Vacation Rentals By Owner In Summerland Key, FL

$254.76

L' archipel | Brand new dock!

Summerland Key, Florida, United States

Summary:brbrCanalfront 2 bedroom retreat on Ramrod Key with brand new dock!brbrbrbrThe Space:brbrWelcome to L’archipel, a charming, newly remodeled monthly rental that offers an ideal retreat for those seeking a relaxing getaway in the Florida Keys. Nestled on a serene canal, this property is a haven for water enthusiasts and nature lovers alike. With 2 bedrooms, 1 1/2 baths, and a host of modern amenities, this home promises a comfortable and enjoyable stay.brbrbrbrAs you step inside, you'll immediately notice the newly updated interior and furnishings. The living area is bright and airy, providing the perfect space to unwind after a day of exploring the Lower Keys or enjoying water activities. The fully equipped kitchen is a delight, featuring stainless steel appliances, granite countertops and ample cabinet space. Prepare delicious meals and savor them at the bar with seating for 4 or outside on the screened porch.brbrbrbrThe two bedrooms are thoughtfully appointed to ensure a restful night's sleep. The primary bedroom boasts a comfortable queen-sized bed, while the second bedroom features a queen bed and a twin-bed bunk set — perfect for small families or friends traveling together. Both bedrooms are tastefully decorated and offer plenty of storage for your belongings.brbrbrbrPower boaters will love the brand new dock! Bring your own boat or rent one locally to explore the surrounding waters at your leisure. Spend your days fishing, paddling or simply basking in the warm Florida Keys sun.brbrbrbrWhen you're not out on the water, take advantage of the covered screened porch. Enjoy alfresco dining or simply unwind while admiring the views of the canal. The property also offers ample parking space for your convenience.brbrbrbrThis monthly rental offers a tranquil and secluded setting while still being within easy reach of local attractions. Explore nearby Bahia Honda State Park, known for its pristine beaches and excellent snorkeling opportunities. Key West, with its vibrant nightlife, shopping, and dining scene, is just a short drive away, allowing you to experience the best of both worlds.brbrbrbrBreezeswept Beach Estates is a quiet neighborhood on the ocean side halfway between Key West and Marathon. Ramrod Key has a small commercial district to make your stay even more convenient: Boondocks Grille & Draft House and Miniature Golf, Looe Key Reef Resort's tiki bar and restaurant, Five Brothers Grocery Two, and a gas station/convenience store. The Key West city bus stops on the island on its way between the Southernmost City and Marathon and offers several stops along the way.brbrbrbrWhether you're seeking relaxation or adventure, L’archipel provides the perfect base for your Lower Keys vacation. Book your stay today and create lasting memories in this newly remodeled canalfront retreat.brbrbrbrThe primary guest must sign a rental agreement. This 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 overnight guests need to be registered with the property manager. No smoking. There's a cap on electric ($250) and water/sewer ($150).

3

Bed

1

Bath

6

Sleeps

$819.84

/ Nightly

Private Vacation Home

Villa Jekjak

Summerland Key, Florida, United States

Summary:brbrVilla Jekjak- 4 BDR, luxury residence with pool & beachbrbrbrbrThe Space:brbrEnjoy 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.brbrAmble of natural light emphasizes the open and easy-flowing design of the main floor. Well-equipped chefs kitchen has top-of-the-line appliances and is a perfect retreat for culinary-inspired guests.brbrHighlighted by the walls of glass doors, Family Friendly floorplan combines the living room, dining room and opens to the oceanfront terrace. The vaulted ceiling adds great drama to the space.brbrLight & Airy Master Suite features King Bed, a private Master Bathroom with a stand-up shower, and a large walk-in closet.brbrThe guest wing offers generously scaled 2 bedrooms and a shared bathroom.brbrThe downstairs Guest Quarter enclosure has an additional private queen bedroom, rec room, TV area, and a wet bar and full bathroom.brbrThe private pool is nestled on a sandy beach and surrounded by meticulously maintained grounds. Deep access to world class fishing and free dockage makes this house a boaters paradise!brbrThis house is truly Paradise Found!brbrThe property is PET-friendly with a non-refundable PET fee.brbrbrbrAdditional features:brbrWasher & DryerbrbrCentral AC & ceiling fans throughoutbrbrStarter supply paper productsbrbrStarter set cleaning productsbrbrLinens, bath, and pool towelsbrbrKitchen cookware, dishes, flatware, glasswarebrbrWireless high-speed internetbrbrFully fenced private residencebrbrHousekeeping services availablebrbrOriginal ArtbrbrPrivate dockbrbrPrivate Beach and a hammockbrbrOutdoor ShowerbrbrbrbrBEDROOMSMaster- King BedbrbrGuest Bedroom #1- Queen BedbrbrKids Room- Bunk BedbrbrDownstairs Guest Quarter- 1 Queen Bed

