Vacation Rentals By Owner In Summerland Key, FL

$351.88

Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!

Summerland Key, Florida, United States

County zoning requires a minimum rental period of 28 nights, and no exceptions can be made. NO PETS. Please review additional policies below. brbr brbrExperience the ultimate in waterfront luxury at Caribbean Cabana, where every moment is a postcard-perfect memory waiting to be made! brbr brbrThis stunning 3-bedroom, 2-bathroom home boasts a prime oceanfront location, offering panoramic views of the azure waters and the mesmerizing sunsets that give the property its name. Step inside to discover a beautifully appointed interior, where coastal-inspired décor and modern amenities blend seamlessly. The spacious living area is ideal for relaxing and unwinding, featuring plush furnishings and a large flat-screen TV. Whip up delicious meals in the fully equipped kitchen, complete with stainless steel appliances, quartz countertops, and a breakfast bar for casual dining. The three bedrooms are elegantly furnished and offer comfortable sleeping arrangements for up to 8 guests. The master suite is a true retreat, boasting a king-sized bed, an en-suite bathroom, and direct access to the outdoor living space. The two guest bedrooms are equally inviting, with a queen-sized bed in one bedroom and two full-sized beds in the other and serene views of the surrounding landscape. Outside, the magic continues with a private outdoor oasis that includes a pool, a spacious deck with lots of seating, and a dining area where you can savor al fresco meals while enjoying the gentle sea breeze. The highlight of the property is its private dock, perfect for boating enthusiasts or those simply looking to soak up the sun. Whether you spend your days lounging by the pool (pool construction begins June 2024), exploring the nearby attractions, or simply relaxing on the deck with a good book, Caribbean Cabana offers the perfect blend of luxury and relaxation for your next vacation. brbr brbrSLEEPS MAXIMUM OF 8 GUESTS: brbr brbrBedroom 1: King Bed, En-Suite Bathroom, Smart TV (no cable/satellite TV) brbr brbrBedroom 2: King Bed, Smart TV (no cable/satellite TV) brbr brbrBedroom 3: Two Full Beds, Smart TV (no cable/satellite TV) brbr brbrLiving Room: Sofa, Chair, Smart TV (no cable/satellite TV) brbr brbrKitchen: Nicely equipped (all things necessary to prepare and serve a meal) brbr brbrAMENITIES: brbr brbr- Saltwater Pool (10' wide by 20' long, 4'-6' deep, heated to ~80 degrees Nov-Apr) brbr brbr- 60' of Seawall (Davits are not for guest use) brbr brbr- Outdoor Seating brbr brbr- Propane BBQ Grill brbr brbr- Keurig, 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 brbrNo Smoking: Smoking is strictly prohibited within the property. For the comfort and safety of all guests, please refrain from smoking indoors. 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. brbr brbrSecurity Cameras: For the safety and security of our guests and property, three exterior security cameras monitor the front driveway, stairs and pool. These cameras are for security purposes only and do not monitor any private interior or outdoor living spaces.

3

Bed

2

Bath

8

Sleeps

$367.5

/ Nightly

Private Vacation Home

Amazing 2 BR Home in Summerland w/ Great Boating Access & Private Heated Pool!

Summerland Key, Florida, United States

Welcome to Summerland Key House! This amazing 2 bedroom home on Summerland Key is a perfect Keys vacation home! It has everything you need and more to enjoy your vacation including quick/easy boating access, a concrete dock for your boat, an in-ground pool, bikes, kayaks and multiple outdoor shaded living spaces for true Keys living.brbrThe inside of the home has 2 large bedrooms, 2 baths and an open concept kitchen and living area. There's an extra sleeping area so the house can sleep up to 6 people. With soaring vaulted ceilings and doors that open to the outside decks, it feels super spacious and comfortable. The kitchen is brand new and well appointed with stainless steel appliances and everything you need to feel right at home!brbrAs wonderful as the inside is, the outside of the home is where you will want to be! The huge covered deck space is mostly shaded and has a full living area, hammock and dining table. Grill right on the deck with a beautiful view of the clean, clear canal! Downstairs you’ll find a large outdoor shower, ping-pong table and an in-ground swimming pool overlooking the canal. There’s plenty of dock space for your boat! The canal system can accommodate larger boats with deep, wide canals and a quick ride out to open water. You can hop in one of the kayaks to explore the water or take a bike ride around the community. There’s absolutely nothing more you will need to enjoy your time here…just pack your bag, Summerland Key House is waiting for you!brbrEnjoy all the unlimited water activities like swimming, fishing, and diving the Keys has to offer. Discover an assortment of Florida Keys wildlife all around the area. Big Pine Key is located a few miles up where you’ll find a shopping plaza hosting Winn-Dixie, Artists in Paradise, Beall’s Outlet, Radio Shack and a branch of the Monroe County Library with Wi-Fi internet access.brbrTake a trip down to Key West for the daily sunset celebration or a romantic sunset cruise. Or visit one of the many venues offering the finest in live entertainment and great food. Be sure to take a stroll up and down Duval Street and visit the art galleries, shops, and more! Take the family for a sunset cruise or go snorkeling, kayaking, or whatever water sport the beautiful Florida Keys has to offer.brbr***NO PETS PLEASE***brbrPLEASE NOTE: This is a monthly rental. During season (Winter and Summer), we only rent full months at a time, ie. all of January, all of February, all of March. We do not split months, ie. Jan 15 - Feb 15.brbrbrNOTE: All images used are for illustrative purposes only. Individual features such as bed sizes/configuration, bedding, décor, appliances, colors, extra amenities, etc. may vary since these are private homes and owners redecorate often. Please also note that pictures are taken in different light conditions and computer screens have different individual settings that moderate colors. Please read the written description and ask questions if you have any specific needs and/or concerns. All furnishings and décor are subject to change at any time.

