Islamorada Vacation Rentals

(57 rentals)
Flamingo Cottage - Adorable 2 bedroom, 2 bath cozy cottage with pool.

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 DaysFlamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like feeling ...

View all property information

Property Type

Islamorada House

Show less

Palms #309 - Exceptional condo with panoramic views of the Atlantic Ocean.

$82

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #309" is an exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen ...

View all property information

Property Type

Islamorada Condo

Show less

Blue Water Retreat - Location!!!! Gorgeous house with Pool and Ocean Views.

$183

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days "Blue Water Retreat" is all about the location, location, location! This home has it all - ocean side Lower Matecumbe location, remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from ...

View all property information

Property Type

Islamorada House

Show less

Villa Riolo - Updated home and perfect for your next holiday in Islamorada

$117

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly

About this property

Minimum Rental: 28 Days"Villa Riolo" is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity ...

View all property information

Property Type

Islamorada House

Show less

Island Conch Cottage

2 BR | 1.5 BA | Sleeps 4 | Quick View

1

Distance to beach: 0.5 miles to Anne Beach

$125

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

Island Conch Cottage A quaint ground level conch style cottage located at the end of a private street in a very quiet setting. Cottage and grounds have privacy fence and gate. The grounds are displayed as a sand beach setting. This property has 60’ of canal frontage located on an extra wide canal ...

View all property information

Property Type

Islamorada House

"Second time Around"
Reviewed September 29, 2018

This is the second time we stayed at this island conch Cottage, this is a beautiful home the neighborhood is very quiet and the locals are always friendly. We caught a variety of snapper just off the patio ...

See all reviews

Show less

Beautiful Ocean Sunrise Views!

3 BR | 2.5 BA | Sleeps 6 | Quick View

3
Owner special: SPECIAL DISCOUNTED RATES FOR APRIL AND MAY. CONTACT ME FOR $$! Weekly &/or Monthly!!

$293

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Enjoy the sunrise over the Atlantic ocean or relaxing on a private, sunny lanai. Take a cruise around the many canals or out to Florida Bay to capture the sunset. A 30' boat slip is included with the rental. Beautifully furnished living spaces, large dining area, granite counter tops and stainless ...

View all property information

Property Type

Islamorada Condo

"Beautiful Condo"
Reviewed August 15, 2018

We love Bay Harbour Condos! We've stayed in the community 3 times so far and this condo- WILL NOT DISAPPOINT. It's beautifully decorated and very spacious. Owners are sweet and communicate very well! We ...

See all reviews

Show less

This beautifully furnished waterfront home with ocean views

$167

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This beautifully furnished waterfront home with ocean views will thrill the most ardent diver or fisherman and his family. You will love the luxury of a heated pool, magnificent view, and protected deep water dockage for multiple boats. It is located on a large harbor with multiple sailing yachts and ...

View all property information

Property Type

Islamorada House

Show less

Mosaic House - A Charming 3 bed/3 bath Waterfront Home with Ocean Views

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

About this property

The MOSAIC HOUSE as it is named is located on one of Lower Matecumbe's (Islamorada) most popular streets and features a very unique floor plan. This home "lives" in the back of the house with glass walls overlooking a tropical paradise. There's an outdoor "play" area which includes ...

View all property information

Property Type

Islamorada House

Show less

Palms #214 - Lovely condo with panoramic views of the Atlantic Ocean.

$73

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days "The Palms #214" is a gorgeous 2 bedroom, 2 bath condo. This is a gated complex located directly on the Atlantic Ocean. This unit has unobstructed views of the ocean from the master suite and the balcony. Wake up every morning, open the curtains and view a panorama ...

