Florida is one of those states where your Airbnb can feel like the trip. You can wake up on the water in the Keys, crash in a design-forward spot near Miami’s energy, or book a full-on family base near Orlando that actually makes the theme park chaos easier.
For this guide, my team and I pulled together the most unique Airbnbs in Florida across the places people really travel to, from Key Largo and Key West to the Gulf Coast beaches and inland nature near the Everglades.
I’ve traveled to 73 countries and I’m picky about stays because I know the wrong one can drag a whole trip down. I built this list around rentals that feel like experiences, not just beds, with standout vibes like treehouses, beach houses, luxury villas, and a few wild curveballs you will not find at a standard hotel. If you want Florida with more wow and less scrolling, start here.
Crystal River, Florida
Waterfront Paradise – Pool, Hot Tub & Private Dock on Crystal River
This is the Florida listing I’d pick over the cookie-cutter Orlando Airbnbs every time. You’re right on the water in Crystal River – manatee country – with a private dock, an L-shaped pool, a built-in hot tub off the master, and a screened lanai that actually feels like outdoor living instead of an afterthought. Bring your own boat or just kayak straight out into the springs. Three bedrooms, sleeps 10, and 66 reviews without a single bad one. That’s rare.
The Coolest Airbnbs in Florida: Top Vacation Rentals in 2026
Here are the best Airbnbs in Florida by category, taking into account different amenities, trip types, and budgets. The subsequent sections will cover each listing in more detail.
- Best-Value Airbnb in Florida: Casa del Sol Vacation Rental
- Best Luxury Rental Florida: Beachfront Luxury Villa
- Top Romantic Airbnb in Florida: 5 Palms Cottage
- Best FL Airbnb for Large Groups: Mediterranean Villa in Cape Coral
- Best Cheap Airbnb Florida: Pensacola Tiny House
- Coolest Treehouse Airbnb in Florida: Tree House in Kissimmee FL
- Top Airbnb Florida with Pool: Siesta Key Pool House Rental
- Best Beach House Rental Florida: Panama City Beachfront Home
- Most Unique Airbnb in Florida: Tiki Suite in Key West
30 Best Airbnb Vacation Rentals in Florida
If beach houses, treehouses, romantic cottages, and luxury rentals all sound good to you, get excited! Below are some of the most unique stays in Florida:
Note: The properties below are featured on Airbnb, VRBO, Booking and Expedia. For each listing, I’ve only included the link to the website with the cheapest rates.
1. Beachfront Pool Home
- 📍 Location: Key Largo
- 💵 Price Per Night: $2,019/night
- 🛏️ Sleeps: 14 guests
- 🔥 Unique Features: Private beach, heated pool & spa, 2 master suites
- 🌟 Perfect For: Large families 👨👩👧👦, beach lovers 🏖️, group getaways
Experience the best of Key Largo at this stunning beachfront pool home—a spacious 6-bedroom retreat with sweeping ocean views. Breezy coastal décor, multiple lounge spaces, and two master suites make relaxing easy, while oversized windows frame the turquoise water.
Outside, your private heated pool and spa overlook the beach. Grab the kayaks for a paddle, dine al fresco by the water, or unwind with sunset cocktails on the patio.
Nearby, snorkel through coral reefs at John Pennekamp State Park, take a boat tour from local marinas, or sample fresh seafood at Key Largo’s waterfront restaurants. From lazy beach days to ocean adventures, this home is your Key Largo paradise.
2. Angie’s Place
- 📍 Location: Bradenton Beach
- 💵 Price Per Night: $297/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Gulf views, two balconies, heated shared pool
- 🌟 Perfect For: Beach lovers 🏖️, couples 🌅, small families 👨👩👧👦
Welcome to Angie’s Place, a charming 2BR/2BA beach cottage tucked into Anna Maria Island’s laid-back coast, just steps from the soft sands of Coquina Beach. This second-floor getaway blends easygoing coastal style with thoughtful amenities to make your stay effortless.
Relax in the bright living area with a smart TV and fast WiFi, or cook your favorite beachside meals in the fully equipped kitchen. At bedtime, drift off in the king bedroom or twin guest room, both featuring soft, hotel-style linens.
The home features two private balconies—one with a peek of the Gulf of Mexico, and another overlooking the heated pool and tropical backyard. Beach chairs, umbrellas, and on-site laundry are all included for a no-fuss stay.
When it’s time to explore, stroll to Bridge Street for dining, shopping, and the local farmers market. The free Anna Maria Island Trolley is right nearby, making it easy to roam the island without a car. Angie’s Place is the perfect spot for a classic Florida beach escape.