Bed

Bath

Sleeps

$618.37

/ Nightly

Private Vacation Home

Torchview Lookout- Secluded Waterfront Retreat With 240’ Dock On Niles Channel

Summerland Key, Florida, United States

Welcome to Torchview Lookout – Your Private Waterfront Retreat!brbrEscape to paradise at Torchview Lookout, a secluded 3-bedroom, 2-bathroom home nestled on 1.4 acres along beautiful Niles Channel in Big Torch Key. Tucked away in the National Key Deer Refuge, this tranquil haven offers the best boating access in the Lower Keys—just 2 miles to the Atlantic and 6 miles to the Gulf!brbrWHY YOU'LL LOVE IT:brbrPrivacy: Enjoy exclusive access to the entire top floor of the home—no other guests or owners will be onsite during your stay.brbrLocation: Ideally located between Marathon and Key West (25–30 minutes in either direction), giving you easy access to dining, shopping, and attractions.brbrWaterfront Living: With a 240-foot dock (4’ draft) that accommodates vessels up to 42’, you can boat, kayak, paddleboard, fish, swim, or snorkel right from your backyard.brbrTurnkey Comfort: Just bring your swimwear, water toys, and fishing gear—we've got the rest covered.brbrHOME FEATURES:brbrLiving Roombrbr35” flat-screen TV with basic cablebrbrHigh-speed internet/WiFibrbrComfortable seating for 6brbrDining & KitchenbrbrFormal dining table for 6brbrFully equipped kitchen with:brbrGas range stove/ovenbrbrRefrigerator with ice makerbrbrDishwasher & microwavebrbrPots, pans, utensils & cutlery for 6brbrBreakfast bar with 4 stoolsbrbrBEDROOMS: brbrMaster Bedroom: King bed, 40 flat-screen tv, work desk, large closet, chest of drawers, en-suite bathroom with dual vanity & shower/tub combobrbrGuest Room 1: King bed with ample closet and storagebrbrGuest Room 2: Two twin beds, large closet, and chest of drawersbrbrBATHROOMS:brbr2 full bathrooms with shower/tub combosbrbrOUTDOOR LIVING:brbrWraparound deck with stunning viewsbrbrOutdoor dining table, chairs, and gas BBQ grillbrbrEXTRAS:brbrLaundry room with washer/dryer, deep freezer, and wash basin (located on the first floor next to the main entry)brbrAmple storage for water toys, boat trailer, vehicle, or RVbrbrBOATERS PARADISE!brbrThe 240' private dock can accommodate boats up to 42’ and offers plenty of tie-off space for jet skis, kayaks, and paddleboards. With quick access to both the Gulf and Atlantic, your ocean adventures start right here.brbrPET POLICY: brbrOne small dog (under 30 lbs) may be allowed with prior approval.brbrYou must request pet approval before booking.brbrNo exceptions on weight or number of pets.brbrPets are not permitted on furniture at any time.brbrUnauthorized pets will not be allowed to stay.brbrbrNEED MORE SPACE:brbrHosting a larger group Check out our sister property, Beachside @ Torchview, located right next door! Perfect for doubling the space and fun.brVRBO Listing #: 2285886brbrTorchview Lookout has welcomed guests for over 20 years and began a new chapter with its current owner in 2020. Come experience the magic of Big Torch Key in your own private slice of the Keys!

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Select Dates for Price

Private Vacation Home

The Bent Anchor-boat lift diving snorkeling fishing key deer 22 miles Key West

Summerland Key, Florida, United States

Welcome to our 3 bedroom, 2 full bath home on canal front Ramrod key. Quite laidback community. Great fishing & diving. 30’ dock with 15,000 lb boat lift for v-hull boat. It’s only a short boat ride out of the deep water canal to Picnic island, Looe key reef and Atlantic Ocean. The covered deck canal side is great for dining or just relaxing. The kitchen has microwave, toaster oven, coffee maker, garbage disposal and all cooking utensils. Kitchen, dining and living room have open floor plan. All 3 TVs are smart TVs or Fire TVs. Access your accounts with high speed Wi-Fi. Master bedroom has king bed full bath large closet tv and dresser. Bedroom 1 has a queen bed and closet. Bedroom 2 has bunkbed with single and double beds closet, TV and desk. Downstairs you will find a picnic table, hanging chairs, gas grill and a bait freezer, Fish cleaning station with water, fan and shade. Beach chairs and towels are located in the wicker cabinet downstairs. Pin fish trap and live bait pen are also available for your use. Looe key dive center, Tiki hut bar and Grill are located at entrance to the neighborhood and there is miniature golf and live music at Boondocks about a mile away. Winn-Dixie CVS and Walgreens pharmacy are six minutes away on Big Pine key. A lot of great restaurants with live music nearby. Free deep water ramp nearby on Little Torch key. A short walk to beautiful sunrises and a short drive to beautiful sunsets.Key West is only twenty two miles away more fun, shopping and nightlife.

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Sleeps

$247.31

/ Nightly

Cottage

Starfish Cottage - Sleeps 4 - ESCAPE THE COLD; OUR POOL IS HEATED!

