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Islamorada Vacation Rentals in the Florida Keys

Book Places to Stay and Vacation Home Rentals in Islamorada Directly Online Here and Save!

We have many choices for Islamorada Vacation Rentals, Homes and Condos with Wi-Fi, Pool, Oceanview, Beachfront and other amenities they have to offer for your visit to Florida.

Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe - Bay Harbour C312

Islamorada Condo 4.4

Beautiful 3 bedroom 2.5 bath luxury condo at MM 74.5 Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and Wifi. The condo boasts some amazing views of the Clear Blue waters of the Atlantic Ocean looking over Sea Oats Beach. Relax on your own private roof top patio and enjoy a beautiful sunrise of the.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Beautiful Oceanfront Property with Pool -- Alligator Reef - Conch & Lobster

Islamorada Private vacation home 4.4

Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to enjoy the trade winds and sip your margaritas. The Con.......read more

5 Bedroom(s)
5 Bath(s) Sleeps 14


Vacation Home


One Day Paradise Retreat

Islamorada Private vacation home

Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port Antigua is one of the best neighborhoods in Islamorada. Not only does it offer a private beach for members only but also has a private boat ramp right inside the neighborhood. With great fishing access to the bay and open ocean.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach

Islamorada Private vacation home 5.0

Paradise is only a click away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation rentals. Our unit has unobstructed direct ocean views, and overlooks the resort style swimming pool. Dock space is available to rent as well for boats up to 31 ft.
This home is great for a family vacation. There is also a beach.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Canalfront 2 bedroom up and 1 bedroom down in Venetian Shores - 107 San Remo

Islamorada Private vacation home 5.0

Comfortable Venetian Shores canal home that has two bedroom/one bath upstairs and a one bedroom/one bath apartment downstairs. The downstairs apartment has a complete kitchen and living room and separate bedroom. There is a screened in porch of the living room upstairs. The home has awesome dockage that is 70\'. Easy ocean or bay access via Sn.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Beautiful 2 Bedroom Oceanfront Bungalow with Pool & Dockage - 75691 Overseas Hwy.

Islamorada Private vacation home 4.4

With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you\'ll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada\'s Lower Matecumbe Key, near mile marker 76, this traditional one-story Keys bungalow is refurbished. .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Panoramic Ocean Views from this 3 Bedroom Islamorada Home - 137 LeSerra

Islamorada Private vacation home 4.8

Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in
Lower Matecumbe (South part of Islamorada). This home is the second one in on a point
and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee
maker, toaster, and blender. There are two flat panel TV\'s in the house, as well a.......read more

3 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Luxury in Paradise, Heated Pool, Kayaks, SUP’s, Bikes, Boat Ramp, BBQ, More

Islamorada Private vacation home 5.0


Luxury in Paradise! Fully remodeled from the floor up, inside and out, all new furnishings in summer of 2022. Your bungalow is one of the original Islamorada bungalows built in the late 60\'s restored to better than new. Come see what the Island Lifestyle in the sportfishing and leisure capital of the world is all about. Castaway Island at Sh.......read more

2 Bedroom(s)
1 Bath(s) Sleeps 5


Vacation Home


Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool

Islamorada Private vacation home 4.8

114 Anglers Way
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many kid friendly features.
Outfitte.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Little Piece of Paradise (AVAIL Oct-Dec)

Islamorada Private vacation home

Our Little Piece of Paradise is a relaxing place to enjoy with family and friends. We look forward to making it your home away from home.
Fully remodeled home on the water, washer and dryer inside the house. TVs in living room and bedrooms. Smart TV and internet are included. Bedrooms include: 1 King Size Bed, 1 Queen Size Bed, 2 Full Size Beds.......read more

3 Bedroom(s)
1 Bath(s) Sleeps 8


Vacation Home


4 Bedroom House In Angler's Reef, Includes 31' Boat Slip

Islamorada Private vacation home 4.9

Beautiful 4-bedroom, 3.5 bath home in Angler\'s Reef. Walk into a brightly decorated, open floorplan, featuring a newly renovated gourmet kitchen including all of the amenities you’ll need for a perfect stay – updated appliances, stone countertops and breakfast bar. A queen bedroom with ensuite bathroom is conveniently located on the first floo.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8


Vacation Home


Islamorada Luxury Waterfront Condo with Boat Slip

Islamorada Condo 5.0

Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo.