View all property information

Property Type

Islamorada Condo

Show less

W. Plaza del Lago - Promises to be a favorite!

2 BR | 2 BA | Sleeps 5 | Quick View

Distance to beach: 0.3 miles to Port Antigua Neighborhood Beach

$133

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly

About this property

Minimum Rental: 28 Days"West Plaza Del Lago" promises to be a favorite. Beautifully remodeled roomy single family stilt home with vaulted ceilings and located in prestigious Port Antigua on a deep and wide canal. You will love the interior of this home as much as the exterior! As you enter ...

View all property information

Property Type

Islamorada House

Show less

Gulfview Getaway - Bayfront Home with Private Beach

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly

About this property

Minimum Rental: 28 Days"Gulfview Getaway" is a FABULOUS BEACH FRONT HOME! This is what you've been dreaming of - your very own single family home with a private sandy beach in the Keys. This home is new to the rental market. It is located in a highly desirable area of Islamorada on ...

View all property information

Property Type

Islamorada House

Show less

A Large Beautiful Home With a Pool in a Peaceful

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Welcome to paradise! This home is a new listing. If you are looking for a large beautiful home with a pool in a peaceful setting and in an absolutely perfect location for your stay in Islamorada, you have found it! We are located in Venetian shores off Snake Creek with a boat slip for your use in the ...

View all property information

Property Type

Islamorada House

Show less

Palms #301 - Darling condo with panoramic views of the Atlantic Ocean.

$77

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool

About this property

Minimum Rental: 28 Days"The Palms #301" is an exceptional condo has been impeccably maintained and is located in one of the finest condo complexes in Islamorada. It features an updated kitchen, remodeled baths and is comfortably furnished. This unit is ready for your arrival. Be sure ...

View all property information

Property Type

Islamorada Condo

Show less

Ocean Front building with Ocean Front pool in beautiful Islamorada!

$129

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

Luxurious and large 2 bedroom 2 bath condo with balcony, large heated swimming pool, stainless steel appliances, flat screen televisions in every room in the beautiful Florida Keys.Huge ocean front dock with plenty of room for fishing! Wifi, deluxe cable, and restaurants within walking distance.2 ...

View all property information

Property Type

Islamorada Condo

"Wonderful location and hosts."
Reviewed January 10, 2019

This home was perfect for our family of five. Spacious bedrooms, living area and bathrooms. We also had use of the storage unit for our fishing gear and coolers. The pier is breathtaking. Our thoughtful ...

See all reviews

Show less

Islamorada water front with free boat tie-up. Available weekly, Saturday to Sat

1 BR | 2 BA | Sleeps 4 | Quick View

8

Distance to beach: 5 miles to Anne's Beach

$185

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

The Osprey Nest (MM 82.3) is a private condo residence which is wonderfully maintained. It is the total upper floor of the building in the foreground. It is operated under FL DBPR license # MOT 5403060 and is inspected annually. This Non-Smoking home is professionally cleaned prior to your arrival. ...

View all property information

Property Type

Islamorada Condo

"Mark and Dolly"
Reviewed July 15, 2018

Absolutely fantastic place to stay, we will definitely be back

See all reviews

Show less

Sunrise on Sunset

3 BR | 3 BA | Sleeps 12 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

**AMAZING SPECIAL! 25% OFF RENT MARCH THROUGH AUGUST 2019!** MINIMUM STAY: 28 DAYS “Sunrise on Sunset” is the ULTIMATE BEACH FRONT HOME. There are BREATH TAKING OCEAN VIEWS from almost every room in this house! Play in the sand, walk into the ocean or sit under the covered ground level ...

View all property information

Property Type

Islamorada House

Show less

Little Bay Lower Duplex - Gated Bayfront Property Shared w/ 2 Other Rental Units

$357

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

Minimum Rental: 7 DaysLittle Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up ...

View all property information

Property Type

Islamorada House

Show less

Southern Diversion Islamorada

5 BR | 3.5 BA | Sleeps 17 | Quick View

$857

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Private Pool

About this property

Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the major restaurants and shopping. This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat ...

