Home Most Beautiful Destinations Around the World19 AMAZING Airbnbs in the Florida Keys (Key West & Key Largo)

19 AMAZING Airbnbs in the Florida Keys (Key West & Key Largo)

by Jon Miksis

Looking to discover the best and coolest Airbnbs in the Florida Keys? Paradise awaits you. The Florida Keys is a tropical oasis filled with endless beaches, sunshine, and outdoor adventures. It’s no wonder that the Florida Keys is also home to some of the coolest Airbnbs and vacation rentals in the state, ranging from exotic villas and bungalows to classic yachts and waterfront rentals.

In this article, we’ve ranked the best Airbnbs in the Florida Keys covering destinations like Key West, Siesta Key, Upper Sugarloaf Key, Marathon, Cudjoe Key, Summerland Key, and Duck Key, among others. Whether you’re looking for a romantic getaway or a trip amongst family and friends, here are the absolute coolest Airbnbs in the Florida Keys!

  • 👉 Pro Tip: If you do ONE thing in the Keys, make it this Key West Sunset Dinner Cruise. Live music, bottomless drinks, a full dinner buffet, and that famous Key West sunset from a 65-foot yacht? I’d recommend this experience to anyone, especially if you’re looking for beautiful photos! Just be sure to book in advance…it sells out fast, especially in peak season.
Spotlight Stay
Oceanedge villa on Seapalm Island with private beach and palm trees in the Florida Keys
Found on Vrbo
From $749/night

Little Conch Key, Florida Keys

Seapalm Island Villa – Private Island Beachfront in the Middle Keys

You can rent a condo on Key West or you can rent a villa on a private island – and somehow the island costs less than most Key West hotels. This Bali-inspired five-bedroom sits on Seapalm Island near Little Conch Key, surrounded by water on all sides with its own white sand beach, pool, and oceanside dock. It’s 4,800 square feet, sleeps twelve, and it’s in the Middle Keys between Islamorada and Marathon – the quieter stretch most tourists drive right past. Long Key State Park is steps away, the snorkeling and diving are world-class, and you wake up every morning feeling like you own the place. For a group trip to the Keys, this is the one.

Guests 12
Type Villa
Rating 9.6/10 ★
Best For Groups
View on Vrbo Why I’d book this one first →
Transparency Note: This post contains affiliate links. If you book through them, I may earn a small commission at no extra cost to you.

The Coolest Airbnbs in the Florida Keys: Top Vacation Rentals in 2026

Here are the best Airbnbs in the Florida Keys by category, accounting for different amenities, trip types, and budgets. The following sections will cover each listing in more detail.

Coolest Airbnbs to book in the Florida Keys

The 19 Best Airbnbs to rent in the Florida Keys

If beach houses, romantic cottages, and luxury rentals all sound good to you, get excited! Whether you’re planning a Florida Keys road trip from Miami or you want a more relaxed, luxury vacation, you’ll love these unique stays in the Florida Keys:

1. Turtles Pace, Key Colony Beach, Florida

  • 👥 4 guests | 🛏️ 2 bedrooms | 💰 ~$262/night
  • 🌴 Beachfront condo with private beach access and a heated pool
  • 🍂 Best in: January to April for warm, dry Keys weather before sargassum season picks up
  • 🚭 Smoke-free community, 4-guest maximum
Bright coastal living room with a large TV, grey sofa, round woven coffee table, and an open doorway to a bedroom
The bright, open living space is designed for relaxation after a long day spent exploring local beaches and shops.
Bright beach house bedroom with a king bed, blue and coral accent pillows, a wooden bench, and a ceiling fan
This bright master suite features a relaxed beach vibe, making it a peaceful retreat to unwind at the end of the day.

Turtles Pace is a two-bedroom condo in the heart of Key Colony Beach, Florida, with direct access to a private beach. Both bedrooms have king beds, smart TVs, and wireless phone chargers, and the primary opens onto its own balcony with ocean views. The kitchen comes stocked with stainless steel appliances, a serving set for eight, a Ninja Barista coffee system, and a blender for smoothies or frozen daiquiris.