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$308.79

/ Nightly

Private Vacation Home

Stunning Sugarloaf, 3 bed house on huge plot to accomodate your RV or boat.

Summerland Key, Florida, United States

Set on the beautiful Sugarloaf Key, our house will offer you comfortable living in the most friendly of communities. brInside there are three bedrooms. One King with en suite. Two further bedrooms with Queen beds and further bathroom. Each bedroom has a TV. There is a large kitchen with all facilities you would need including a dishwasher, washing machine and dryer. The comfortable lounge has fabulous views down the canal. The Wi Fi is fast and there is a printer if needed. Working from here is easy!brOutside living is what its all about with comfortable seating and dining furniture, grill, fridge freezer and W.C. brThe Wooden Swimming Platform can accommodate a small boat and provides access to our crystal clear swimming canal. brDownstairs is fully lit so enjoy your warm evenings drinking cocktails with a wonderful view.brThe large plot has plenty of room for any vehicle or boat that you travel with. brWith superb bars and restaurants a short drive away, you can mix with the locals or take the 20 min drive into Key West. Sugarloaf Marina is 2 mins away for all your boating needs including a public ramp. Easy access to the Sand Bars brCome and immerse yourself in local life- fabulous neighbours who will make you most welcome!

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Bath

Sleeps

$231.78

/ Nightly

Private Vacation Home

Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite Community.

Summerland Key, Florida, United States

28 consecutive day minimum rental. Lower Keys Living at its very best. This This Modern 1,700 sq ft Old Florida Keys Waterfront House is located on Lower Sugarloaf Shores at Mile Marker 17, a half mile off of US 1 in an extremely quiet neighborhood and is available for 28+ day rentals. It is a three bedroom, three baths elevated house. All of the bedrooms are located on the second floor with two full bathrooms. Each bedroom has a queen size bed, closet, dresser, nightstand and TV. The bathroom in the master bedroom has a shower/tub. The second bathroom has a shower only. The third bathroom is conveniently located on the ground floor in the garage. This is a great vacation property, not a party house... This house is completely furnished with everything you will need for your vacation stay. The Full-sized kitchen has a beautiful granite countertop and is complete with a glass top stove, microwave, dishwasher, refrigerator/freezer and garbage disposal. A complete collection of cookware and flatware is provided. All of the essential linens and towels are provided and there is a full-sized washer and dryer available downstairs. TVs and Wi-Fi are provided in every room. Every TV is supported with a fire stick to access your streaming services. There is no Cable TV coming into the house. brbrThere is a spacious 40’ x 15’ screened in lanai overlooking the waterfront with canal and bay views. For your comfort, there is a trestle table and benches for a relaxing morning coffee or outdoor dining any time of the day. There is also a couch and comfortable chairs for conversation or a glass of wine. The walk around balcony surrounding the house provides a view of the entire property without having to leave the second floor.brbrThe house is located on a crystal-clear deep-water canal that's great to swim in with 100’ of dock space and overlooks a beautiful bay. This wonderful location allows access to the Gulf of Mexico with world class back water fishing, as well as the Atlantic Ocean with fantastic patch reefs and deep water fishing in the Gulf Stream. Beautiful reefs in the Lower Keys provide some of the best diving and snorkeling in all of Florida. A word of caution, the waters in Sugarloaf Key can be shallow in areas, so navigational care and a good understanding of the local waterway is required. For your recreational enjoyment there are ocean kayaks and bicycles available for use. There is a gas grill, beach chairs and umbrellas.brbrLocated halfway between historic Key West and Big Pine Key with its endangered Key Deer. Both are good for shopping and restaurants. Grocery shopping is within minutes of the house. Key West is also very popular for its night life, museums, beach, airport as well as many other attractions.brbrThis family friendly, and pet friendly house is used frequently throughout the year by the owners and is being offered for rental to those who are willing to care for it as much as we do.