Summerland Key, Florida, United States

brThe Star Fish Cottage is a one bedroom unit that includes a Queen-sized bed and TV in the bedroom, a full kitchen, bathroom with a tub/shower, living area with a sofa, TV, table with 4 chairs and some outdoor space on the side of the unit with a table and chairs. It can comfortably sleep 3 adults or 2 adults and 2 small children. The unit is air conditioned and WiFi service is available throughout the resort. Enjoy the communal outdoor pool and covered patio that has a gas grill, griddle and picnic area. There is a laundry room with washers/dryers for guests to use free of charge.brbrFor those who would like to venture out to the beach, the unit has 2 beach chairs, a beach umbrella, a cooler and beach towels for your convenience. brbrGuest may request to have their pet, 1 dog of 40 pounds or less, accompany them on their vacation and will be required to sign and abide a pet occupancy agreement as well as pay $75 in additional cleaning fees for the in-depth cleaning required after a dog has stayed in the unit. Guests that bring a dog that has not been pre-approved by management or do not follow resort rules will be asked to leave the resort and all payments will be forfeited.brbrFishing adventures, bird watching, water sports or some down time relaxing in nature and the beauty of the most desired key in Florida. We’re twenty-five miles to Key West for dinner and nightlike or walk down the block to the local tiki bar, Tonio’s. brbrWe have plenty of space for your boat and trailer. There is a boat ramp just down the block at Tonio's that can handle flat boats 21' or smaller and the boat ramps at Cudjoe Gardens Marina (477 Drost Ave.) and Little Torch Key (SR 4A & County Road) can handle larger boats for a minimal fee.brbrWe’re located twenty-five miles from Key West for dinner and nightlife. Walk 2 minutes down the block to Tonio's Seafood Shack & Tiki Bar. Bahia Honda State Park, with its beautiful beaches is a 15 minute drive from HIDDEN HAMMOCK RESORT. Our property is not on a waterfront and there are no public beaches in Summerland Key.brbrGuests are provided with the following amenities: a small bottle of dish soap, hand soap and a sponge, a roll of paper towels and toilet paper, a few laundry pods and hotel-size toiletries in the bathroom. This is to help our guests off to a good start. There are grocery and convenience stores in the areas for guests to purchase anything else that they may need.

1

Bed

1

Bath

4

Sleeps

$228.75

/ Nightly

Cottage

Ocean Front Access - just 30 miles to Key West

Summerland Key, Florida, United States

These cottages are not fancy, but clean and comfortable. Plenty of space for your boat trailer, public ramp just around the corner. We have 2 cottages on this property. This is unit #1. This cottage does not have an ocean view but is on the open water. Just a few steps you can walk out and lounge by the ocean. brTo see our other units features and availability please see VRBO listing #789269brbrYou're in the tropics... listen to the waves, rest, relax or fish, kayak and snorkel, if you wish to lose a few pounds. One bedroom cottage with direct ocean access. Sunrise view, ocean breezes. Fully furnished, linens, cable/internet. Kiki's restaurant and bar within walking distance. Shuttle to Key West at the end of the street. Come and stay with us, you're sure to have a wonderful vacation.

1

Bed

1

Bath

2

Sleeps

$270.17

/ Nightly

Private Vacation Home

Cudjoe Bay Overlook

Summerland Key, Florida, United States

This really nice custom Keys home is located in a very quiet area with good boating access to both the Atlantic with its coral reefs and Gulf Stream or the Gulf and backcountry. The home features three bedrooms and two baths, a screened porch, and a rooftop star deck for spectacular views of Cudjoe Bay and sunsets. There is a modern and fully equipped kitchen adjacent to the main dining area and porch. The living area is large and opens onto the porch through pocketed sliders. You will have TV, DVD, Stereo with CD and plenty of room to relax. The master bedroom has a king-sized bed and private bath. The other two bedrooms feature two twin beds in each. Amenities include a washer/dryer, barbecue grill, and central A/C. From the concrete dock the fisherman, diver, or boater will have easy access to the ocean-side waters as well as the backcountry by way of a nearby bridge and channel going north. The reef edge is about 5 miles offshore and the Gulf Stream lies just beyond. Here you can experience diving and snorkeling, sample reef fishing or tackle the big blue water species like dolphin, sailfish, and marlin. Nearby you can find shopping, fuel, bait, post office, banks, restaurants, and groceries. Just 23 miles down US1 is Key West for its world-class dining, unique shopping, and unusual history. The airport in Miami is about a three-hour drive. This is a non-smoking home. Ask about our pet policies. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE.

3

Bed

2

Bath

6

Sleeps

$294.83

/ Nightly

Private Vacation Home

3/2 waterfront home w/54ft dock near Key West

Summerland Key, Florida, United States

This peaceful retreat in the heart of all the Florida Keys fun.brplenty of space and comfort to enjoy a tranquil sunrise, a breathtaking Florida Keys sunset, or a serene evening of stargazing. Downstairs, you’ll find ample seating and room for entertaining, outdoor kitchen, and relaxing. The outdoor fire pit is a perfect spot to unwind after a long day at sea!brThe spacebrThe property included Smart TVs in the living room and master bedroom give you access to international, local and premium movie channels and Pay-per-view, YouTube, and over 400 channels to surf through. Downstairs kitchen, 2 kayak, and fire pit.brOther things to notebrProperty includes a 54 ft dock that can accommodate vessels up to 30 feet long, and a small vessel on a 6000lbs boat lift ( boat lift is temporarily out of service). The home has plenty of parking space to fit a 50 ft trailer (or an RV). Large ice machine ideal for fishing or drinks. Chest freezers for bait and an above ground pool to enjoy the keys warm days.

3

Bed

2

Bath

8

Sleeps

$236.33

/ Nightly

Private Vacation Home

3/2 waterfront home w/54ft dock with WiFi, AC in wonderful Summerland Key

Summerland Key, Florida, United States

Summerland Key is waiting for you This peaceful retreat in the heart of all the Florida Keys fun.brplenty of space and comfort to enjoy a tranquil sunrise, a breathtaking Florida Keys sunset, or a serene evening of stargazing. Downstairs, you’ll find a large shaded cleaning table, outdoor kitchen, above groundpool, ice maker machine, freezer, extra fridge, grill, and relaxing ample seating and room for entertaining, The outdoor fire pit is a perfect spot to unwind after a long day at sea!