Downstairs there’s a heated pool ringed with sun loungers and umbrellas, plus a tiki hut with a grill for cooking dinner outside. The condo is stocked well past where a rental usually stops, with beach chairs, a soft-side cooler and Yeti tumblers, resort robes in the primary bedroom, and a bar area with shakers and glassware. I could settle into one of the balcony chaises with a coffee and lose an entire morning.

You’re in the middle of Key Colony Beach, with walking and biking paths outside the door and kayak, paddleboard, bike, and boat rentals under a quarter mile away. Sunset Park is a half-mile walk, and there’s a playground a quarter mile off if you’re traveling with kids. Plan around sargassum, the seaweed that washes ashore in the Florida Keys depending on wind and tide, since conditions change day to day and the host doesn’t refund for it.

2. Captain’s Quarters, Key Colony Beach, Florida

  • 👥 5 guests | 🛏️ 2 bedrooms | 💰 ~$245/night
  • 🌴 Renovated bayfront duplex with its own dock and tiki hut
  • ☀️ Best in: December through April for calm water and prime Keys fishing
  • ⚓ 40-foot deep-water dock with shore power
Covered tiki hut patio with wicker lounge furniture and a dining set next to a waterfront dock with palm trees
The outdoor tiki hut patio sits right on the water, offering a perfect shade setup to watch boats pass by the private dock.
Open-concept beach house living room and kitchen with a tile floor
This open-concept layout makes it easy to transition from cooking a family meal to relaxing in the living room after a fun day out.

Captain’s Quarters is a renovated two-bedroom, two-bath duplex on the bay in Key Colony Beach, with open water in front and behind the property. One bedroom has a king and the other a queen, and the family room adds a sofa and two recliners under a wall of bay views. The full kitchen has a dishwasher, there’s a separate laundry room with washer and dryer, and Rokus on all three TVs.

Out back sits a 40-foot deep-water dock with shore power and water, a fish cleaning station lit for after-dark cleanups, and an outdoor rain shower for rinsing off. The tiki hut, gas grill, porch seating, and three sun loungers give you plenty of places to land between trips out on the water. I’d tie up the boat, clean the day’s catch at the dock, and grill it 20 feet away without changing out of my swim trunks.

Curry Hammock State Park is about a five-minute walk, and Sunset Park, golf, restaurants, and shops all sit within the walkable stretch of town. The airport is five minutes out, which makes this an easy landing spot if you’re flying in rather than driving down. If you’re towing a boat, arrange trailer parking directly through the city of Key Colony Beach, which charges $150 per week separately from your booking.

3. Turtle-by-the-Sea, Key Colony Beach, Florida

  • 👥 2 guests | 🛏️ 1 bedroom | 💰 ~$110/night
  • 🌴 Canal-side guest suite with a private entrance, steps from the water
  • ☀️ Best in: December through April for warm, dry Keys weather and calm paddling
  • 🏄 Free paddleboards and dock access
Cozy beach cottage studio with a bed, a small dining table, and green walls
This cozy beach studio offers a relaxed basecamp for exploring the local shops, dining spots, and surrounding nature trails.
Beach cottage kitchenette and a built-in dining booth with a colorful geometric table
The compact dining space and kitchenette offer a perfect setup to enjoy a morning coffee before heading out for the day.

Turtle-by-the-Sea is a one-bedroom guest suite on a canal in Key Colony Beach, reached through a garden gate and its own private entrance. The bedroom has a queen, and the kitchenette covers a cooktop burner, microwave, toaster, fridge, and a coffee machine with free coffee for the length of your stay. A window-side breakfast nook gives you room to eat or set up a laptop, and the custom tropical rain shower is a standout for a suite this size.