3

Bed

3

Bath

6

Sleeps

$465.4

/ Nightly

Private Vacation Home

Bayside Beauty, 3 bedroom with pool

Summerland Key, Florida, United States

Indulge in the ultimate tropical escape at Bayside Beauty, a stunning 3-bedroom home nestled in the exclusive South Point neighborhood on Lower Sugarloaf Key!br brPerched along the shores of Sugarloaf Sound, this luxurious vacation rental offers unrivaled panoramic views that paint an enchanting picture of paradise. Step into your own private oasis, where the allure of the Florida Keys comes alive. The expansive living spaces seamlessly blend with the breathtaking outdoor scenery, creating an ambiance of tranquility and luxury. With a design inspired by the tropics, Bayside Beauty is a true haven for those seeking relaxation and rejuvenation. The highlight of this retreat is the private 60 ft. grotto-style pool, adorned with a magnificent sailfish fountain, offering a unique and refreshing swimming experience. Lounge on the spacious deck, basking in the warm sunshine, or take a dip in the pool to cool off while enjoying the serene surroundings. Located a mere 25 minutes from the vibrant energy of Key West and 45 minutes from the charming town of Marathon, Bayside Beauty is perfectly situated for those seeking both adventure and relaxation. Immerse yourself in the local culture, savor delicious cuisine, and explore the unique attractions of the nearby islands. Escape to Bayside Beauty and experience the perfect blend of luxury, natural beauty, and convenient access to the best that the Keys have to offer!br brSLEEPS A MAXIMUM OF 8 GUESTS:br brBedroom 1: King Bed, En-Suite Full Bathroom, Flat Screen TVbr brBedroom 2: King Bed, En-Suite Full Bathroom, Flat Screen TVbr brBedroom 3: Twin/Full Bunk Bed, Twin Bedbr brLiving Room: Sofa, Loveseat, Two Chairs, Flat Screen TVbr brKitchen: Nicely equipped (all things necessary to prepare and serve a meal)br brAMENITIES:br br- Saltwater Heated Pool (Heated to ~80 degrees Nov-Apr)br br- 60' Waterfront (limited boat dockage, owner's boat stored on boat lift)br br- Fish Cleaning Station with Waterbr br- Outdoor Seatingbr br- Propane BBQ Grillbr br- Parking for a maximum of 4 vehicles (including boat trailers) on the property. Recreational Vehicles may not be parked on the property.br br- Linens and towels providedbr brThis is a non-smoking home. This home is a 28-day minimum rental per Monroe County Code. The security deposit on the quote also includes utilities which consist of electric and water.

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$232.76

/ Nightly

Private Vacation Home

Relax at the flying hogfish

Summerland Key, Florida, United States

Located on beautiful Summerland Key, this is the perfect vacation home for any family. Just 20 minutes from Key West and minutes from Looe Key. Enjoy the private pool and large sun deck for BBQing or relaxing. Canal access is perfect for kayaking and there is only a 10 minute boat ride to the ocean. A canoe and Four kayaks are provided for vacationers (2 adult and 2 childrens kayaks) as well as use of kayak dock, fish cleaning table, and bait freezer. The kids are sure to be entertained by the private air strip located on the street side of the home. All linens are provided and other amenities include table tennis, cable television, internet, central A/C and washer & dryer. Please call or email with all your vacation stay requests.