View all property information

Property Type

Islamorada Estate

Show less

Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities

$269

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo ...

View all property information

Property Type

Islamorada Condo

Show less

Islamorada Beachfront Apartment - Great Sunsets! Private Beach!

$120

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Oceanfront
  • Rentals by Owner

About this property

The Jetson's House apartment (Located on the prestigious White Marlin Beach - which is considered one of the nicest natural sand beaches in the Florida Keys) features great swimming, snorkeling, and spectacular sunsets right off the beach! Have fun exploring an artificial reef! What makes the beach ...

View all property information

Property Type

Islamorada Apartment

"The perfect vacation for two"
Reviewed November 11, 2018

Have spent a month here with my girlfriend the past two summers. Jerry and Lisa are great hosts, Jerry knows a lot about the keys having lived there nearly his whole life and is great to talk to. The location ...

See all reviews

Show less

Matecumbe Jewel - 3 bedroom home with pool and dockage is a jewel of a home!

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Minimum Rental: 28 Days"Matecumbe Jewel" is a jewel of a home! Located in Lower Matecumbe, this charming canal front home offers a swimming pool, dockage, direct access to the ocean, covered fish cleaning station, a screened lanai, inviting décor and comfortable accommodations. ...

View all property information

Property Type

Islamorada House

Show less

Islamorada Paradise Vacation Home on the Water

$229

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Pool
  • Rentals by Owner

About this property

Great house! Great location!House On Canal… 60 foot concrete dock with fish cleaning stand, water, electricity and dock ladder. Bring your boat, great boat ramps. The house is a short distance to supermarkets, movie theaters, dive shops, and full service marinas with fuel, bait and tackle. ...

View all property information

Property Type

Islamorada House

Show less

Luxury Home with Dock, Waterfall Pool, HotTub, Wi-Fi deep water dock up to 60 ft

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

About this property

Venetian Shores 4-Bed/4-Bath Luxury Pool Home with 100' Dock & Opt. ElevatorMINIMUM STAY: 29 DAYS Dreaming of a Florida Keys vacation where you can boat, fish, dive, snorkel, or stay home and swim in your own private heated pool? This is it. This home offers a professionally-designed living environment ...

View all property information

Property Type

Islamorada House

Show less

Islamorada Luxurious Private Sandy Beach Access Tiki Huts Hammocks & more

3 BR | 2 BA | Sleeps 6 | Quick View

4

Distance to beach: 0.5 miles to White Marlin Beach

$457

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

About this property

House, 3 Bedrooms, 2 Baths, Sleeps 6Villa Marlin , 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three bedrooms, two bath, private home totally renovated and remodeled, new furniture ...

View all property information

Property Type

Islamorada House

"Beautiful Home on the channel to the Gulf"
Reviewed January 27, 2019

My friends and I (total 6 adults) rented this beautiful home for a birthday celebration. The home is absolutely beautiful and in close proximity too many features within the Keys. The house has water craft ...

See all reviews

Show less

Palms #405 - Totally Remodeled Condo with Ocean Views

$103

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool

About this property

Minimum Rental: 28 Days"The Palms #405" is a diamond! Be among the first to rent this gorgeous two bedroom condo. It has been completely renovated from floor to ceiling. The floors have been replaced with tile and the old popcorn ceilings are gone. You'll adore the comfortable living ...

View all property information

Property Type

Islamorada Condo

Show less

Beacon Reef 406 - Charming condo with lovely views of the ocean and pool.

$100

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. "Beacon Reef 406" is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient ...

View all property information

Property Type

Islamorada Condo

Show less

Palms #407 - Beautiful condo with panoramic views of the Atlantic Ocean.

$97

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"The Palms #407" is a charming 2 bedroom, 2 bath condo with updated kitchen and baths. Walk out onto your balcony and enjoy the sea breezes and ever changing ocean views. The comfortable furnishings and convenient floor plan provide an inviting place to call home. ...