Out back, the deck and dock are shared with owners Mallory and Steve, who leave paddleboards free for guests to take out on the canal. Manatees and spotted eagle rays turn up in the water regularly, and dolphins pass through on a lucky morning. Steve is a local scuba instructor, and I’d take him up on the dive advice before booking anything through a shop.

Sparky’s Landing sits within 100 yards of the door, along with Sole Watersports and several fishing charters, and the Fairfield Inn sells daily access to its waterside pool and pool bar through ResortPass. The Island Fish Company and two convenience stores are a two-minute walk. Fifteen minutes on foot or five by car brings you to Key Colony Inn, the nine-hole par 3 Key Colony Golf Course, Havanna Jacks, and Sunset Beach. The suite caps at two guests, and the hosts offer a 10% boat rental discount if you ask.

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4. The Royal Compound

  • 📍 Location: Key West
  • 💵 Price Per Night: $2,827/night
  • 🛏️ Sleeps: 8 guests
  • 🔥 Unique Features: Three separate dwellings, pool with waterfall, outdoor kitchen
  • 🌟 Perfect For: Luxury groups ✨, milestone celebrations 🎉, privacy seekers 🏡, culinary enthusiasts 👨‍🍳
The Royal Compound
Credit: Vrbo
The indoor living area
Credit: Vrbo

The most exclusive address in Key West comes with bragging rights that money can’t usually buy, and The Royal Compound in Truman Annex delivers exactly that level of prestige. This estate occupies an entire block as the largest single property in the gated community, featuring three separate dwellings and a dramatic pool with waterfall.

Five bedrooms sleep eight guests across multiple buildings, including two private master suites in their own houses. The professional-grade kitchen features double ovens and Sub Zero appliances, while the outdoor kitchen creates resort-level entertaining spaces.

Mallory Square becomes my sunset ritual destination just 6 minutes away for those legendary Key West sunsets with street performers. Duval Street provides world-famous nightlife 5 minutes on foot, while the Southernmost Point offers iconic photo opportunities 18 minutes through charming Old Town streets.

5. Casa Loca

  • 📍 Location: Key West
  • 💵 Price Per Night: $1,042/night
  • 🛏️ Sleeps: 8 guests
  • 🔥 Unique Features: Heated private pool, lush garden, designer decor
  • 🌟 Perfect For: Families 👨‍👩‍👧‍👦, couples 💕, group getaways 🌴
Casa Loca is one of the most unique Airbnbs in the Florida Keys
Credit: VRBO
Casa Loca vacation rental in the Florida Keys
Credit: VRBO
Beautiful pool area at the vacation rental
Credit: VRBO

Casa Loca is a vibrant island retreat just one block from Duval Street in the heart of Old Town Key West. With tropical gardens, custom design touches, and a private pool, this stylish home offers the best of island living steps from the action.

Within, elegant furnishings and hardwood floors complement an open layout with a full kitchen, dining area, and cozy living room. Three bedrooms sleep 8, including a private suite with French doors to the pool.

Head outside to your private paradise, featuring a heated pool, stone fountain, lush landscaping, and a gas grill—perfect for alfresco dining or lounging in the sun.

Walk to local favorites like the Hemingway House and Southernmost Point, or spend your days exploring the vibrant shops, cafés, and nightlife of Duval Street. With room to unwind and everything close by, Casa Loca is your island escape made easy.

6. Luxurious Private Home

  • 📍 Location: Marathon
  • 💵 Price Per Night: $2,565/night
  • 🛏️ Sleeps: 28 guests
  • 🔥 Unique Features: Private beach with floating dock, basketball/volleyball courts
  • 🌟 Perfect For: Epic reunions 👨‍👩‍👧‍👦, wedding venues 💒, corporate retreats 💼, multi-family vacations 🏖️
Tiki Looking Over The Pool
Credit: Vrbo
Upstairs King Suite Overlooking The Zero Entry Pool
Credit: Vrbo

This is the Florida Keys vacation rental that makes everyone else look small by comparison. This Marathon estate delivers your own private resort complete with basketball court, volleyball court, private beach, floating dock, and zero-entry pool with swim-up bar seating.

