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.
The Coolest Airbnbs in the Florida Keys: Top Vacation Rentals in 2025
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.
- Top Airbnb in the Florida Keys: Cozy Cottage with Porch
- Best Luxury Rental Florida Keys: Casa Loca in Key West
- Top Romantic Airbnb in the Florida Keys: Beach Bungalow with Cabana Club Access
- Best Florida Keys Airbnb for Large Groups: Casa Victoria Old Town Villa
- Best Cheap Airbnb Florida Keys: Sunset Bungalow Rental
- Top Airbnb Florida Keys with Pool: Windsor Townhome in Key West
- Best Beach House Rental Florida Keys: Palms Resort at Sugarloaf
- Most Unique Airbnb in the Florida Keys: Viking Yacht Getaway in the 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. Southern Diversion Estate
- 📍 Location: Islamorada
- 💵 Price Per Night: $1,661/night
- 🛏️ Sleeps: 16 guests
- 🔥 Unique Features: 200 feet oceanfront, private beach with tiki hut, 200-foot dock
- 🌟 Perfect For: Luxury groups ✨, fishing enthusiasts 🎣, family reunions 👨👩👧👦
When you want the Florida Keys experience without compromise, this gated oceanfront estate in Islamorada delivers everything you’ve imagined. Southern Diversion sits on two private acres with 200 feet of pristine oceanfront, complete with your own beach, tiki hut, and extensive dock system.
Five bedrooms sleep 16 guests with creative bunk configurations perfect for multi-generational families. The 5,500 square foot house features a heated pool with marble decking, while the private beach provides direct access to snorkeling at Cheeca Rock Reef and bonefishing right from your backyard.
Theater of the Sea becomes my go-to recommendation for dolphin encounters just 3 minutes away, while Robbie’s of Islamorada offers boat rentals and the famous tarpon feeding experience 5 minutes down the road. Florida Keys Brewing Co. provides excellent craft beer tastings just 2 minutes away for evening relaxation.
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2. Windsor Townhome #6
- 📍 Location: Key West
- 💵 Price Per Night: $871/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Private heated pool, en-suite baths in all bedrooms
- 🌟 Perfect For: Couples 👩❤️👨, families 👨👩👧👦, wedding guests 💐, snowbirds ☀️
Welcome to Windsor Townhome #6 – a peaceful island retreat just three blocks from iconic Duval Street in the heart of Old Town Key West. This tropical home offers a perfect balance of privacy and convenience for families or friends traveling together.
Inside, enjoy an open-concept living space with a modern kitchen, a bright dining area, and a cozy living room that opens to the garden. All three bedrooms feature en-suite baths, including a spacious king suite with a tiled shower and dual vanities.
Step outside to the private heated pool, where swaying palms and a sunny patio invite you to grill, dine, or unwind in true Florida style.
Nearby, stroll to Duval Street’s restaurants, bars, and galleries, or visit the Ernest Hemingway House and Southernmost Point. Whether you’re unwinding poolside or exploring Key West’s vibrant culture, Windsor #6 is your ideal home base.
3. Papa’s Hideaway
- 📍 Location: Key West
- 💵 Price Per Night: $2,477/night
- 🛏️ Sleeps: 22 guests
- 🔥 Unique Features: Five separate homes in one compound, 100-year-old Conch cottage
- 🌟 Perfect For: Large celebrations 🎉, wedding parties 💒, family reunions 👨👩👧👦
Finding accommodations for 22 people in Key West usually means compromising on location or splitting up the group, but Papa’s Hideaway solves both problems brilliantly. This secluded tropical compound features five separate homes sharing a heated pool and palm-covered courtyard, all just one block from Duval Street.
Six bedrooms across the compound sleep 22 guests with individual kitchens in each home, giving everyone privacy while maintaining the group dynamic. The property centers around a heated swimming pool with wraparound sundeck, newly furnished in 2022.
The Ernest Hemingway Home and Museum becomes my favorite morning destination just 5 blocks away before the crowds arrive. South Beach offers excellent swimming and snorkeling 5 minutes on foot, while the Key West Lighthouse provides panoramic island views from its historic tower just 5 blocks north of your compound.
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 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.
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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 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 🏖️
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. Chick-A-Pea Cottage
- 📍 Location: Key West
- 💵 Price Per Night: $1,052/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Private pool with waterfall, cabana lounge, Dade County pine accents
- 🌟 Perfect For: Families 👨👩👧👦, friend getaways 🍹, pet lovers 🐾
Chick-A-Pea Cottage is a cheerful island escape just steps from Duval Street. Surrounded by swaying palms and blooming bougainvillea, this colorful Key West retreat blends classic charm with tropical flair.
Indoors, Dade County pine, an open layout, and cozy seating create a warm island vibe. The home sleeps 8 across four bedrooms, including a king suite and two upstairs rooms with a shared Jack-and-Jill bath.
Move outside to your private oasis with a heated pool and waterfall feature. Lounge on the sunny deck, grill and dine al fresco, or unwind in the shaded cabana with a ceiling fan and outdoor seating.
In the vicinity, explore Key West on foot—just one block to Duval, and a short stroll to the Hemingway House, Butterfly Conservatory, and the Southernmost Point. From sightseeing and shopping to relaxing under the palms, Chick-A-Pea Cottage puts it all within easy reach.
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 ⛵
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 🗓️
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 👨👩👧👦
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 🎉
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 👥
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 👨👩👧👦
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 🛶
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 🐾
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 🌴
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 💑
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 💰
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.
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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 🌅
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!
Looking to plan another luxury vacation? Check out these other destinations:
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