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.
Charming 3-Bed, 2-Bath Canal Home in Tavernier, FL, with Private Pool!
Islamorada Private vacation home 
9.0
128 Tequesta Street - The perfect vacation home! This charming two-bedroom two bath home has everything you need for the perfect Florida Keys Vacation. With dockage, a pool, and a great outdoor bar and tiki hut, you'll never want to leave your private oasis. You can hang out and have a drink by the pool or take out the kayaks and paddle your way to.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 6
Enjoy stunning views at Bay Harbour C-312, a 3BR condo in picturesque Islamorada.
Islamorada Private vacation home 9.2
Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete with two tennis courts, weight room, pool, dockage, fish cleaning station, and Wi-Fi. 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 t.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 6
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
Islamorada Private vacation home 9.8
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
Spacious 5BR home in Islamorada, perfect for 14 guests with ocean views.
Islamorada Private vacation home 9.2
Conch & Lobster Homes - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a privately gated oceanfront estate. The Conch House (pronounced conk) is a three bedroom, two bath ocean front home featuring beautiful views, ocean breezes, your own private pool, plus a private balcony to enjoy the trade winds and sip.......read more
5 Bedroom(s)
5 Bath(s) Sleeps 14
Paradise Retreat
Islamorada Private vacation home 10.0
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, but also has a private boat ramp right inside the neighborhood. With great fishing access to the bay and open ocean just through chan.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 8
Enjoy a serene stay at 137 LeSerra Lane, a 3-bedroom canal retreat in Islamorada.
Islamorada Private vacation home 9.4
137 LeSerra Lane - 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 on the point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffeemaker, toaster, and blender. There are two flat panel TVs in the house, as wel.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 6
Charming 3BR canal home in Islamorada, perfect for your tropical getaway!
Islamorada Private vacation home 10.0
107 San Remo Drive - 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 porch off the living room upstairs. The home has an awesome dockage that is 70'. Easy ocean or b.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 4
Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
Islamorada Private vacation home 10.0
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
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
Islamorada Private vacation home 10.0
We are so proud to say our tropical Bungalow now has 65 Straight 5 STAR REVIEWS on VRBO
What sets us apart from "just a vacation rental"? As your hosts, we have spent a lifetime in the hospitality industry. When we chose to purchase, remodel and refurnish the property we set out to achieve 6 main goals. LACBSC, or Location, Amenities, Comfo.......read more
2 Bedroom(s)
1 Bath(s) Sleeps 5
Pet Friendly 3 Bedroom in Venetian Shores Sleeps 6
Islamorada Private vacation home
The Salty B is located in the popular neighborhood of Venetian Shores! Canal front home on Snake Creek gives you fast access to both Ocean & Bay, fuel, bait, and provisions.
Key Features of Salty B:
- The House: Upstairs has Two Bedrooms, with a king-size bed in the Master, and a Full/Twin Bunks (2) in the other guest suite, There i.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 10
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 26-0169
Islamorada Condo 10.0
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.
Located .......read more
2 Bedroom(s)
3 Bath(s) Sleeps 4
Charming 2-bedroom retreat in Islamorada with stunning open water views.
Islamorada Private vacation home 9.2
75130 Overseas Highway - 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. View beautiful sunsets from the screened porch that includes tables and .......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Amazing Sandy Beach Sunsets + New Pool + Best Location w/ Park - Bikes & Kayaks
Islamorada Private vacation home 9.8
Now available January and part of February - You will see amazing sunsets in our community sandy beach, fish or relax on pier, dip in the heated pool, take a few bikes for ride to Founders Park next door, slide over the water on our kayaks. You can also simply work from home from one of our TWO ready-to-go functional offices
Yes - Last minu.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Discover the Charm of Island Living
Islamorada Condo 9.4
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
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
Islamorada Condo 10.0
“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
Fabulous Island Getaway! Easy access to Florida Bay, Private Beach, Elevator
Islamorada Private vacation home
Enjoy watching the ospreys and manatees from the dock at this beautiful Port Antigua home on Biscayne Blvd. You have access to a large private sandy beach with zero entry to waist deep water to sit and sun bathe and bring the kids for a splash. 4 beach cruiser bicycles are included for riding around the neighborhood. The dock has a large fish cle.......read more
5 Bedroom(s)
3 Bath(s) Sleeps 10
Charming Ocean Front Pool Home with dockage & pool
Islamorada Villa 10.0
Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two living spaces, downstairs and upstairs. You will enjoy amazing ocean views from the 3rd floor-viewing porch. Enjoy a nice lunch out on the dock, which includes a round concrete picnic table. Midnight Runner has all the amenities for .......read more
5 Bedroom(s)
5 Bath(s) Sleeps 10
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
Islamorada Villa 9.4
Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features an exotic wood deck surrounding a custom pool overlooking a private sugar sand beach on the Atlantic Ocean. Newly built-in outdoor shower! This home features an inviting living room with a sliding glass wall and a stunning 180-deg.......read more
4 Bedroom(s)
5 Bath(s) Sleeps 12
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
Islamorada Villa 9.8
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
Beautiful Bayfront Home with Amazing Sunsets
Islamorada Private vacation home 10.0
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
Keys Paradise with Private Beach and Pool
Islamorada Private vacation home 10.0
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
Beautiful 4/3, pool home in lovely White Marlin beach, Islamorada, FL
Islamorada Private vacation home 10.0
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
Experience coastal bliss at Oceanside Isle, a spacious 3-bedroom condo in Long Key.
