Vacation Rentals By Owner In Summerland Key, FL

Summerland Key House is all about open air living. Cypress plank cathedral ceilings extend through the bedrooms, bathrooms and over 2 large porches on the side and back of the house.brDouble French doors in the master bedroom and living room open to a lounging area and hammock on the large back covered wooden porch. Double French doors in the kitchen open onto a large covered tile side porch for dining. There are skylights in the living room as well as both bathrooms.brSleeps four. Primary bedroom has a queen bed. Second bedroom has a king bed. brWasher and dryer are located in garage and workshop below the house.brAn outdoor shower is located below the back steps and a fish cleaning station is located at the back corner of the property.brBrand new swimming pool with Badu swim system for exercise.brOceanside, protected canal, deep water, flow thru and crystal clear for swimming . Just minutes from open water. A single and double kayak as well as 2 bicycles are provided with the house.

Summerland Key House Open Air Living

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$544.25

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. Please review additional policies below. brbr brbrWelcome to 'The Blue Pearl' – the ultimate destination for large families or multiple families seeking an expansive and accommodating retreat! brbr brbrWith two distinct living areas, this spacious haven offers ample room to gather together or find your own space for relaxation. Step onto the sand and revel in the 125 feet of oceanfront that's all yours. Watch the breathtaking sunsets paint the sky with vibrant hues. As the day transitions to evening, gather around the Boat Bar, where tales are shared and favorite cocktails savored. While 'The Blue Pearl' offers a wealth of activities, if you're itching to explore the Keys, Key West is just 25 minutes away, and Marathon is a short 40-minute drive. Your ideal vacation awaits at 'The Blue Pearl.' Secure your reservation now and embark on a journey of relaxation, adventure, and the splendor of the Florida Keys! brbr brbrSLEEPS MAXIMUM OF 12 GUESTS: brbr brbrBedroom 1 (2nd Floor): King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2 (2nd Floor): Queen Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3 (1st Floor): Queen Bed brbr brbrBedroom 4 (1st Floor): Queen Bed & Twin Bed, Smart TV (no cable/satellite TV) brbr brbr2nd Floor Loft: Three Twin Beds brbr brbr2nd Floor Living Room: Sectional Sofa, Two Chairs, 75 Smart TV (no cable/satellite TV) brbr brbr1st Floor Living Room: Sofa, 65 and 55 Smart TV's (no cable/satellite TV) brbr brbrTwo Kitchens: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- 65' of Private Dockage brbr brbr- Private Boat Ramp to launch up to a 22' boat brbr brbr- Fish Cleaning Station brbr brbr- Outdoor Seating brbr brbr- Tournament Size Pool Table brbr brbr- Parking for a maximum of 4 vehicles, including boat trailers. 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 50 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.

The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$473.3

FOLSOM'S FOLLY... Summerland Key, Florida brbrInteresting architecture with breezy views of the water. All rooms beautifully furnished in relaxed Keys style, including the 'Nautical Room', the 'Captain's Room', the 'Fish Room', and a private master suite with private bath, twin sinks, and French doors onto a deck with teak chairs. Interesting natural history mounts, area-related books and other reading material. Ceiling fans everywhere. Tile and hardwood floors downstairs.brbrIn-ground heated swimming pool with jets. Covered hammock overlooking beautiful tropical landscaping with bromeliads, coconuts and flowers; pelicans, herons, seagulls, hummingbirds, butterflies, tree frogs, and lizards galore. Even an occasional iquana. brbrLovely panoramic southern view over open water; easy access by boat to great fishing & scuba diving; ground floor lockable storage room for stowing scuba/fishing gear; bait freezer and fish cleaning station; screened porch for relaxing & dining, nice breezes; covered parking. Private deep draft boat dock; large deck for sunbathing & and swim platform on the Atlantic Ocean for swimming.brbrOUTDOOR TIKI SHOWER!brbrKeywords: House