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Bath

Sleeps

$602.23

/ Nightly

Private Vacation Home

Blue Pearl of Summerland Key 4 Bedrooms, 3 Baths with Dock, Heated Pool and Spa

Summerland Key, Florida, United States

Welcome to this Florida Keys gem, The Blue Pearl. The Blue Pearl is a beautiful, updated waterfront home with pool in a quiet neighborhood on Summerland Key (mile marker 24). Your stay here will relieve you of stress and warm your soul. The beautiful tropical landscaping provides privacy and a soothing atmosphere for your island adventures. It has a great location and convenient to world famous ocean and back country fishing and diving spots such as Looe Key, American Shoal (lighthouse built in 1880), Content, Marvin, Snipe, and Sawyer Keys, restaurants and shopping. Some of the best boating in the Key can be found on Summerland Key. Key West is only minutes away and offer endless entertainment, activity attractions, and dining options. brIt’s time for your tropical vacation and this house and upscale location will assure your needs are met. This wonderfully furnished waterfront home is available for monthly rental. The home is fully furnished with everything you will need. Just bring a toothbrush and a change in attitude. The house has Wireless internet and cable TV. In addition to the living room, TV’s are in all 4 bedrooms. There is one room with a king size bed (Tommy Bahama Ivory Key furniture), two bedrooms have queen size beds, the 4th bedroom has to two single beds. The living room also has a queen size pull out bed. The house is located on a flow-through canal, consequently the water is clear and clean. Tropical fish such as Anglefish and Parrot fish are seen on a routine basis. On the main levle there is a large covered porch overlooking the canal with a couch, table and chairs. Off the master suite, there is a small balony with two chairs and a small talble perfect for watching the stars on clear nights. We have a large ice maker (500lbs per day) available for the boaters and fishermen to use. brLocated between Marathon and Key West, Summerland Key is close enough to visit both in the same day. One of Florida's top beaches at Bahia Honda is only minutes away. There are several tackle and dive shops in the area and a boat ramp is near by. brThe location offers quick access to local fishing and diving spots. You can easily navigate access to Gulf via Niles Channel or a direct shot to the Atlantic ocean. Tarpon enthusiasts, we have easy access to some of the best bridge and flats tarpon spots in Florida. Tarpon are also common in the canal behind the house. Both the Seven Mile and Bahia Honda bridges are close by and there are a multitude of flats and cuts in the area that tarpon, permit, and bonefish frequent. The Sawyer and Content Keys are easily reached from our house via Niles Channel. Marvin Key sandbars are also within easy access through Niles or Kemp chanels. Don't forget the reef and offshore fishing which is also excellent off of Summerland Key where you will find snapper, dolphin, sailfish, Kingfish, and grouper just to name a few of the local species! In the Gulf, you will find cobia, snapper, trout, grouper, bonefish, permit, tarpon, and mackerel.brFor the diver, we are close to numerous (Content Keys, Sawyer Key, etc.) excellent lobster spots in the gulf and Atlantic. Looe Key, Adolphus Busch wreck and American Shoal Lighthouse are easily reached due south of our location and there are many other great dive sites close by. brBoat rentals, fishing guides, and a boat ramp are available. We are only a short distance from Looe Key, which is renowned for its beautiful coral reefs. Bahia Honda beach is rated as one of the top beaches in Florida and is a short distance from our house.brThe home is just a 25 minute drive to Key West Florida. This is a great location as the island is close to many restaurants, grocery stores (Winn Dixie, Murray’s Market), CVS and Walgreens drug stores, fishing, diving, clothing and gift stores several tackle shops, and marinas. brThis recently updated home accommodates up to 8 and has 4 bedrooms and 3 full bathrooms. Tastefully decorated with Keys-style/Tommy Bahama furniture and wall hangings, you will feel the true spirit of the tropics. With 2 bedrooms upstairs and 2 bedrooms downstairs there is plenty of room for your family and friends. Two of the bedrooms are masters with on-suite bathrooms. The first floor has a full-size washer and dryer. The modern updated kitchen includes stainless steel appliances and is a pleasure to cook in and serve your guests. The dining area has a large dining table that will accommodate 8 and there is a breakfast bar with seating for 3. You can also eat outside on the covered porch.brDownstairs the house features a tropical pool area with plenty of comfortable seating as well as a large table with chairs great for that afternoon BBQ using the available gas grille. A large capacity ice machine is also located downstairs. There is a pool heater for the cooler months and a separate jacuzzi which is also a great place for small kids. An enclosed downstairs shower area is great for washing off the salt or sand after a day on the boat or at the beach. brA large covered porch upstairs overlooks the water and is a great place to watch the boats go buy or spend a peaceful evening. There is a 70-foot dock with a fish cleaning table. The canal usually has an abundance of snapper and you may see the occasional manatee. brThe large eat-in kitchen is fully equipped and includes a dishwasher, microwave, coffee maker, blender, pots/pans, silverware, etc. Sheets, towels, pillows are provided. The rooms are nicely furnished with ceiling fans, central air conditioning, cable TV, and VCR/DVD. brNo boat, not a fisherman or diver, no problem Mon! Fish off the dock behind the house. Three kayaks are provided for our guests. The area has hiking trails (Big Pine Blue Hole and Bahia Honda State Park), biking, and is an excellent area to kayak. Jet ski and kayak tours and/or rentals are available at several locations in the area. See the little Key Deer on Big Pine Key.brThere are several good restaurants in the area including Little Palm Island, Square Grouper/My New Joint, Galley Grille, Boondocks Grille, KikiI's Sandbar, Big Pine Rooster, Tonio’s Seafood, and Mangrove Mamas. Looe Key Tiki bar and Boondocks usually have nightly entertainment featuring great local and regional bands. Of course, Key West offers endless fine dining establishments. brThere is a minimum 28 day rental period, no exceptions. County and state taxes are collected (combined at 12.5%) and the renter must be 25 or older. Nightly occupancy is limited to a maximum of 8 people. Absolutely no smoking and no pets and failure to comply will forfeit your security deposit. Not available for temporary employee housing. of more than one family unit.brSecurity cameras monitor the front door, dock area, and the spa/pool. br