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👉 Send me cheap 2026 flights3. The Best Sunsets in the World, Indian Rocks Beach, Florida
- 👥 6 guests | 🛏️ 2 bedrooms | 💰 ~$445/night
- 🌴 Beachfront Gulf Coast condo with sunset views from the balcony
- 🌅 Best in: November to April for dry, sunny Gulf Coast evenings
- 🏊 Pool shared by only seven units
The Best Sunsets in the World is a beachfront condo on a private stretch of Indian Rocks Beach along Florida’s Gulf Coast. It has two bedrooms and two bathrooms for up to six guests, with an open kitchen flowing into a combined living and dining room. The kitchen comes fully equipped, and complimentary internet plus a full washer and dryer make longer stays easy.
The balcony faces straight out over the sand toward the water, and a spiral staircase leads down to the pool. With only six other units on the property, you’ll often have the pool to yourselves, and beach equipment comes included for your days on the sand. I’d plan every evening around this balcony, because the sunsets here live up to the listing’s bold name.
Several restaurants sit just across Gulf Blvd, including Anecdote Brewing Company and The Original Crabby Bills, both under a five-minute walk. Splash Harbour Water Park is a three-minute walk away, and John’s Pass Village & Boardwalk is a 24-minute drive. Fly into St. Pete-Clearwater International Airport if you can, since it’s 23 minutes by car compared to 48 minutes from Tampa International.
4. Personal Paradise Getaway
- 📍 Location: Pompano Beach
- 💵 Price Per Night: $319/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Heated pool, tiki hut with TV, private fenced yard
- 🌟 Perfect For: Families 👨👩👧👦, beach lovers 🏖️, outdoor entertainers 🍹
Your tropical escape starts here in sunny Pompano Beach. Just a mile from the ocean, this fully renovated 4-bedroom home offers resort-style amenities in a quiet, family-friendly neighborhood.
Inside, you’ll find a bright and open layout with a spacious living area, smart TVs in every room, a fully stocked kitchen, and a luxurious master suite with direct pool access.
Out back, the private fenced yard is your oasis—lounge by the heated pool, grill out under the tiki hut with an outdoor TV, or dine al fresco beneath the palms.
Hit nearby spots like Las Olas Boulevard in Fort Lauderdale, Mizner Park in Boca Raton, or enjoy local golf, biking, and fishing. From poolside lounging to coastal adventures, this getaway captures the best of Florida living.
5. Luxe Waterfront Retreat
- 📍 Location: Marathon
- 💵 Price Per Night: $3,107/night
- 🛏️ Sleeps: 16 guests
- 🔥 Unique Features: Two pools, private beach, spa, dock, tiki bar, Bali guest house
- 🌟 Perfect For: Large families 👨👩👧👦, milestone celebrations 🎉, water lovers 🌊
Escape to The Retreat, a private luxury resort set on the sparkling waterfront of Marathon in the Florida Keys. With a main house and a charming Bali guest home, this property is built for unforgettable group getaways.
Spread out across seven bedrooms and five bathrooms, with stylish interiors and plenty of space for everyone. The kitchen comes stocked with food and drinks for your first day, so you can start relaxing the moment you arrive.
Spend your days lounging by two pools, kayaking from the dock, or playing beach games like cornhole. There’s also a shaded game room, paddle boards, outdoor grills, and a tiki bar for evening cocktails.
Explore nearby Sombrero Beach, dive into the Florida Keys National Marine Sanctuary, or take a short drive to Key West for shopping and nightlife. Celebrate, recharge, or simply unwind—The Retreat has something for everyone.
- Read also: The Absolute Best Florida Keys Airbnbs
6. Lakeview Cottage, Anna Maria Island, Florida
- 👥 4 guests | 🛏️ 2 bedrooms | 💰 ~$428/night
- 🌴 Updated island cottage with a private heated pool and spa
- 🌅 Best in: November to April for warm, dry island days
- 📅 Weekly stays, with shorter options off-season
Lakeview Cottage is a two-bedroom island cottage one block from Pine Avenue and the Gulf beaches of Anna Maria Island. Both bedrooms have king beds and share one bathroom, which works well for couples or a small family of four. Vaulted ceilings open up the living area, and the updated kitchen has island seating plus a wine fridge for evenings in.
Out back, the private heated pool and spa are surrounded by lush tropical landscaping and a brick patio lined with loungers. A screened porch and an outdoor hot-and-cold shower complete the setup, and the cottage even comes stocked with beach equipment and a bicycle. Pool heat is an extra charge, and I’d add it in any month since the shade trees keep the water cool even in summer.
