Home Vacation Home Rentals By Owner In Summerland Key, FL

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Exceptional(5)

$289.01

/ Nightly
Private Vacation Home

3/2 on the Water in Paradise Monthly Rental 28 Day min.

Summerland Key, Florida, United States

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 small community that is only 24 miles north of Key West. Amazing fishing, diving, snorkeling, kayaking and paddle boarding available right here in this fantastic area. We also have 3 bicycles and 3 kayaks (one is a double) on property for your use as well. Our kitchen is brand new, with quartz Carrera marble countertops. All stainless appliances. Top of the line appliances include dishwasher, refrigerator, microwave, Kuerig coffee maker, toaster and of course a blender. All pots, pans, dishes, cups and utensils you need in a fully stocked kitchen to enjoy your stay and cook at home if you chose. Living room boasts a 55” smart tv with Ruku, Netflix and WiFi. We have a Bose bluetooth speaker to hook up your favorite music to. Games, magazines and books should you want to just chill and relax. Central air throughout the home and a ceiling fan in every room. Master bedroom has a pillow top mattress with quality linens, extra pillows and blankets. Full bathroom is adjoining the master. Queen pillow top bed in second bedroom with top quality linens, extra pillow and blankets. The 3rd bedroom has two twin beds, with a 43” smart tv with same system as living room. The other full bath is located in the hallway from living room to bedrooms. This home will comfortably hold your family or group of 6. Up on the deck, we have a dining table and chairs to enjoy the sunrise/sunset or have a fantastic dinner outside while looking at the amazingly calm water. Downstairs, at the TiKi area we have a comfortable fire pit/seating area. This is a great place to unwind and enjoy your keys time. BBQ grill located on deck to cook your catch of the day. Inside by the TiKi, there is a full size washer/dryer and an extra fridge for your drinks and for freezing bait. There is also public transportation to Key West from our neighborhood. brbrThis is a once a month rental only so the days are flexible.
Bed 3

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Bath 2

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Sleep 6

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Exceptional(19)

$444.09

/ Nightly
Private Vacation Home

Ocean Front Modern Home

Summerland Key, Florida, United States

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.brbrThere 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 because monkey research was once performed there. brbrInterestingly, the research was stopped due to 'monkey business,' i.e that the primates began swimming to the mainland, creating some havoc and threatening to eventually outnumber the local inhabitants. The spectacular view is effectively captured by virtue of numerous expansive windows and sliding doors, all of which complement an already-bright and cheery interior.brbrWhile virtually every room is afforded this unique ocean panorama, the top floor, housing only the master bedroom suite, is especially unique. Here, one is treated to an ocean-front balcony, king-size bed fronting the Atlantic, walk-in closet, bidet, and a spacious bathroom with two-headed shower for those who enjoy joint bathing. There are two bedrooms, on the main level, likewise roomy suites, tactfully furnished and endowed with their own bathrooms and balconies. Icing on the cake - Each bedroom has its own flat-screen HD TV with surround sound. The final bedroom is on the 1st floor and has a beautiful view of the ocean out back and furnished with 2 twin beds.brbrThe spacious living/family area, bordered on the ocean side by a cozy sun room, is bright, tastefully furnished, and, above all, comfortable and inviting. A 55-inch flat-screen LED TV, with surround sound, tops off this unique ocean setting. Also on this level, in addition to the two bedrooms and baths, is a gourmet kitchen equipped with stainless-steel appliances. brbrThe kitchen is bordered by an enclosed washer and dryer, breakfast bar/snacking area, a full dining room, and a balcony overlooking the tropical pool and ocean. The balcony, with a small seating area, is equipped with a gas grill, anxiously awaiting the fresh fish and lobsters to be caught off a large deck on the lower level. (see below).brbrThe lower level, with ample storage space for fishing/snorkeling/swimming gear and other needs, opens, in the front, to a large circular driveway surrounded by lush greenery, and, in the back, to a tropically-landscaped pool and patio area. Here, one enjoys the comfort of a table and chairs and numerous chaise lounges. Attached to the in-ground pool is a hot tub and, along side, a shower. A few steps down from the pool/patio area is an expansive concrete deck, suitable for sunning, fishing, boat docking (off the back sea wall, boat lift not included), or simply viewing the boats gliding by, with the ocean and islands as a backdrop. brbrIn summary, this tropical paradise, which enjoys a post-card type sunset and surroundings, awaits those with a penchant for a 'margaritville-like' atmosphere. Located some 25 miles north of Key West and just south of Deer Key and Marathon Key, one is treated to the peace and tranquility of family-oriented Summerland Key, albeit with proximity to the night life, shopping, and other advantages of the larger keys. This is not to say, however, that restaurants, with rustic nautical decor and savory food, do not exist nearby, both by land and sea, as do stores for basic shopping and groceries.brbrOne final, but highly significant, note - The highly-affable and capable manager of the home is a long-time local resident who lives nearby and is a readily-available troubleshooter and purveyor of valuable tidbits and suggestions. His value is attested to by the comments below from previous tenants. In short, come relax in this tropical abode. You will almost certainly want to return.
Bed 4