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Bath

Sleeps

$423.75

/ Nightly

Private Vacation Home

44ft Seawall at Sportsman's Paradise

Summerland Key, Florida, United States

44ft Seawall at Sportsman's ParadisebrbrTrue Island Paradise. Brand New in the rental program, this 2020 Stilted 2Bd/2Ba is located on a wide 60' sparkling canal with immediate ocean access in just seconds! 1 king bed and 1 queen bed plus a queen pull out sofa. Mini split air conditioners allow you to set your temperature in each room. The most perfect sportsman's retreat, with everything you will need, with oversized seawall to accommodate PLUS SIZE BOAT! Features a newly poured sprawling 44' concrete dock, equipped with dock posts, mooring whips, fish cleaning table, cleats and swim ladder. 20 and 30 amp receptacles at dock. Use of the downstairs locking enclosure, the 350# per day commercial ice maker and large chest freezer is available for guests. Being an oversized lot, there is more room to enjoy the outdoors, with a spacious side yard garden oasis, surrounded by tropical oversized planters to add privacy, while at night, lounge around and view the stars and moon under the clear night sky. Share a cocktail or two with your friends at the “Tipsy Turtle Bar” downstairs. High speed internet and cable tv installed and also wired for Directv. Just bring your directv box(s) to enjoy all your programming from home. Walk or drive to The Square Grouper without ever getting on U.S.1. A mural called My Happy Wall was hand painted by a local artist, and depicts the beauty of our natural surroundings, from roosters and flamingos to a conch house, a dingy boat, to turquoise blue waters, this wall will make you smile!brbrSECURITY DEPOSIT REQUIRED, NO SMOKING, NO PETS,br7 DAY MINIMUM LOBSTER SEASON, WIFI IN REC HALL, OVERFLOWbrPARKING IS NOT GUARANTEED. IT IS A FIRST COME, FIRST SERVE LOT AND CANNOT BE RESERVED AHEAD OF TIME.brVO REGISTRATION FEE effective Jul 1, 2023 of $125.00DUE UPON ARRIVAL CASH OR CC ONLY. PAID DIRECTLY TO VENTURE OUT WHEN YOU ARRIVE.

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Sleeps

$507.95

/ Nightly

Private Vacation Home

Tides & Tranquility - Venture Out Unit 053

Summerland Key, Florida, United States

Escape to paradise in Cudjoe Key. This charming ocean front home has breathtaking views of the Atlantic Ocean and spectacular sunrises. Just steps from the water, it provides easy access for boating, kayaking, paddling, swimming and fishing enthusiasts. Enjoy modern conveniences including free Wi-fi, TV, a fully equipped kitchen and outdoor grill for memorable gatherings. The master bedroom has a queen mattress and TV for streaming. The guest bedroom features a bunk bed with a full mattress on the bottom, twin on top. There are two full bathrooms and a sleeper sofa for a comfortable experience. Added amenities include a swim ladder, dock posts and and elevator.(note that the elevator is not a guarantee if a maintenance issue occurs)brVenture Out's exceptional amenities include a large pool, ocean swimming area, hot tub, tennis, pickleball and basketball courts and a recreation center with a pool table, library and games. Contact us today to book your relaxing getaway in the beautiful Florida Keys!

2

Bed

2

Bath

6

Sleeps

$244.9

/ Nightly

Private Vacation Home

Blue Heaven

Summerland Key, Florida, United States

If you are looking for a great place to kick back and enjoy the easy Keys lifestyle, then Blue Heaven is just for you. This ground-level three-bedroom, two-bath home is located on the ocean side of Cudjoe Key with a great deep canal and a marina just around the corner. The home features eclectic and colorful decor with a mix of antiques and Caribbean/Keys colors and art. Inside there is a bright and comfortable living room area with an adjacent dining area as well. There is also a large Florida Room which opens out to a huge screened and covered dining/party area. The three bedrooms feature a queen in one bedroom, another queen in the second bedroom, two double beds in the third, plus a sofa sleeper in the Florida room. The kitchen is well-equipped and ready for you. Amenities include central AC, five TVs, DVD, stereo with CD, dishwasher, washer/dryer, and barbecue grill. From the full-length concrete seawall/dock you have excellent boating access to the ocean, Gulfstream and coral reefs, or the backcountry and Gulf. There is a built-in step-down access to the canal for swimming or snorkeling. Nearby there are excellent restaurants, a dive shop, and a marina. Within a short drive, there are also groceries, banks, post offices, bait and tackle, boat rentals, kayak rentals, and shopping. Key West and its unusual nightlife, world-class dining, and unique shopping are 20 miles south. The airport in Miami is about a three-hour drive. This is a non-smoking home. Ask about our pet policies. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE.

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Sleeps

$421.98

/ Nightly

Private Vacation Home

Florida Keys Paradise!