Oceanfront Sunsets in the Florida Keys

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$216.27

The Crab House 28 day rental offers 2 spacious bedrooms 3 bathrooms (1 full bath in garage to use after coming in from boating or diving), on beautiful clear canal. Home offers 60 ft of bulkhead for docking your boat, deep canal, neighborhood marina just 5 blocks away to launch your boat. Marina also sells fuel, bait and fishing supplies. The Bent Prop Restaurant is located next to the marina. Canal is great for swimming and paddle boarding. We have 2 paddle boards for your use. 21 miles to Key West makes this a convenient location to everything the lower keys has to offer! Looe Key is located 6 miles away and offers snorkeling day trips an jet ski rentals! 10 miles from Big Pine Key. Bring your clothes and groceries and enjoy paradise! brMaster bedroom has king size bed with memory foam mattress and full bath. Guest bedroom has a two twin beds and full size bed, living room has a full size futon and two couches. Kitchen offers pots and pans, dinnerware, silverware, gas stove, electric oven, microwave, refrigerator, small coffee maker, toaster and blender for your frozen tropical drinks! Grocery store located on Big Pine Key 15 minutes away. Boat/trailer can be parked in front yard of property. No fixed bridges in ocean in 5 minutes/ gulf and ocean access.

2 Bedroom/3 Bath Waterfront 28 day rental

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$454.65

Nestled in the heart of Summerland Key, this 3-bedroom vacation home offers a tranquil escape for your Florida Keys getaway. Enjoy the stunning water views from the balcony or relax on the beach loungers with a good book. The fully stocked kitchen is perfect for whipping up delicious meals, complete with a stove, oven, grill, and all the necessary appliances and utensils. Unwind in the living room or catch up on your favorite shows with the smart TV. Refresh and rejuvenate in the 2 bathrooms, equipped with towels and basic soaps, and take advantage of the in-unit washer and dryer. Explore the nearby Florida Keys Beaches all within a short drive. With free WiFi, air conditioning, and a desk for remote work, this vacation home has everything you need for a comfortable and memorable stay in the Florida Keys.

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

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$563.47

Quiet, secluded Keys house with a pool. Ideal for larger groups of friends and family's. Equal distance to Marathon and Key West. Larger wrap around screen porch. Deep water canal , easy boat ride to golf and ocean access. Watch the stars at night. Bring you toys and boat. Big deep water dock , can bring up to 33 foot boat. You can also fish off the dock. This area has lots wildlife and deer. Come enjoy and relax

Great Location , Great Vibes, Great Pool

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$663.75

Mariner's Cove is a private island oasis. Featuring 5 large guest rooms, 3 full bathrooms and 2 1/2 bathrooms, Gourmet Chef's kitchen, formal dining room, breakfast nook, living area, private theater with 70 HD flat screen, oversized washer/dryer, ample outdoor seating, pool chase loungers & umbrellas, hammocks, outdoor gazebo/ wet bar with full outdoor kitchen and entertainment area, over .5 acres of lush tropical landscaping, outdoor fire pit, private boat dock on canal and lots of room to entertain. brbrThis home is essentially your own private resort and offers boaters quick access to the Gulf or Atlantic in just minutes from the private dock. brbrLocated just 30 minutes from Historic Key West or 30 minutes from Marathon you are close enough to the excitement of Duval Street but far enough away for a tranquil evening on the back porch watching the stars. Great home for multiple families, private functions, corporate retreats or just a perfect place to relax.brbrRoom Specifics: brThe Downstairs master bedroom features a full power adjustable King size canopy bed so you can tilt it up to watch TV or lay it down flat to sleep. The master bathroom has huge walk-in closets and a walk-in shower. Relax in the soaking tub or get to work at the Tommy Bahama desk in the attached office.brbrUpstairs has 4 bedrooms and 2 full baths. There are two rooms with King size fully power adjustable beds. These rooms are joined by a full bath. There is a bunk bedroom great for kids and both bunk beds are full size beds (upper & lower). And lastly a large room with two queen beds with on-suite bathroom, walk in closet and 55 smart TV. brbrFor special requests and questions please reach out to us as we are always available to assist with your Florida Keys destination needs. brbrNOTE: Security Cameras on site: brLocations: brFront Deck Pointing Toward DrivewaybrBulkhead: Pointing Toward Dock brUnder Deck: Pointing Toward Kayaks & EquipmentbrOn Pool Equipment brThere are two others one on back deck and one on tiki bar and are disconnected and covered during guest stays.

