Islamorada Rentals
From $399 per night (USD)VRBO
Ocean & Bay Views. Welcome To Paradise!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sleeps 4, 1 Bedroom - King Bed, 2 Full Bathrooms, Queen Sleeper Sofa, 2 TVs, Balcony, fully stocked kitchen, towels & l ...
From $399 per night (USD)VRBO
From $430 per night (USD)VRBO
Cozy 1-bedroom Hawksbill Cottage in Islamorada, perfect for a romantic getaway.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hawksbill Cottage - The Hawksbill Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all wi ...
From $430 per night (USD)VRBO
From $859 per night (USD)VRBO
Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 8
Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages al ...
From $859 per night (USD)VRBO
From $327 per night (USD)VRBO
Cozy 1-bedroom Kemp Cottage in peaceful Islamorada, perfect for a romantic getaway.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kemp Cottage - The Kemp Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their o ...
From $327 per night (USD)VRBO
From $429 per night (USD)VRBO
Bayside Retreat: Enjoy stunning open water views in this 3-bedroom home in Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayside Retreat - Completely renovated bayfront duplex home. This bayfront home consists of three bedrooms and three bat ...
From $429 per night (USD)VRBO
From $399 per night (USD)Expedia
Ocean front paradise, 6th story balcony ocean view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Islamorada is the fishing capital of the world, and home to the famous Islamorada sandbar. 🏖️ This condo is a 6th floor ...
From $399 per night (USD)Expedia
From $366 per night (USD)VRBO
Beachfront Islamorada Villa with Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect Islamorada getaway awaits. Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, ...
From $366 per night (USD)VRBO
From $366 per night (USD)VRBO
Bayfront Islamorada Townhome with Dock & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy all the wonders Sandy Pointe Townhome has to offer. With breathtaking bay views, deep water dockage and a private ...
From $366 per night (USD)VRBO
From $562 per night (USD)VRBO
Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Islamorada is considered the fishing capitol of the world!You can do deep sea,offshore game and back country fishing!It ...
From $562 per night (USD)VRBO
From $562 per night (USD)VRBO
Relax in this 3-bedroom canal getaway in Islamorada, perfect for families!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
125 Porto Vista Ct - No shoes, No shirt, No problem! In this Pt Antigua Pool Home, you will need to go nowhere to have a ...
From $562 per night (USD)VRBO
From $145 per night (USD)VRBO
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautiful modern Studio apartment has just been completely remodeled and new to the rental market. Every detail has ...
From $145 per night (USD)VRBO
From $664 per night (USD)VRBO
Experience paradise at Green Cottage, a charming 2-bedroom oceanfront retreat in Islamorada!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Green Cottage - The Green Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their ...
From $664 per night (USD)VRBO
From $239 per night (USD)VRBO
Embrace island living at 132 Atlantic Lane, a cozy 2-bedroom canal retreat in Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Cute Keys-style 2 bedroom, 2 bathroom canal-front home located on Atlantic Lane with dockage and a quick ride out to the ...
From $239 per night (USD)VRBO
From $214 per night (USD)VRBO
Wake up in Paradise. Islamorada Florida - 6-month minimum without boat lift.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
(6 month minimum rental) - $4,800 per month (boat slip not included). Conveniently located on a quiet street in Port An ...
From $214 per night (USD)VRBO
From $645 per night (USD)VRBO
Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
VILLAGE. RENTAL LICENSE # VR-007 Please always send email request with dates desired , as sometimes the dates on the ca ...
From $645 per night (USD)VRBO
From $336 per night (USD)VRBO
Relax in this 3-bedroom canal home with stunning views in Islamorada!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
141 Ocean Lane - "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of thi ...
From $336 per night (USD)VRBO
From $183 per night (USD)VRBO
Lovely Islamorada Studio in the Heart of the Keys
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Rates are based on 28 day rental with check in and check out on Saturday. Contact owner for flexible check in dates. C ...
From $183 per night (USD)VRBO
From $147 per night (USD)VRBO
Beautiful 1 bedroom apartment, king size bed, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a beautiful, recently renovated, one bedroom apartment at Summer Sea Condo. A wonderful garden view with a side ...
From $147 per night (USD)VRBO
From $397 per night (USD)VRBO
POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your own tropical paradise in Islamorada overlooking the fabulous Florida Bay - this family favorite is just 67 miles s ...
From $397 per night (USD)VRBO
From $279 per night (USD)Expedia
Oceanfront Private Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Paradise Cottage!! This downstairs portion of a dual family dwelling is fully renovated a 1/1 cottage with ...