3

Bed

2

Bath

6

Sleeps

$322.95

/ Nightly

Private Vacation Home

Waterfront Oceanside 200' Seawall 3/2 Sleeps 6

Summerland Key, Florida, United States

Hello ! My name is Debra and I run our VRBO account for our family. We love our salty slice of paradise and I look forward to sharing it with you!brbrOur oceanside 3/2 home features a large lot, 200ft of concrete dockage, fish cleaning station, & plenty of parking for boats, cars & trailers. You will have a full kitchen, living & dining room, TV, wifi, screened porch, tiki hut & plenty of outdoor space to fish, play, kayak, and Florida Keys sunsets. Quick boat access to both Atlantic & Gulf.brThe spacebrOur house offers seclusion, privacy and plenty of room to play, perfect for you and your family to relax & unwind. We have a large double lot with Tiki Hut and 200' of concrete seawall and dockage for all of your toys. Fish right off our seawall, take a dip in the canal, relax and float, or go kayaking and explore.brbrWe have a fisherman's paradise here. A deep water canal that quickly takes you directly out into the Atlantic and quickly over the reef to experience the world's best fishing ! There is a public boat ramp, fuel, bait and snacks (Cudjoe Gardens Marina) located about 7 minutes away, and about a 10 minute boat ride back to the house. Cudjoe Sales is 2 minutes away for tackle and specialties as well as Low Key Fisheries, the perfect place to buy daily fresh caught fish, lobsters and stone crab.brbrDining out Gotta try Boondocks about a 5 minute car ride. Live entertainment every night, and a Putt-Putt Golf course too. Square Grouper, fine dining at it's best is only 2 minutes away. Winn Dixie, Walgreens and CVS is only 10 minutes away.brbrNo chance of getting bored !! By boat you are about a 20 minute ride to Looe Key reef, and 10 minutes to American Shoal reef. Two of our favorite places to go every time we come down. The grandkids LOVE it.brbrNo boat No problem. Reserve a Looe Key boat tour, You will NOT be disappointed. It is breath taking. And a 15 minute drive to Bahia Honda State Park for a picnic on the beach with gorgeous emerald waters to enjoy snorkeling, fishing and relaxing on the beach, and their nature walk is awesome. You are only 5 minute walk to Kemp Channel bridge to enjoy fishing off the bridge.brbrAnd you can't go to the Florida Keys without a trip to Key West. Just a short and scenic 20 minute drive and you in the world famous Key West. Discover the historic Conch Republic, schedule a tour to visit the Dry Tortugas National Park (one of my favorites), and have a drink on Duval Street while you take in the world famous sunsets.brGuest accessbrThe entire upstairs of house is yours we just ask that you respect and love it (and all the wildlife that you may come across) as if it was you own.brOther things to notebrWhen requesting a booking please specify the following:br1. How many people, names and ages of each.br2. How many (if any) watercrafts you will be bringing with you.br3. No smokingbr4. No pets

3

Bed

2

Bath

6

Sleeps

$264.77

/ Nightly

Private Vacation Home

Private 1 Acre property outdoor retreat on boatable canal- Monthly Rental!

Summerland Key, Florida, United States

Private 1 acre property nestled in Little Torch Key, this unique property offers a pleasant retreat for a couple looking for peace, space and outdoors. This property offers 1 king bedroom 1 full bath, living room, dining room, kitchen, and office with a cozy sofa bed in the main house. 1 queen bedroom 1 full bath under the main house with a screened in florida room TV and sofas. Laundry room with storage and extra refrigerator all under the main house. A detached guest house that makes up the third bedroom and bathroom on this property which consists of 1 queen bed and 1 full bathroom, sofa and TV, with a screen porch upstairs and screened in florida room underneath and commercial ice machine. Guest house and Main house all located on 1 acre property. Every couple or family member will have their own space for comfort. The property offers a fully fenced in yard with gates, screened in porch upstairs out the back door with stairs that lead you to the lower pool deck with table, chairs and loungers just off the above ground pool. Large yard with plenty of parking. Property located on a boatable canal to accommodate up to a 25-foot boat and within 10 minutes to closest grocery store. We hope you will enjoy the peacefulness and relaxing time we have spent on this property. It is truly a very unique property in this area.

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$448.63

/ Nightly

Private Vacation Home

Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapid Open Water Access!