Summerland Key, Florida, United States

Looking for the ultimate vacation experience Our vacation home has everything you need to relax and have fun. We are located on a beautiful flow through canal with dockage to fit a 26’ boat. Take a 5 minute boat ride to open water or explore the mangroves by kayak. The fish cleaning station is perfect for your fresh catch. Enjoy your stay with the heated pool, hot tub, tiki hut, putting green, and fire pit. We are located between Key West and Marathon, enjoy the best of both! 28 day minimum stay, must start at the beginning of the month. The boat lift is not available at this time.

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$1074.96

/ Nightly

Private Vacation Home

~Reel Em' Inn~ Luxury Oceanfront Summerland Key home with deep water and pool!

Summerland Key, Florida, United States

Completely remodeled, high-end Summerland Key home! Meticulously designed vacation property with exquisite furnishings throughout the home, quartz countertops, and top-of-the-line stainless steel appliances. This newly remodeled home has a lovely open & entertaining feel to the living, dining, and large outdoor spaces! The home consists of four large bedrooms plus a separate office space. The master suite has two separate en suite full bathrooms and contains a king bed, a single-size pullout chair, and a queen pullout couch located in the office. The two other bedrooms each have king beds and the third bedroom has four separate full-size mattresses located on bunk beds. The living room has been furnished with a very inviting couch consisting of a queen, high-quality pillow top pullout mattress as well. Each coastal-designed bedroom also has its own flat screen tv as well as a large flat screen tv in the living room for family movie nights. The spacious outdoor area (including the covered space underneath the house as well as the large pool deck area) is sure to be perfect for your entertaining pleasure! Enjoy fishing right off the seawall or just grab a cocktail and sit under the Tiki hut with a great view! Bring your hammock to hang near the pool and enjoy the professionally landscaped tropical oasis yard or watch the Coconut Palms blow in the breeze! The pebble tech pool was thoughtfully designed with a perfectly angled shallow sunning deck which has bubblers and an umbrella to relax under as well as two water features at each corner. We have cornhole and ledge loungers for your use with your guests located in the garage. This allows you to lay back and relax as you watch your guests play and boats travel by across the open water view! The canal is deep water and nice and wide so bring your large boat to take pleasure in. The property has over 100 feet of docking seawall for your boat/s! Enjoy a lobster dinner with your guests on the main balcony at the back of the house which has enough seating for six or eat inside at the dining table which also seats six and the peninsula off the kitchen which seats three. All water-view windows and sliders have remote-controlled shades so you can lay in bed and just push a button to watch the golden sunrise in the morning as you wake! Just a 10-minute short boat ride straight out of the canal to the famous LOOE Key national reef and amazing snorkeling! Hop in the car for only a 30 minute ride either way to Marathon or Key West so you can enjoy the wonderful restaurants and nightlife as you choose! Don't miss out on making lifelong memories with your family or friends vacationing at this exquisite Florida Keys home!

Bed

Bath

Sleeps

$790.93

/ Nightly

Private Vacation Home

Waterfront Captain House with Boat Basin & Ramp!

Summerland Key, Florida, United States

Welcome to Paradise!brStay in the amazing Keys and beautiful waterfront home with boat basin for your boat. The property lot is almost an acre with an island point surrounded by sea life. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!brbrThe Space:brCaptain House has an airy floor plan from living room to kitchen. Sofa bed, smart TV, and relaxing heated massage recliner chair! Dining area with high back chairs. Master bedroom has a king size bed, TV, en-suite bath, and a separate entrance. Cozy queen bedroom with smart TV near the second bath. Third bedroom has a trundle bed (full over full and one roll out single bed) with board games for entertainment! Tile and wood thoughout. Awesome fishing quarters for family and friends. Pet friendly!brbrAmenities:brCable, wifi, central air, 4 free parking spaces, 3 private entrances, full kitchen, stove, oven, refrigerator, dishwasher, dishes, silverware, cooking basics, regular coffee maker, coffee, tea, microwave, toaster oven, blender, washer, dryer, bathtub, showers, hot water, toiletries, first aid kit, hangers, iron, three smart TV's, board games, bed linens, extra pillows and blankets, bath and beach towels, hair dryer, laptop friendly workspace, beach chairs, patio table and chairs, BBQ grill, outdoor bait freezer.brbrBasin and Ramp:brAvailable to guests with one boat per home up to 40 foot included in your stay. The basin basin has water hose, catch cleaning station, and power outlet. Low tide is around six feet and one foot near the shoreline. Use the shared ramp two doors down or at 751 State Road 4A, Little Torch Key to launch your boat then tie it or explore the area for some fun in the sun!brbrLocation:brCaptain House is located mile marker 28.5 on the Gulf side. Only a 10 - 15 minute boat ride to open waters towards Gulf or Atlantic. No RV hookups, no RV/camper/tent/outdoor accommodations provided (we are not campground zoned).brbrActivities:brEnjoy the stunning views of our nearby beaches! Bahia Honda State Park and Beach around 10 minute car ride. Sombrero Beach in Marathon is a 25 minutes drive with iconic beach views! Fort Zachary Taylor Beach in Key West is the westernmost beach and worth the 45 minutes drive.brbrRent fishing rods and kayaks at Jig's Bait and Tackle in Big Pine Key. Rent boat, snorkel and fishing gear, paddle boards, charters, and specialty cruises at Captain Hooks in Big Pine Key.brbrWalking distance to Kiki's Sandbar Restaurant. Minutes from Little Palm Island and ferry. Only 15 minute boat ride to the famous Looe Key reef for diving/snorkeling. Picnic Island is great for swimming and relaxing on the beach, a 10 minute boat ride. Big Pine Key is 5 to 10 minutes by car, the habitat of beautiful key deer and has an amazing park with panoramic water view! The Blue Hole trails in Big Pine are great for biking, hiking, and walking. Also has a lake with sea life! Snipe Key has swing on tree and spectacular beach about 45 minute boat ride.brbrSquare Grouper Restaurant in Cudjoe Key is best for everything (main floor) and My New Joint (second floor) is great for raw bar. Santiago's Bodega is one of the best of Key West. Walk Duval Street Key West for restaurants, shops, and touring. The Guidebook for things to do, places to see, where to eat, and where to shop is provided in the home during your stay.brbrWatch the sunrise and sunset on the point or go to the famous Key West Mallory Square to catch the western most sunset of the Florida Keys! Sight-see on the Key West Conch Tour train for a some Key West history. Tour Ernest Hemingway Home and Museum in Key West to see his six toed cats. Or visit treasure hunter Mel Fisher Maritime Museum, also in Key West. Only 28 miles to Key West!brbrEasy Check-in:brSelf check-in with keyless entry or lockbox key.brbrWe look forward to accommodating!

