
Beachfront holiday rentals in Islamorada
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Islamorada
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

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.

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"

🏝 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.

NEW! CASA AZUL - Golf Cart, 2 Kings, Pool, Kayaks
NO RESORT, GUEST OR MANAGEMENT FEES WHEN BOOKING MY HOMES! Welcome to your Key Largo vacation rental. This oceanside villa is family friendly and filled with amenities, including a private Golf Cart, pools, one adult kayak, and three kids, kayaks, pickleball and tennis courts, and a unique swimming lagoon. Spend your days kayaking, fishing, boating, snorkeling, or visit the beach at John Pennekamp. Our villa has earned hundreds of 5-star reviews on all major platforms. No Hidden Fees!

Coastal Key Colony Beach Condo, Oceanfront Complex
Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Tropical Getaway
This light, airy two bedroom condo is located in the community of Kawama. Overlooks a small lake, where people swim, kayak and paddleboard. The condo community features two pools, tennis courts, playground, fishing, beach and marina. A long jetty extends out in the ocean where you can watch the beautiful sunrises or sunsets in the afternoons. Centrally located in Key Largo near restaurants, shopping and attractions. Come down and enjoy the peaceful atmosphere of our tropical area.

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.

Turtle Nest 1 Private beach,Pool, 2bed 2bath
Ocean Pointe Suite is located on the Atlantic. Featuring ocean views from living room, master bedroom and balconies. King bed in master bedroom, Queen bed in guest bedroom, pull out queen sofa, 2 bathrooms, Smart TV's with cable WIFI. Completely stocked kitchen with all appliances. Amenities include heated swimming pool, private beach, marina with boat launch & dockage for extra fee book through marine info in pictures. Tennis courts, gazebo, located on 60 tropical acres.

Beachside Unit 37 - Come Relax on the Atlantic!
Unit 37 Details: Second Floor, Walk-in shower, Two Queen Beds, Twin Sofa Sleeper, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.” Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean.

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.
Popular amenities for beachfront rentals in Islamorada
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

Sale! Lux Home, Walk to Beach, 90' Dock, Pool

RV In The Keys | Tropical Retreat

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Relaxing Town home with great water views

New Private 4/3 Single Family - Kayaks & Bicycles+
Beachfront home rentals with a pool

Seaside Villa~ Charming Beachfront Condo w/ Pool!

Bayside Townhome in Islamorada with Boat Slip

Private Beach in Marathons Key Colony Beach

Canal/Dock - Cabana Club - Pickleball - Remodeled

Beach Front

2 Bdrm Oceanfront Complex Private Beach & Pool

Welcome to Paradise

Paradise found! Sea-Esta Condo beach and pool.
Private beachfront home rentals

BayFront Cottage,Bay Front Porch,Central AC,Beach

Sunny Beach Suite. 2 beds bath

Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool

Oceanfront community 114 Anglers Reef Islamorada

Vibrant Beachfront Villa

Endless Bay Views, Sues Promise Islamorada FL

Waterfront Villa & Sunset Views

Feb availability in Angler's Reef Islamorada
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £237 | £289 | £278 | £231 | £429 | £231 | £284 | £271 | £268 | £231 | £218 | £245 |
| 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 beachfront rentals in Islamorada

Total holiday rentals
Explore 250 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at £66 per night before taxes and fees

Verified guest reviews
Over 1,620 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 180 rentals that welcome pets

Holiday rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
240 of Islamorada holiday rentals include wifi access

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

4.5 Average rating
Islamorada stays receive an average rating of 4.5 out of 5 from guests
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- Beachfront rentals Monroe County
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- Everglades Alligator Farm
- Schnebly Redland's Winery & Brewery
- Conch Key
- Bahia Honda State Park
- Long Beach
- Theater of the Sea
- Monkey Jungle
- Key Largo Kampground And Marina
- Founder's Park
- Calusa Campground
- Homestead-Miami Speedway
- Sunset Park
- Florida Keys Aquarium Encounters
- Dolphin Research Center
- Seven Mile Bridge
- The Turtle Hospital




