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Summerland Key Vacation Rentals in the Lower Florida Keys

Book Your Summerland Key Florida Vacation Rental Homes Here and Save! Many to choose from!

Browse Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer 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 in Summerland Key to choose from, we now have the selection and value to offer our visitors going to Florida.

The Tiki

3 bedroom accommodation in Summerland Key

Separate living areas make this beautiful canalfront pool home ideal for extended families or friends wintering together. In the spacious upstairs, there's a master suite with king bed and a queen bedroom with adjacent hall bath; fully equipped kitchen with bar seating and 4-person dining area; comfy living area with large flat-screen TV; small scr.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 Summerland Key House Rental

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Blackbeard's Hideaway

Blackbeard`s Hideaway

Open floor plan with warm pine floors, vaulted ceilings and newly updated kitchen with stainless appliances and quartz countertops. The two downstairs bedrooms have king beds and share a nice jack-and-jill bath with bath/shower combo. There's a small loft with a full-sized bed accessible by spiral staircase, and there's a comfortable fold-out couch.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Summerland Key House Rental

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LIVING IN BEAUTIFUL PARADISE

LIVING IN BEAUTIFUL PARADISE

Enjoy the view from the large porch overlooking a deep, wide, crystal blue, clear canal with quick boating access to both the Atlantic Ocean and Gulf of Mexico. Looe Key Coral Reef is a short distance away by boat for some of the best diving & fishing the keys has to offer. If you prefer to stay home, enjoy the canal loaded with marine life, and ca.......read more

3 Bedroom(s)
3 Bath(s) - Sleeps 8 Summerland Key House Rental

Details

Villa Paradise

4 bedroom accommodation in Summerland Key

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 Summerland Key House Rental

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Latitude Adjustment

3 bedroom accommodation in Summerland Key

3 bedroom/2 bathroom canalfront home on Summerland Key just a few homes in from open water. Vaulted ceilings, updated and spacious kitchen, tile throughout. Dining for 6 inside. Flat-screen TV in the living area, which has canal views. Primary bedroom features king bed and en-suite with a huge shower. The 2nd bedroom has a queen bed and a futon. Th.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Summerland Key House Rental

Details

Foster's Folly

3 bedroom accommodation in Summerland Key

Beautifully decorated and recently remodeled, this 3 bedroom/2 bath stilted home sits along a great boating canal on Cudjoe Key and features a waterfront pool. Enjoy the large outdoor living area with seating and dining space, or watch the sun rise and set from the rooftop deck. This home's upscale yet cozy interior is the perfect place to relax at.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Summerland Key House Rental

Details

Paradise in the Keys

Paradise in the Keys

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 charge). About 27 miles from Key West. Gated yar.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 6 Summerland Key House Rental

Details

Sunshine 23

2 bedroom accommodation in Summerland Key

All the comforts of home, with none of the cold weather! Dog-friendly 2 bed/2 bath monthly vacation rental on a boating canal on Cudjoe Key! Open main living area with two comfy seating areas with TVs, large dining table and a small bar. Roomy kitchen features a breakfast bar with room for four, tile counters, stainless steel appliances and a pantr.......read more

2 Bedroom(s)
2 Bath(s) - Sleeps 5 Summerland Key House Rental

Details

TARPON RANCH

TARPON RANCH - Live the Resort Life at Tarpon Ranch, Open Water, Pool/Spa, Dockage & Dog Friendly!

Welcome to TARPON RANCH! The epitome of relaxed elegance -- a masterful combination of architectural splendor within the casual atmosphere that defines the Keys lifestyle. Exquisite estate w/ 6 bedrooms, 6 full baths & two 1/2 baths, evenly split between the Main House & the Guest House. Interior is executed with superb craftsmanship where soaring.......read more

7 Bedroom(s)
7 Bath(s) - Sleeps 14 Summerland Key House Rental

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Sugarloaf Serenity

3 bedroom accommodation in Summerland Key

Great views of Sugarloaf Sound from this ground-level midcentury-era home that offers expansive sound frontage perfect for kayaking and paddleboarding, plus a dock on the canal to the side for your small power boat. Light and bright, with lots of windows throughout. Scandinavian-inspired furnishings. The kitchen is well-equipped, and you have your .......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Summerland Key House Rental

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286 Colson Drive

4 bedroom accommodation in Summerland Key

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.  Amble of .......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 Summerland Key House Rental

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Reel Caribbean Getaway

Reel Caribbean Getaway

Fantastic deep-water boating from this spacious, gated, 4 bedroom / 2.5 bath home on Summerland Key's Caribbean Drive East that features open water views and sunset hues. Large and deep heated pool, plenty of dockage, tiki and screened porch. Water views from nearly every room. Great boating. Ample parking. The first floor has a king bedroom, queen.......read more

4 Bedroom(s)
3 Bath(s) - Sleeps 8 Summerland Key House Rental

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Kokomo

3 bedroom accommodation in Summerland Key

Beautifully remodeled 3 bedroom 2 bath home with 60’ concrete dockage in Cudjoe Key. Home is perfectly appointed with everything you could need for your Keys vacation. Easy boating access via Cudjoe Bay, gas up at Venture Out across the bay. Oversized fenced-in lot, covered parking under the house. Lightning fast fiber optic internet provided and.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 6 Summerland Key House Rental

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Vacation Rental

Lower Keys Waterfront Getaway

Our private studio is located on beautiful Cudjoe Key. It has a private entrance with no accessibility to the main house. We are located at 22.5 mm from Key West. It’s a great room to stay in while visiting the Florida Keys. The space is great for couples or single travelers. Great studio apartment with kitchenette that has a full size refrige.......read more

Studio
1 Bath(s) - Sleeps 2 Summerland Key Studio Rental

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Vacation Rental

3/2 waterfront home w/54ft dock near Key West with lots of amenities and great 🎣

Sunny Lei Keys house is your slice of paradise away from home! This 3 bedroom/2 bathroom beach-themed house sleeps 8 guests comfortably, and boasts a spacious kitchen with an adjacent dining area. Smart TVs in the living room and master bedroom give you access to international, local and premium movie channels and Pay-per-view, Netflix,YouTube, and.......read more

3 Bedroom(s)
2 Bath(s) - Sleeps 8 Summerland Key House Rental

Details

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