The Anna Maria Island Museum and Historical Park is a five-minute walk away, and the Anna Maria City Pier is about nine minutes on foot. For dinner, The Waterfront Restaurant and The Sandbar Restaurant are both within a ten-minute walk, and the free Island Trolley stops nearby for exploring the rest of the island. One dog up to 25 pounds is welcome for a $150 non-refundable fee covering the first week, with certain breeds excluded, and the office asks you to confirm details before your trip.
7. Fabulous Gulf Front Home
- 📍 Location: Redington Beach
- 💵 Price Per Night: $2,045/night
- 🛏️ Sleeps: 16 guests
- 🔥 Unique Features: Direct beachfront, lagoon-style pool & hot tub, game room
- 🌟 Perfect For: Large families 👨👩👧👦, beach lovers 🌊, sunset chasers 🌅
Welcome to Fabulous Gulf Front Escape, a stunning 6-bedroom, 5-bath home with 80 feet of private beach in Redington Beach. This spacious retreat combines luxury, comfort, and laid-back coastal living.
The home features six king bedrooms, all with private baths. Two of the bedrooms have balconies with sweeping Gulf of Mexico views. Gather in the chef’s kitchen or unwind in the open-concept living room and game room with pool and darts.
Outdoors, the private beachfront yard has a lagoon-style pool, hot tub, grill, and shaded dining area—perfect for coffee at sunrise or cocktails at sunset.
Close by, explore John’s Pass Village for waterfront dining and shopping, or take the kids to Splash Harbour Water Park. With Downtown St. Pete and the airport just a short drive away, this home is the perfect base for your beach vacation.
8. Florida Modern Mediterranean Villa
- 📍 Location: Cape Coral
- 💵 Price Per Night: $459/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Gulf access canal, 5 full baths, custom pool & spa, pet-friendly
- 🌟 Perfect For: Families 👨👩👧👦, boaters 🚤, sunseekers ☀️
This modern Mediterranean villa sits at the southern tip of Cape Coral, with direct sailboat access to the Gulf of Mexico. Hop in your boat and reach Sanibel Island or Fort Myers Beach in just 10 minutes.
The home features five bedrooms and five bathrooms, including three king suites with spa-like en-suites. All rooms have memory foam beds and LG Smart TVs with Netflix.
Spend time in the open-concept living area, unwind in the game room with foosball, arcade machines, and a Nintendo 64, or relax in the custom pool and spa while watching boats cruise by the canal.
Pet-friendly and close to Tarpon Point Marina and Yacht Club Beach, this villa is perfect for families and groups looking to soak up the Florida sunshine in style.
9. Cozy Premium Apartment
- 📍 Location: Miami
- 💵 Price Per Night: $392/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Free spa & gym access, balcony views, modern amenities
- 🌟 Perfect For: Business travelers 💼, couples 🌇, city explorers 🌴
Stay in the heart of Miami’s Brickell neighborhood, where world-class restaurants, nightlife, and shopping are right outside your door. This sleek high-rise apartment offers 1,386 sq ft of modern comfort and city views.
The unit features a full kitchen, open dining space, a bright living room with balcony access, two cozy bedrooms, and two modern bathrooms—perfect for families or business travelers.
Guests have access to the building’s spa, gym, and hot tub, plus sweeping skyline views. The rooftop pool is open on weekends, adding another way to unwind when available.
Walk to Brickell City Centre, Bayfront Park, and Bayside Marketplace, or take a quick drive to Miami Beach and Wynwood Walls. Whether you’re working remotely or exploring the city, this stay offers a stylish Miami home base.
- Read next: My Favorite Free Things to Do in Florida
10. La Playa Casa Bonita
- 📍 Location: Bonita Springs
- 💵 Price Per Night: $2,029/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Four floors with elevator, heated pool and spa, game room
- 🌟 Perfect For: Families 👨👩👧👦, luxury travelers 💼, beach lovers 🏖️, sunset seekers 🌅
La Playa Casa Bonita is a luxury beachfront estate in Bonita Springs, offering four levels of coastal living and panoramic Gulf of Mexico views.
Inside, the 5-bedroom home features a chef’s kitchen, open living space, and ensuite baths in every bedroom—some with private balconies. A top-floor game room and tiki bar add fun with darts, ping pong, and poker.
Step out to your private beachfront paradise with a heated pool, spa, outdoor shower, and grill area—perfect for sunset cocktails or lazy afternoons.
