This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation
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Summerland Key Vacation Rentals Show this location only Back to top
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Seas the Keys! Vacation Paradise on Deep Water Flow Through Canal
3BR+/3BA
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Sleeps 6-8
– Summerland Key #436601
$2100 - $2450 per week 7 night min stay
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Open Water View Home with Pool and Spa
3BR/2BA
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Sleeps 6
– Summerland Key #396273
$5,500 MTH
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Private Island, Weekly Luxury Escape's
3BR+/3.5BA
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Sleeps 6
– Summerland Key #438052
Please Call US
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Luxury Eco Friendly Private Island in Florida
4BR/3.5+BA
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Sleeps 10
– Summerland Key #3503655ha
$1500 per night 3 night min stay
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Oceanfront Home-Pool, Dock-Available Weekly or Monthly
3BR+/2BA
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Sleeps 8-10
– Summerland Key #15888
$2,500- $4,500/wk
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"Caribbean Cottage" Ocean Side Pool Boat Dock Sunset Sleeps 8
4BR+/2BA
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Sleeps 8
– Summerland Key #19286
$6500- $7500/mo
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Atlantic Mansion-Estate on Private Paradise Peninsula
4BR/4BA
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Sleeps 8
– Summerland Key #303222
$2950.00- $6000.00
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Your Own, Private Resort; Pool with 3 Waterfalls Near Key West
4BR+/3.5BA
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Sleeps 8
– Summerland Key #334495
Call pricing starting from $5000+
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Canal Front (Deep Water) Tropical Villa
2BR+/2BA
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Sleeps 8
– Summerland Key #155489
$3000- $5000/mth
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Lagoon Keys Paradise at Your Door - Corner Canal Lot End of St
2BR/2BA
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Sleeps 4
– Summerland Key #376262
$4000- 5,000 monthly;
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Summerland Estate
5BR/4BA
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Sleeps 12
– Summerland Key #282258
$3000- $6000/wk
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Private, Estate Like, Oceanside Open Water Home in the Keys!
3BR+/3BA
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Sleeps 6-8
– Summerland Key #217646
$6825- $8400/mo
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Summerland Key-2 Bedrooms Pool-Deep Water Canal; Ocean Access
2BR/2BA
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Sleeps 4
– Summerland Key #376273
$4000- 5000 mo
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Fabulous Florida Keys
5BR/4.5BA
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Sleeps 10
– Summerland Key #322572
$16,500- $19,500./mo
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Open Plan Canal Front Tropical Villa with Boatlift, Dock & Swim Spa
2BR+/2BA
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Sleeps 6-8
– Summerland Key #475762
$3720 per month 31 night min stay
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Florida Keys, Mile Marker 25
3BR/2BA
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Sleeps 2-6
– Summerland Key #422495
$5000.00 _ $6500.00 per month
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New Listing! Waterfront Cottage
3BR/2BA
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Sleeps 7
– Summerland Key #458782
Starting at $1200
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Oceana Estate with Pool and Hot Tub
4BR+/3.5BA
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Sleeps 8-12
– Summerland Key #410747
$715/nt, minimum stay required
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Tropical - Private Deep Water Canal Home
2BR+/2BA
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Sleeps 5
– Summerland Key #151980
$1750 per week 7 night min stay
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Changes in Latitudes -Even Better Than Before with New Changes
4BR/2.5BA
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Sleeps 7
– Summerland Key #5943
$4500- $7500/mo
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Come for the Holidays! Direct Oceanfront Home W/Dock/Ramp
2BR+/2BA
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Sleeps 4-6
– Summerland Key #87007
$3000- 4200/mo
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Paradise Found... a Reel and Diver Retreat!
3BR/3BA
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Sleeps 6
– Summerland Key #196245
$3950- $6100/mo
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Oceanfront Home Endless Sunsets Pool with Deepwater Dockage
3BR/3.5BA
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Sleeps 6
– Summerland Key #307025
$2800- $7900
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Hogfish Hideout
3BR+/2BA
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Sleeps 8
– Summerland Key #418782
$3800 - $4500 US
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Florida Keys Waterfront Cottage W/Pool and Ocean Views
1BR+/1BA
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Sleeps 2-4
– Summerland Key #364224
$2800 per month 28 night min stay
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Air & Sea Cottage on Private Airstrip.