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Bath 3

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Sleep 9

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$569.65

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Private Vacation Home

Summerland Serenity Elevated Waterfront Luxury with Private Elevator & Pool

Summerland Key, Florida, United States

Summerland Serenity Elevated Waterfront Luxury with Private Elevator & PoolbrbrWelcome to Summerland Serenity, an exceptional five-bedroom, five-and-a-half-bath waterfront estate designed for refined Florida Keys living. Thoughtfully curated for extended stays, this exclusive retreat blends modern coastal elegance, effortless accessibility, and resort-style amenities in a serene Summerland Key setting.brbrFrom the moment you arrive, soaring ceilings, expansive windows, and sophisticated finishes create an atmosphere of understated luxury. The home's private in-residence elevator provides seamless access to every level, offering both convenience and comfortideal for multi-generational groups and long-term guests.brbrEach of the five bedrooms serves as a private sanctuary, featuring its own en-suite bathroom and carefully selected furnishings. Four suites offer king beds, while the fifth bedroom is appointed with four custom built-in bunks, perfectly suited for families or guests seeking flexible sleeping arrangements. Two additional half baths add to the home's thoughtful design.brbrAt the heart of the residence, the gourmet kitchen showcases premium appliances, custom cabinetry, and an expansive island designed for both casual mornings and elegant entertaining. The open-concept layout flows effortlessly into multiple indoor and outdoor living spaces, allowing for a seamless connection to the surrounding waterfront environment.brbrOutdoors, indulge in your private pool oasis, complemented by a fully equipped outdoor kitchenideal for alfresco dining, sunset cocktails, and relaxed evenings under the Keys sky. Boating enthusiasts will appreciate the 60 feet of private dockage, complete with Gulf access, a 10,000 lb boat lift, shore power, and wateroffering effortless access to world-class fishing, diving, and island exploration.brbrAdditional conveniences include under-home boat trailer storage, ample parking, and a 4-person electric golf cart, included for stylish neighborhood cruising and island exploration.brbrPerfectly positioned in Summerland Key and just a short drive from Key West, Summerland Serenity delivers a rare blend of privacy, sophistication, and waterfront lifestylean elevated escape for those who expect nothing less than exceptional.brbrWhy Guests Love Summerland Serenity: brbrPrivate in-home elevator for effortless access to every levelbrbrPrime waterfront setting with 60 ft of dockage and Gulf accessbrbrResort-style private pool with a fully equipped outdoor kitchenbrbrFive spacious en-suite bedrooms for ultimate privacybrbr10,000 lb boat lift, shore power, and water at the dockbrbrElectric golf cart included for easy island cruisingbrbrQuiet Summerland Key location, just minutes from Key WestbrbrThis property is Not pet friendly so pets are not allowed on the property. Owners are highly allergic to dogs. Failure to adhere to this rule will result in a charge up to $500 and asked to vacate without a refund.brbrConcierge Services - Enhance your stay with our concierge services, designed to create a seamless and memorable Florida Keys experience. Our concierge agent, Kasey Platt, can assist with everything from private boat charters, snorkeling, fishing trips, and eco-tours to in-home massages, private chefs, and unique entertainment like fire shows or dancers. She can also help arrange grocery deliveries, kayak or fishing gear rentals, charcuterie boards, and more.brbrBorn and raised in Marathon, Kasey has strong local connections, allowing for personalized recommendations and exclusive experiences. More details on available services and how to coordinate them are shared with guests after booking. If you have any questions in advance, please let us knowwe're happy to help! brbrVacation Rentals of the Florida Keys (Vrotfk) has Terms and Conditions that apply to this property and all properties we manage. By booking this propertywhether directly with us or through a third party siteyou and your party expressly agree to these Terms and Conditions. A deposit or completed booking serves as acknowledgment and acceptance of these terms. After your reservation is confirmed, the Terms and Conditions will be sent to you via an e-sign document, which is required to be completed. If the e-sign is not completed, access to the virtual guidebook and arrival details will not be provided. Please feel free to reach out with any questions. Additionally, we will request certain information that third-party sites may not collect, as we are required to have specific details on file per company policy and local city regulations.brbrThings to Note:brbr- This property has a 28 night min brbr- Must be 25 years or older to book and must be present for the entire staybrbr- 12 guests: Max occupancy reflects the number of guests allowed per city regulations and does not guarantee sleeping accommodations for that numberplease review the bed description carefullybrbr- Check-in: 4:00 PM on the day of arrival brbr- Check-out: 10:00 AM on the day of departurebrbr- Dockage is available at this property; please verify maximum boat size and dockage details with the property manager prior to booking brbr- This property is not pet friendly brbr- Vacation Rentals of the Florida Keys provides a complimentary starter set of items, including soap, toilet paper, paper towels, dishwasher detergent, and laundry detergent. Guests are responsible for providing additional supplies for the remainder of their stay. Starter items are typically located in the bathrooms, at the kitchen sink, and in the laundry area.brbrAmenities Include:brbr- Air Conditioning: yes - centralbrbr- Kitchen: yesbrbr- Private Entrance: yesbrbr- Smoke Detector: yesbrbr- Bait Freezer: yesbrbr- Bed Size 1st/Master: King with en suite bathbrbr- Bed Size 2nd Rm: King with en suite bathbrbr- Bed Size 3rd Rm: King with en suite bathbrbr- Bed Size 4th Rm: King with en suite bathbrbr- Bed Size 5th Rm: 4 twin bunk beds (built in)brbr- Child Friendly: yesbrbr- Coffee Maker: yesbrbr- Pool: private - heated & chilledbrbr- Stand Alone Ice Machine: yesbrbr- Balcony: yes - each room has its own (except bunks)brbr- Bbq Grill: yes - outdoor kitchen downstairsbrbr- Ceiling Fans: yesbrbr- Elevator: yesbrbr- Internet Access: yesbrbr- Micro/Dishwash/Disp.: yesbrbr- Refrig And Ice Maker: yesbrbr- Stove/Oven Elec/Gas: yesbrbr- TV Cable/Satellite: Smart TVs - Youtube TVbrbr- View: canal view, waterfront, near oceanbrbr- washer dryer: yes in housebrbr
Bed 5