View all property information

Property Type

Islamorada Condo

Show less

Beacon Reef #310 - Beautiful condo with lovely views of the ocean.

$107

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days"Beacon Reef 310" is one of the most desirable condominium complexes in the Upper Keys. Located in Islamorada it is convenient to everything - restaurants, fishing, diving, snorkeling, swim with the dolphin programs and much more. Picture yourself relaxing on your ...

View all property information

Property Type

Islamorada Condo

Show less

2 Master Bedrooms, Waterfront, Pool, Hot Tub, Gym/Tennis, Marina, Bikes, Jacuzzi

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Condo is immaculate, has one of the best locations in the complex! FEELS LIKE YOU ARE LIVING RIGHT ON TOP THE WATER!!!Check out our (69) - 5 STAR REVIEWS on VRBO # 50672. FYI: This site does not charge you booking fees VRBO does.Fantastic Gated Waterfront Resort Style Community:Heated Pool, ...

View all property information

Property Type

Islamorada Condo

"Location, Location, Location"
Reviewed January 25, 2019

The condo and the complex were just as advertised. The condo was clean and outfitted with everything you need. The complex is gated and of very high quality. The owner provided excellent information ...

See all reviews

Show less

Beacon Reef #222 - Gorgeous condo with panoramic views of the Atlantic Ocean.

$147

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront

About this property

Minimum Rental: 28 Days"Beacon Reef 222" is an extraordinary ocean front condo with panoramic views of the Atlantic Ocean. Relax on your own balcony or use the spiral stairs to access the sandy beach below. This condo is located in one of the most prestigious condo complexes in Islamorada. ...

View all property information

Property Type

Islamorada Condo

Show less

Beacon Reef 522 - Oceanfront 5th floor (top floor) condo at Beacon Reef.

$147

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. PHOTO UPDATES COMING SOON. "Beacon Reef 522" offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy ...

View all property information

Property Type

Islamorada Condo

Show less

Waterfront Elegance: Heated Pool/Spa/Dock Ultimate Vacation Rental

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

This tropical waterfront beauty has it all...heated pool, spa, dock, boat lift and custom elevator. It is beautifully appointed and fully equipped for your ultimate holiday rental. Located on a deep water canal, it has direct access to the Bay or Ocean. Enjoy unforgettable sunsets while relaxing on one ...

View all property information

Property Type

Islamorada House

Show less

Sunshine Place - Ground Level Unit with Ocean Views.

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

Minimum Rental: 7 Days"Sunshine Place" is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people ...

View all property information

Property Type

Islamorada House

"Absolutely perfect!"
Reviewed November 16, 2018

My boyfriend and I stayed at The Sunshine Place to celebrate both of our November birthdays. I have been visiting the keys for many years and this is the best place I have found. The property was very ...

See all reviews

Show less

Sea Grape - Serene, quaint part of paradise that the entire family will enjoy..

$400

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly

About this property

*******THIS PROPERTY IS NOT CURRENTLY AVAILABLE FOR RENT*******MINIMUM STAY: 28 DAYSFABULOUS BEACH HOUSE located directly on a mile long sandy beach. The original "Sea Grape" was destroyed by Hurricane Irma in September 2017. The decision was made to tear down and rebuild. The ...

View all property information

Property Type

Islamorada House

Show less

Mitchell's Keys Villa - Private, Secluded House on the Bay

2 BR | 1 BA | Sleeps 4 | Quick View

Distance to beach: 5 miles to Five Miles

$185

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Oceanfront
  • Pet Friendly
  • Rentals by Owner

About this property

Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a quiet residential area (rare). The villa is approx. 50 feet from the water. The property contains a wading beach and a free marina with night lights, power and water.The villa itself ...