Mariners Cove - The Kraken House

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$302.59

Custom designed Tropical Keys Home located on one of the nicest flow through deep water canals leading to the ocean in Summerland Key! Privacy 6' Walls surround the Villa to allow sunbathing delights!brbrThe Custom Canal Front Dock has Fenders, Cleats, and water spigots for all your boat needs. The Dock also has a swim platform and ladder to make all your water accessibility needs easy.brbrOpen floor plan that flows to the outside porch allows for tropical breezes and spacious entertainment. Plenty of parking area in front of house allows for storage of RV's, Boats, Cars and Planes if so desired.brbrSpacious kitchen to include all stainless appliances and large seating for 6 or more at the granite island bar! You can flow from the island bar to the open living room with wrap around leather sofa to view your favorite movies on the 50 Flat Panel TV.brbrMaster Bedroom has large California Walk-In Closet and King Bed with views of Outside porch and large Jacuzzi. Guest Bedroom has two spacious queen beds, 42 Flat Panel TV, and California Closets. Living Room has large pull out full sectional sleeper leather sofa.brbrThe Master and Guest Showers are a hedonistic experience with Rainfall Showers and 8 surrounding water sprays to immerse you in water pleasure.brbrThe Screened in Tropical private porch overlooks the Deep Water canal with great views of the ocean while the overhead porch fans cool you in the 8 person Hot Spring Jacuzzi. Enjoy the state of the art Jacuzzi with enough massaging jets to keep you smiling for some time. There is seating for 6-8 with comfortable Sofas, chairs and coffe table for tropical style conversations. Large sliding Porch doors open the house and master bedroom to the outside for great access to Jacuzzi and Screened in Porch.brbrThe House overlooks a beautiful private airstrip that allows for private aircraft and owners to fly in and access their tropical homes.brbrAnd speaking of world class entertainment! The State of the art Audio-visual system with surround sound fills the house and porch with the music of your choice. Flat Panel Plasma TV's in each room allow for majestic visual experiences. brbrAll the Audio and visual entertainment is controlled by a easy to use LCD remote. The house was designed with a unique lighting system that allows you to create endless moods of lighting for your pleasure. Have fun directing the lights! brbrThe house is Internet Ready with high speed wireless access for your laptop computer needs. Printer and copier also available if needed. brbrbrbrKeywords: House

Canal Front (Deep Water) Tropical Villa

Summerland Key, Florida, United States

Bed

Bath

8

Sleeps

$349.1

Welcome to this charming house in Summerland Key. This phenomenal property boasts 3 bedrooms, including a king bed, queen bed, and murphy bed. With 3 bathrooms equipped with hair dryers, guests can freshen up with ease. The house also features amenities like an iron, AC, and heating for a comfortable stay. Enjoy all that Summerland Key has to offer when you stay at our place.