Stroll to Bonita Springs Public Beach or unwind at Barefoot Beach Preserve. For dining and shopping, head to Bonita Beach Park, or drive 30–40 minutes to Downtown Fort Myers and the airport.
- Read next: These Are the Coolest Hidden Gems in Florida
11. Floating Cottage
- 📍 Location: Sanford
- 💵 Price Per Night: $134/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Floating on St. Johns River, front porch with river views, stained glass loft bedroom
- 🌟 Perfect For: Nature lovers 🐢, peaceful retreats 🌿, river explorers 🚤
Settle into the Floating Cottage, a one-of-a-kind houseboat anchored on the serene St. Johns River in Sanford. This peaceful retreat invites you to relax among turtles, herons, and gentle manatees.
Cathedral ceilings and hardwood floors brighten the open kitchen and living space, which leads to a porch with river views. Upstairs, the loft bedroom has a queen bed, a walk-in closet, a stained glass window, and A/C.
Guests enjoy access to marina perks like a pool, deli, restaurant, poolside bar, and laundry. Plus, you’ll get discounts on boat rentals to cruise the St. Johns River or nearby Lake Monroe.
Explore Historic Downtown Sanford, home to art galleries, local shops, and vibrant markets. End your day with sunset views along the Riverwalk—a peaceful way to experience life on the water at your own pace.
12 Luxury Beachfront Escape
- 📍 Location: Bonita Springs
- 💵 Price Per Night: $1,978/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Double-lot beachfront, dolphin sightings, expansive patios, firepit
- 🌟 Perfect For: Large families 👨👩👧👦, beach lovers 🏖️, sunset seekers 🌅
Unwind at this rare double-lot beachfront home on Bonita Beach, where Gulf views, direct beach access, and daily dolphin sightings set the tone for a relaxed coastal stay. This 5-bedroom retreat blends upscale comforts with easygoing beach vibes.
Inside, soaring ceilings and oversized windows bring in natural light. The kitchen is designed for gathering, complete with a breakfast bar, island, and walk-in pantry. Several bedrooms feature en-suite baths and private balconies, with space for up to 12 guests.
Spend your day at Bonita Springs Public Beach, explore Barefoot Beach Preserve, or dine and shop at Bonita Beach Park—all just minutes away. For a day trip, head 30–40 minutes to Fort Myers or Naples for more Gulf Coast adventures.
End the evening by the fire pit or watch the sunset from the patio—this coastal escape offers the perfect mix of relaxation and scenic beauty.
13. Palm Breeze Home
- 📍 Location: Cape Coral
- 💵 Price Per Night: $238/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Swim-up pool bar, integrated spa, outdoor grill & fire pit
- 🌟 Perfect For: Relaxation seekers 🏖️, families 👨👩👧👦, pool party lovers 🍹
Welcome to Palm Breeze, where poolside living meets laid-back luxury. This 4-bedroom, 2.5-bath home is built for fun, with a swim-up pool bar, integrated spa, and plenty of space to unwind with friends or family.
Indoors, the open-concept living area flows into a chef’s kitchen and spacious dining space. The master suite offers dual marble vanities, walk-in closets, and a spa-style bath.
Step out to the tropical backyard, where the pool bar is ready for cocktails, the grill is prepped for dinner, and the fire pit sets the mood for relaxed evenings. A Tommy Bahama bar cart and ample poolside seating complete the setup.
When it’s time to explore, Fort Myers Beach and Sanibel Island are just a short drive away, making Palm Breeze the perfect home base for Southwest Florida beach days and nightlife.
14. Cozy Upscale Retreat
- 📍 Location: Naples
- 💵 Price Per Night: $243/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Private heated pool, covered lanai with summer kitchen, screened backyard
- 🌟 Perfect For: Beach lovers 🏖️, families 👨👩👧👦, and relaxing getaways 🌴
This upscale retreat in Naples Park offers a quiet hideaway just minutes from Vanderbilt Beach. With a private fenced yard, heated pool, and covered lanai, it’s made for relaxed Florida living.
The home features two bedrooms and two baths. The primary suite includes a king bed, double sinks, a walk-in closet, and direct pool access. For beach days, you’ll have bikes, chairs, towels, and toys all ready to go.
High ceilings, stainless steel appliances, a built-in wine cooler, WiFi, and a SONOS sound system round out the modern amenities.
Nearby, explore the shops and restaurants at Mercato, stroll Delnor-Wiggins Pass State Park, or soak up the sun on Naples’ white sand beaches—this home combines comfort, convenience, and coastal style.