3BR+/2BA
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Sleeps 6-8
– Summerland Key #65059
$1200/wk - $3800/mo
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Summerland Key Oceanfront
3BR+/3BA
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Sleeps 8-10
– Summerland Key #375105
From $5000 to $7000/mo
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Pool, Dock, Sandy Beach, Privacy, Open Water Estate
7BR+/5BA
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Sleeps 12-14
– Summerland Key #257454
$5000- $7000/wk
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Oceanfront Sunsets in the Florida Keys
4BR+/3.5BA
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Sleeps 8-10
– Summerland Key #2032
$8500/mo
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Large Comfortable Home on Great Canal!
4BR/3.5BA
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Sleeps 8-10
– Summerland Key #14840
$3500- $4000/mo
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Summerland Key Bungalow
3BR/2BA
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Sleeps 6
– Summerland Key #253562
$4000/mo
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Large House with Pool. Sleeps 8, Deep Water Canal!
2BR+/2BA
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Sleeps 8
– Summerland Key #106212
$4500 and up monthly
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Direct Oceanfront, Beautiful Inside!
2BR/2BA
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Sleeps 8
– Summerland Key #441508
$2200- $4600 Monthly
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The Flying Hogfish!
3BR/2BA
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Sleeps 6
– Summerland Key #442915
$3500/mo
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Breathtaking Open Waterfront Home, Dock, Open Water & 2 Canals!
2BR+/2.5BA
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Sleeps 8
– Summerland Key #213669
$350 - $365 per night 6-7 night min stay
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'the Pisces House' Oceanside Cottage
1BR+/2BA
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Sleeps 2-4
– Summerland Key #106235
$2600- $3400
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Summerland Key Cottage on Deep Canal with Pool
3BR+/2BA
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Sleeps 6-8
– Summerland Key #90320
4000- 4500/mo
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The Royal Retreat House
5BR/3BA
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Sleeps 2-10
– Summerland Key #437161
$500 - $800 per night 5-7 night min stay
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Tropical Deep Water Canal with Beautiful Sunsets, Good Rates
3BR/2BA
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Sleeps 6
– Summerland Key #119467
$3400/mo
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Oceanfront Home on Summerland Key
4BR/3BA
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Sleeps 9-10
– Summerland Key #249627
$ 2600-$2800/wk - $8500-$9000/mo
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Casita Marina
6BR+/4BA
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Sleeps 10-12
– Summerland Key #256032
$19600 per month 28 night min stay
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Ocean Front Summerland Home/Keys to Paradise
3BR/2.5BA
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Sleeps 2-6
– Summerland Key #241017
$2500- $7500
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Fishing and Diving or Relaxing in Paradise!
3BR/2BA
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Sleeps 6-7
– Summerland Key #374931
From $1200/wk - $3400/mo
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Wonderfull Oceanfront Home with Pool & Spa Sunsets Are Unbelievable
3BR+/3BA
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Sleeps 8
– Summerland Key #236175
10,000.00 per month
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Palm Mansion Fantastic Pool Home on Deep Water Canal in Summerland Key
5BR/3BA
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Sleeps 10-12
– Summerland Key #451644
$3800- $4500 Monthly
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Oceanfront Experience You Won't Forget!
3BR+/2.5BA
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Sleeps 8-9
– Summerland Key #211800
$7,000
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Ocean Front Cottage with Pool, (Monthly Only) Awsome Views
2BR+/3BA
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Sleeps 6
– Summerland Key #307503
5000.00
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Old Florida Style Mini-Estate
2BR/1BA
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Sleeps 6
– Summerland Key #443256
$1400 - $1603 per week 7 night min stay
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Summer Months Available!!!