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 brbrIntroducing Casa Rosada, a delightful canal front haven nestled within the enchanting Cudjoe Gardens on Cudjoe Key! brbr brbrOffering an invitation to tropical relaxation, this charming abode provides a tranquil escape from the everyday. Dock your boat along the seawall and embark on fantastic fishing escapades in the pristine waters of the Atlantic or the Gulf, a mere stone's throw away. Rejuvenate with a refreshing dip in the inviting pool, cocktail in hand, as boats gracefully pass by, adding to the serene ambiance. While Casa Rosada offers a plethora of activities to enjoy, including its own array of offerings, if you're enticed to explore the wonders of the Keys, the vibrant allure of Key West awaits a convenient 30-minute journey, while the captivating charm of Marathon beckons within the same short span. Unveil the essence of island living at Casa Rosada! brbr brbrSLEEPS MAXIMUM OF 6 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV brbr brbrBedroom 2: King Bed brbr brbrBedroom 3: Two Twin Beds brbr brbrLiving Room: Sofa, Chair, Flat Screen TV brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Private Heated Pool (heated to ~85 degrees Nov-Apr) brbr brbr- 85' of Seawall (Davits are not for guest use) brbr brbr- Fish Cleaning Station with Water brbr brbr- Tiki brbr brbr- Outdoor Seating brbr brbr- Electric BBQ Grill brbr brbr- Hamilton FlexBrew (drip & single serve), Toaster, Blender brbr brbr- Parking for a maximum of 4 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 brbrSmoking Policy: Smoking is strictly prohibited to maintain a smoke-free environment. brbr brbrNo Pets: Pets are strictly prohibited. To help maintain a pet-free environment for all, we require every guest to confirm they are not bringing a pet/animal. It's free, and does not require creating an account. After booking, you'll receive a link to complete the process. 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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Sleeps

$326.83

/ Nightly

Private Vacation Home

Summer Month's Just Opened Up!!! Canal Front Pool Home in Summerland Key

Summerland Key, Florida, United States

Atlantic Chateau, is a beautiful 3 bedroom 2 bath house on Cruikshank Island. Cruikshank Island is a peaceful private island off East Caribbean Drive, Summerland Key Florida only a 20 minute drive to Key West for a night on the town.brEnjoy the gorgeous sunsets in the evening while relaxing on the porch where the tropical breezes flow through or relax by the new pool & spa. The house is tastefully furnished for your comfort. Spacious kitchen to cook your lobsters and fish. brbrKeywords: Beautiful Sunsets from this property located on private island only 25 miles from Key West. Excellent boating,20 foot deep canal,150 foot dock, 5 mins by boat to open waterbrRent Rate Per Month inc utilities pool/spa heating not includedbrbr** This is a 28 day rental ** Must Rent from the 1- 30/31. Can not separate months, unless prior arrangements have been made.brPool Heater fee for the month is $250.00

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Bath

Sleeps

$334.17

/ Nightly

Private Vacation Home

Florida keys Waterfront,Forever Summer

Summerland Key, Florida, United States

MINIMUM STAY OF 28 DAYS REQUIERED BY THE COUNTY.Booking from the 1st of the month. Waterfront house with heated pool. Located on the canal of Summerland Key, has a 60 ft dock. Short access to Atlantic and Golf side. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Open kitchen concept with quartz countertops, stainless steel appliances, and an eat in kitchen island, separate dining room.Outdoor chest/bait freezer and ice maker provided, fish cleaning station,2 kayaks with paddles.Pet fee $150

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Bath

Sleeps

$343.13

/ Nightly

Private Vacation Home

New pool & Huge master suite! Open water views , 2 stories of wrap around decks

Summerland Key, Florida, United States

Captivating views from sunrise to sunset overlooking expansive salt ponds and open water from this newly renovated 2-story, waterfront home. This waterfront Little Torch Key home is situated on a tranquil corner lot in the Mates Beach neighborhood. This home has been stylishly upgraded and features a spacious free-flowing floor plan with granite countertops and stainless appliances. The views from every window will make you feel like you're in paradise at each glance. After a day on the water, dock your boat at the new concrete dock and enjoy your fresh catch on one of the many spacious wrap-around decks overlooking the canal and salt ponds. 2 charming guest bedrooms will greet your guests with a sun-filled welcome and a private door in each leading out to a relaxing deck. The massive owner's suite comes complete with a large, private balcony with open water views, offering an oasis of peace and relaxation. The natural light floods the ensuite spa-like bathroom, featuring a soaking tub, large walk in closet and custom tile shower. Just a short boat ride awaits world class fishing, diving and boating. Relax on a nearby sandbar like the content keys or picnic island or explore nearby Looe Key National Marine Sanctuary.brbrThe Pool was completed in 2024 and is a salt water system complete with a heater for those cold months and a chiller for those hot summer days. The two waterfalls provide calming sounds and even provide a little massage when you stand under them. The deep end hosts a cocktail bench for the big kids while the shallow end has a sun shelf for tanning or the little ones to play safely. Enjoy the light show as the colored lights provide a fun atmosphere. brbrThe lower level has a 500lbs/day commercial ice machine so no more running into town before those fishing trips. A bait freezer to store as much bait as you could need. And a Pit Boss smoker to cook the day’s catch. You will also find power and water at the dock for your boat needs. Additionally there is a 100 gallon fuel bulk tank with a 12 V pump to save you time and money by getting a fuel truck straight to the house.brbrEnjoy after hours with drinks around the fit pit table or make s’mores with the kids. The private font swinging porch with twinkling lights also makes for a great after hours hangout. brbrBikes are available to cruise around the neighborhood, to Kiki’s bar or up and down the many bike paths. Two kayaks and paddle board are also included a short paddle will get you into the salt flats and neighboring bird sanctuary.

