Vacation Rentals By Owner In Upper Sugarloaf Key, FL

$317.42
/ Nightly

Private Vacation Home

Waterfront Escape

Upper Sugarloaf Key, Florida, United States
Enjoy a wonderful relaxing vacation in this Keys-styled open-water home located on the east side of Sugarloaf Key. This three-bedroom two two-bath home features all you need to get away from the grind. Located on the open water facing the trade breezes, the home has a large screened porch facing the water and the dock. You will find a fully equipped kitchen with all the amenities and a comfortable living area. For sleeping, there is a queen bed in the master, a queen in the second bedroom, and a day bed (2 twins) in the third bedroom. Other amenities include a washer/dryer, barbecue grill, central A/C, 2 TVs, DVD player, and stereo. For the boater, there is a wood piling dock on the open water, with a boat ramp/picnic area adjacent to the property. Access for fishermen and divers to the backcountry and Gulf is easy, while Oceanside access is under a bridge with some height restrictions. By auto, there is nearby shopping, groceries, great restaurants, marinas, fuel and convenience stores, banks, and much more. Key West and its unique history, world-class dining, and shopping, is only about 18 miles south. Big Pine Key and its wildlife refuge, dive shops, major grocery store, and pharmacy is about 12 miles north, while the world-renowned beach at Bahia Honda State Park is just a short drive further. The international airport in Miami is about three hours away. This is a designated nonsmoking home. Ask about our pet policies. THIS HOME IS A 29-DAY MINIMUM RENTAL PER MONROE COUNTY CODE.

3
Bed

2
Bath

6
Sleeps

$147.33
/ Nightly

Private Vacation Home

Our Happy Place

Upper Sugarloaf Key, Florida, United States
Summary:brbrBeautiful 3BDR 2BA Home on the canal, with boat liftbrbrbrbrThe Space:brbrWelcome to Your Sugarloaf Key Retreat! Escape to this sun-filled, single-level 3-bedroom, 2-bathroom haven situated on Lower Sugarloaf Key, perfectly perched on a pristine canal. Nestled on over a quarter acre, this spacious home is designed for relaxation and entertaining, featuring an open-concept great room that seamlessly connects generous living and dining areas to a beautifully equipped kitchen. You'll love the abundant cabinetry, granite countertops, stainless steel appliances, and a handy pantry and laundry closet. Step outside to your large screened-in porch, where dining and lounging come with breathtaking canal views—an ideal spot for year-round al fresco meals or sipping your morning coffee in the gentle sea breezes. The well-planned split floor layout ensures privacy for everyone, with two spacious guest bedrooms (one offering stunning canal views) sharing a thoughtfully designed bathroom. The expansive primary suite provides a personal sanctuary, featuring serene water views, patio access, double closets, and an en suite bathroom. Take full advantage of your 100 feet of waterfront with a composite dock and a 15K boat lift installed in 2020, making your fishing and diving adventures easily accessible. The property includes a substantial carport, ample open parking, and room for trailer storage on this impressive 12,500 sq. ft. lot. Located in the tranquil and exclusive Sugarloaf neighborhood, this home is just minutes away from fantastic restaurants and entertainment.

3
Bed

2
Bath

8
Sleeps

Exceptional(7)

