......read more

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

Vacation Home

Summerland Key Private vacation home 5.0

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 5.0

Welcome to the captivating retreat of Blue Fish Point, a haven nestled on a sprawling 3-acre expanse, offering an exclusive boating sanctuary like no other. Embrace the ultimate Keys experience as you revel in the seclusion of your private beach and boat ramp, boasting an impressive 200 feet of open water frontage and 900 feet of canal, complete wi.......read more

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

Vacation Home

Summerland Key Private vacation home 4.7

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 5.0

Watch spectacular sunsets from this brand new high-end ocean front home with panoramic water views. Immaculate condition throughout. Very private back yard with heated swimming pool and hot shower. Covered entertainment area with dining table, sofa set, TV and BBQ. Ocean-side fire pit and beach chairs. Sonos sound system inside and out. Dock wit.......read more

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

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 4.7

Kiki's Casa - Your Beautifully Updated Canal Front Retreat in the Florida Keys! Discover the ultimate vacation experience at Kiki's Casa, a charming canal front home located on Summerland Key. Nestled in an area known for some of the cleanest and clearest canals in the Lower Keys, this delightful getaway invites you to bring your boat and explore t.......read more

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

Vacation Home

Summerland Key Private vacation home 5.0

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 Cottage 4.3

VO333
70' Seawall 2Bd/1.5Ba Large Covered Porch

Lovely 2Bd/1.5Ba vacation home in desirable boating community only 15 minutes to the deep blue waters of the Florida Keys for world class fishing and diving! WiFi. Features include 70' Concrete Seawall with dock post, swim ladder,fish cleaning table and cleats. Located right off the marina.......read more

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

Vacation Home

Summerland Key Private vacation home

Magnificent Ocean Front Estate! Enjoy breathtaking views of the ocean from the large screened in porch. Prepare freshly caught fish from the private dock in the chefs kitchen. Cool off in the huge secluded pool or lounge pool side as you watch the ocean and hear the breeze rustle the palms. Tropical dreams await you in the four beautiful bedrooms. .......read more

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

Vacation Home

Summerland Key Private vacation home 5.0

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

Welcome to "Way To The Ocean," your updated canal front home on Cudjoe Key. This charming retreat offers a convenient location, just a stone's throw from some of the area's best restaurants and bars. Start your day with a cup of coffee on the screened porch, taking in the refreshing island breeze. Later, as the day turns into evening, gather with f.......read more

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

Vacation Home

Summerland Key Private vacation home

Beautiful cozy house for rent in Ramrod Key. The place features;
Three bedrooms, two baths, large dock with a lift to accommodate
any vessel up to 30 ft. Nice outside area with a tiki hut to bbq or just relax.
See Pictures.

Location and surroundings:

Ramrod is conveniently located at 25 miles drive from Key West which is a.......read more

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

Vacation Home

Summerland Key Private vacation home 4.5

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 4.8

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 4.9

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 4.7

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 4.5

Welcome to Key Blessing, your gateway to experiencing the quintessential Keys Life! This charming 3-bedroom canal front home, nestled on Ramrod Key, offers the perfect blend of relaxation and adventure. As you arrive, you'll appreciate the convenience of docking your boat along the sea wall, allowing you to indulge in fantastic fishing just moments.......read more

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

Vacation Home

Summerland Key Private vacation home

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 5.0

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