Fourteen bedrooms sleep 28 guests with smart layouts including bunk rooms for kids and multiple king suites. The property features a tiki bar, game room with pool table, and direct ocean access where guests regularly catch tarpon and redfish right from the dock.

Sombrero Beach becomes my favorite morning destination for swimming and snorkeling just a 6-minute walk away with its famous curved shoreline. The Turtle Hospital provides fascinating marine wildlife education 7 minutes by car, while Curry Hammock State Park delivers excellent kayaking through mangrove trails 10 minutes from your dock.

7. Captain’s Choice, Key West, Florida

  • 👥 6 guests | 🛏️ 2 bedrooms | 💰 ~$410/night
  • 🌴 Renovated resort condo with a shared pool and hot tub
  • ☀️ Best in: December through April for dry, warm Key West weather
  • ♨️ Shared pool and hot tub open year-round
Modern condo interior with a white quartz kitchen island, a living room, and large balcony doors
The bright open layout lets you easily chat between the modern kitchen island and the living area while looking out toward the balcony.
Cozy bedroom with a white headboard, bedside lamps, and a Key West sign on the wall
The bedroom offers a cozy place to recharge with a relaxed design inspired by the laid-back atmosphere of Key West.

Captain’s Choice is a renovated two-bedroom, two-bath condo at Sunrise Suites Resort in the center of Key West. The master suite has a king, a walk-in closet, a 50-inch smart TV, and an ensuite bath with a quartz vanity and glass shower, while the second bedroom has a queen and the living room adds a full-size sleeper sofa. The open kitchen came out of the renovation with new stainless appliances, and there’s a Keurig alongside a drip coffee maker plus a full-size washer and dryer in the unit.

The shared pool and hot tub sit steps from the building and stay open all year, which is unusual for a condo complex at this price point. Beach towels are stocked, the living room has a 60-inch smart TV with Netflix, and your booking includes one free parking space with no charge. I’d float in the hot tub after a long day out on the water and call it a good use of an evening.

The condo sits near Key West International Airport, with Smathers Beach close by and restaurants and a convenience store within reach. Cozumel Park is about a 20-minute walk. Park on either side of the building rather than under the carports, which are private, and note the unit caps at six guests.

8. Private Oceanfront Home

  • 📍 Location: Marathon
  • 💵 Price Per Night: $1,292/night
  • 🛏️ Sleeps: 8 guests
  • 🔥 Unique Features: Private gated peninsula, putting green, tiki hut with HDTV
  • 🌟 Perfect For: Luxury families ✨, fishing enthusiasts 🎣, golfers ⛳, yacht owners ⛵
Backyard area
Credit: Vrbo
Family room
Credit: Vrbo

Some Florida Keys properties claim to be exclusive, but this gated Coco Plum Beach estate actually delivers on every luxury promise. The 3,000 square foot home sits on its own private peninsula with heated pool, spa, putting green, and a tiki hut positioned perfectly for watching both sunrises and sunsets.

Three bedrooms sleep eight guests with the master suite opening directly onto oceanfront porches. The property features a dock capable of mooring 100-foot yachts, fire pit on the peninsula, and Sub Zero appliances in the gourmet kitchen. Daily beach raking maintains resort-level standards.

Curry Hammock State Park becomes my go-to kayaking destination through pristine mangrove tunnels just 3 minutes away, while Coco Plum Beach provides secluded swimming right outside your door. The property’s dock delivers incredible tarpon fishing plus regular dolphin and manatee sightings from your private peninsula.

9. Copa Cabana

  • 📍 Location: Key West
  • 💵 Price Per Night: $249/night
  • 🛏️ Sleeps: 4 guests
  • 🔥 Unique Features: Private cocktail pool, separate guest cabana, 1920s shotgun-style home
  • 🌟 Perfect For: Couples 💑, solo travelers ✈️, long-term stays 🗓️
One of the best Airbnb vacation rental in Florida Keys
Credit: VRBO
Great and spacious living room
Credit: VRBO

Copa Cabana is a classic 1920s Key West cottage tucked behind a white picket fence in historic Bahama Village. This cozy home blends Old Town charm with breezy island living.

