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Summerland Key Vacation Rentals in the Lower Florida Keys

Book Your Summerland Key Vacation Rentals Here and Save! Many to choose from, including Rental Homes or Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities to make your Florida stay enjoyable.

Vacation Rentals by Owner in Summerland Key Florida.

We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places to Rent in Summerland Key Florida.

Gorgeous 3 bedroom 2 bath canal front home

Summerland Key Private vacation home

Beautiful 3 bedroom 2 bath canal front home on Summerland Key. This home features deep water dockage, great access to the Atlantic or the Gulf and just minutes away from world famous Looe Key Reef. The split floor plan boast spacious bedrooms, fully equipped kitchen, dining area and screened porch overlooking the turquoise waters. Book your stay a.......read more

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


Vacation Rental


Gorgeous Canal Front Home! Come stay at 'Casa Key Ramrod'

Summerland Key Private vacation home Star 4.7 Star Review

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

High Season Jan 1st to March 31st $4500/month
Mid Sea.......read more

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


Vacation Rental


The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17

Summerland Key Private vacation home Star 5.0 Star Review

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 Rental


The Blue Pearl - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The Whole Family & Fido!

Summerland Key Private vacation home Star 5.0 Star Review

Welcome to The Blue Pearl!

The perfect destination for large families or multiple families. Two living areas provide plenty of room to accommodate everyone, but also separate when needed. Relax with your toes in the sand along your 125\' of oceanfront and enjoy the amazing sunsets or kick back under the gazebo and catch up on a book. At the .......read more

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


Vacation Rental


Waterfront house conveniently located.

Summerland Key Private vacation home

From here you can enjoy all that the Keys have to offer.
Conveniently located at the 23 mile marker. Walk to Square Grouper for lunch or dinner. Have a cocktail at "My New Joint" after a day of fishing and fun. Diving, snorkeling or fishing? You can launch your boat nearby at Cudjoe Gardens Marina. Dock the boat on the 60’ dock in back .......read more

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


Vacation Rental


4 bedroom accommodation in Summerland Key

Summerland Key Private vacation home

Enjoy the unobstructed 270-degree ocean view in this newly renovated beachfront residence. Located in the most exclusive part of Cudjoe Gardens this 2- story house is surrounded by the water on 3 sides. Three bedrooms and two bathrooms are impressively decorated in a soft coastal palette and are located on the second main living floor. 

Amb.......read more

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


Vacation Rental


Green Turtle - Waterfront Vacation rental with pool and dockage

Summerland Key Private vacation home

Welcome to Green Turtle! A luxurious 4 Bedroom, 2 Bath, Canal Front Vacation home with a Private Pool

Beautiful and bright luxurious 4 bedroom 2 bathroom home on a crystal clear wide canal on presitigious Sugarloaf Key. After a day of world class fishing & diving, which is within minutes from the home, enjoy the true Florida Keys vacation an.......read more

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


Vacation Rental


WEEKLY Oceanfront Home-Pool, Dock-Available Weekly or Monthly.

Summerland Key Private vacation home Star 4.8 Star Review

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 Rental


Spectacular sunsets and open water views at this 3 BR 3 BA

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 Rental


Open Water ~ Pool Home in Summerland Key

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 Rental


Conveniently located Canal Front whole house!!

Summerland Key Private vacation home Star 5.0 Star Review

Water front house in very convenient area. Fish from the dock or bring your boat and have access to the Atlantic Ocean or the Gulf. The fishing is excellent as much for little kids to seasoned fisherman. House is in close distance to convenience stores, markets and excellent restaurants. Feel like enjoying nightlife that Key West has to offer? A 20.......read more

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


Vacation Rental


Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key Private vacation home Star 4.9 Star Review

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.......read more

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


Vacation Rental


Florida Keys Waterfront House w/Pool & Spectacular Ocean Views/Minimum 28 Nights

Summerland Key Private vacation home Star 4.3 Star Review

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 v.......read more

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


Vacation Rental


Ocean Front Modern Home

Summerland Key Private vacation home Star 4.9 Star Review

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 Rental


Gasparilla Villa - your home away from home in the Fabulous Florida Keys

Summerland Key Private vacation home

Located just 23 miles from the ever popular Key West with all the restaurants, history and night life you can find in a tropical paradise. Yet once you arrive at the Gasparilla Villa in Cudjoe Key you are in a quiet, peaceful lifestyle that is unique to the Florida Keys. Fully fenced property with some of the most beautiful sunsets you will see co.......read more

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


Vacation Rental


Cozy 2 Bedroom home in Summerland Key

Summerland Key Private vacation home Star 2.0 Star Review

Our home is located in a quiet and cozy area 5 minutes away from the famous Ramrod Swim Hole; a local treasure. It is also less than 5 minutes away from Boondocks, a super fun bar where you can also mini golf. Our home is thoughtfully accommodated with everything you will need in your stay. Our home is your home and we hope that you have a pleasant.......read more

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


Vacation Rental


3/2 two story home with pool and 80' dock on canal ocean side.

Summerland Key Private vacation home


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 th.......read more

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


Vacation Rental


August/September discounts - Vacation like a local

Summerland Key Private vacation home Star 5.0 Star Review

Newly renovated 3 bedroom/ 2 bathroom + loft, corner canal lot. Fully equipped home.

Plenty of room for boat and great location. 5 minutes to marina, 20 minutes to Key West and 30 minutes to Marathon.
.......read more

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


Vacation Rental


Charming and Private

SUMMERLAND KEY Private vacation home Star 3.8 Star Review

20 Miles from Key West and mini golf, private pool & hot tub, deluxe outdoor kitchen, outdoor shower, screened in porch all around, bait freezer in work shop area, davits, 50 & 35 amp shore power boat basin, fish cleaning station, with 2 bikes and kayak, washer/dryer, dishwasher, refrigerator, ice maker, full kitchen, microwave, phone, air conditi.......read more

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


Vacation Rental


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