
Holiday rentals with outdoor seating in Islamorada
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Islamorada
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Islamorada bungalow 2 bed & pool
Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

Island Sanctuary Islamorada
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Charming 2BR cottage in prime keys location w/pool
Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Tiny Home on Waterfront | Bay Views | Deck | Pool
Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Florida Keys Houseboat, unique waterfront stay-
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫

Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Best View Ocean Pointe Pool Beach King Bed, Gated
***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Cottage By The Sea
Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals

Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.
Popular amenities for outdoor seating rentals in Islamorada
House rentals with outdoor seating

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Beachfront Villa - Florida Keys

Viamarhe House-Private beach, Kayak, yard games

Waterfront Oceanside, 60 Ft Dock, As seen on HGTV

Private Pool! Luxury Paradise Pointe, Pet Friendly

Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!
Apartment rentals with outdoor seating

Oceanfront Bliss • Wall-to-Wall Water Views + Pool

New Coastal Escape 2BR/2BA Oceanfront Condo

Beachside Unit 22 - Private Beach on Atlantic

New Waterfront Views | Pool & Tiki Bar

Key's Cottage Escape

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Little Peace of Haven

Welcome to the Pelican Lodge !
Apartment rentals with outdoor seating

Villa 5087 on Duck Key BOAT SLIP available

Your Happy Place - Oceanfront

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

2BR - Key Largo Sunshine Getaway

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Waterfront Apt Key Largo #4, 10% Off 7+, 5% Off 4+

Ocean views at “Sangria Sunrise” 10% off Charters

🏝 Oceanfront Paradise Awaits You
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $464 SGD | $511 SGD | $511 SGD | $455 SGD | $443 SGD | $447 SGD | $447 SGD | $409 SGD | $394 SGD | $390 SGD | $447 SGD | $477 SGD |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Quick stats about holiday rentals with outdoor seating in Islamorada

Total holiday rentals
Explore 310 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 4,360 verified reviews to help you choose

Family-friendly holiday rentals
250 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Holiday rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
160 properties have a dedicated workspace

Wifi availability
310 of Islamorada holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islamorada rentals

4.9 Average rating
Islamorada stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with outdoor seating Monroe County
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Long Beach
- Coral Castle
- Sea Oats Beach
- Homestead-Miami Speedway
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Theater of the Sea
- Everglades Alligator Farm
- Conch Key
- Calusa Campground
- Key Largo Kampground And Marina
- Sunset Park
- Seven Mile Bridge
- Monkey Jungle
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Founder's Park
- Florida Keys Aquarium Encounters
- The Turtle Hospital