3

Bed

2

Bath

8

Sleeps

$260.61

/ Nightly

Private Vacation Home

Serene 3-bedroom oceanfront house and dock in Sugarloaf Key

Summerland Key, Florida, United States

Consider this house your home away from home while you visit Sugarloaf Key. This welcoming retreat features three bedrooms, including a king, queen, and twin bed, plus an office with a comfy sofa bed. Guests enjoy two bathrooms, one with a jetted bathtub and a separate shower for ultimate relaxation. The brilliant 2004 sq foot layout offers plenty of space to unwind or work comfortably. Whether you’re lounging or catching up on emails, this phenomenal house has you covered. Our place will help you feel at home while you're traveling in Sugarloaf Key.

3

Bed

2

Bath

8

Sleeps

$263.79

/ Nightly

Private Vacation Home

Oceanfront 2 bedroom, Pet friendly on Ramrod Key with screened porch and kayaks

Summerland Key, Florida, United States

Welcome to our house in Breezeswept Estates on Ramrod Key. With two cozy bedrooms featuring a queen bed, a bunk bed, and a full bed, sleeping 5. Pet friendly with fenced in yard. Oceanfront with a screened in porch for great views of sunrises and moonrises. 5 kayaks and bikes available to use. Ac and heat mini splits throughout house. Washer and dryer on main level. 2 full bathrooms. Open concept living room and kitchen with ocean view. Wifi provided. Floating dock is great place to read, feed the fish in the mangroves, or watch the sea turtle swim by. Small, comfortable home in quiet neighborhood away from highway noise. Limited boat access through Newfoundland Harbor, gets very shallow. Picnic Island within view. Bahia Honda 10 min drive. Boondocks and Looe Key Tiki right down the road. 28 day min stay. You will never want to leave the porch with the breeze and amazing view.

Bed

Bath

Sleeps

$655.26

/ Nightly

Private Vacation Home

Oceanfront Gated Corner lot Amazing Sunsets. 90” BoatDock & 12 person Swim Spa!

Summerland Key, Florida, United States

Vista de Sirenas translates to ‘Mermaid Views’ is a piece of paradise with an unobstructed sunset view over open water year round! 3,200 sq ft living space on oversized fenced corner lot at the very end of a private road offering picture perfect sunsets! Boasting 323' of water frontage, this property includes 175' of open water and 148' of canal frontage featuring a 90' concrete dock, and a private kayak launch. brbrThe main level of the home features a wrap-a-round deck, a spacious living area, including a large master bedroom and bathroom, 2nd bedroom, half bathroom and a large kitchen area. The third level has a private bedroom, bathroom and balcony accessible by a spiral staircase. On the opposite side of the home is a private mother-in-law/teen suite with an open floor plan that includes a large living area, 2 Story tongue & groove West Indies Great room with wet bar and it's own kitchen with views for days!brbrWe have a 12 person Calspa Swim Spa with Vertical massage plus benches for up to 12 people, 55 jets, surround sound and open year round along with outdoor couches, pool table, lounge chairs and grill to complete the outdoor living! The entire property is pricacy fenced & Gated!brbrWe have plenty of toys including Kayaks, Fishing Rods, Paddle Boards, Bike cruisers, a pool table and plenty of inside games also. Boat Dockage is super with room for up to 42 ft boat plus a floating Jet Ski Dock that holds 2 Skis! We have boat rentals available also! Plenty of parking for all the guests! Easy access with super fishing spots and reefs! brbrOnly 20 mins to Key West with plenty of shopping, Nightlife and super restaurants. Check out our Instagram page for reviews! @vistadesirenasbrbrThe best of all is the wide open water & gorgeous sunset views! We searched for the right property for three years for our family to enjoy. We hope you love it just as much as we do!