From $279 per night (USD)Expedia
From $429 per night (USD)VRBO
Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
80ft Dock and Boat Lift very close to Islamorada Sandbar and Alligator Reef. Great fishing, diving, snorkeling and boat ...
From $429 per night (USD)VRBO
From $962 per night (USD)Expedia
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation Rental License No VR-001 WEEKLY RENTAL Located on the peaceful upper Keys, in Islamorada, this home is situat ...
From $962 per night (USD)Expedia
From $403 per night (USD)VRBO
Tarpon Bend ocean view with boat lifts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
3/2 Waterfront Home in Lower Matecumbe Key in Islamorada, Florida. Featuring a 70' ft private dock with 2 boatlifts (1- ...
From $403 per night (USD)VRBO
From $488 per night (USD)Expedia
3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay - this family favorite is just 67 miles south of Miami! ...
From $488 per night (USD)Expedia
From $601 per night (USD)VRBO
Holly’s Hideout (Fisherman's Dream)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This amazing home is centrally located on a clean, clear canal with deep water access to either the bay or ocean via Tav ...
From $601 per night (USD)VRBO
From $339 per night (USD)VRBO
2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features ...
From $339 per night (USD)VRBO
From $1788 per night (USD)VRBO
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamor ...
From $1788 per night (USD)VRBO
From $451 per night (USD)VRBO
Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unit B106 Village of Islamorada: License Number: 24-0368. BOOK MONTHLY AND SAVE $$$$ Bay Harbour is a gated community ...
From $451 per night (USD)VRBO
From $179 per night (USD)VRBO
Summer Sale! Stunning 2-Bedroom with a million-dollar Open Water View!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This Fantastic Condo is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacular sunsets and ...
From $179 per night (USD)VRBO
From $459 per night (USD)VRBO
Breezy Beach Waterfront home in Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept ...
From $459 per night (USD)VRBO
From $634 per night (USD)VRBO
Bay Harbour Islamorada Oceanfront Views 3/2.5 UPDATED condo DOCK
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful views from this condo dock 32 available- Unit C109 License Number: VR-194 Bay Harbour is a gated community l ...
From $634 per night (USD)VRBO
From $632 per night (USD)VRBO
3200sqft Masterpiece Home, Fishing Paradise ,Waterfront, Beach, Pool, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
"Monthly rentals only, no split months, thank you." Day 1, of the month , to end of the month. Welcome to, GULFVIEW 150 ...
From $632 per night (USD)VRBO
From $537 per night (USD)VRBO
Breathtaking ocean views for your Paradise vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house s ...
From $537 per night (USD)VRBO
From $206 per night (USD)VRBO
Executive Bay - Next to Beach and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come to Paradise and Enjoy it in comfort.! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), par ...
From $206 per night (USD)VRBO
From $428 per night (USD)VRBO
Charming 2-Bedroom Futura Townhome 731 in Islamorada, with heated pool and modern amenities.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Townhome #731 - Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a tw ...
From $428 per night (USD)VRBO
From $693 per night (USD)Expedia
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
😊This Beautifully renovated Compound / Property Comes With A recently completed and Magnificent Landscape Oasis , That ...
From $693 per night (USD)Expedia
From $646 per night (USD)VRBO
The PERFECT ESCAPE with Private Pool and Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful 4 bedroom/ 4 bathroom home has a 60' dock. Its canal leads straight out to Snake Creek and has immediate ...
From $646 per night (USD)VRBO
From $422 per night (USD)VRBO
Boater's Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—per ...
From $422 per night (USD)VRBO
From $549 per night (USD)VRBO
Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to Paradise! This fabulous Keys home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dre ...
From $549 per night (USD)VRBO
From $230 per night (USD)VRBO
Islamorada Spectacular Vacation At Executive Bay Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come, Enjoy and Relax in our beautiful piece of the paradise in the Florida Keys. The Executive Bay Club is located in I ...
From $230 per night (USD)VRBO
From $271 per night (USD)VRBO
Oceanfront Views From Every Room! SEPT. DISCOUNT! RESERVE QUICKLY! Lic #26-0403
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Huge terrace! Right on the water with unobstructed views! Accessible from every room! Spacious and clean. Fully Renovate ...
From $271 per night (USD)VRBO
From $1032 per night (USD)VRBO
Ultimate luxury vacation home in Islamorada, Florida!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
SPECTACULAR HOME AND FISHERMAN'S PARADISE IN VENETIAN SHORES! This home is located in close proximity to many shopping ...
From $1032 per night (USD)VRBO
From $588 per night (USD)VRBO
Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and priv ...