3

Bed

2

Bath

8

Sleeps

$374.79

/ Nightly

Private Vacation Home

Sugarloaf Sunrise

Summerland Key, Florida, United States

Located on the open water in Sugarloaf with absolutely gorgeous views and excellent boating, this newly renovated home is the perfect spot for relaxation. Also throughout the home is brand new furniture that will certainly provide a comfortable space after a long day on the water to kick back and lounge. This home is equipped with wifi, central A/C, a washer/dryer, and a gas grill. For your sleeping, there is a queen bed in all bedrooms. The home also sits next to a canal for excellent boating access to open water. A 15-minute drive will put you in Key West for all your shopping needs, world-class dining, and unique history. The international airport in Miami is about a 3.5-hour drive with the Key West airport is about 20 minutes. This a non-smoking home. No pets. THIS HOME IS A 28-DAY MINIMUM RENTAL PER MONROE COUNTY CODE. br

Bed

Bath

Sleeps

$488.95

/ Nightly

Private Vacation Home

Beachside @ Torchview Waterfront Retreat

Summerland Key, Florida, United States

Welcome to Beachside at TorchviewbrLocated on the serene shores of Big Torch Key in the Florida KeysbrbrBeachside at Torchview is a charming 2-bedroom, 2-bathroom waterfront home offering breathtaking ocean views and the quintessential Keys lifestyle. Whether you're here to fish, boat, snorkel, or simply unwind, this peaceful retreat puts it all right outside your door.brbrPROPERTY HIGHLIGHTS:brbrWaterfront Views: Enjoy panoramic ocean views from the open-concept living area.brbrSplit Floor Plan: Offers privacy for guests and includes a full laundry room.brbrSpacious Grounds: Set on over one acre of lush, natural beauty – perfect for relaxing or exploring.brbrPrivate Dock: A 180’ dock accommodates vessels up to 50’ with deep water access via Niles Channel to the Atlantic. Just seconds to world-class fishing!brbrSLEEPING ARRANGEMENTS:brbrMaster Bedroom: King bed with en-suite bathroom and walk-in showerbrbrGuest Bedroom: Two twin bedsbrbrLiving Room: Sleeper sofabrbrSecond Bathroom: Full bath with showerbrbrHOME FEATURES:brbrLarge, open living area with sliding glass doorsbrbrScreened-in porch with dining area, ceiling fans & ocean breezesbrbrIndoor & outdoor dining areas (seating for 6)brbrFully stocked kitchen with essentialsbrbrBuilt-in desk – perfect for working remotelybrbrSpacious living room with 35” flat screen TV (Dish Network)brbrFull-size washer & dryer in unitbrbrSun deck with loungers & BBQbrbrDownstairs breezeway with bait freezer and fridgebrbrPLEASE NOTE: Dock does not have shore power or water hookup.brbrThe Perfect Florida Keys EscapebrbrBeachside at Torchview is ideal for families and friends seeking a peaceful, authentic Keys experience in a timeless setting. With privacy, comfort, and adventure at your fingertips, it’s everything you need for an unforgettable stay.brbrPET POLICY:brbrSorry, no pets allowed at Beachside. If you are traveling with a pet, please check availability at our pet-friendly sister property, Torchview (VRBO Listing #2072371), located directly next door.brbrNEED MORE SPACE brbrIf your group is larger than 6, consider renting both Beachside and Torchview to double your space and fun!brbrWe hope you’ll join us at Beachside at Torchview for a stay unlike any other – where the beauty of the Keys meets the comfort of home.

