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

Floating Luxury Home-steps from Food Fun & Relaxin
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers a unique blend of comfort, adventure, and waterfront living. Wake up to breathtaking sunrises, sip your morning coffee with all the marine life, and fall asleep to the gentle movement of the boat. Whether your celebrating something special or simply want a one of a kind getaway-it's the perfect home base for Keys adventures or peaceful retreats. An amazing experience Free park

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

Exquisite Oceanfront Paradise - Key Colony Beach
Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Romantic cozy peaceful Guesthouse beach Sunsets.
Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

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!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Beach House - Kayak 2/2.5 Villa - OS Slip/Ramp/Pkg
Welcome to Beach House Getaway, a charming villa tucked away on the serene island of Duck Key and perfectly situated in the heart of the Florida Keys. Nestled between Key Largo and Key West, Duck Key serves as a peaceful yet convenient base for your island getaway. Its central location means you’re just a short drive from some of the most iconic destinations in the Keys, including the natural wonders of Bahia Honda State Park, the famous waters around Islamorada, and the lively Key West.

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.

Waterfront Studio 2| Couples Oasis | Kayaks | Pool
Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

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.

2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!
Popular amenities for Islamorada outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Sea Ray Cove w/ Pool, Beach, 80' Dock & Tiki hut

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Waterfront Home 37.5-ft dock, Cabana Club Included

NEW! 4-Story Villa, Private Rooftop, Pool, Marina

Luxury Boating Paradise+Pool+Sailing Kayaks

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

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

Captain’s Quarters Ahoy Mateys! Florida, Keys
Apartment rentals with outdoor seating

Beachside Unit 22 - Private Beach on Atlantic

Kawama Lagoon, 3D corner chickee 2bdr , 2 baths

Dive Into Comfort – 2BR Key Largo Retreat

Key's Cottage Escape

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

Little Peace of Haven

Boho FL Keys Condo

2 Bdrm Oceanfront Complex Private Beach & Pool
Condo rentals with outdoor seating

Villa 5027 on Duck Key BOAT SLIP available

Your Happy Place - Oceanfront

Key Largo Paradise - Remodeled Townhome in Kawama

2BR - Key Largo Sunshine Getaway

Island Vibes / 1BR + Den & 2 Balconies

Enjoy sunsets & sunrise in your home away home.

Raya Islamorada

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $622 NZD | $685 NZD | $685 NZD | $610 NZD | $595 NZD | $600 NZD | $600 NZD | $548 NZD | $528 NZD | $492 NZD | $538 NZD | $649 NZD |
| 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 290 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $69 NZD per night before taxes and fees

Verified guest reviews
Over 4,060 verified reviews to help you choose

Family-friendly holiday rentals
260 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 120 rentals that welcome pets

Holiday rentals with a pool
200 properties feature pools

Rentals with dedicated workspaces
170 properties have a dedicated workspace

Wi-Fi availability
290 of Islamorada holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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
- Coral Castle
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Sea Oats Beach
- Far Beach
- Everglades Alligator Farm
- Conch Key
- Theater of the Sea
- Long Key State Park
- Monkey Jungle
- Long Beach
- Horseshoe Beach
- Schnebly Redland's Winery & Brewery
- EAA Air Museum
- Bahia Honda State Park
- Windley Key Fossil Reef Geological State Park
- Sandspur Beach
- Keys' Meads