Indoors, enjoy a bright open layout with a cozy living area, kitchen, and dining nook with a built-in desk. The main house includes a queen bedroom, while the guest cabana offers a sleeper sofa, a half bath, and a private retreat.

Venture outside to your tropical retreat, where a jetted cocktail pool, shaded deck, outdoor shower, and grill invite you to unwind. Enjoy coffee on the rocking chair porch and sunset dinners beneath the swaying palms.

Just minutes away, stroll to the Ernest Hemingway Home, snap a photo at the Southernmost Point, or unwind at the White Street Pier. From walking and sightseeing to relaxing by the sea, Key West offers endless charm and adventure.

10. The Keys Compound

  • 📍 Location: Tavernier
  • 💵 Price Per Night: $2,125/night
  • 🛏️ Sleeps: 20 guests
  • 🔥 Unique Features: 2.5-acre gated compound, 155 feet private beach, deep-water dockage
  • 🌟 Perfect For: Mega celebrations 🎉, wedding venues 💒, corporate retreats 💼, multi-family reunions 👨‍👩‍👧‍👦
Beach Cottage Living Room View
Credit: Vrbo
Beach Cottage King Master Bedroom
Credit: Vrbo

Occasionally, you find a vacation rental that redefines what’s possible in the Florida Keys, and this 2.5-acre Tavernier compound represents the absolute pinnacle. The Keys Compound features three separate cottages on 155 feet of private beachfront with deep-water dockage for 45-foot boats, two pickleball courts, and legendary sunsets.

Six bedrooms across the three cottages sleep 20 guests with individual kitchens and Weber grills in each cottage. The property includes swimming pool, hot tub, artificial grass areas, basketball hoop, and boat launch ramp for jet skiing in the expansive bay waters.

Laura Quinn Wild Bird Sanctuary provides fascinating wildlife rehabilitation education just 2 minutes away, while Florida Keys Dive Center offers world-class scuba and snorkeling adventures 4 minutes by car. Harry Harris Park delivers excellent family beach activities 5 minutes away, perfectly positioned between Key Largo and Islamorada dining scenes.

11. Real World MTV House

  • 📍 Location: Key West
  • 💵 Price Per Night: $2,198/night
  • 🛏️ Sleeps: 22 guests
  • 🔥 Unique Features: MTV Real World filming location, 500 feet oceanfront, tennis court
  • 🌟 Perfect For: Bachelor parties 🕺, reality TV fans 📺, large groups 👥, milestone celebrations 🎉
Sunken Living Room and Whirlpool
Credit: Vrbo
1st Floor Back Porch with Open waterview
Credit: Vrbo

Reality TV history meets Key West luxury at this legendary oceanfront compound where MTV filmed Real World Key West in 2006. The 9,600 square foot property spans 500 feet of prime oceanfront with resort-level amenities including tennis court, racquetball court, multiple docks, and that famous sunken living room with whirlpool.

Ten bedrooms sleep 22 guests across the main house and optional guest house built around the racquetball court. The property features 11 plasma TVs, pool table, basketball hoop, kayaks, paddleboards, and both deep-water and shallow docks for serious boating.

Key West Golf Club becomes my morning escape for tee times just 3 minutes away, while Stock Island Yacht Club & Marina provides excellent dining and charter fishing 6 minutes by car. Smathers Beach offers the island’s longest sandy shoreline 11 minutes away for a change from your private oceanfront.