This unit located in the complex of Bay Harbour offers a private 50\' boat slip, heated swimming pool, hot tub, club house, fitness center, tennis courts, gas barbequ.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Beautiful 'Keysey' Condo in Gated Community (VR-196)

Islamorada Condo 4.9

Enjoy the spirit of the Florida Keys in this \'keysey\' furnished condo with everything provided. All you have to do is show up with your shorts and swimsuit. Boat slip is optional. You can be in your boat and heading out to enjoy spectacular fishing, diving, snorkeling, boating, or just cruising and watching the sunset in a flash.

Locate.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4


Vacation Home


Location. Location. Location.

Islamorada Private vacation home 5.0

Our home is in the perfect location in Islamorada....across the street from The Worldwide Sportsman, Morada Bay and Pierre\'s and within walking distance to restaurants, shops and galleries. We are situated on the ocean side of the Overseas Highway at MileMarker 81. There is enough room for a trailered boat in the driveway. Relax on the large scree.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Amazing Islamorada Sunsets, 2 Sandy Beaches, Pier Fishing, Pool, WiFi, Cable

Islamorada Private vacation home 4.9

For a relaxing & fun family vacation experience. It is time to change your latitude, attitude & immerse your body & mind in the calming, soothing waters that surround this Florida Keys paradise. So come enjoy Gulf waterfront sunsets in Islamorada, Florida. (OK. I agree, it\'s kind of corny but oh so very true.)

QUICK OVERVIEW:
We offer yo.......read more

4 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Unique 2 Bedroom Bay Front Home with Roof Top Terrace - 75130 Overseas Hwy.

Islamorada Private vacation home 4.8

Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs makes for a great sunset watching area. The house has .......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Executive Bay Club Condo (2 bds + loft & 3 full baths)

Islamorada Private vacation home

Come stay and watch the sunsets at our beautifully updated Keys townhouse at Executive Bay Club located in Islamorada on the bay. It has 2 bedroom with a loft, 3 full bathrooms and washer/dryer in the unit. It is a private, gated community with a clubhouse, heated swimming pool, a private beach area, a fishing dock and 2 tennis courts. Founders .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 9


Vacation Home


Discover the Charm of Island Living

Islamorada Condo 4.6

Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf of Mexico and is a gated complex consisting of 70 units. Enjoy wonderful Bay views and sunsets from our two bedroom / two bath condominium unit that sleeps up to 4 people. Stay in touch with family & friends with free wireless int.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 4


Vacation Home


Tastefully Renovated Townhome with Great Community Amenities - Executive Bay G5

Islamorada Private vacation home 4.5

This townhome at Executive Bay will sure make your home away from home! This unit has been completely renovated and decorated beautifully. This
2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a Bayside complex. It is a gated community with 24 h.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Vacation Condo at Futura Yacht Club

Islamorada Condo 4.9

Beautifully renovated second floor condo at Futura Yacht Club, a private, gated complex with a fabulous marina and pool, just 67 miles south of Miami, at mile marker 88.5 in Islamorada, considered the Sportfishing Capital of the World.
Excellent access to the Ocean through Tavernier Creek or Snake Creek for boating, fishing or snorkeling. Relax.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,

Islamorada Condo 5.0

“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much more.

This 2 Bedroom condo at Bay Harbour sleeps 4 adults & two children 6 and under. Easy access to the Gulf or Ocean makes this the perfect home port for any fishing vacation. Bring your own boat or rent from any of.......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4


Vacation Home


Beautiful Townhouse in the heart of the Florida Keys

Islamorada Private vacation home

SNOW BIRD.. COME TO PARADISE. 2/2 with a Loft (can be a 3rd bedroom) beautifully located in the heart of the Florida Keys. Amazing sunset, great community pool and beach. Next to founders park with many amenities that can be used when staying at this home away from home. Boat access, slips and marina. Great pier for fishing and watching the best s.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 10


Vacation Home


OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada

Islamorada Villa 4.9

Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches, shopping, fishing, diving, snorkeling, bike riding, etc.

We provide bikes, kayaks and you can snorkel right from our dock. There are some resident iguanas in our mangroves and with luck you will see a manatee or great wh.......read more

1 Bedroom(s)
1 Bath(s) Sleeps 4


Vacation Home


Beautiful Bayfront Home with Amazing Sunsets

Islamorada Private vacation home 4.9


This Property has a large kitchen and living area open to amazing views of the bay with 4 bedrooms and 3 full baths. You cannot go wrong with the protected boat basin for your boat or jet skis. If snorkeling, swimming or kayaking is your thing, look no further! Either enjoy amazing sunsets in the comfort of the backyard or walk to a fun local h.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8


Vacation Home


Private Pool, Completely Renovated Lovely Cottage Home in Islamorada

Islamorada Private vacation home 4.9

Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Home has been completely renovated in the last year. Serene and spacious outdoor area with brand new wooden deck, private pool and private homeowners beach. Two bedrooms/ two baths upstairs. Master Suite with ensuite bathroom. Second Master downstairs with ful.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8


