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Summerland Key Vacation Rentals in the Lower Florida Keys

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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. There are many home rentals to choose from, and we now have the selection and value to offer our visitors going to Florida.


Summerland Key House

The Tiki - Summerland Key House

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....

4 Bedrooms 3 Baths - Sleeps 8
Summerland Key, FL

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Summerland Key House

Blackbeard's Hideaway - Summerland Key House

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....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key House

LIVING IN BEAUTIFUL PARADISE - Summerland Key House

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....

3 Bedrooms 3 Baths - Sleeps 8
Summerland Key, FL

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Summerland Key House

The Hideaway - Summerland Key House

The Hideaway - Find Us and Get Lost! Newly Decorated Canal Front Home, Great Dockage & Dog Friendly. Welcome to The Hideaway! This lovely canal front home is located on Big Torch Key and offers a relaxed, tropical escape from your everyday life. Dock your boat along the sea wall and enjoy fantastic fishing only minutes away. Relax on the porch while enjoying your morning coffee or favorite cocktail and soak in the nature that surrounds you! There....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key House

Solstice Seaside - Summerland Key House

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

4 Bedrooms 2 Baths - Sleeps 8
Summerland Key, FL

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Summerland Key House

HappyOurs by Sea. - Summerland Key House

Perfection in Paradise by the Sea / Coastal jewel home with Pool/Heater.. . Fully renovated coastal jewel This home has been fully and beautifully renovated. The first floor living level offers a spacious, open layout with a modern coastal feel and a sensational kitchen. The bedrooms are split; two bedrooms are on one side. On the other side, the master bedroom features an adjacent room separated by double barn doors. This....

4 Bedrooms 3 Baths - Sleeps 10
Summerland Key, FL

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Summerland Key House

Latitude Adjustment - Summerland Key House

3 bedroom accommodation in Summerland Key. 3 bedroom/2 bathroom canalfront home just three homes in from open water on a deep-boating canal on Summerland Key. Vaulted ceilings, updated and spacious kitchen, tile throughout. Dining for six inside. Flat-screen TV in the living area, which has canal views. Master bedroom features king bed and en-suite with a huge shower. Second and third bedro....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key House

Foster's Folly - Summerland Key House

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....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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SUMMERLAND KEY House

Summerland Hideaway - SUMMERLAND KEY House

Charming and Private. 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....

2 Bedrooms 3 Baths - Sleeps 6
SUMMERLAND KEY, FL

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Summerland Key House

Paradise in the Keys - Summerland Key House

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 27miles from Key West.     Ga....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key House

Sunshine 23 - Summerland Key House

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....

2 Bedrooms 2 Baths - Sleeps 5
Summerland Key, FL

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Summerland Key House

Tarpon Ranch - Summerland Key House

New Listing!!! 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....

7 Bedrooms 7 Baths - Sleeps 14
Summerland Key, FL

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Summerland Key House

Sugarloaf Serenity - Summerland Key House

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 ....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key House

The Yellow House - Summerland Key House

Acreage Multi-Million Dollar Beach Mansion w/ Pool & Billiards . This is a newly remodeled four bedrooms multimillion-dollar elegant mansion. The house has its own private beach located in the heart of Summerland Key. It is the perfect Key for a vacation getaway. Summerland Key is an island in the lower Florida Keys about 20 miles east of Key West. The island has a private airport located 3 blocks from the house....

5 Bedrooms 3 Baths - Sleeps 10
Summerland Key, FL

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Summerland Key House

22940 Sharp Lane - Summerland Key House

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

5 Bedrooms 3 Baths - Sleeps 12
Summerland Key, FL

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Summerland Key House

Open Ocean View Summerland Key - Summerland Key House

Open Ocean View Summerland Key. 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....

4 Bedrooms 3 Baths - Sleeps 9
Summerland Key, FL

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Summerland Key House

Vacation Rental - Summerland Key House

3/2 on the Water in Paradise Monthly Rental 28 Day min. . Wonderful, open concept, 3/2 stilt, canal front home in Summerland Key. On the beautiful, blue/green flow through canal only 5 minutes to open water on the Atlantic Ocean side. 80’ of dock space can accommodate large boats. You can also store your trailer on the property to avoid additional fees many other properties charge for. Our home is in a ....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key House

Kokomo - Summerland Key House

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....

3 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key Studio

Vacation Rental - Summerland Key Studio

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....

Studio 1 Baths - Sleeps 2
Summerland Key, FL

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Summerland Key House

Summerland Key House - Summerland Key House

Summerland Key House Open Air Living. Summerland Key House is all about open air living. Cypress plank cathedral ceilings extend through the bedrooms, bathrooms and over 2 large porches on the side and back of the house. Double French doors in the master bedroom and living room open to a lounging area and hammock on the large back covered wooden porch. Double French doors in the kitc....

2 Bedrooms 2 Baths - Sleeps 6
Summerland Key, FL

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Summerland Key House

Folsom's Folly - Summerland Key House

Oceanfront Sunsets in the Florida Keys. 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....

5 Bedrooms 6 Baths - Sleeps 8
Summerland Key, FL

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Summerland Key House

4 bedroom 4 bath on swim canal - Summerland Key House

spring& summer sale, quiet waterfront private swim canal, boat dock"PET FRIEN. Monroe Count requires 28 day contract to rent a property. Please contact us so we can work with you regarding your particular rental needs. Beautiful sunsets with privacy in your secluded paradise. Enjoy the best of both worlds snorkeling, kayaking, diving & swimming in the pristine swim canal behind the house or boating from the dock. Jus....

4 Bedrooms 4 Baths - Sleeps 8
Summerland Key, FL

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Summerland Key House

Oasis - Summerland Key House

Oceanfront tropical home with pool and dock . Spacious home for large family gatherings. Amazing 4 bedroom/3 bath Ocean Front Home on Cudjoe Key with; heated pool, dock, large screened in porch and great ocean views. Sleeps 10+ There are beds for 8 people. There are additional sleeper sofas in several bedrooms. Please contact host for more than 10 guests. Master suite with king bed overl....

4 Bedrooms 3 Baths - Sleeps 12
Summerland Key, FL

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Summerland Key House

A Paradise in the Florida Keys - Summerland Key House

Cudjoe Gardens Estate With Ocean View & Pool. This beautiful Eco-friendly Ocean view home is away from the hustle-bustle of Key West. Welcome to this luxury deluxe vacation home that can comfortably accommodate for a large family union or wedding. Come to Beautiful Key West and stay in this immaculate, beautifully furnished Home in the beautiful 2-acres green lush tropical Estates. Enjoy the....

5 Bedrooms 2 Baths - Sleeps 10
Summerland Key, FL

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