Vacation Rentals By Owner In Summerland Key, FL

Showing 130 Of 130 Vacation Rentals

$343.51

Views Views! Direct Oceanfront, Beautiful Inside!

Summerland Key, Florida, United States

View, views, views! Totally beautiful modern home has a very large balcony which provides an opportunity for endless dreaming and relaxation as you look at the ocean and the islands directly offshore. There is also a dock for your boat and many palms to ensure you feel like you are in Paradise in the Keys!brbrThe kitchen has granite countertops and stainless appliances. Both bathrooms have dual sinks. brbrEverything is light and bright with lots of windows and doors for the view. The living room is furnished with 2 leather couches to watch the view or the flat screen TV's. There is another hideaway couch in the 2nd bedroom. brbrThe property is in Summerland Key, a short 25 minutes away from Key West.

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Exceptional(1)

$257.25

/ Nightly

Private Vacation Home

Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly

Summerland Key, Florida, United States

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to 'Lake It Easy' – Your Canal Front Oasis on Summerland Key! brbr brbrIndulge in the laid-back Florida Keys lifestyle in this beautifully updated canal-front home. Dock your boat along the sea wall, offering convenient access to world-class fishing just minutes away. Whether you're cooling off with a dip in your private pool or unwinding on the back porch with your morning coffee or a favorite cocktail, this house provides the perfect backdrop for relaxation. While there's plenty to keep you entertained on the property, 'Lake It Easy' also serves as a fantastic base for exploring the Keys. You'll discover several excellent restaurants just moments away, and the vibrant charm of Key West is a mere 35-minute drive, while the captivating town of Marathon awaits you in just 25 minutes. Whether you're seeking solace by the water's edge or eager to uncover the treasures of the Florida Keys, 'Lake It Easy' promises an unforgettable escape where relaxation and adventure go hand in hand! brbr brbrSLEEPS MAXIMUM OF 10 GUESTS: brbr brbrBedroom 1: King Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: King Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3: Queen Bed & Twin Bunk Beds, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Sectional Sofa with Pull Out Full Bed, Two Chairs, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Saltwater Pool (heated to ~85 degrees Nov-Apr, 18' x 10', depth 3.5' to 5.5') brbr brbr- 20' of Dockage available (owners boat on lift & lift is not available for guest use) brbr brbr- Fish Cleaning Station brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Parking for a maximum of 3 vehicles (including boat trailers) on the property. Recreational Vehicles may not be parked on the property. brbr brbr- Linen's and towels provided brbr brbrIMPORTANT POLICIES FOR YOUR STAY: brbr brbrAge & Occupancy: The booking tenant must be 25 years or older and must occupy the property for the entire duration of the stay. This property is exclusively available as a vacation rental and not for worker housing. brbr brbrPeak Season Monthly Bookings: All bookings from December through March must be for the entire month, starting at the beginning and ending at the end of the month. Consecutive months may be booked if they follow this requirement. Bookings that do not adhere to this policy are subject to cancellation. If you are interested in alternative dates, please contact us for approval before booking. brbr brbrPet Policy: Up to two friendly and well-behaved dogs 100 LBS OR LESS will be considered with a $10/night pet fee. To help maintain a safe and welcoming environment for all, we require every guest to submit pet or assistance animal information through BetterPet Passport. Guests will simply submit household pet information, request an accommodation for an assistance animal, or confirm they are not bringing a pet/animal. It's free, and only requires creating an account if you're bringing a pet or animal. After booking, you'll receive a link to complete the process. brbr brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrMid-Stay Cleaning: For stays of 28 nights or more, we reserve the right to require a mid-stay cleaning to maintain the quality of the property. For longer stays, a mid-stay cleaning will be required every 28 nights thereafter. The cost will be collected separately, and the number of cleanings depends on the length of your stay. brbr brbrBoating & Dockage Advisory: Due to bridges and varying water depths, it is your responsibility to ensure that your boat can safely navigate local waters, access the canal, and fit the listed dockage before booking. While we are happy to provide general information based on our knowledge of the area, guests must exercise extreme caution when boating and ensure all activities comply with local regulations. brbr brbrLocal Wildlife & Pest Control: The Florida Keys are home to various insects (mosquitoes, no-see-ums, termites), reptiles, chickens, Key deer, and other wildlife. While routine pest control is in place, complete elimination is not possible. Guests should take precautions, such as using insect repellent and keeping doors closed, to minimize exposure. brbr brbrConstruction & Renovation Notice: Due to ongoing growth in the Florida Keys, renovations, construction, and road repairs may occur without prior notice. While we strive to provide a peaceful stay, iTrip Key West is not liable for any inconveniences caused by nearby construction. brbr brbrPhoto Disclaimer: All images are for illustrative purposes only. Individual features such as bed sizes, bedding, décor, appliances, colors, and amenities may vary, as these are privately owned homes and updates occur regularly. Lighting conditions and screen settings may also affect how colors appear. Please refer to the written description and reach out with any specific questions or concerns. All furnishings and décor are subject to change at any time.