15. Stunning Home on The Beach
- 📍 Location: Panama City Beach
- 💵 Price Per Night: $878/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Gulf-front hot tub, private beach access, spacious 1-level floor plan
- 🌟 Perfect For: Large groups 👥, families 👨👩👧👦, beach lovers 🏖️, couples retreats 💑
Stay beachfront in this spacious, single-level home with sweeping Gulf of Mexico views—just steps from Pier Park. Inside, enjoy a wall of windows, an open-concept living space, and a fully stocked kitchen.
Four bedrooms sleep up to 12 guests, including two king suites, a queen bedroom, and a fun bunk room for kids. The highlight? A private 7-person hot tub with front-row views of the pier, plus dual grills and an outdoor shower for easy beach living.
Out the front door, you’re just steps from Russell-Fields Pier for fishing and surfing, and Pier Park, home to Margaritaville, Dave & Buster’s, Ron Jon Surf Shop, and more.
With everything walkable, there’s no need to drive once you arrive—just relax and enjoy the beach life.
16. Stunning Gulf-Front Getaway
- 📍 Location: Panama City Beach
- 💵 Price Per Night: $2,084/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Private beach walkover, infinity pool & spa, kids’ bunk suite
- 🌟 Perfect For: Luxury travelers 🌅, families 👨👩👧👦, beach lovers 🏖️
This custom-designed home in Carillon Beach delivers next-level beachfront living. With private beach access, a Gulf-facing infinity pool, and top-tier amenities, it’s built for luxury getaways.
The open-concept design includes a chef’s kitchen, wet bar, and ocean-facing windows. The master suite has its private balcony, while three king suites and a bunk room comfortably host up to 12 guests.
Outside, enjoy sunset terraces, an outdoor fireplace, and a direct beach walkover. The gated Carillon Beach community offers pools, tennis courts, and local dining near Rosemary Beach and 30A.
Nearby, visit Camp Helen State Park, fish on Lake Powell, or bike the scenic coastal trails. From quiet retreats to festive gatherings, this home blends comfort, space, and location for a truly memorable stay.
17. Spacious West Palm Retreat
- 📍 Location: West Palm Beach
- 💵 Price Per Night: $950/night
- 🛏️ Sleeps: 19 guests
- 🔥 Unique Features: Rooftop hot tub, 50-ft heated lap pool, tiki hut, crow’s nest
- 🌟 Perfect For: Large families 👨👩👧👦, golfers ⛳, reunions 🎉, snowbirds ☀️
This West Palm Beach retreat blends Key West-style charm with 5,000+ square feet of indoor and outdoor living space—perfect for large groups and family reunions.
Inside, you’ll find a chef’s kitchen, multiple dining areas, and private balconies off each bedroom. With four bedrooms plus extra sleeping spaces, the home sleeps up to 19 guests.
The backyard is pure Florida fun: a 50-ft heated lap pool, rooftop hot tub, and tiki hut create a private resort vibe. Climb to the crow’s nest for panoramic Intracoastal Waterway views.
Walk to the scenic waterfront along Flagler Drive, or head into Downtown West Palm Beach for dining, golf, and beaches. Poolside lounging, rooftop dinners, and sunset views are all part of the experience.
18. Star Wars Game Room Villa at Solara, Kissimmee, Florida
- 👥 24 guests | 🛏️ 9 bedrooms | 💰 ~$619/night
- 🏰 Gated-resort villa 15 minutes from Disney with a private pool and spa
- ☀️ Best in: Spring and fall, when warm nights keep the heated pool comfortable
- 🎮 Star Wars game room
Star Wars Game Room Villa at Solara is a 4,700-square-foot home inside Solara Resort, a gated community in Kissimmee built for big family trips. Nine bedrooms and 14 beds sleep up to 24, with a king master suite on the ground floor and a Mickey and Minnie themed kids’ room among the eight bedrooms upstairs. The upgraded kitchen opens into a sprawling living and dining area, and the hosts will even put away a grocery delivery before you arrive.
The ground-floor game room is decked out in Star Wars style, with a PlayStation 5, an Xbox, two Pandora arcades holding over 1,000 games, air hockey, and foosball. Unlike many rentals in the area, it’s fully finished and climate-controlled, and out back the screened pool and spill-over hot tub are heated at no extra charge. After a long park day, I’d claim a spot in that 99-degree hot tub while the kids settle their air hockey rivalries inside.
Walt Disney World is 15 minutes away, and the Solara Resort clubhouse is an eight-minute walk with free access to its kids waterpark, resort pool, poolside bar, and fitness center. The route is fully sidewalked with no major roads to cross, and the hosts leave a large cloth wagon for hauling little ones and pool gear. Pets aren’t allowed, and the driveway fits four compact cars with overflow parking nearby since the garage is off-limits.