$534.38
/ Nightly

Private Vacation Home

Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

Upper Sugarloaf Key, Florida, United States
Castaway – Your Ultimate Vacation Home on Sugarloaf KeybrbrWelcome to Castaway, a stunning 4-bedroom, 3-bathroom vacation home perfectly situated on a large corner double lot in a private cul-de-sac on Sugarloaf Key. This is a getaway like no other—surrounded by uninterrupted panoramic views of the Gulf of Mexico, where water stretches as far as the eye can see.brbrUnmatched Location & PrivacybrEnjoy the privacy of no neighbors on three sides and ample space for your boats, water toys, and vehicles. With your own 10-ton boat lift accommodating vessels up to 26’ and 6,500 lbs, a dock with a fish cleaning station, outdoor power, and a boat basin for kayaks and other watercraft, this is a water enthusiast’s dream come true.brbrLight-Filled, Spacious InteriorbrThe home’s interior boasts oversized floor-to-ceiling windows, flooding the space with natural light and framing breathtaking Gulf views from every room. The open-concept kitchen and dining area are designed for both comfort and entertainment, featuring a gas range stove, breakfast nook, dining table for six, and a breakfast bar with stools.brbrLiving Spaces Designed for RelaxationbrbrLiving Room: Relax on the sectional couch and recliner while watching your favorite shows on the 50” flat-screen TV.brbrMaster Bedroom: A spacious retreat with a king-size bed, ample closet and storage space, chest of drawers, en-suite bathroom with shower, and spectacular Gulf views from four large windows.brbrBedroom 2: Queen-size bed, flat-screen TV, large closet, and dresser.brbrBedroom 3: Oversized room with one full-size bed, one single bed, and an organizer-equipped closet.brbrBedroom 4 (Bonus Room): Downstairs family room featuring bunk beds (single over full), queen bed, and sofa sleeper. Note: This room is included only for groups of 9 or more; additional charges apply.brbrBathrooms:brbrMaster bath with full showerbrbrShared full bath with oversized jet jacuzzi bathtub/shower combobrbrDownstairs half bath with an outdoor showerbrbrOutdoor Living & EntertainmentbrA partial wrap-around deck offers outdoor dining and sitting areas ideal for entertaining. Dine waterfront for four or relax on four lounge chairs and Adirondack chairs around the outdoor fire pit.brbrImportant Rental DetailsbrbrMinimum Stay: 28 daysbrbrCheck-in: 4 PM | Check-out: 10 AM (No early check-ins or late check-outs to ensure thorough cleaning and sanitation)brbrOccupancy Restrictions:brbrUp to 8 guests include use of the 1st floor only.brbrFor 9-12 guests, the 4th bedroom (Bonus Room) is included for an additional charge.brbrNo baggage holding or extra bedding/supplies provided to reduce cross-contamination.brbrEnhanced cleaning protocols are strictly enforced for guest safety.brbrCome Castaway on Sugarloaf Key—your peaceful sanctuary surrounded by nature’s beauty and endless water adventures. We look forward to hosting you!

4
Bed

2
Bath

12
Sleeps

Exceptional(11)

$954.23
/ Nightly

Private Vacation Home

The Lighthouse - Beach Houses Key West

Upper Sugarloaf Key, Florida, United States
Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our cozy nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings relaxing and sipping your coffee or cocktails.brbr1 of 5 secluded bungalows nestled in a 10 acre ocean / beach front paradise. This unique property has close to 1000’ of private sandy beach, 2 docks extending out 450’ from the shore, great for docking your boat, jet ski or enjoying the great fishing action right off our pier. At the heart of our resort is our featured amenity, our newly remodeled grotto style pool inspired by natural Coral coast such as you would find in South Florida. The pool area features 2 pools; a smaller chill pool with a cascading waterfall bench. Our larger pool includes water slide, a waterfall hidden grotto, a swim up bar and a hot tub for those days you need to relax after a great day out fishing. Amenity’s also include complimentary paddle boards, our fitness center, 8 bikes to cruise the island, 2 tiki huts on the beach great for grilling as you feel the ocean breeze, or just soaking it all in on a hammock.brbrAlso a Great place for weddings, corporate retreats and family reunions (fees apply) brbrOther Amenities include :brJet ski rentalbrGolf cart rentalbrIn suite massagebrFishing charter toursbrbrOur guests are our top priority, and we are dedicated to exceeding their expectations. Your host is available 24/7, 365 days a year, ready to assist with anything you need—from providing extra towels to recommending the perfect restaurant.brbr*The Florida Keys even though surrounded by water is not known for its beaches. Our unique property does have a natural setting beach, meaning that seaweed and debris from the ocean does make its way to our shoreline. Specifically in the hotter months, extreme amounts of seaweed will accumulate on our shoreline and beyond.brbrSecluded island neighborhoodbrbrA vehicle is requiredbrbr***Self check inbrbr*Upon check in, a refundable damage deposit will be collected*brbr****During Hotter Months seaweed mixed with debris from the ocean will accumulate on our beach and beyond.brbr****Our property is located on what is considered to be a turtle nesting beach. We must follow environmental guidelines when trying to remove any type of seaweed that washes ashore.brbr****Its is strongly recommended to bring mosquito and no see um repellent (No-see-ums are tiny flying insects that are incredibly difficult to spot. Also known as biting midges, punkies, sand flies or biting gnats, these flying insects are small enough to fit through the mesh screens of windows and doors. They are also easy to overlook when they swarm around you or land on your skin.brNo-see-um bites are painful and itchy.brbrWe are committed to the conservation and protection of all our resources. We are constantly looking for ways to improve our efforts. Water is one of our most important life resources. You can protect and conserve this vital source by turning the faucet off while brushing your teeth or shaving, not using the toilet as a trash receptacle, being sure faucets are turned completely off, report leaky faucets and re using towels.brbr*In the event of a cancellation, guest will be refunded what is applicable per the cancellation guidelines minus the credit card transaction feebrMUST BE AT LEAST 30 YEARS OF AGE TO BOOK THIS HOUSEbrbr- NO SMOKING- $200.00 fee will charged for smoking inside the house.brbr- Bonfire prohibitedbrbr-Pets must be on a leash when outside. Pets are not allowed in the pool area.brbr- Protective footwear suggested while in the waterbrbr- We ask our guest not to remove any items found through out the house and property such as any type of sea items including drift wood that wash ashore that are used as decorative piecesbrbr-Guest shall take care of the premises, its appliances and furnishings and maintain the house in a neat and sanitary condition. Guest will leave house in the same condition as at check-in, including furniture placement. Excessive trash/garbage and or leaving the house in an unsanitary condition will be subject to an additional cleaning fee.brbr-$75.00 lost key fee