Paradise house 3-bedroom house with AC in Summerland Key

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$1321.88

Large oceanfront home with breathtaking open water views! Seaclusion is a unique 3,400 square foot custom built home set on over an acre of tropical landscaping with a sparkling newly resurfaced heated pool on beautiful Summerland Key in the Lower Florida Keys. This house is permitted for daily, weekly or monthly rental. (Daily and weekly rental permits are rare in the Florida Keys!) br brEnjoy watching sunrise views over the open water of the Florida Keys. Our Non-Smoking home, Seaclusion, is comfortable and beautifully furnished for your stay. This three bedroom, two bath, uniquely designed home offers elegant living spaces including a palatial living area with carpet and tiled floors, a kitchen with new appliances, and an open staircase leading to the master suite. brbrRelax and enjoy the luxury, space, comfort, and beauty of Seaclusion's wide open living space where you'll find vacationing is easy. The master bedroom is located on the third floor. This spacious master suite features a king size bed, wet bar, and lavish his and her bath with jacuzzi tub.brbrMake yourself at home, Seaclusion gives you a whole new relaxed perspective on life. This picture-perfect home-away-from-home is open and airy. You'll enjoy the ocean breezes while dining and sipping frozen Pina Coladas at the kitchen bar or in the dining area while viewing the sparkling blue waters of the Atlantic Ocean. You'll also find a queen sleep sofa in the living area along with a full entertainment center for your family and friends. There are also two bedrooms with queen beds and a full bath on the second floor.brbrThe sliding doors lead to a screened in porch and outside shower. Follow the steps that lead to the 200 foot dock for swimming and boating. Highlights of this 3,400 square foot home include the master suite's private screened balcony and open sunbathing, the screened porch on the ground floor and a sparkling in-ground pool - a sea of tranquility right here on earth. brbrActivities: Our home is centrally located at Mile Marker 25 and is within minutes to Florida Keys style recreation, restaurants, shopping, and night life. Bahia Honda State Park with its world-famous beach is only 12 minutes away, Looe Key Reef and Marine Sanctuary is only 15 minutes away. We're located just 20 miles north of Key West where you'll love the great many eateries and shops. It's only a ten minute boat shuttle to take you to the exclusive Little Palm Island. Every water activity is at your back door just minutes from exceptional deep sea and flats fishing. Enjoy the very best the Florida Keys has to offer.br brIndulge yourself. Relax the body, lift the spirit, and invigorate the soul. It isn't hard to fall in love with a Florida Keys sunrise in this oceanfront estate. Seaclusion is a place where each day is better than the one before.br brMust be 25 years or older to rent this property.brKeywords: House

Oceanfront Home-Pool, Dock-Available Daily, Weekly or Monthly.

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$532.5

Kelly's Kabin is a recently renovated property freshly painted in tropical blues. It's a private home without neighbors. There is ample parking for multiple vehicles and your boat. The property is fully licensed for nightly, weekly, or monthly rentals.brSummerland Key is located at mile marker 24, which allows you to enjoy short drives north to Big Pine Key, Bahia Honda National Park, and Marathon Key. The major attractions of Key West are only 35 minutes to the south. Public transportation is conveniently accessible immediately adjacent to the cottage. No need to drive or find parking! Looe Key, with its phenomenal snorkeling and diving, is accessible through a variety of local charters. Kayaks, paddleboards and bicycles can be rented nearby. Fishing options include back country fishing, ocean fishing or bridge fishing. A lovely bike path is located at the back of the property. This property is close to favorite local restaurants as well as a small gourmet grocery. Food delivery is also available.brThe private lighted back patio overlooks a mangrove area, which leads to the Gulf of Mexico. The outdoor area includes a patio table, fire pit, charcoal grill, and fish cleaning station. You can observe native birds and often the endangered Key Deer from the patio.brInside the cottage, the main bedroom has a new king size bed. The pull-out couch has a comfortable gel foam mattress, and the front area has a comfortable single day bed.brThe full kitchen is equipped with new appliances, ample counter space and a breakfast bar.brThe bathroom has a bathtub and shower equipped with shampoo, conditioner, soap, clean towels, iron and a first aid kit. All linens, as well as beach towels and a beach umbrella are provided.brThe living area has a smart TV. The house is equipped with free Wi-Fi and a landline for emergencies.brWe hope you'll come relax in this welcoming tropical oasis and make new Low Key friends while here in paradise!brWe live locally and are available to assist to make your rental experience relaxing and enjoyable.

Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key, Florida, United States

3

Bed

1

Bath

5

Sleeps

$338.74

Ramrod Key is calling you to your next adventure at this vibrant and welcoming 4 bedroom island home.brbrUpstairs, the primary bedroom offers a king bed and an updated full bathroom with a tub... perfect for recharging after a day on the water. The second upstairs bedroom opens directly onto the wraparound deck, where sunlight pours in and ocean breezes set the tone for your morning.brbrDownstairs, you’ll find a queen bedroom and a twin bedroom, along with a second bathroom and a full kitchen, an ideal setup for guests who want their own space to gear up for the day’s excursions.brbrBoth levels include their own washer and dryer, so you can pack light and stay ready for whatever the Keys throw your way.brbrStep outside and the adventure continues: a brand‑new dock awaits your boat, paddleboard, or sunset cocktails. The outdoor shed is stocked with a chest freezer and an outdoor shower, perfect for cleaning up after fishing trips, snorkeling runs, or long days exploring the backcountry.brbrWith air conditioning and heating throughout, the home stays comfortable no matter the season. brbrWhether you’re plotting your next outing or unwinding after a full day of island fun, this home is the perfect launch point for experiencing everything Ramrod Key has to offer.