12. Beautiful Waterfront Home

  • 📍 Location: Key West
  • 💵 Price Per Night: $1,665/night
  • 🛏️ Sleeps: 12 guests
  • 🔥 Unique Features: Gated community, pet-friendly fenced yard, free gym membership
  • 🌟 Perfect For: Boating families ⛵, pet owners 🐕, fishing enthusiasts 🎣, group getaways 👥
Private Heated Pool Inside Fenced in Yard
Credit: Vrbo
Open Concept Living Space
Credit: Vrbo

The best Key West vacation combines waterfront access with family-friendly amenities, and Spindrift House in Lunara Bay delivers both without compromise. This contemporary home features a private heated pool, dock for boats up to 50 feet, and a fully fenced yard that keeps kids and pets safe.

Four bedrooms with individual bathrooms sleep 12 guests, while the open-concept design encourages group gathering. The gourmet kitchen handles serious meal prep, and the private dock offers excellent fishing opportunities right from your backyard.

I love grabbing waterfront dinner at Hogfish Grill just minutes away, while Hurricane Hole offers scenic happy hour views perfect for watching boats navigate the channels. Key West Golf Club sits within a 12-minute walk for morning tee times, and Stock Island Yacht Club & Marina delivers charter fishing and upscale dining 5 minutes by car.

13. Bumpa’s Big House

  • 📍 Location: Marathon
  • 💵 Price Per Night: $1,921/night
  • 🛏️ Sleeps: 22 guests
  • 🔥 Unique Features: 10 bedrooms with en-suites, 6-hole putting green, swim-up bar
  • 🌟 Perfect For: Multi-gen families 👴👶, grandparent getaways 👵, milestone celebrations 🎉, family reunions 👨‍👩‍👧‍👦
Pool area
Credit: Vrbo
Interior design
Credit: Vrbo

Multi-generational family vacations require serious space and amenities, and Bumpa’s Big House delivers exactly what grandparents dream of when planning the ultimate family gathering. Ten bedrooms with individual en-suites mean everyone gets privacy, while the 6-hole putting green, swim-up bar, and basketball hoop keep multiple generations entertained.

The property spans two levels with dual full kitchens, three full-size refrigerators, and enough outdoor space for 22 guests. Features include shuffleboard, cornhole, fish cleaning station, and a 35-foot dock for serious boating families.

Sombrero Beach sits just an 8-minute walk away for that famous curved shoreline perfect for morning walks with grandkids. The Turtle Hospital provides educational marine wildlife experiences 7 minutes by car, while Marathon’s central location offers easy day trips to both Key Largo and Key West.

14. Pelico Palms Estate

  • 📍 Location: Monroe County
  • 💵 Price Per Night: $1,924/night
  • 🛏️ Sleeps: 20 guests
  • 🔥 Unique Features: 2 private pools, hot tub, tiki hut bar, fire pit, game room
  • 🌟 Perfect For: Large groups 👨‍👩‍👧‍👦, retreats 🌴, nature lovers 🦜, island adventurers 🛶
Pelican Palms luxurious villa
Credit: VRBO
beautiful Airbnb for large groups in Florida
Credit: VRBO
Spacious pool area at the Pelican Palms
Credit: VRBO

Pelico Palms Estate is a private tropical resort just 30 minutes from Key West. Nestled on 6 gated acres, this peaceful oasis blends privacy, space, and island charm for unforgettable group getaways.

Step inside, the main villa features Dade County Pine ceilings, a Coquina fireplace, and a baby grand piano. With 9 bedrooms and 9 bathrooms, there’s room for everyone to relax, spread out, and reconnect.

Outdoors, swim in the pools, lounge by the tiki hut, or sip a drink by the fire pit. The estate also includes a private beach launch, hammocks, games, and a fully equipped grill deck.

Close by, hike the Crane Blvd Trail, or boat from Cudjoe Marina. Grab coffee at Baby’s, dine at Square Grouper, or explore reefs and the Hemingway House. From early morning dips to golden hour cocktails, your tropical escape begins here.