2
Bed

1
Bath

4
Sleeps

Exceptional(15)

$925.1
/ Nightly

Private Vacation Home

Private and Exclusive Florida Keys Getaway

Upper Sugarloaf Key, Florida, United States
The best time of the year to visit us is now!! brbrOne of a kind two bedroom beach bungalow right on the beach, deck with direct ocean views, sandy beach, a tropical ambiance and a family friendly setting that will make you feel like you are in your own private island and where memories are made.brbrThe Palm is 1 of 5 secluded bungalows nestled in a 10 acre ocean / beach front paradise. This unique property has close to 1000’ of private sandy beach, 2 docks extending out 450’ from the shore, great for docking your boat, jet ski or enjoying the great fishing action right off our pier. At the heart of our resort is our featured amenity, our newly remodeled grotto style pool inspired by natural Coral coast such as you would find in South Florida. The pool area features 2 pools; a smaller chill pool with a cascading waterfall bench. Our larger pool has a water slide, a waterfall hidden grotto, a swim up bar and a hot tub for those days you need to relax after a great day out fishing. Amenity’s also include complimentary paddle boards, our fitness center, 8 bikes to cruise the island, 2 tiki huts on the beach great for grilling as you feel the ocean breeze, or just soaking it all in on a hammock.brbrOur guests are our top priority, and we are dedicated to exceeding their expectations. Your host is available 24/7, 365 days a year, ready to assist with anything you need—from providing extra towels to recommending the perfect restaurant.brbrAlso a Great place for weddings, corporate retreats and family reunions (fees apply) brbrOther Amenities include :brJet ski rentalbrGolf cart rentalbrIn suite massagebrFishing charter toursbr*fees applybrbr*The Florida Keys even though surrounded by water is not known for its beaches. Our unique property does have a natural setting beach, meaning that seaweed and debris from the ocean does make its way to our shoreline. Specifically in the hotter months, extreme amounts of seaweed will accumulate on our shoreline and beyond.brbrA vehicle is suggested.brbr***Self check inbrbr*Upon check in, a refundable damage deposit will be collected*brbr**** During Hotter Months, extreme seaweed mixed with debris from the ocean will accumulate on our beach and beyond, (Please contact us if needed to get up the moment seaweed condition)brbr****Our property is located on what is considered to be a turtle nesting beach. We must follow environmental guidelines when trying to remove any type of seaweed that washes ashore.brbr****Its is strongly recommended to bring mosquito and no see um repellent (No-see-ums are tiny flying insects that are incredibly difficult to spot. Also known as biting midges, punkies, sand flies or biting gnats, these flying insects are small enough to fit through the mesh screens of windows and doors. They are also easy to overlook when they swarm around you or land on your skin.brNo-see-um bites are painful and itchy.brbr**** Must be at least 30 years old to bookbrbr**** We are committed to the conservation and protection of all our resources. We are constantly looking for ways to improve our efforts. Water is one of our most important life resources. You can protect and conserve this vital source by turning the faucet off while brushing your teeth or shaving, not using the toilet as a trash receptacle, being sure faucets are turned completely off, report leaky faucets and re using towels.brbr*In the event of a cancellation, guest will be refunded what is applicable per the cancellation guidelines minus the credit card transaction feebr**MUST BE AT LEAST 30 YEARS OF AGE TO BOOK THIS HOUSE** brbr** **No day visitors allowedbrbr** Max 4 guests allowed per booking brbr** NO SMOKING brbr**NO FRYING FISH, TURKEYS OR ANYTHING ON THE DECK brbr**Pets must be on a leash when outside. Pets are not allowed in the pool area.brbr**Quiet time 10:00PM - 7:00AM brbr **Protective footwear suggested while in the water brbr**Check out 10:00AM (Check out strictly enforced additional $50.00 will be charged for every hour up to four hours, after four hours a full day charge will be accessed) brbr **All dirty dishes, pots, pans, cups, glasses, silverware must be left in the dishwasher brbr**All dirty towels to be left in a in a corner of the bathroom floor brbr**We ask all guest to please wipe their feet prior to entering the house in order to keep the sand to a minimum inside the house brbr**Leaving the house with excess trash and in a unsanitary condition would be subject to an additional cleaning fee brbr We love our guests to enjoy our beach house. Please bear in mind that our property is situated on the Ocean and from time to time we get items and seaweed that wash a shore. **Depending on the season and weather, seaweed could accumulate in our beach. brbrWe are committed to the conservation and protection of all our resources. We are constantly looking for ways to improve our efforts. Water is one of our most important life resources. You can protect and conserve this vital source by turning the faucet off while brushing your teeth or shaving, not using the toilet as a trash receptacle, being sure faucets are turned completely off, report leaky faucets and re using towels.