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Sleeps

$493.85

/ Nightly

Private Vacation Home

Starlight Serenity - Hideaway with Stunning Views

Summerland Key, Florida, United States

Summary:brbrEscape to paradise at this serene 1-bedroom, 1-bath home in beautiful Sugarloaf Key sleeping up to four guests. Enjoy breathtaking views from the expansive wrap-around balcony, perfect for sunrise coffee or sunset cocktails. The spacious outdoor area is ideal for dining, lounging, and soaking in the tropical ambiance.brbr Whether you're relaxing indoors or savoring the outdoors, this home offers the perfect blend of comfort and tranquility.brbrbrbrBook your next getaway for 3 nights or more!brbrbrbrThe Space:brbrWelcome to your perfect getaway! This charming home features a spacious open-concept floor plan designed for relaxation and connection. The main living space includes two twin sleeper sofas, while the bedroom features a queen bed - making it ideal for families or groups of friends.brbrbrbrNatural light pours into the airy interior, complementing the seamless flow between the living, dining, and kitchen areas. Whether you’re enjoying quiet moments or gathering for meals, this inviting space offers the comfort and convenience you need for a memorable stay.brbrbrbrBedroom 1: Queen Bed brbrExtra sleeping: two twin sofa beds in living roombrbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrHow to access: Stair access onlybrbrbrbrThe Neighborhood:brbrStarlight Serenity is located on Sugarloaf Key, just 19 miles from Key West. This private oasis is conveniently situated right off US-1.brbrbrbrCheck out our favorite must-do activities and eateries, all within 5 minutes of your front door:brbrbrbrLooking for a day away Visit Sugarloaf Lodge, where you can take a boat to the South of Seven Restaurant & Marina.brbrBook a day on the water! Enjoy local fishing, eco tours, kayaking, paddleboarding, snorkeling, and more.brbrSeeking adventure Experience the trip of a lifetime at Sky Dive Key West.brbrSavor local flavors. Dine at local favorites like Square Grouper and My New Joint.brbrCoffee lover Vacation isn’t complete without a great brew. Check out Morning Joint and Baby’s Coffee for your morning fix!brbrbrbrGetting Around:brbrParking Information: Private parking is available in front of the home.brbrbrbrThis home is conveniently located, offering easy access to everything Sugarloaf Key and the surrounding Keys have to offer but still maintaining peacefulness surrounded in nature. A car is recommended for exploring the area, with ample parking available at the property.brbrbrbrEnjoy a short drive to nearby beaches, marinas, and local attractions. Key West, with its vibrant nightlife, unique shops, and historic sites, is just a 25-minute drive away. For those looking to explore by bike or foot, the scenic Overseas Highway provides stunning views and plenty of spots to stop and take in the beauty of the Keys.brbrbrbrOther Things to Note:brbrPrivate Washer/Dryer: Conveniently located in the home.brbrParking Information: Private parking is available in front of the home.brbrPet-Friendly Home: Dogs under 25 lbs are welcome! $15 per night, per pet, Maximum of 2 petsbrbrThis property is a 3-night minimum stay.

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Sleeps

$319.14

/ Nightly

Private Vacation Home

Canalfront house with private pool, WiFi, private washer/dryer, and central AC

Summerland Key, Florida, United States

With three separate living areas and a private heated pool, this charming home is full of comfortable spaces for guests to enjoy. Stay in the main house, the downstairs lounge, or in the guest house complete with a full bathroom - each area has its own private entrance. But no matter where you decide to relax, there's room for you by the pool! Feel free to set up the private gas grill and enjoy a relaxing night near the canal. Inside, guests will be able to cool down in central air conditioning. Board games and a DVD player are on hand for relaxing evenings. The private washer/dryer will ensure you have everything you need for your days enjoying the sunshine.brbrThings to KnowbrA futon in the downstairs area of the main house provides an extra sleeping space.brThe upstairs bedroom and bathroom in the guest house is only accessible via spiral staircase.brThis property is managed by Seven Keys Vacations by Casago.