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$354.75

/ Nightly

Private Vacation Home

Summer Breeze on Summerland Key

Summerland Key, Florida, United States

Relax on the large porch overlooking a beautiful,flow through,crystal brclear,deep water canal with excellent boating access to the Atlantic bror the Gulf.Looe key reef is only ten minutes by boat along with brsome of the best diving and fishing the keys has to offer.Or you may brjust want to fish from the dock,as there is a abundance of brsnapper,grouper,tarpon and lobster just steps from the door.This is a brnew home with a fenced in yard with plenty of parking and dock brspace.The interior decor and tropical colors compliment this brbeautiful custom home.And fuel and bait is just right down the brcanal.Master bedroom has king size bed ,bedroom two has a queen size brbed,room three has two sets of bunkbeds twin-full and the couch also brpulls out as a bed.brNo SmokingbrNo Pets

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Exceptional(7)

$380.73

/ Nightly

Private Vacation Home

PARADISE on Sugarloaf Key! 704-650-8105 Summer and Fall low rates.

Summerland Key, Florida, United States

Breathtaking Open Water Views. This spectacular home is in impeccable condition. New Custom Pool. Dock up to a 31' boat. 2 kayaks and 2 bicycles for your use. Beautiful landscaping. Oversized covered porch. Super fast WiFi Cable 75inch TV. Gourmet kitchen. Washer and dryer. Extra refrigerator and freezer in the air conditioned downstairs space. Super Clean. Plenty of parking. 6 person maximum. LOCAL Laws require a 28 Day minimum rental.

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$511.32

/ Nightly

Private Vacation Home

New 3BR Ocean-Side Home on Little Torch Key, hidden gem - 28 Miles from Key West

Summerland Key, Florida, United States

If it’s hidden gems you’re after, Little Torch Key is calling.brTucked away at Mile Marker 28, this quiet island is one of the Florida Keys’ best-kept secrets—offering a more relaxed, authentic Keys experience without the crowds.brbrWelcome to your perfect island retreat: a bright, breezy 3-bedroom, 3-bathroom home just steps from the water. With 1 king bed and 2 queen beds, it comfortably sleeps up to six—ideal for families, couples, or friends seeking sun-soaked adventure or total relaxation.brbrInside, you’ll find everything you need: air conditioning, WiFi, heating, and a washer/dryer to make your stay as effortless as it is unforgettable. Each bathroom includes a refreshing shower, and the serene coastal decor sets the tone for easy island living.brbrSpend your days snorkeling, fishing, kayaking, or venturing into vibrant Key West—just a 30-minute drive away. Afterward, return to peace, privacy, and ocean breezes. Stroll down the street to Kiki’s Sandbar Bar & Grille, where you can enjoy fresh seafood with your toes in the sand, live music every night, and a great happy hour with water views.brbrWhether you're here for the quiet or the adventure, you'll find it on Little Torch Key.brBook your stay today—we’d love to welcome you.