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Bath 6

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Sleep 12

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Exceptional(1)

$280.82

/ Nightly
Private Vacation Home

FLORIDA KEYS PARADISE! DEEP WATER CANAL WITH FAST OCEAN ACCESS.

Summerland Key, Florida, United States

Carribean Paradise is a beautiful 3 bedroom 3 bathroom house in a quiet, beautiful neighborhood. Large corner lot with boat ramp, dock and plenty of parking. There is a king in the master and a queen in the two rooms. There is a sectional couch in main living area with pullout queen. This house has an open living and dining room area, new stainless steel appliances in the kitchen and a screened in back porch. Large TVs in all living spaces and bedrooms, wireless internet, wireless printer, full size washer/dryer. Huge backyard with lots of comfortable seating for relaxing and eating. The dock features fresh water, electricity and two fish cleaning tables. Best part is the deep water flow through canal with less than a minute travel time to the Atlantic or the Gulf. Just a short boat ride to the great deep sea fishing or to the famous Looe Key coral reef for some of the best snorkeling/diving in North America. Sightseeing and shopping in Key West is just 24 miles away. brbrYou can drive over to Bahia Honda State Park (named among the United States’ top 25 beaches), a short 15 minutes away. Key West is a short drive away, through the most breathtaking, scenic section of the famous overseas highway. In Key West, take the Conch Train tour; visit Ernest Hemingway's house, and then Mel Fisher's Museum where they display the remarkable treasures from the Spanish Galleon the Atocha, shipwrecked in 1622. Have your picture taken at the Southernmost Point, then head over to famous Duval Street and do the Duval Crawl down to Sloppy Joe's, Margaritaville, the Hog's Breath Saloon, Captain Tony's, Schooner Warf, and finally head over to Mallory dock, Mallory Square, for the nightly sunset celebration.brbrCheck out the restaurants and nightlife a little closer to home. brSquare Grouper and My New Joint are just two miles way. You can enjoy classic cocktails and swanky tapas upstairs at My New Joint while listening to live music. Then head downstairs to Square Grouper for an unforgettable meal at the annually rated top restaurant of all the keys. Both the Kiki's Sandbar and Boondocks are fun local hangouts, and feature good food, full bar, and live music nightly. Kiki's is a short 5 mile drive with corn hole and swings. The famous No Name Pub is on Big Pine Key, bring your dollar bills so you can personalize and staple to the wall. Other great restaurants close by are: Galley Grill for a wonderful breakfast, Tonio's on Summerland Key, Mangrove Mamma's on Sugarloaf Key, Looe key for excellent live music.brbrThere is something for everyone at this well equipped home, so what are you waiting for Start planning your own good times, down in the lower keys. Contact us today!
Bed 3

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Bath 3

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Sleep 8

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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.
Bed 3

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Bath 2

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Sleep 10

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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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Bath 2

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Sleep 6

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