2
Bed

2
Bath

4
Sleeps

Exceptional(8)

$1133.12
/ Nightly

Private Vacation Home

The Hemingway - Beach Houses Key West

Upper Sugarloaf Key, Florida, United States
If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you.brbrWe are pet friendly !!!brbrOff the beaten path you will find a unique location and a beach front bungalow with endless unobstructed views of the ocean from every bedroom. Featuring an open family area, full kitchen, deck and its own tiki, excellent for grilling, having a cold drink or just gazing at the ocean. Enjoy you day on the beach, dock or our coral inspired pool, with swim up tiki bar, waterslide and grotto. brbrThe Hemingway is 1 of 5 secluded bungalows nestled in a 10 acre ocean / beach front paradise. This unique property has close to 1000’ of private sandy beach, 2 docks extending out 450’ from the shore, great for docking your boat, jet ski or enjoying the great fishing action right off our pier. At the heart of our resort is our featured amenity, our newly remodeled grotto style pool inspired by natural Coral coast such as you would find in South Florida. The pool area features 2 pools; a smaller chill pool with a cascading waterfall bench. Our larger pool has a water slide, a waterfall hidden grotto, a swim up bar and a hot tub for those days you need to relax after a great day out fishing. Amenity’s also include complimentary paddle boards, our fitness center, 8 bikes to cruise the island, 2 tiki huts on the beach great for grilling as you feel the ocean breeze, or just soaking it all in on a hammock.brbrAlso a Great place for weddings, corporate retreats and family reunions (fees apply)brbrOther Amenities include :brJet ski rentalbrGolf cart rentalbrIn suite massagebrFishing charter toursbr*fees applybrbrOur guests are our top priority, and we are dedicated to exceeding their expectations. Your host is available 24/7, 365 days a year, ready to assist with anything you need—from providing extra towels to recommending the perfect restaurant.brbr*The Florida Keys even though surrounded by water is not known for its beaches. Our unique property does have a natural setting beach, meaning that seaweed and debris from the ocean does make its way to our shoreline. Specifically in the hotter months, extreme amounts of seaweed will accumulate on our shoreline and beyond.brbrA vehicle is required to get aroundbrbr***Self check inbrbr*Upon check in, a refundable damage deposit will be collected*brbr****During Hotter Months, extreme amounts of seaweed mixed with debris from the ocean will accumulate on our beach and beyond (Please contact us if needed to get up the moment seaweed condition)brbr****Our property is located on what is considered to be a turtle nesting beach. We must follow environmental guidelines when trying to remove any type of seaweed that washes ashore.brbr****Its is strongly recommended to bring mosquito and no see um repellent (No-see-ums are tiny flying insects that are incredibly difficult to spot. Also known as biting midges, punkies, sand flies or biting gnats, these flying insects are small enough to fit through the mesh screens of windows and doors. They are also easy to overlook when they swarm around you or land on your skin.brNo-see-um bites are painful and itchy.brbr**** Must be at least 30 years old to book.brbr**** We are committed to the conservation and protection of all our resources. We are constantly looking for ways to improve our efforts. Water is one of our most important life resources. You can protect and conserve this vital source by turning the faucet off while brushing your teeth or shaving, not using the toilet as a trash receptacle, being sure faucets are turned completely off, report leaky faucets and re using towels.brbr*In the event of a cancellation, guest will be refunded what is applicable per the cancellation guidelines minus the credit card transaction feebr**MUST BE AT LEAST 30 YEARS OF AGE TO BOOK THIS HOUSE**brbr**No day visitors allowedbrbr** Max 6 guests allowed per bookingbrbr**Pets must be on a leash when outside. Pets are not allowed in the pool area.brbr** NO SMOKINGbrbr**NO FRYING FISH, TURKEYS OR ANYTHING ON THE DECKbrbr**Quiet time 10:00PM - 7:00AMbrbr**Protective footwear suggested while in the waterbrbr**Check out 10:00AM (Check out strictly enforced additional $50.00 will be charged for every hour up to four hours, after four hours a full day charge will be accessed)brbr**$250.00 fee per dog per stay, smaller non aggressive breeds only ( Failure to advice on pet in the house will cause an additional cleaning fee)brbr**All dirty dishes, pots, pans, cups, glasses, silverware must be left in the dishwasherbrbr**All dirty towels to be left in a in a corner of the bathroom floorbrbr**We ask all guest to please wipe their feet prior to entering the house in order to keep the sand to a minimum inside the housebrbr**Leaving the house with excess trash and in a unsanitary condition would be subject to an additional cleaning fee of up to $300.00brbrWe love our guests to enjoy our beach house. Please bear in mind that our property is situated on the Ocean and from time to time we get items and seaweed that wash a shore. brbr**Depending on the season and weather, seaweed could accumulate in our beach. brbrWe are committed to the conservation and protection of all our resources. We are constantly looking for ways to improve our efforts. Water is one of our most important life resources. You can protect and conserve this vital source by turning the faucet off while brushing your teeth or shaving, not using the toilet as a trash receptacle, being sure faucets are turned completely off, report leaky faucets and re using towels.