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Exceptional(11)

$139.26

/ Nightly

Mobile Home

Little Torch Tropical Oasis April Available

Summerland Key, Florida, United States

LITTLE TORCH TROPICAL OASISbrbrThis Beautiful Oasis is a recently renovated Manufactured Home on the corner of 2 Crystal Clear Swimming Canals. The backyard has a Sun Deck with custom Swim Ladder. Please note this is not a boating canal but you can swim, float or snorkel in your own back yard. This home has all the amenities you may need and more. It has a gas BBQ Grill. It's on a large fenced in lot with a nice shady area under Florida Native Gumbo Limbo Trees. Enjoy your own private spa on the large front deck. Wifi and Ethernet connection for Internet use included.brbrThis home is located about 30 minutes from Historic Key West where you can enjoy Shops, Restaurants and World Famous Entertainment. If you like Boating, Fishing and Snorkeling it is located in a great area minutes from the Ocean and about 6 miles by boat to the amazing Coral Reefs of Looe Key Sanctuary. This home is not on a boating canal but there is plenty of space for parking a boat and the local boat ramp is less than a mile away. Bait shops are minutes away. Roku Smart TV available. brbrNearby are local Restaurants, Grocery Stores, Pharmacy, Bait and Tackle Shops, Banks, Post Office, Boat Rental and a Weekend Flea Market. High season and low season rates, please inquire. Please make sure to contact the me, the owner, before booking online as availability can change daily. No pets allowed. No Smoking permitted.brbrbrbrThank you!brbrAdditional photos and information are available upon request.brbrbrbrKeywords: Manufactured Home

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$213.75

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Private Vacation Home

Spectacular waterfront views! Boaters Paradise! 2bd/2-1/2bath. Dock space too!

Summerland Key, Florida, United States

Your cozy getaway awaits in Summerland Key at this charming townhome. Inside, guests find two comfortable bedrooms with king and queen beds with private baths and a first floor half bath. Boaters paradise with dock space for an additional charge. Pets welcome too with an extra fee.brUpscale living with many amenities which include two heated pools, gym, sauna, kayaks, beach and game area. Local bar and restaurant next door. A great place to enjoy the best of the Florida Keys, brThis is a month to month rental only with a minimum of 3 months preferred. Monthly fee $5,500. This rental is available until June 30th, 2026. Not available after this date!brPlease contact us for more photos and information! All renters are screened before booking!

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$295.03

/ Nightly

Private Vacation Home

Island Comfort at Cudjoe Key

Summerland Key, Florida, United States

Your Keys Getaway! Escape to paradise with this charming 3-bd, 2-ba canal-front home, perfect for those looking to unwind after a long day of fishing and exploration. Equipped with a concrete dock and davits, enjoy easy boat access to Cudjoe Bay. Head out to your favorite fishing spots directly from your backyard! Relax on the deep screened porch, offering expansive space for outdoor living. Just 23 miles from Key West. Come see why this is the perfect spot for your next getaway!

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Exceptional(2)

$155.44

/ Nightly

Private Vacation Home

Cozy 2-bedroom house in charming Little Torch Key

Summerland Key, Florida, United States

Discover the beauty of Little Torch Key from this beautiful 2-bedroom house. With 1 queen bed and 2 full beds, guests can enjoy a comfortable stay. The property offers amenities like AC, heating, WiFi, and a washing machine and dryer. 1 bathroom is equipped with shower and tub and master bath is equipped with a shower. Home is 28 miles from Key West and 10 miles from Bahia Honda State Park. We look forward to welcoming you to our place.