View all property information

Property Type

Islamorada House

Show less

The PERFECT Escape with pool & jacuzzi

$429

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

This beautiful 4 bedroom/ 4 bathroom home has a 60' dock directly behind the home . Canal leads out to Snake Creek and has immediate Ocean and Bay access. The home is located in one of the finest neighborhoods of the Florida Keys- Venetian Shores. Upstairs there are 2 bedrooms/ 2 baths and there is a ...

View all property information

Property Type

Islamorada House

Show less

The Perfect Getaway with Heated Swimming Pool, Jacuzzi and Boat Slip

$357

per night

View Details

Key Amenities

  • Air Conditioning
  • Private Pool
  • Rentals by Owner

About this property

This beautiful, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a beautiful upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is extra clean and modernly furnished.Upstairs ...

View all property information

Property Type

Islamorada House

Show less

BAYSIDE CONDO, MARINA, POOL AND BEACH

$114

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Rentals by Owner

About this property

Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for your ...

View all property information

Property Type

Islamorada Condo

"First time to to Keys!"
Reviewed January 20, 2019

My family and I had a great time in the Florida Keys this year. I have family that moved there in the last year or so and we wanted to visit. It was amazing!! We really had a great time and I was so happy ...

See all reviews

Show less

Brand New Waterfront Home with Pool and Dock

$450

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

This gorgeous, newly constructed, Islamorada home has 4-bedroom, 3+ bath and is located in the quiet neighborhood of Venetian Shores MM86. It provides immediate access to both the Atlantic Ocean and Florida Bay via Snake Creek.The deep-water dockage is ideal for the avid boater or fishing enthusiast. ...

View all property information

Property Type

Islamorada House

"Friendship & Festivities in Paradise"
Reviewed January 4, 2019

We rented this gorgeous home to gather with friends(4 couples) to celebrate my 50th and it was a perfect choice. There is a wonderful balance of entertainment in the Keys and entertaining ourselves at the ...

See all reviews

Show less

Pool Home Fisherman's Dream Ocean Side

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool
  • Rentals by Owner

About this property

4 Bedroom 2 bath home with private dock and private pool with direct open access to the ocean and convenient access to the bayside through Tavernier Creek. This is both family friendly and a fisherman's dream. Our home sleeps 8 (max) with every comfort you would want while on vacation in the keys...Large ...

View all property information

Property Type

Islamorada House

Show less

Waterfront Paradise with Free Dockage - Contact us to price your stay!!

1 BR | 1 BA | Sleeps 2 | Quick View

Distance to beach: 12 miles to Founders Park

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Rentals by Owner

About this property

Secluded Waterfront Studio with Tiki hut, dock, King bed, 1 Bath, Sleeps 2.Please contact us for all of our rates for different length of stays! For shorter stays, make you have a minimum of 28 days entered in your contact form! We do not use the rate feature or the calendar feature on this listing. ...

View all property information

Property Type

Islamorada Studio

Show less

Oceanfront End Unit, Pool, WiFi, Panoramic Ocean Views

2 BR | 2 BA | Sleeps 4 | Quick View

1

Distance to beach: 1 miles to Harry Harris

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

Welcome to this 5th floor end unit condo in an art deco inspired building right on the Atlantic Ocean in a peaceful neighborhood. Enjoy full panoramic ocean views right from your own condo and balcony. Oceanfront clean heated pool and private covered parking space. Free high speed WiFi included. Sandy ...

View all property information

Property Type

Islamorada Condo

"Great Views, Comfortable Condo, Great Bargain!"
Reviewed September 9, 2018

My wife and I stayed here the first week in September, 2018 and wouldn't you know it, we got a tropical storm! It was just one rainy day however. This condo is on the 5th floor of a 7 story building, ...

See all reviews

Show less

Bayside: 1st Floor Apartment in Native Hammock on Florida Bay

1 BR | 2 BA | Sleeps 4 | Quick View

Distance to beach: 4 miles to Founders Park

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a native hammock on Florida Bay. An easy 90 minute drive from Miami International Airport, this property is located in the heart of Islamorada, directly on Florida Bay. Bayside is fully air ...