- Read Next: 12 Orlando Hidden Gems So Beautiful, They Feel Like a Dream
- More Central Florida adventures: Surprising Things to Do in The Villages for Young People
19. Beautifully Remodeled Home
- 📍 Location: Holmes Beach
- 💵 Price Per Night: $583/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Sugar sand gulf front, private pool, heated jacuzzi
- 🌟 Perfect For: Couples 💑, families with kids 👨👩👧, beach lovers 🏖️
Stay just steps from Palmetto Ave Beach at this beautifully remodeled duplex in Holmes Beach. It’s the ideal blend of coastal simplicity and modern comfort.
The home includes a fully equipped kitchen, a cozy king-size bed, and a queen sofa sleeper in the living room—perfect for small families or couples.
Relax by the shared pool and jacuzzi, with optional heating available. Beach chairs and umbrellas are ready for your days in the sand.
Explore nearby spots like the Anna Maria Pier, local seafood restaurants, and the shops of Holmes Beach. From peaceful getaways to family fun, this home offers everything you need for a memorable island stay.
20. Unique Private Canal Home
- 📍 Location: Sarasota
- 💵 Price Per Night: $525/night
- 🛏️ Sleeps: 12 guests
- 🔥 Unique Features: Private canal frontage, pool & spa, Spanish castle facade
- 🌟 Perfect For: Families 🏖️, beach lovers 🌊, water sport enthusiasts 🚣♂️
This Siesta Key home stands out with its Spanish castle-style design and private canal frontage. With a pool, spa, and dock, it’s perfect for family gatherings or group getaways.
The two-story layout offers spacious living areas and room for up to 12 guests. Lounge poolside, watch boats pass from the terrace, or head to Siesta Key Village for shops and restaurants.
Beach days are easy with Siesta Key Beach and Crescent Beach just minutes away. For more adventure, explore Sarasota’s marinas, art galleries, and theaters. Disney World and other theme parks are about a two-hour drive if you want a day trip.
This home is your all-in-one retreat for relaxation, exploration, and family fun.
21. “ROYS PLACE” Home
- 📍 Location: Sarasota
- 💵 Price Per Night: $205/night
- 🛏️ Sleeps: 2 guests
- 🔥 Unique Features: Outdoor bamboo shower, lush tropical landscaping, urban jungle feel
- 🌟 Perfect For: Couples 💕, romantic getaways, alternative lifestyle friendly 🌴
Welcome to Roy’s Place, an 800 sq. ft. boutique villa offering total privacy in the heart of Sarasota. Spend your days swimming in your heated, clothing-optional pool, surrounded by tropical greenery—just one block from the Sarasota Bay sunsets.
The villa features chic decor, quality furnishings, and a fully stocked kitchen for home-cooked meals. Dine poolside on the covered lanai or shower beneath the stars in the bamboo outdoor shower.
Set in a quiet, bike-friendly neighborhood, you’re minutes from the Ringling Museum, Downtown Sarasota, and the soft sands of Lido Beach. Local restaurants, shops, and nightlife are just a short stroll away.
22. Fontainebleau Sorrento Oceanview Junior Suite
- 📍 Location: Miami Beach
- 💵 Price Per Night: $260/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Partial ocean views, access to 11 pools, fitness center
- 🌟 Perfect For: Couples 💑, beach lovers 🏖️, resort enthusiasts 🌴
Stay at the Fontainebleau Sorrento Oceanview Junior Suite, a serene Miami Beach escape on the 4th floor of the iconic Fontainebleau Resort.
This spacious suite features a king bed, queen sofa sleeper, sitting area with desk, kitchenette, and a marble bathroom with a jetted whirlpool tub.
Enjoy access to 11 pools, the fitness center, two daily Lapis Spa passes, beach chairs, valet parking, and dining options from casual cafes to Michelin-starred restaurants, with no resort fees.
Relax poolside, stroll along the beach, or unwind in your suite—this is Miami luxury, made easy.
23. Roe Family Lake House
- 📍 Location: Eagle Lake
- 💵 Price Per Night: $266/night
- 🛏️ Sleeps: 7 guests
- 🔥 Unique Features: Lakefront on over an acre, kayaks, screened patio, family-friendly
- 🌟 Perfect For: Families 👨👩👧👦, nature lovers 🌿, water sports enthusiasts 🚣♂️
The Roe Family Lake House offers a peaceful, renovated cottage retreat on Lake McLeod—perfect for relaxing or adventuring. With proximity to Legoland, Disney World, and Tampa, it’s both central and serene.