From $588 per night (USD)VRBO
From $510 per night (USD)VRBO
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Flori ...
From $510 per night (USD)VRBO
From $119 per night (USD)VRBO
Oceanfront Luxury Condo. Step on to the beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seagulls Condominiums Islamorada Tavernier Key Largo Florida Keys New Lazy Boy recliner added to our open concept livin ...
From $119 per night (USD)VRBO
From $659 per night (USD)Expedia
Islamorada Waterfront Paradise with 5 Bedrooms, Pool and Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Escape to your tropical island paradise in the heart of the Florida Keys! Nestled in cross keys location, to Tavernier C ...
From $659 per night (USD)Expedia
From $451 per night (USD)VRBO
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Oceanside 3/3 located in a beautiful naturally protected harbor on the Atlantic Ocean. See manatee, tarpon and many bea ...
From $451 per night (USD)VRBO
From $364 per night (USD)Expedia
Villa located on the water Free marina, and trailer parking.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a q ...
From $364 per night (USD)Expedia
From $161 per night (USD)VRBO
New 2/1 Remodeled Cozy Home in Tavernier Key
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Relax at this peaceful and centrally-located 2/1 remodeled private home in Tavernier Key. Located near Tavernier Creek M ...
From $161 per night (USD)VRBO
From $1544 per night (USD)VRBO
Experience luxury at The Sapodilla House, a stunning 5-bedroom waterfront retreat in Islamorada.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The Sapodilla House - The Sapodilla House is one of Islamorada's gems. This tropical, sprawling estate has every amenity ...
From $1544 per night (USD)VRBO
From $343 per night (USD)VRBO
Casa Mia 7862778706
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Absolutely comfortable keys Home , great location to restaurants and activities, two bedroom and two full bath upstairs ...
From $343 per night (USD)VRBO
From $387 per night (USD)Expedia
AQUAMARINE OCEANVIEW+””SPECIAL RATES””+ DOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE EMAIL US WITH ANY QUESTIONS??? WE ARE HAPPY TO PROVIDE THE ANSWERS ABOUT OUR PROPERTY, OUR RESORT, RESTAURANTS, ...
From $387 per night (USD)Expedia
From $233 per night (USD)VRBO
Tropical Escape | Sea Gulls 407 ~ Weekly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Located right on the Atlantic Ocean, in the heart of the Florida Keys on Plantation Key - the sport fishing and ...
From $233 per night (USD)VRBO
From $833 per night (USD)VRBO
Large Canal Front Family home in the heart of Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 14
Make yourself at home at this beautiful stay in Islamorada. Minutes away from the open ocean and the bay, this home is o ...
From $833 per night (USD)VRBO
From $632 per night (USD)VRBO
Charming 3-Bedroom Canal Home in Islamorada with Private Pool & Balcony
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located on Cortez Drive on Lower Matecumbe Key, this beautifully maintained waterfront home offers everything you need f ...
From $632 per night (USD)VRBO
From $311 per night (USD)VRBO
Sunset from our own Private Balcony Directly over the Bay
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Paradise in the Upper Keys. Just under 1 1/2 hrs. from Miami you can rent a piece of Heaven this Winter Season. Prime co ...
From $311 per night (USD)VRBO
From $343 per night (USD)VRBO
Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This opulent condo is located within Ocean Harbour which is one of Islamorada’s most sought after gated communities feat ...
From $343 per night (USD)VRBO
From $593 per night (USD)VRBO
A Piece of Paradise Islamorada, Fl. On the water 3/2, 90 Ft of dock New Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. T ...
From $593 per night (USD)VRBO
From $341 per night (USD)VRBO
Relax at Ocean Harbour K-35, a 3-bedroom oceanfront condo with dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour K-35 - This newly renovated unit is located in Ocean Harbor, one of the most exclusive condominiums in Isl ...
From $341 per night (USD)VRBO
From $1014 per night (USD)VRBO
Experience luxury at Maison 307 in Islamorada, 3 bedrooms with resort-style pool.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Maison Matecumbe #307 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centra ...
From $1014 per night (USD)VRBO
From $1082 per night (USD)VRBO
You will never want to leave
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Ocean Retreat offers breathtaking views from every room, with a 60' covered balcony that overlooks the 32' Pool/Spa ...
From $1082 per night (USD)VRBO
From $1794 per night (USD)Expedia
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Spectacular property - two stories of true keys paradise in a relaxed basin-front setting. Newly renovated, the proper ...
From $1794 per night (USD)Expedia
From $358 per night (USD)VRBO
Oceanfront home ON Tavernier Creek
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
This home is a fisherman`s dream come true. New dock right on Tavernier Creek. You will be in open ocean in minutes!! ...
