Summerland Key Vacation Rentals in the Lower Florida Keys

Summerland Key Vacation Rental

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 Bedrooms - Sleeps 8
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 8
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental

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 Bedrooms - Sleeps 10
Vacation Rental Home in Summerland Key

SUMMERLAND KEY Vacation Rental 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 Bedrooms - Sleeps 6
Vacation Rental Home in SUMMERLAND KEY

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 6
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental

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 Bedrooms - Sleeps 6
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 8
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental

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 Bedrooms - Sleeps 6
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 5
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 10
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 8
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental

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 Bedrooms - Sleeps 6
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 7
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental

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 Bedrooms - Sleeps 8
Vacation Rental Home in Summerland Key

Summerland Key Vacation Rental 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 Bedrooms - Sleeps 6
Vacation Rental Home in Summerland Key