
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.

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.

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 💫

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!

🏝 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.

Waterfront, GROUND LEVEL, Awesome Sunsets!!!
This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

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.

Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Exquisite Oceanfront Paradise - Key Colony Beach
Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.

SaltSpray Bungalow Oceanside, 1 bedroom
Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Your Keys Getaway!
Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.
Popular amenities for outdoor seating rentals in Islamorada
House rentals with outdoor seating

Pristine pool front home w/ocean views Anglers 148

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

Spacious 3Br/3Ba, 70ft Dock, Hidden Gem!VACA23-16

TheSandbar: Ocean view,Pool,Free Dockage,Gameroom

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

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

Waterfront House with 37 ft Dock & Cabana Club
Apartment rentals with outdoor seating

Ocean View Duplex Penthouse | Pool | Vista Two

Beachside Unit 22 - Private Beach on Atlantic

Dive Into Comfort – 2BR Key Largo Retreat

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

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

Welcome to the Pelican Lodge !

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina

Studio apartment in Calusa Resort & Campgrounds
Apartment rentals with outdoor seating

1st Floor, Boat Slip, King Adj Bed, Heated Pool

Villa 5087 on Duck Key BOAT SLIP available

2BR - Key Largo Sunshine Getaway

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

Enjoy sunsets & sunrise in your home away home.

Gone Coastal @ Ocean Pointe

Just a Few Friends - Ocean View and Bring your Boa

Tropical Escape | Sea Gulls 407 ~ Weekly Rental
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $461 SGD | $508 SGD | $508 SGD | $452 SGD | $441 SGD | $444 SGD | $444 SGD | $406 SGD | $391 SGD | $387 SGD | $444 SGD | $474 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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- Beach apartment rentals Islamorada
- Rentals with outdoor seating Monroe County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
- 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
- Conch Key
- Everglades Alligator Farm
- Bahia Honda State Park
- Theater of the Sea
- Homestead-Miami Speedway
- Monkey Jungle
- Seven Mile Bridge
- Key Largo Kampground And Marina
- Calusa Campground
- Sunset Park
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- The Turtle Hospital