Kraken's Cove: 4‑bedroom Ramrod Key escape, minutes from open water

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$289.01

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.

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

Summerland Key, Florida, United States

3

Bed

Bath

6

Sleeps

$464.39

Secluded lower keys oasis on 4 acres. Incredible sunrises and sunsets over the water and jungle. Room for the whole family. Close to boat ramps. Sleeps 8 easily with the possibility for more. 4 bedrooms, 3.5 baths. 20 mins to KW. 30 mins to Marathon. House has undergone a major remodel and will continue to be updated. Come enjoy our tropical paradise! Great base camp for lobstering and fishing!

Secluded Jungle Paradise

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$444.09

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.

Ocean Front Modern Home

Summerland Key, Florida, United States

4

Bed

3

Bath

9

Sleeps

$337.12

brbrA beautiful place to escape—your very own fisherman’s dream in the Florida Keys. Open dock space to bring your boat with a gas dock right across the way. Ideally situated just 27 miles from Key West, this serene retreat offers the perfect blend of relaxation and adventure. Walking distance to the tiki bar with live music every night. brbrThis thoughtfully designed home comfortably sleeps up to six guests, featuring two inviting bedrooms plus an additional full bed—ideal for kids or extra visitors.brbrEnjoy year-round comfort with both air conditioning and heating, ensuring a perfect stay in any season. Spend your days unwinding on the private dock, or relax with a morning coffee or evening cocktail on the screened-in porch while taking in the peaceful surroundings.brbrWhether you're out on the water, working remotely in a tranquil setting, or simply embracing the laid-back island lifestyle, this home offers the perfect balance of comfort and convenience.brbrYour stay here isn’t just a getaway—it’s where lasting memories are made.

Our little slice of paradise

Summerland Key, Florida, United States

Bed

Bath

6

Sleeps

$569.65

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

Summerland Serenity Elevated Waterfront Luxury with Private Elevator & Pool

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$280.82

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!

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

Summerland Key, Florida, United States

Bed

Bath

Sleeps

$135.1

Experience Marathon to Key West (right smack dab in the middle) like a local in this freshly painted 2-bedroom mobile home with RV hook up for additional guests. This is a crystal clear canal front residence with direct open water access to the Gulf and Atlantic Ocean. Bring your boat/jetski and dock in front of the Tiki Hut in front of the home. The boat ramp is less than a mile from da lobster shack. This cozy space features 2 brand new queen beds in the bedrooms and 1 brand new full bed pull out couch in the living room. With brand new AC to keep you cool and a refreshing shower in the bathroom, guests will feel right at home. There is a brand new 86 inch TV in the living room and 2 brand new 55 in TVs in the bedrooms. All brand new appliances including gas stove/oven, microwave (4 in one), fridge and freezer, ice maker, Capresso coffee and capachino maker, Keurig, washer/gas dryer. Additional fridge/freezer outside for additional refreshments. Built in brand new propane grill. (no need for a tank, just turn on). Easy access digital keyless entry making key life much more enjoyable. Book now and enjoy everything this welcoming property has to offer.brbr*sea wall updated and new concrete poured.br*fenders, 5 step swim ladder, and fish cleaning station installed on sea wall. br*Fence installed for added privacy on left and right sides of property. br*New outdoor furniture delivered. brbr*home inside and out treatment by Orkin with monthly pest control visits to ensure quiet, peace and enjoyment for tenants. brbr*We highly recommend travel insurance. peace of mind is worth more than the cost of the insurance.*

Mobile Home

Charming 46 ft lg canel ft 2-bed in delightful Little Torch Key with RV hook up.

Summerland Key, Florida, United States