The master bedroom has a queen bed and walk-in closet, while the second bedroom features twin bunks with a trundle. The kitchen includes Keurig and drip coffee makers and everything you need to cook at home.
Spend time on the screened patio overlooking the lake or enjoy kayaking, fishing, and boating with the provided gear. The yard is shaded by mature trees and fruit trees in season.
- You may also like: Hidden Gems in The Villages for Young Adults
24. Cozy Balcony Apartment
- 📍 Location: St. Augustine
- 💵 Price Per Night: $367/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Complimentary drink cards, free parking spot, live music, and top restaurants
- 🌟 Perfect For: History buffs 🏰, foodies 🍽️, nightlife lovers 🎶, city explorers 🚶♂️
Stay in the heart of historic St. Augustine in this cozy 1-bedroom, 1-bath apartment perched above one of the city’s best Italian restaurants. A king bed and pull-out couch comfortably sleep up to 4 guests.
Relax on your private balcony, watching the energy of St. George Street unfold below—think live music, festivals, and local charm. The kitchen is stocked with essentials, including coffee, tea, and complimentary drink cards.
You’re steps from gastropubs, live entertainment, and historic landmarks. Whether you’re here for the food, history, or nightlife, this apartment puts you right in the middle of it all.
25. Private Waterfront Retreat
- 📍 Location: Boynton Beach
- 💵 Price Per Night: $1,710/night
- 🛏️ Sleeps: 10 guests
- 🔥 Unique Features: Private white sand beach, heated pool & spa, 300-ft intracoastal dock
- 🌟 Perfect For: Families 🏖️, water lovers 🚤, luxury seekers ✨
This private waterfront retreat in Boynton Beach is set along the Intracoastal, offering stunning water views and your white sand beach. The villa’s outdoor spaces include multiple patios, a heated pool and spa, and a 300-foot dock.
Inside, find spacious bedrooms, multiple living areas, and a kitchen stocked for entertaining. Kayaks and paddleboards are included for easy fun on the water.
Nearby, explore Ocean Ridge Hammock Park, shop and dine at Boynton Beach Mall, or head to Boynton Harbor Marina for boating and fishing. This villa offers the ideal blend of seclusion and adventure.
26. Villa Maya, Miami, Florida
- 👥 24 guests | 🛏️ 12 bedrooms | 💰 ~$3,958/night
- 🌴 Gated 14,000-square-foot estate in Little Havana built for big groups
- ☀️ Best in: November to April, Miami’s warm and dry season
- 🪩 Private disco nightclub with a full bar
Villa Maya is a gated 14,000-square-foot estate in Little Havana, a few minutes from Calle Ocho in central Miami. Its 12 bedrooms hold 19 beds for up to 24 guests, and nine of those beds are kings. Three kitchens and an elevator make feeding and moving a group this size much easier, and the huge dining area brings everyone together at mealtime.
The standout is a 4,700-square-foot ballroom that doubles as a private disco nightclub, with a full-length bar running along one side. Outside you’ll find a sleek pool and deck with a hot tub, plus a basketball court, a pickleball court, and even mini golf, while a sauna and a yoga studio with a gym round out the wellness side. I’d book a private chef through the hosts for one big group dinner, then take the party straight to the dance floor.
South Beach, Wynwood, Brickell, and Coconut Grove are each about 10 to 15 minutes by car, along with Downtown Miami, the Design District, and Coral Gables. Grapeland Water Park is a one-minute drive for a family afternoon, and El Palacio de los Jugos is an 18-minute walk from the villa. Miami International Airport is only seven minutes away, and the hosts can arrange transportation and yacht charters for you, which saves a lot of coordinating when you’re moving 24 people around the city.
27. The Tiki Suite
- 📍 Location: Key West Harbor
- 💵 Price Per Night: $700/night
- 🛏️ Sleeps: 2 guests
- 🔥 Unique Features: Floating tiki hut, custom oak bed, hammock & water sports gear
- 🌟 Perfect For: Romantic getaways 💕, adventure seekers 🌊, off-grid enthusiasts 🏝️
Experience The Tiki Suite—a floating glamping oasis anchored in Key West Harbor. This off-grid escape offers surprising comfort with a custom oak bed, vaulted ceilings, and a 65″ TV hidden in the bed’s footboard.
Outside, unwind in your hammock over crystal-clear waters, or take the paddleboards and snorkeling gear for a spin. Watch dolphins and tropical fish swim just beneath your suite.