Islamorada Private vacation home 10.0
Oceanside Isle - Oceanview Isle is a hidden gem located in a gated condominium complex on Long Key, a quiet location conveniently located between Islamorada and Marathon. This 3/2 end unit has a large private patio with breathtaking views of the ocean, a boat slip that will accommodate boats up to 34' and access to a shared pool. Located on the fir.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Just a Few Friends - Ocean View and Bring your Boat!
Islamorada Condo 10.0
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 p.......read more
2 Bedroom(s)
3 Bath(s) Sleeps 4
Just relisted! Discounts on longer stays ~ Heart of Islamorada ~ Boat Dockage
Islamorada Private vacation home 10.0
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
Oceanfront Luxury - Heated Pool, Boat Slip, Beaches & Spectacular Sunrise Views
Islamorada Private vacation home 10.0
*****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
Spacious 5BR San Remo Canalfront iwith hot tub in Islamorada, perfect for 10 guests.
Islamorada Private vacation home
San Remo Canalfront - Venetian Shores five bedroom and four 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 three bedrooms and three bathrooms upstairs, plus tw.......read more
5 Bedroom(s)
4 Bath(s) Sleeps 10
Venetian Shores Pool Home
Islamorada Private vacation home 10.0
Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenient access either bay or ocean with protected dockage. This canal front home has 2 king en-suites upstairs and a relaxing screen porch off of the living room. There is a downstairs apartment with 2 bedrooms and 1 bathroom and small.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 6
Spacious 4BR canal home in Islamorada with private heated pool and beach access.
Islamorada Private vacation home 10.0
Cozy, canal front, pool home at MM 74 in Islamorada's desirable Port Antigua (Lower Matecumbe Key) with quick Florida Bay access and a short ride to the Atlantic Ocean. Excellent outdoor living and entertaining areas, summer kitchen, Wi-Fi, 65ft of deep-water dockage, a fish cleaning station, and a pool. Downstairs apartment with kitchenette and tw.......read more
4 Bedroom(s)
3 Bath(s) Sleeps 8
Charming 2-bedroom condo in Islamorada with pool access and ocean views.
Islamorada Private vacation home 9.8
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 on the bay side in Islamorada. The unit comes fully furnished with a full kitchen, dining room, large living room with sleeper sofa, expansive balcony with great views of the Florida Bay and the community's two tennis courts, alon.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Charming 2BR condo in Islamorada with pool, hot tub, and beautiful views.
Islamorada Private vacation home 6.8
Beacon Reef 404 - Beautiful two-bedroom two baths, condo with everything that you need for a perfect relaxing vacation. Balcony access off your living room and master bedroom that overlooks the newly remodeled pool and jacuzzi as well as the beach and ocean. The complex is oceanfront and has amazing views of the Atlantic. Some additional amenities:.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4
Experience paradise at Oceanfront Maison Matecumbe 303 in beautiful Islamorada!
Islamorada Private vacation home 9.8
Oceanfront Maison Matecumbe #303 - Maison Matecumbe is a premier gated oceanfront complex in the heart of Islamorada. This prime oceanfront three bedroom, two bath flat unit offers an open concept living and dining room with ocean views, an expansive kitchen with an island and bar seating, and large screened in porch overlooking the Atlantic. The m.......read more
3 Bedroom(s)
2 Bath(s) Sleeps 6
Paradise Found - Three Story Beach House w/ private beach, dock and Ocean Views
Islamorada Villa 10.0
3 story bayside home with its own beach. Great location. Private residential area, yet close to Everything. Due to unique location, one of only a hand full of homes on the island with views of both the Bay and the Ocean. Three (3) good sized bedrooms and 3 baths. Each bedroom has its own distinct views. The practical - high speed internet, s.......read more
3 Bedroom(s)
3 Bath(s) Sleeps 6
WATERFRONT FISHING COTTAGE/ DOCKAGE + Walking distance to world famous Lorelei
Islamorada Cottage 10.0
1940s Keys Cottage with *dockage available. Waterfront and walking distance to world famous Lorelei Cabana Bar & Restaurant as well as local breweries too ! We can arrange custom days of stay, less than 7 days, if you are booking a sunset/sandbar/fishing charter with our family. Enjoy the peace and privacy of the large, natural waters edge property.......read more
1 Bedroom(s)
1 Bath(s) Sleeps 2
EMAIL WITHIN FOR ALL INQUIRES DIRECT OCEANFRONT JEWEL,Heated Salt Pool,70Ft Doc
Islamorada Private vacation home 10.0
PLEASE INQUIRE WITHIN FOR STAYS AND SPECIAL DEALS!!!
OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access.
This Open Water home HAS IT ALL.
-Brand New (Sept 2017) Huge, heated salt water swimming pool
-Brand New (Jan .......read more
4 Bedroom(s)
3 Bath(s) Sleeps 12
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
Islamorada Private vacation home 9.8
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of Islamorada. Located within a gated community with 24 hr. security. Includes fully equipped kitchen w/ granite countertops, microwave and s/s appliances; With washer & dryer, plasma TV, electric outdoor grill, cable, and phone. S.......read more
2 Bedroom(s)
2 Bath(s) Sleeps 4