
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.

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.

Waterfront Sunsets, Great Price, Relaxing Spot!!!
Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Paradise Casa Bayfront sunsets,pool,King bed ,dock
Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

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.

🏝 Oceanfront Paradise Awaits You
Bring your boat to next vacation in tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise Fl. Keys waters. Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in Tavernier, Florida Keys. The resort offers a private sandy beach, heated swimming pool, jacuzzi, tennis courts, oceanfront marina with boat ramp and dockage, boat & trailer storage, and more - all situated on 60 lush tropical acres.

Your Happy Place - Oceanfront
Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

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.

Seaside Bungalow
Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

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.
Popular amenities for outdoor seating rentals in Islamorada
House rentals with outdoor seating

Conch Cottage at Hawks Cay - Chic Tropical Retreat

Blue House Marine in Key Largo

Beachfront Villa - Florida Keys

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks

Gorgeous Ocean View Home!

Marathon one-level home on the Marina - with slip!

Walk to Sombrero Beach, 50’Dock, SPA, Kayaks,Bikes

Little Venice Paradise~ 55' Dock Atlantic Access!
Apartment rentals with outdoor seating

Ocean View Duplex Penthouse | Pool | Vista Two

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

New Coastal Escape 2BR/2BA Oceanfront Condo

Port Largo Villas Escape 5A

Beachside Unit 22 - Private Beach on Atlantic

Dive Into Comfort – 2BR Key Largo Retreat

Key's Cottage Escape

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
Apartment rentals with outdoor seating

Villa 5027 on Duck Key BOAT SLIP available

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

2BR - Key Largo Sunshine Getaway

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Enjoy sunsets & sunrise in your home away home.

Florida Keys Getaway - Slps 4 - Ocean View

Ocean views at “Sangria Sunrise” 10% off Charters

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $463 SGD | $511 SGD | $511 SGD | $455 SGD | $443 SGD | $447 SGD | $447 SGD | $409 SGD | $393 SGD | $389 SGD | $447 SGD | $476 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 280 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 4,180 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Holiday rentals with a pool
190 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wifi availability
280 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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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Long Beach
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Theater of the Sea
- Conch Key
- Everglades Alligator Farm
- Homestead-Miami Speedway
- Monkey Jungle
- Seven Mile Bridge
- Key Largo Kampground And Marina
- Dolphin Research Center
- Sunset Park
- Calusa Campground
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- The Turtle Hospital