Close by, explore Duval Street, or head to Fort Zachary Taylor State Park for beaches and snorkeling. From sunrise paddles to sunset cocktails, this stay is pure island magic.
- Read Next: 17 Airbnb Boat Houses With Availability
28. Unique Penthouse Condo
- 📍 Location: Hallandale Beach
- 💵 Price Per Night: $365/night
- 🛏️ Sleeps: 5 guests
- 🔥 Unique Features: Private rooftop terrace, penthouse views, full kitchen
- 🌟 Perfect For: Couples getaways 💕, beach lovers 🏖️, luxury seekers ✨
Discover this luxurious penthouse condo with panoramic views of the Intracoastal Waterway and the Atlantic Ocean.
The open-concept design features sleek, modern furnishings, a fully equipped gourmet kitchen, and two spacious bedrooms with king beds and private bathrooms—perfect for couples or small groups.
Head up to your private rooftop terrace, an exclusive spot for morning coffee, sunset cocktails, or late-night stargazing under the Miami sky.
Spend the day at Gulfstream Park Racing & Casino, browse the shops at Aventura Mall, or experience the energy of South Beach after dark. This penthouse blends luxury living with the best of South Florida’s coast and city life.
- Read next: Coolest Penthouses on Airbnb
29. Stylish Miami Retreat
- 📍 Location: Miami
- 💵 Price Per Night: $1,059/night
- 🛏️ Sleeps: 14 guests
- 🔥 Unique Features: Heated pool, hot tub, tropical landscaping, spacious layout
- 🌟 Perfect For: Art lovers 🎨, friend groups 👯, family gatherings 👨👩👧👦
Escape to this bright and stylish five-bedroom home in the heart of Miami’s trendiest neighborhood—just steps from local galleries, shops, and buzzing restaurants, all wrapped in a bold, vibrant design.
Inside, the open floor plan showcases colorful decor, a chef’s kitchen, an oversized TV, and flexible spaces perfect for both relaxing and entertaining. With five bedrooms, four bathrooms, and a cozy loft studio, the home comfortably sleeps up to 14 guests.
Step into your private backyard oasis featuring a heated pool, hot tub, pergola, and teak dining table. Lounge poolside, sip cocktails beneath the string lights, or unwind after a day of exploring.
Nearby, discover the Design District, Wynwood, and Bal Harbour for shopping, art, and dining. Public beaches, golf, nightlife, and cruise terminals are just minutes away—perfect for family trips, group getaways, or special celebrations.
- Read next: Coolest Stays with Bowling Alleys
30. Nest on the Beach
- 📍 Location: Anna Maria
- 💵 Price Per Night: $1,221/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Beachfront location, heated saltwater pool, oversized hot tub
- 🌟 Perfect For: Beach lovers 🏖️, families 👨👩👧👦, relaxation seekers 🌅
Nest on the Beach is a designer coastal retreat on the peaceful north end of Anna Maria Island. With direct beach access, it offers the perfect blend of luxury and laid-back island living.
Bright wood floors, coastal-inspired decor, and panoramic Gulf views create an airy, open feel. The sleek kitchen and comfortable living space flow seamlessly onto the beachfront deck.
Spend your days lounging by the heated saltwater pool or soaking in the oversized hot tub. Dine alfresco, unwind in the outdoor shower, or sip cocktails with your toes in the sand.
Take a stroll to the boutiques and cafés along Pine Avenue, paddle out to serene Bean Point Beach, or explore quiet waters by kayak or paddleboard. It’s all part of the laid-back rhythm that makes this Anna Maria Island retreat so special.
- Read next: My Favorite Experiences in the Everglades
Best Places to Stay in Florida for Unique Villas and Beach House Rentals
Still unsure of where you’d like to stay in Florida? Here are my favorite cities, towns, and beach destinations where I recommend staying:
- Top Cities and Towns: Destin, Fort Lauderdale, Key West, Kissimmee, Miami, Orlando, Sarasota, St. Augustine, Tampa
- Best Beaches: Clearwater Beach, South Beach, Panama City Beach
- Coolest State/National Parks and Nature Spots: Florida Keys, The Everglades, Rainbow Springs
If you’re looking for another tropical vacation paradise, check out these destinations:
– Epic Airbnbs in the French Riviera
– Coolest Tuscany Vacation Rentals
– Turks and Caicos Airbnbs for Rent
– Best Portugal Accommodations to Rent
For more Airbnb inspiration, here are my other ‘best stay’ articles:
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.