3BR/2BA
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Sleeps 2-6
– Summerland Key #403469
$4800 a mo
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Cozy & Private Conch Home in Florida Keys Tropical Paradise
3BR/1BA
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Sleeps 2-4
– Summerland Key #406659
$3000.00/mo
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Nature Lover's Retreat
2BR+/2BA
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Sleeps 6-8
– Summerland Key #315985
$1600- $1800/wk Canadian Dollars
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Oceanfront Heaven - 4 / 4 , Sleeps 8, Rates: Low $6,500.00/28 Days - High $8,000
4BR/4BA
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Sleeps 8
– Summerland Key #3552534ha
$267 per night
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Charming Waterfront Home in the Lower Keys
2BR/2BA
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Sleeps 4-6
– Summerland Key #367129
$1400-$1800/wk or $4000-$5000/mo
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Charming and Private
2BR/2BA
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Sleeps 4
– Summerland Key #169213ha
$180 - $286 per night
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Living on Key West Time
3BR/2BA
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Sleeps 6
– Summerland Key #211102ha
$200 per night 6 night min stay
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Enjoy an Affordable Blissful Keys Getaway!
2BR/2BA
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Sleeps 4
– Summerland Key #271572ha
$2000 - $2500 per month 30 night min stay
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Waterfront Beauty: Kayaks, Sun Porch, Dock, Minutes to Bay or Ocean
3BR/2BA
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Sleeps 8
– Summerland Key #248807ha
$150 - $213 per night
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Caribbean Sunsets - 10 Feet from the Ocean!
3BR+/2BA
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Sleeps 8
– Summerland Key #3012143ha
$571 per night
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4 BR Summerland Key Perfect Getaway
4BR+/2BA
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Sleeps 8-12
– Summerland Key #3013471ha
$133 per night
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Summerland Seduction - Gated Ocean Front Home Along Millionaires Row!
5BR/4BA
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Sleeps 12
– Summerland Key #3013414ha
$1000 per night
- Summerland Supreme 7BR/5BA – Sleeps 12 – Summerland Key #3012141ha
- Murphy's Landing 4BR/3.5BA – Sleeps 8 – Summerland Key #102121ha
- Fishing, Diving or Relaxing in Paradise!! 3BR/2BA – Sleeps 7 – Summerland Key #911492ha
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Paradise Views
3BR/3BA
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Sleeps 6
– Summerland Key #3490836ha
$8820 per month 28 night min stay
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Seas the Keys! Vacation Paradise on Deep Water Flow Through Canal
3BR+/3BA
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Sleeps 6-8
– Summerland Key #436601
Overview of Summerland Key Vacation Rentals
Get Everything You Need for a Florida Holiday with Summerland Key Vacation Rentals
Summerland Key, a tropical paradise about twenty minutes from Key West, lets you relax and play to your heart's content. Sunbathe or watch the sun set from the deck of your Summerland Key vacation rental, or enjoy private pools or hot tubs available with many Summerland Key resort rentals. Some Summerland Key vacation rentals come with personal boat docks, fishing gear, water vehicles, and barbecues, so you can be sure to have all the amenities you desire during your stay in this island haven.
Summerland Key Resort Rentals Provide Easy Access to the Best of Lower Keys
Florida Lower Keys travel puts you on the biggest and least crowded of the islands, which means more space for you to enjoy the Atlantic Ocean, the deep canals, and beaches near Summerland Key resort rentals. Bahia Honda State Park and its famed white sand beach are close with plenty of ocean activities, bird watching, and a nature center.
From many Summerland Key vacation rentals, you can snorkel right outside your front door, but for the best local underwater scenery, take a trip to the Looe Key Reef and Marine Sanctuary less than twenty minutes away. World-class reef and deep sea fishing are available, too, and you can bring your own boat or rent one nearby. A ten-minute ride on a shuttle boat will take you to the elite and secluded Little Palm Island for a romantic picnic.
Delicious Seafood Awaits near Summerland Key Vacation Rentals
Of course, the freshest fish is whatever you catch and bring home to cook in your Summerland Key resort rental. But for meals when you want to be served, the highly recommended Square Grouper Bar and Grill has great seafood and fantastic service. Sugarloaf Food Company and The Wharf Bar and Grill are other good bets for Florida Lower Keys travel dining.
Other equally beautiful and popular but also affordable Florida Keys vacation destinations include Key Colony Beach vacation rentals, lodging in Marathon, Islamorada beach house rentals, Key Largo lodging, or Key West rentals. You are sure to find many recommended by others ideal vacation rentals available to you during your next family trip to Florida Keys.