From $358 per night (USD)VRBO
From $799 per night (USD)VRBO
The Beach House-Luxury Oceanfront Home, Outstanding Views, Pool & Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to ‘The Beach House’ at Tarpon Point in Islamorada – This luxurious oceanfront home is in a private gated enclav ...
From $799 per night (USD)VRBO
From $394 per night (USD)VRBO
Tavernier Keys Home w/ 70’ Dock & 20k Boat Lift on Bayside! 3/2.5 Plus Game Room
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Gorgeous and Spacious Bayside Tavernier Keys Home with a 70’ foot Dock for your Boat and 20,000 lb Boat Lift. Be in the ...
From $394 per night (USD)VRBO
From $720 per night (USD)Expedia
Bay Front Home With Magnificent Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Located in Islamorada, the fishing capital of the world, this house is tucked away in a quite neighborhood on the bay si ...
From $720 per night (USD)Expedia
From $357 per night (USD)VRBO
Stunning Keys home w/pool, jetted tub, elevator & more!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Paradise. Come and relax in our Bayside home and enjoy the coastal breeze and rustling palms in your own pri ...
From $357 per night (USD)VRBO
Click For PricingExpedia
Spring Break in the Sun! Islamorada townhome w/ beach, pool in gated community!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just reduced for last minute Spring Break family!! Enjoy Townhome in the heart of the Florida Keys, under 1.5 hours fro ...
Click For PricingExpedia
From $851 per night (USD)VRBO
Island pool home awaits in Islamorada's Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Your island pool home awaits in Islamorada's Port Antigua! 3,500 square foot, 4 bedroom, 3 bathroom, high ceilings, til ...
From $851 per night (USD)VRBO
From $505 per night (USD)VRBO
Islamorada, Indian Waterways, waterfront retreat - heated pool, 30’ dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your private slice of paradise in the heart of Islamorada, Florida Keys! This spacious and beautifully ...
From $505 per night (USD)VRBO
From $1711 per night (USD)VRBO
Oceanfront 2 Homes | Private Beach & Pool | 3 Acre
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Oasis4rent! Escape to 2.75 acres of private oceanfront paradise in the heart of Islamorada. Two beautifully ...
From $1711 per night (USD)VRBO
From $868 per night (USD)VRBO
Ocean Front Contemporary Beach House, Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in the sweet spot of the Florida Keys - Islamorada. Custom built and designed by an Award winning architect in 2 ...
From $868 per night (USD)VRBO
From $595 per night (USD)VRBO
Waterfront Pool Home w/ Boat Lift - Easy Ocean & Bay Access
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Waterfront canal home with pool, spa, and 15,000 lb boat lift just minutes to both the ocean and Florida Bay. Located j ...
From $595 per night (USD)VRBO
From $695 per night (USD)VRBO
Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
SANCTUARY FOUND… At the intersection of two very wide sparkling canals sits this lovely, four bedroom, two and a half ba ...
From $695 per night (USD)VRBO
From $126 per night (USD)VRBO
Very Nice 3 Bedroom Home With Large Lot! Built to entertain! Boat Ramp!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This is a beautiful property that offers a home like atmosphere as well as complete privacy. The property is in the comm ...
From $126 per night (USD)VRBO
From $113 per night (USD)VRBO
Beautiful Efficiency Apartment - Bayfront, Islamorada Apt 232
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summer Sea Condominium Unit 232 is a brilliant, clean and modern efficiency apartment, newly upgraded in 2023 with tile ...
From $113 per night (USD)VRBO
From $1013 per night (USD)VRBO
3 Bedroom Private Oceanfront House - Sol
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overl ...
From $1013 per night (USD)VRBO
From $734 per night (USD)Expedia
Happy Tarpon: Boat Dock - Private Heated Pool - Fisherman and Family Fun!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Happy Tarpon - A special place for you in the beautiful Florida Keys. Enjoy our renovated home in the heart of Islamor ...
From $734 per night (USD)Expedia
From $265 per night (USD)VRBO
Best Location for Your best vacation!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Spacious Waterfront Vacation Home – Perfect for Families & Groups This beautiful property features two separate levels, ...
From $265 per night (USD)VRBO
From $276 per night (USD)VRBO
New saltwater pool, pet friendly, waterfront house with dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Lower Matecumbe waterfront home, pet friendly for 1 dog. New concrete saltwater pool (heated/cooled) in 2022. New 20,0 ...