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$265.82

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Private Vacation Home

Tarpon Canal | Like-new retreat

Summerland Key, Florida, United States

Summary:brbrCozy waterfront 3 bed/2 bath home on Ramrod KeybrbrbrbrThe Space:brbrNicely appointed and nearly new, this 3 bedroom/2 bathroom home sits on a clear swimming canal on the gulfside of Ramrod Key. It's the perfect spot for your Florida Keys getaway.brbrbrbrEnjoy the spacious great room and open deck with canal views. Comfortable living room furnishings and a table for 6. Tons of cabinets and new appliances in the roomy kitchen with breakfast bar. The primary bedroom features a king bed, flat-screen TV and an en-suite bath with double sinks, large shower and walk-in closet. The two guest bedrooms feature queen beds. The shared hall bath has a tub and shower. Separate laundry room.brbrbrbrThis home features 30-foot observation dock and swim ladder. There's no open water access via the plugged canal, but you can swim, canoe and kayak through the neighborhood. There are several boat ramps nearby and plenty of room for you to park your boat trailer. Tropical landscaping. Gas grill.brbrbrbrHigh-speed Internet and WiFi.brbrbrbrRamrod Key is a quiet, mostly residential island conveniently located midway between the cities of Marathon and Key West. There's also a small commercial district -- Boondocks Grille & Draft House and Miniature Golf, Looe Key Reef Resort's tiki bar and restaurant, Five Brothers Grocery Two, and a gas station -- for your convenience and enjoyment. The Key West city bus runs between Marathon and key West stops on the island several times a day.brbrbrbrThis home requires a minimum 28-day stay per county ordinance. Proper county and state taxes are collected regardless of booking platform. Renter must be 25 or older. Overnight occupancy is limited to a maximum of 6 people, and all guests need to be registered with the property manager. No smoking on the property. Small dog under 20 lbs permitted with manager approval and nonrefundable $150 fee. There's a cap on electric use ($200) and water/sewer ($150).

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Rent a place that suits your needs

Private vacation home

View 115 Private vacation home

Most popular vacation rentals in Summerland Key

$493.85

/ Nightly

Private vacation home

Starlight Serenity - Hideaway with Stunning Views

Summerland Key, Florida, United States

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$444.09

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Private vacation home

Ocean Front Modern Home

Summerland Key, Florida, United States

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$444.87

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Private vacation home

Oceanfront Home With Large Private Deck with boat dockage

Summerland Key, Florida, United States

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$449.68

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Private vacation home

Sunset Serenity – 3BR Open Water Oasis On Summerland Key Boat Dockage, Stunning Views & Pet Friendly

Summerland Key, Florida, United States

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$454.65

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Private vacation home

PEACEFUL PARADISE DEEP WATER CANAL! MINUTES TO OCEAN Fishing and Lobster season

Summerland Key, Florida, United States

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$473.19

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Private vacation home

Sea Glass House of Summerland Key! Pool, 70 feet of Seawall, deep water canal!

Summerland Key, Florida, United States

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$473.30

/ Nightly

Private vacation home

Oceanfront Sunsets in the Florida Keys

Summerland Key, Florida, United States

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$481.97

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Private vacation home

Warm and relax 3-bed 2 bath home in charming Summerland Key minutes from K.West

Summerland Key, Florida, United States

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$488.95

/ Nightly

Private vacation home

Beachside @ Torchview Waterfront Retreat

Summerland Key, Florida, United States

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$927.03

/ Nightly

Private vacation home

Waterfront Beach House with Dock & Heated Pool!

Summerland Key, Florida, United States

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Vacation Rentals By Owner In Summerland Key, FL

$343.51

$257.25

$354.75

$380.73

$511.32

$139.26

$213.75

$295.03

$155.44

$265.82

Rent a place that suits your needs

Most popular vacation rentals in Summerland Key

$493.85

$444.09

$444.87

$449.68

$454.65

$473.19

$473.30

$481.97

$488.95

$927.03

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