15. Lower Keys Escape

  • 📍 Location: Little Torch Key
  • 💵 Price Per Night: $375/night
  • 🛏️ Sleeps: 6 guests
  • 🔥 Unique Features: Private pool, pet-friendly, resort-style shared amenities
  • 🌟 Perfect For: Couples 💑, small families 👨‍👩‍👧‍👦, remote workers 💻, dog lovers 🐾
Sunset bungalow Airbnb rental
Credit: VRBO
Unique vacation rentals in Florida
Credit: VRBO
Stunning sunset bed and breakfast
Credit: VRBO

Step into Lower Keys escape—a cozy two-bedroom, two-bath retreat with a private pool, just a short stroll from tranquil water views. Enjoy laid-back comfort and easy access to resort-style amenities in peaceful Little Torch Key.

Within, two king bedrooms, two full baths, and a pull-out sofa provide space for up to six. The kitchen is well-equipped for meals at home, while the open living and dining area is perfect for relaxing or remote work.

Step outdoors to enjoy your private pool, screened porch, and quiet fenced yard, ideal for morning coffee, evening dips, or letting your pup roam free.

In the vicinity, explore the National Key Deer Refuge, relax at Bahia Honda State Park’s White-Sand beaches, or paddle the local backwaters. From nature trails to island adventures, the perfect Keys escape begins here.

16. The Flower Power House

  • 📍 Location: Key West
  • 💵 Price Per Night: $1,084/night
  • 🛏️ Sleeps: 13 guests
  • 🔥 Unique Features: Vintage 1938 home, boho-chic design, shared pool
  • 🌟 Perfect For: Large groups 👯‍♀️, creative travelers 🎨, beach lovers 🌴
One of the most unique Airbnb rental in the Florida Keys
Credit: VRBO
Rustic and charm interior decor
Credit: VRBO

Step back in time at The Flower Power House—an eclectic 1938 Key West retreat blending vintage charm with artistic flair. Nestled in the White Street Gallery District, this boho hideaway features 5 bedrooms, including a whimsical cottage and breezy sunlit porches.

Head inside, two kitchens and a cottage kitchenette offer space to gather, while the lush garden and shared 40′ pool provide a serene retreat just blocks from Higgs Beach.

Close by, walk or bike to Duval Street, Salute! on the Beach, or sandy shores for volleyball, snorkeling, and sea breezes. From morning mimosas to sunset swims, this boho beauty is a celebration of Old Key West’s free-spirited soul.

17. The Grey Lady

  • 📍 Location: Tavernier
  • 💵 Price Per Night: $450/night
  • 🛏️ Sleeps: 6 guests
  • 🔥 Unique Features: Authentic houseboat experience, marina location, spiral staircase
  • 🌟 Perfect For: Budget travelers 💰, unique experiences 🌟, fishing enthusiasts 🎣, couples’ getaways 💑
Dining area
Credit: Vrbo
Property grounds
Credit: Vrbo

Living on the water doesn’t have to cost a fortune, and The Grey Lady houseboat at Mangrove Marina proves that authentic Florida Keys experiences come at every price point. This floating home features four bedrooms sleeping six guests, spiral stairs leading to the main living area, and sliding glass doors opening to spectacular open water views.

The compact but efficient layout includes a full kitchen, two bathrooms, and a back patio positioned at the end of the pier for maximum privacy and sunset viewing. The houseboat gently rocks with weather conditions, creating that authentic on-the-water experience.

Florida Keys Wild Bird Rehabilitation Center becomes my favorite educational stop for pelican feeding just a 7-minute walk away. Florida Keys Dive Center provides world-class scuba adventures 3 minutes by car, while Harry Harris Park offers excellent family beach activities 6 minutes from your marina.

18. Key Largo Oceanfront Retreat

  • 📍 Location: Key Largo
  • 💵 Price Per Night: $531/night
  • 🛏️ Sleeps: 8 guests
  • 🔥 Unique Features: Gated oceanfront community, free golf cart, marina views
  • 🌟 Perfect For: Resort lovers 🏖️, active families 🎾, boaters ⛵, budget-conscious luxury seekers 💰
Living area
Credit: Vrbo
Kitchen area
Credit: Vrbo

Resort-style amenities without resort prices make this gated Key Largo villa an incredible value for families wanting it all. The oceanfront home overlooks both marina and Atlantic Ocean with access to two heated pools, tennis court, pickleball court, playground, and that amazing 3-acre saltwater lagoon with diving board.