View all property information

Property Type

Islamorada Condo

Show less

Futura Yacht Club Bayside Condominium and Marina Dockage, Islamorada

$164

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean via Snake ...

View all property information

Property Type

Islamorada Condo

Show less

PARADISEPOINT- SMACK OCEANFRONT, POOL, 30' DOCK, EASY BAY ACCESS

3 BR | 2.5 BA | Sleeps 6 | Quick View

Distance to beach: 3 miles to ANNES BEACH

$465

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Private Pool
  • Rentals by Owner

About this property

YOU MAY SEE COMMENTS ON 'HOMEAWAY LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS. MINIMUM STAY 7 NIGHTS, MAXIMUN OCCUPANCY 6 PEOPLE, RENTAL PATTERN SATURDAY TO SATURDAY, SORRY NO PETS A SLICE OF PARADISE. This is it...Search no More -you ...

View all property information

Property Type

Islamorada House

Show less

Dream Home in the Keys

5 BR | 3 BA | Sleeps 12 | Quick View

1

$357

per night

View Details

Key Amenities

  • Air Conditioning
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

Deam home in they keys is one of the very few legal weekly rentals in Islamorada. It is a 4000 square foot home on water with heated Pool. Located in an exclusive area of all waterfront homes. This immaculate two-story home offers a luxurious and very private setting. Ryan's place has 5 large bedrooms ...

View all property information

Property Type

Islamorada House

"Large luxury waterfront home"
Reviewed August 26, 2018

We had the most exceptional time at this home. It’s spacious with enough rooms for everyone. The house was clean and well put together. The linens in every room are luxurious and majority of the beds ...

See all reviews

Show less

Keys Cottage; Remodeled Villa in Native Hammock on Florida Bay

$214

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Rentals by Owner

About this property

The Cottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on Florida Bay. The Cottage is a “conch-style” cottage which was just completely remodeled and renovated and is completely new, from the tile floors to the new tongue-and-groove ...

View all property information

Property Type

Islamorada Cottage

Show less

Paradise in Islamorada

2 BR | 2.5 BA | Sleeps 6 | Quick View

$300

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool
  • Rentals by Owner

About this property

2 Bed & 2.5 Bath Villa in Anglers Reef with Boat slip.Upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, upstairs balcony. Spacious ...

View all property information

Property Type

Islamorada Villa

Show less

Five Bedroom Pool home with Boat Slip in Marina..... Your Florida Keys Getaway!

$200

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Welcome to paradise! This home is a new listing. If you are looking for a large beautiful home with a pool in a peaceful setting and in an absolutely perfect location for your stay in Islamorada, you have found it! We are located in Venetian shores off Snake Creek with a boat slip for your use in the ...

View all property information

Property Type

Islamorada House

Show less

Anglers Reef-Rent Now for Summer- May/June Special

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Welcome to Anglers, a newly renovated luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated swimming pool and two private beaches. Our availability calendar is always up to date and current.Our beautiful ...

View all property information

Property Type

Islamorada House

Show less

Expand map | Close map
Islamorada Vacation Rentals

Islamorada Weather

 | 

7524°  6217°
JANUARY
Ocean 7423°
7624°  6217°
FEBRUARY
Ocean 7423°
7826°  6518°
MARCH
Ocean 7624°
8228°  7021°
APRIL
Ocean 7926°
8529°  7423°
MAY
Ocean 8127°
8731°  7725°
JUNE
Ocean 8329°
8932°  7926°
JULY
Ocean 8530°
8932°  7826°
AUGUST
Ocean 8730°
8731°  7725°
SEPTEMBER
Ocean 8530°
8429°  7423°
OCTOBER
Ocean 8328°
8027°  7021°
NOVEMBER
Ocean 7926°
7624°  6518°
DECEMBER
Ocean 7625°

The “Village of Islands” awaits you: Islamorada vacation rentals by owner


Sunny, friendly Islamorada is a smart choice for those who want a quiet escape away from the hustle and bustle of the major Florida hot spots. Located between Mile Marker 91 and Mile Marker 74, Islamorada is situated halfway between Miami and Key West along Florida’s scenic Route 1. Islamorada itself is spread out over six islands, each surrounded by tranquil ocean and soft sands.