2

Bed

4

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6

Sleeps

$486.1

/ Nightly

Private Vacation Home

Waterfront home with boat/canal access, screened lanai, & renovated interior

Summerland Key, Florida, United States

Everything you need for a carefree Florida Keys escape is right at your fingertips in this laid-back bungalow. Boasting direct canal access by way of a private dock, this waterfront retreat also features a tropical outdoor area and recent home upgrades including an all-new kitchen and primary bathroom. A fully screened-in lanai offers a breezy perch to start your day with a cup of coffee or cap it off with a cold drink. Local charter services and great dining options can be found between Upper Sugarloaf and Little Torch Keys. Key West is just over a 20-mile drive from the house.brbrThe home features a stilted interior with an open-concept layout designed with group gatherings in mind. Updated kitchen appliances are equipped to help you whip up island-inspired creations. Large smart TVs are equipped in the living room and each bedroom for flexible home entertainment.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10 p.m. to 8 a.m.brNo smoking is permitted anywhere on the premises.brThis property is managed by Seven Keys Vacations by Casago.

3

Bed

2

Bath

6

Sleeps

$273.21

/ Nightly

Private Vacation Home

Summerland Canal-Front Escape w/ Plunge Pool, Dock, Tiki Bar, WiFi & Laundry

Summerland Key, Florida, United States

Boasting a canal-front location, this two-bedroom home is a dream retreat on Summerland Key. Tie up a boat of up to 24 feet at the private dock. Cruise the canal with ease, travel mere minutes to prime fishing and diving locations, and come home to take a dip in the backyard plunge pool and sip tropical drinks in the festive tiki lounge.br brKick back in the sunny living area after a fun-filled day, where a large sectional sofa provides comfortable seating and the 32-inch Smart TV offers streaming capability. Home chefs will appreciate the modern kitchen, newly appointed with a full suite of stainless steel appliances and granite countertops. When it's time to eat, you can share home-cooked meals around the table for four in the dining area.br brThe wrap-around balcony offers space to bask in the sun or relax in the shade. Unwind on the covered back patio, take a refreshing dip in the private plunge pool, make use of the gas grill for an afternoon cookout, and enjoy a tropical retreat to the covered tiki bar. Additional amenities include free WiFi, a washer/dryer, and driveway parking.br brFrom fishing equipment to boat rentals, retailers along Overseas Highway provide all the gear you'll need for aquatic adventures. You'll also find several local eateries in the area, conveniently located about a mile from home. For a beautiful beach day, travel 13 miles to Bahia Honda State Park.brbrThings to KnowbrFull kitchenbrAccess to this stilted home is via a flight of external stairsbrThere is a 28-night minimum staybrThis canal-front home is located across the street from the Summerland Key Cove Airport. While the private airport receives little traffic, passing airplanes may occasionally be heard.br brThis property is managed by Seven Keys Vacations by Casago.

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Sleeps

$395.63

/ Nightly

Private Vacation Home

Sunny Hideaway - Venture Out Unit 276

Summerland Key, Florida, United States

Sunny Hideaway - Venture Out Unit 276brThis beautifully decorated home is located on the water and is located within walking distance to the pool and marina. Features 35' concrete seawall for docking a boat that equipped with heavy duty dock posts, cleats, swim ladder, whips and fish table and offers quick access to the open water! Main living area features an open floor plan with high ceilings throughout. Living room is surrounded by windows that overlook the water with sleeper sofa and large flat screen television. Kitchen offers full line of appliances with dining room that leads to the covered porch. Master bedroom queen bed features lots of closet storage, flat screen television and private full bathroom. Guest bedroom features a queen bed with closet storage and private entrance. Additional amenities include wireless internet, central air conditioning/heat, washer/dryer, ceiling fans, BBQ grill, dishwasher, microwave. Use of golf cart NOT allowed.brSECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL,brOVERFLOW PARKINGIS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.VO REGISTRATION FEE $113.00- **EFF 7-1-23 new fee is $125**DUE UPON ARRIVAL CASH OR CREDIT CARD ONLY PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.

2

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2

Bath

4

Sleeps

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