Three bedrooms sleep eight guests, while the included golf cart, bikes, kayaks, snorkeling gear, and tennis equipment eliminate rental fees. The gated community provides 24-hour security and free boat ramp access.

Jimmy Johnson’s Big Chill becomes my go-to spot for waterfront dining just 2 minutes away. Dolphins Plus provides incredible dolphin swimming experiences within walking distance, while Baker’s Cay Resort Beach offers day passes to pristine beach facilities 6 minutes by car.

19. Waterfront Cozy Cottage

  • 📍 Location: Little Torch Key
  • 💵 Price Per Night: $457/night
  • 🛏️ Sleeps: 6 guests
  • 🔥 Unique Features: 250′ dock, private boat ramp, water views, bait freezer
  • 🌟 Perfect For: Boaters 🚤, anglers 🎣, families 👨‍👩‍👧‍👦, sunset lovers 🌅
Cozy cottage waterfront Airbnb rental in the Florida Keys
Credit: VRBO
Waterfront view from the living room and kitchen area
Credit: VRBO

Welcome to this cozy waterfront cottage on Little Torch Key—set on nearly an acre with a 250-foot dock, private boat ramp, and endless water views. A laid-back base for fishing, boating, and soaking up the sun.

Inside, the open layout blends the living area, full kitchen, and dining space. A king bedroom and bunk room sleep six, with Smart TVs, tile floors, games, and a heated massage chair for added comfort.

Outside, enjoy sunrise views from the long dock or dine on the shaded patio with a grill. The property includes a bait freezer, fish station, and full dockside setup—water, power, and ramp access for your boat.

Nearby, explore Looe Key Reef or cruise around Picnic Island. Visit Bahia Honda State Park for white sand beaches, or head to Big Pine Key to spot Key deer. With fishing, boating, and island adventures all around, this Lower Keys cottage is your gateway to it all.

Best Airbnbs in the Florida Keys

Have you ever stayed in a unique Airbnb or vacation rental in the Florida Keys? Let me know in the comments or on Insta, as I’m always looking to add to this list of the coolest Airbnbs in the Florida Keys!

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Global Viewpoint is a personal blog. All content is for informational and entertainment purposes only and does not constitute professional financial, medical, or legal advice.

Jon Miksis

About Jon Miksis

Award-winning Travel Writer • Founder of Global Viewpoint • 70+ countries visited • 10 Million+ readers

Since 2017, I’ve traveled 3–6 months a year, sharing detailed guides that help my readers travel smarter, deeper, and better. My work blends firsthand experiences - from U.S. road trips and cold-plunge cabins to Michelin-starred dining and business-class flights — with honest, independent reviews.

I’ve been hired by leading tourism boards in 7 countries across Europe, North America, and South America, as well as international travel brands. My travel tips and insights have been featured in Forbes, HuffPost, Yahoo Travel, and The Boston Globe. I’ve personally reviewed 500+ hotels, retreats, and flight experiences. And I never recommend a place I wouldn’t return to myself.

I also save $10K-15K+ per year on airfare using flight tools and 10+ travel credit cards, and I’ve invested over $100K into personal development through transformational retreats and coaching since 2021.

When I’m not road-tripping across the Northeast or writing guides for Global Viewpoint, you’ll find me cold plunging in local lakes, sipping espresso in quiet cafes in Vienna, or chasing fall foliage across New England. I split my time between exploring the world and soaking up life in Boston, my lifelong home base. Some of my favorite places I keep going back to? Switzerland, Spain, Iceland, Italy, Greece, the Faroe Islands, Guatemala, California, Montana, Vermont, the UK, the Philippines, Argentina, the Caribbean, and coastal Maine in autumn.

See my latest adventures on Instagram and TikTok.

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