Next time you’re looking for fun & sun, skip the traditional beachside hotel and opt for a vacation rental in Islamorada instead from FloridaRentals.com. When staying in a beach condo instead of hotel, you’ll have much more space and privacy, plus cost savings when booking a property for a large group. Some of our rentals even come with special amenities like a backyard pool, washer/dryer units, and bicycles. Whether you’re looking for a super-sized modern villa with an indoor pool, or a cozy beachfront bungalow, you can find it on our site.

Islamorada, Florida travel advice


This destination is a tropical paradise for those looking to get away from it all. In fact, celebrities have made the secluded Islamorada a second home for decades, including the island’s most famed resident, baseball player Ted Williams. Be careful, or you might just fall in love with the area, too.

With a tropical climate and daytime temperatures that rarely dip below the 70s (F), Islamorada is a fantastic vacation spot any time of the year. During the summer, temperatures typically hover in the upper 80s. The ocean breeze cools temps down in the afternoon, and the conditions are just perfect for fishing (more on this below).

Getting here from Miami International Airport or Key West Airport is easy with a rental car, and the views on Route 1 and connecting bridges are incredible. Worth the drive! Once you’ve arrived, island hopping via boat is a fun way to see the entire area.

Named by early Spanish explorers, Islamorada literally translates to “purple isles” – a nod to the colors one might see during one of the legendary sunsets.

Top activities and attractions


The sport fishing capital of the world, this city offers activities for anglers of all ages and skill levels. The surrounding ocean and shallow bays teem with a variety of fish, including sailfish, bonefish, swordfish, marlin and tarpon. Hop aboard a deep sea fishing charter to try your hand at grabbing one of these fish and cooking your own catch for dinner. If you’d rather stay on land, explore try fly fishing in the backcountry.

Fishing not your thing? That’s fine, there’s plenty of other activities in the area. Grab a towel and head to Anne’s Beach for a full day of sand castles and snorkeling. It’s also private and quiet, so you will feel a long way away from the crowds on South Beach. If you’re feeling adventurous, try your hand at kite surfing since the shallow waters here provide an ideal environment.

Bring your family to the Theater of the Sea and take a live snorkeling tour or swim with dolphins. If you prefer nature surroundings, Windley Key Fossil Reef Geological State Park has nature trails for hiking. Don’t miss the underwater shipwreck site at San Pedro Preserve where scuba divers love the scenery and adventure.

Music lovers enjoy warm, tropical evenings and daylong music festivals on the lawn of the outdoor, waterfront ICE Amphitheater located inside Islamorada Founders Park, a 40-acre expanse that features an Olympic-sized pool, shallow water beach, water sports rentals, ball fields, fishing jetty, exercise opportunities, skatepark and a dog park.

Dining


Known for delicious seafood, Islamorada’s restaurants serve up the day’s freshest catch. Starting at breakfast, stop in to the Midway Cafe & Coffee Bar where guests can start their day off with an omelette or pancakes. For lunch, grab a wrap at Chef Michael’s where they feature daily seafood dishes that “wow” eaters. Want to eat with a view? Grab an outside table at Morada Bay and watch the palm trees sway as you grub. Lastly, the Green Turtle Inn has more seafood dishes and soups that come with rave reviews.

Islamorada homes for rent on FloridaRentals.com


Islamorada condo rentals on FloridaRentals.com can save you up to 20% over our competitors. Plus, we have a wide array of inventory appealing to any group size or traveler tastes. Happy planning!