
Waterfront holiday rentals in Islamorada
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Top-rated waterfront rentals in Islamorada
Guests agree: these waterfront rentals 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.

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.

Turtle-By-The-Sea: the Best Deal in KCB!
A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

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!!!

Ocean Pointe 2309 with Ocean Views
Come and enjoy all the activities the Florida Keys has to offer from this new inviting oceanfront condo. Your vacation begins the moment you drive into our 60 acre Ocean Pointe property. The Jr. Olympic sized heated pool is surrounded by beautiful landscaping, a hot tub, & the Mermaid bar. Other amenities include: a sandy beach, a Marina for boats up to 28ft, a ramp, tennis courts, pickle ball court, children's swings, charcoal grills, picnic tables, pier, cafe bar & lounging areas.

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.

Blue Haven Key Largo | Ocean Pointe 1315
Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

Ocean Views at Ocean Pointe
Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

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.

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated & is beautifully designed with comfortable, beach chic decor. It offers an abundance of natural light surrounded by windows overlooking lush landscaping and the Atlantic Ocean. Ocean Pointe Suites offers a private sandy beach, a junior Olympic sized pool, a 14-person spa, a boardwalk, a pickleball court, deep-water marina, gazebo, 2 tennis courts & more!
Popular amenities for waterfront rentals in Islamorada
Waterfront apartment rentals

New Coastal Escape 2BR/2BA Oceanfront Condo

Oceanfront Getaway in Marathon!

Beachside Unit 22 - Private Beach on Atlantic

Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Panoramic Ocean Views, Ocean Pointe Condo

Lush Views from Cozy Top Floor [Ocean Pointe 1415]

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
Waterfront house rentals

Dock, Beach Club, Ocean & Gulf Access, Pickle Ball

Oceanfront Rooftop Views w/ 75ft of Dockage

Cancellation Deal: March 21 thru March 28

Florida Keys Cottage with Pool - Hawks Cay Resort

Charming Beach House directly ON the beach

Waterfront Home 37.5-ft dock, Cabana Club Included

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

Escape to the Seaside!
Waterfront apartment rentals

Villa 5087 on Duck Key BOAT SLIP available

Reel Large END Unit in Ocean Point Suites

Your Happy Place - Oceanfront

Island Vibes / 1BR + Den & 2 Balconies

Beach Heaven-Private Beach, Pool

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

Enjoy sunsets & sunrise in your home away home.

Tequila Sunrise
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £258 | £287 | £292 | £244 | £334 | £238 | £247 | £223 | £223 | £229 | £215 | £260 |
| 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 waterfront rentals in Islamorada

Total holiday rentals
Explore 460 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at £67 per night before taxes and fees

Verified guest reviews
Over 3,720 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 280 rentals that welcome pets

Holiday rentals with a pool
370 properties feature pools

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wifi availability
450 of Islamorada holiday rentals include wifi access

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

4.7 Average rating
Islamorada stays receive an average rating of 4.7 out of 5 from guests
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Calusa Campground
- Biscayne National Park
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Coral Castle
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- Monkey Jungle
- Long Beach
- Theater of the Sea
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Seven Mile Bridge
- Dolphin Research Center
- Curry Hammock State Park
- Sunset Park
- Robbies Marina Of Islamorada