Vacation Home


Keys Paradise with Private Beach and Pool

Islamorada Private vacation home 4.9

NOTE:
--PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE.
--DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT NEXT DOOR FOR A FEE. NO DOCKAGE AND NO TRAILERS ALLOWED ON PROPERTY. (Condo rules, not ours!!)
The bed configuration is different than the photos but the same beds are all there, as follows: Large bedroom with King bed an.......read more

2 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


Pristine Pool Front Anglers Reef Home - Ocean Views, Beach & Boat Slip

Islamorada Private vacation home 4.9

Welcome to Angler’s Reef Resort Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths wind through this Caribbean fishing village-styled retreat, dotted with 52 cottages inspired by Native Conch and British West Indies themes and adorned with metal roofs and gingerbread trim. More than five hundred feet of .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 6


Vacation Home


Family/Pet Friendly Venetian Shores Home

Islamorada Private vacation home 5.0

This beautiful Venetian Shores pool home with plenty of space to relax and play. Situated on a deep water canal with quick access to the Atlantic Ocean and Florida bay. The property offers lush tropical landscaping, 100 foot dockage. Outdoor covered living area with grill, dining table, and TV. The main floor has 1 master king with shower, and 2 ad.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 6


Vacation Home


Incredible Bayside Home in the Florida Keys!

Islamorada Private vacation home 5.0

**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommended standards for disinfecting in our all our cleaning protocols.

As soon as you walk into this home you will feel like you just walked into a comfortable, cozy home. With its cool laid-back style and subtle sophistication .......read more

3 Bedroom(s)
3 Bath(s)


Vacation Home


Islamorada 3/2 condo. Dockage, swimming pool, sunsets

Islamorada Condo 4.8

Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that tranquil tropical getaway you\'ve always imagined.

Futura Yacht Club is a gated community. This is a 4th floor condo with 3 bedrooms, 2 baths and a fan.......read more

3 Bedroom(s)
2 Bath(s) Sleeps 8


Vacation Home


BAYSIDE PARADISE ~ Heart of Islamorada *Private Boat Dockage Upon Request*

Islamorada Private vacation home 5.0

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle to every place in town.
Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and a half bathrooms, to comfortably accommodate u.......read more

4 Bedroom(s)
4 Bath(s) Sleeps 8


Vacation Home


Just a Few Friends - Ocean View and Bring your Boat!

Islamorada Condo 5.0

Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in Bay Harbour, Islamorada Florida. This quiet gated community allows one to truly escape. Have the trip of a lifetime with Just a couple of friends & BRING YOUR BOAT too (up to 30\')!

Amenities include; Large heated/cool .......read more

2 Bedroom(s)
3 Bath(s) Sleeps 4


Vacation Home


Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage

Islamorada Private vacation home 4.9

I am a legal weekly rental in Islamorada!!! Commercial Ice Machine, bait freezer, and fish cleaning station!! SUPER PRIVATE!!!


Amazing waterfront restaurants close by!!! Boat rental and paddle board/kayak company that will deliver boat to dock for your stay.

Dream home in they keys is one of the very few legal weekly renta.......read more

5 Bedroom(s)
3 Bath(s) Sleeps 12


Vacation Home


Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach

Islamorada Private vacation home 4.9

*****New Owners/Listing so you may not see reviews yet for that reason******

***** Please email and I will answer any questions you have!*****


Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 bath home has endless views of the ocean from every room. If you enj.......read more

4 Bedroom(s)
3 Bath(s) Sleeps 8


Vacation Home


San Remo Canal Front

Islamorada Private vacation home

Venetian Shores 5 bedroom and 4 bath home with 70 ft. dock just minutes to Snake Creek for instant ocean and bay access. Totally renovated 3800 sq. ft home with all new furnishings. Open concept kitchen, dining room and living room...ready for your extended family with 3 bedrooms and 3 bathrooms upstairs, plus two more bedrooms and a full bath do.......read more

5 Bedroom(s)
4 Bath(s) Sleeps 10


Vacation Home


Luxury Oceanfront Villa with Resort Amenities

Islamorada Villa 5.0

WELCOME TO THE ISLANDS OF ISLAMORADA
Designed for those who love the bounty and beauty of the ocean, The Islands of Islamorada seamlessly weaves the allure of tropical beauty with familiar luxurious comforts, creating a captivating experience for the whole family. Spend meaningful time in this natural haven, and relax in privacy among family and.......read more

4 Bedroom(s)
5 Bath(s) Sleeps 8


Vacation Home


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