Bed

Bath

Sleeps

$713.31

/ Nightly

Private Vacation Home

Private Secluded Ocean View & Pool Near Key West

Summerland Key, Florida, United States

This beautiful Eco-friendly Ocean view home is away from the hustle-bustle of Key West. Welcome to this luxury deluxe vacation home that can comfortably accommodate for a large family union or wedding. brbrCome to Beautiful Key West and stay in this immaculate, beautifully furnished Home in the beautiful 2-acres green lush tropical Estates. Enjoy the peaceful surroundings while also being only 15 minutes from Key West Golf Club, the Beach, Restaurants, and Shopping.brbrThe spacebrOur property makes an excellent location for wedding or any large party gathering, we are a very private and secluded property for you to enjoy a quiet and peaceful time. The best part is to watch the stars after sunset from our yard or pool deck area.brbrSleeping Arrangements:brbrMaster Bedroom: 1 King bed (sleeps 2)brSecond Bedroom: 1 Queen bed (sleeps 2)brThird Bedroom: 1 Queen bed (sleeps 2)brFourth Bedroom: 2 Bunk beds (sleeps 2)brbrAdditional Sleeping Option: 1 Queen air mattress (available for use in the living area)brbrWe have added to all of our mattresses with an odor-neutralizing, anti-bacterial feature designed memory foam mattress to help you fall asleep easily and stay asleep throughout the night and greatly relieve back pains, and wake up feeling fully rested. brbrWe have one of the 10 best beaches (Bahia Honda) in the USA (Washington Post/Conde Nast Traveler) just a minute away from our property. brbrIf you are into *Biking * Fishing * Bicycling * Birding * Hiking * Paddling* Picnicking * Walking and Running * Wildlife Viewing * Nature Trail, then you got all, just a few minutes away Florida Keys Overseas Heritage Trail.brbrOur goal is to create guest accommodation that is environmentally responsible and non-detrimental to the local flora and fauna. According to NASA, there is greater than a 95% probability that the reason the Earth is warming up at alarming rates is due to human activity. Among the luxuries our home offers is higher-quality bedding and linens, cleaned with non-toxic, eco-friendly detergents, so that our guests can have a good night’s sleep.brbrDuring your stay, you will see many local species of deer, frogs, turtles, butterflies, birds, and other animals living on and around the property. In order to avoid harming these island residents, we are trying to uphold policies that are more environmentally-friendly, such as not using extremely harsh bleaches or chemical sprays on the house and around the yard. We also try to use environmentally-sensitive detergents and cleaning supplies when tidying the houses, as we are making efforts to be mindful about how our actions affect nature.brbrThe fresh, tropical breeze that you will feel upon arrival on our property is the result of a careful balance in nature, and it is our hope that the starry skies will continue to be clear in our beloved Florida Keys for many years to come. We aim to do our part in protecting the environment that we love.brbrThere is a basketball half-court near the pool, and foosball table located outside the home, allowing you to have some fun and get some exercise without going too far.brbrAs a Vrbo host, we work really hard to provide guests the most clean, comfortable and our beautiful home in the Florida Keys for an unforgettable vacation. Our home is a very unique, lush green, a peaceful tropical paradise in the fabulous Florida keys. brbrWe request that you respect our quiet neighborhood for calm and peace and no loud noise and music after 10pm as you would expect the same for yourself. Our property makes an excellent location for wedding or any large party gathering, we are a very private and secluded property for you to enjoy a quiet and peaceful time. The best part is to watch the stars after sunset from our yard or pool deck area.brbrThe nightly base rate assumes that up to 6 guests are occupying the listing. The home is designed to accommodate up to 10 guests, two per bedroom/sleeping space. For every additional guest after the first 6, the rate increases by $25 per person, per night when a reservation is made. The rate increases further prior of check-in, or after check-in according to what is outlined in the Rental Agreement.brbrWe Welcome Pets – With Care and Policy:brWe’re one of the few pet-friendly accommodations in the area and are happy to welcome guests with their furry companions.brbrHowever, due to past issues—such as pet hair, waste left behind, and property damage—we paused our pet policy for nearly a year. We’ve decided to welcome pets again because we want you to fully enjoy your vacation, including the company of your pet.brbrMaximum of 2 petsbrEach pet must weigh under 25 lbsbrPet fee: $100 per petbrbrWe kindly ask that you be fully responsible for your pet to help us keep this policy in place. Failure to follow these rules may result in additional cleaning or damage fees.brbrNearby Fitness & Marina AccessbrFor fitness-minded guests, a fully equipped 24/7 gym is located just a block away — perfect for maintaining your health and wellness routine while on vacation.brbrOnly two streets away (2–3 minutes) is the Cudjoe Gardens Marina, a family-run, eco-friendly marina on the beautiful island of Cudjoe Key (Mile Marker 21). The marina features 135 slips accommodating boats from 15 ft to 250 ft, with a dock depth of 14 ft, and is known for having the best boat ramp in the Lower Keys. You’ll find everything from frozen and live bait to a friendly, knowledgeable staff and a spectacular ocean view.brbrPlease inquire with us directly for usage rates or assistance if you’d like to access these facilities during your stay.brbrWe are licensed by the State of Florida, (DWE5403957), and require a rental agreement to be signed before check-in. It contains more information on the county bylaws pertaining to vacation rentals, and our complete home rules and will be emailed to you prior your check-in for acceptance and signed. brbr*** There may be additional charges for a large party or wedding, please inquire prior of making a reservation.brbrPlease take note that the management team may be on-site to inspect or maintain the gardens and landscaping, composed of over 300 coconut trees and innumerable exotic flowering plants, which requires constant care due to the property’s proximity to the salt ocean and intense exposure to south Florida sun and strong Atlantic winds. This maintenance will not impede your ability to enjoy the private amenities.

4

Bed

2

Bath

10

Sleeps

$309.76

/ Nightly

Private Vacation Home

10 minutes away from Bahia Honda and 30 minutes away from Key West

Summerland Key, Florida, United States

Outside you will find hammocks to relax in, bikes to check out the area and a dock that will accommodate most type boat. Located on the ocean side of Ramrod Key in canal, there are no bridges to the open water and it's a quick easy shot out of the canal. You will enjoy beautiful surroundings and have plenty to do. Enjoy all the unlimited water activities like swimming, fishing, and diving the Keys has to offer. Discover an assortment of Florida Keys wildlife featuring birds, iguanas, and Key Deer. You’ll find a shopping plaza hosting Winn-Dixie, Artists in Paradise, Beall’s Outlet, Radio Shack and branch of the Monroe County Library with Wi-Fi internet access nearby as well. Take a trip down to Key West for the daily sunset celebration or a romantic sunset cruise. Or visit one of the many venues offering the finest in live entertainment and great food. Be sure to take a stroll up and down Duval Street and visit the art galleries, shops, and more! Hire a charter boat captain, or go for a sunset cruise on one of the Schooners down at the wharf. Plenty of restaurants and bars down every street, Key West is a hot spot for travelers and locals.

3

Bed

1

Bath

6

Sleeps

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