From $276 per night (USD)VRBO
From $304 per night (USD)VRBO
Keys Comfort: 1BR Condo with Den, Kitchen & Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Welcome to your island retreat! This spacious ground-floor Den Suite offers the perfect blend of relaxation and fun, com ...
From $304 per night (USD)VRBO
From $304 per night (USD)Expedia
Anchor Here: Oceanfront 1BR Condo with Marina Access
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 6
Immerse yourself in the tranquility of island living with this spacious first-floor pool-view suite, perfectly designed ...
From $304 per night (USD)Expedia
From $301 per night (USD)VRBO
Direct Oceanfront Corner Condo, WiFi, Pool, Gym, Panoramic Ocean Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
FOR VIEW LOVERS and a favorite of returning visitors. EVERY ROOM has a gorgeous OCEAN view. Enjoy this rare Licensed I ...
From $301 per night (USD)VRBO
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Beautiful Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state ...
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From $813 per night (USD)VRBO
Venetian Shores Home -DOCK remodeled 3/3 POOL/Hot Tub! Deep water Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
126 Palermo Drive Check out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, ...
From $813 per night (USD)VRBO
From $249 per night (USD)Expedia
Idyllic Tropical Paradise Overlooking the Fabulous Florida Bay.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This condo is located in your tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada in Futura Yac ...
From $249 per night (USD)Expedia
From $346 per night (USD)VRBO
Wonderful Retreat at relaxing Paradise. Everything like new!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
MINIMUM STAY: 29 DAYS - Very comfortable 50ft wide canal home located in Islamorada close to Snake Creek Channel with ...
From $346 per night (USD)VRBO
From $306 per night (USD)Expedia
Water Front 3/3 Family and Boat Friendly Home, Great Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful well-kept and spacious two story bay-side waterfront home is a perfect rental home for you and your famil ...
From $306 per night (USD)Expedia
From $154 per night (USD)VRBO
Charming Summer Sea 203 in Islamorada: 1 bed, heated pool, and ocean views!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This studio makes the best of the space. Living room by day bedroom by night with the convenient Murphy bed. All newly u ...
From $154 per night (USD)VRBO
From $1368 per night (USD)Expedia
4 Bedroom Private Oceanfront House - Bahia
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 4 bedroom private oceanfront house overl ...
From $1368 per night (USD)Expedia
From $772 per night (USD)VRBO
Gulf access, private dock and private neighborhood beach!
- Bedrooms:
- 1
- Bathrooms:
- 5
- Sleeps:
- 4
Recently updated Islamorada waterfront rental. Fully furnished and equipped kitchens! Come bring your boat or rent one t ...
From $772 per night (USD)VRBO
From $732 per night (USD)VRBO
\" Endless Summer\" Awaits!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Sure you can drive another 1.5 hours to reach Marathon but why would you do that when the best restaurants and events ...
From $732 per night (USD)VRBO
From $435 per night (USD)VRBO
Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers ...
From $435 per night (USD)VRBO
From $1778 per night (USD)VRBO
Luxury home, Heated pool, Hot tub, Chefs kitchen, Sundeck, 100 ft of dockage.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
*** MINIMUM 28 NIGHT STAY *** Once you check-in, you’ll never want to leave 216 Johnny Road With quick ocean access, a ...
From $1778 per night (USD)VRBO
From $700 per night (USD)VRBO
Bayfront Home In Florida Keys
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy your stay at your own private oasis! You will approach this stunning home down a secluded road that leads into pa ...
From $700 per night (USD)VRBO
From $432 per night (USD)Expedia
Peacock Shores Islamorada - Vacation On The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The ocean is your front yard at this modern, luxurious townhome hidden away in a small, private seaside community. Enjoy ...
From $432 per night (USD)Expedia
From $435 per night (USD)VRBO
Canal Front Beautifully Renovated Home w/ Great Deck, Private Boat Ramp + WI-FI
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This comfortable house, located in the quiet neighborhood of Plantation Key Colony, Offers three inviting bedrooms and 2 ...
From $435 per night (USD)VRBO
From $529 per night (USD)VRBO
NEW POOL ** Waterfront Paradise with Amazing Sunsets on Beach**
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra ...
From $529 per night (USD)VRBO
From $180 per night (USD)VRBO
Beautiful 2 bedroom Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful, modern, upgraded 2-bedroom, 1.5 bath apartment at Summer Sea has everything you would want for your fabu ...
From $180 per night (USD)VRBO
From $336 per night (USD)VRBO
Breezy Happy Hours in Port Antigua Beach Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This 2,500sf home has been completely renovated. With 4/3.5 this comfortable home is located in one of the most desirabl ...
From $336 per night (USD)VRBO