3
Bed

2
Bath

6
Sleeps

$277.95
/ Nightly

Private Vacation Home

Waterfront Sugarloaf Key Home

Upper Sugarloaf Key, Florida, United States
Escape to Sugarloaf Key!! Waterfront Home. Enjoy your vacation from this 2 bedroom 2 bath ground level home. You won't want to leave this rental. Endless water views with beautiful SUNRISES . The open floor plan is ideal for entertaining. Sliding glass doors open from the living room to the screen patio so you can enjoy the water views from inside or out.br World class fly fishing, deep sea fishing, diving and snorkeling are just a short boat ride from this home. There is dockage for your boat with a beautiful wide canal. brbrOnly 19 Miles Away is the Exciting, Eccentric and Much Beloved City of Key West, with its many attractions.brThis home will make your vacation one you will never forget! Activities: Bahia Honda State Park with its world-famous beach is only 20 minutes away, Looe Key Reef and Marine Sanctuary is only a short boat ride away. It's only a ten minute boat shuttle to take you to the exclusive Little Palm Island.brTHIS IS A 28 DAY RENTALbr

2
Bed

2
Bath

6
Sleeps

$925.10
/ Nightly

Private vacation home

Private and Exclusive Florida Keys Getaway

Upper Sugarloaf Key, Florida, United States

2
Bed

2
Bath

4
Sleeps

$954.23
/ Nightly

Private vacation home

The Lighthouse - Beach Houses Key West

Upper Sugarloaf Key, Florida, United States

2
Bed

1
Bath

4
Sleeps

$1133.12
/ Nightly

Private vacation home

The Hemingway - Beach Houses Key West

Upper Sugarloaf Key, Florida, United States

3
Bed

2
Bath

6
Sleeps

$534.38
/ Nightly

Private vacation home

Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

Upper Sugarloaf Key, Florida, United States

4
Bed

2
Bath

12
Sleeps

$147.33
/ Nightly

Private vacation home

Our Happy Place

Upper Sugarloaf Key, Florida, United States

3
Bed

2
Bath

8
Sleeps

$277.95
/ Nightly

Private vacation home

Waterfront Sugarloaf Key Home

Upper Sugarloaf Key, Florida, United States

2
Bed

2
Bath

6
Sleeps

$317.42
/ Nightly

Private vacation home

Waterfront Escape

Upper Sugarloaf Key, Florida, United States

3
Bed

2
Bath

6
Sleeps