
Islamorada Rentals

- From $134 per night (USD)
VRBO
ISLAMORADA AFFORDABLE 2023 2\/2\n Ocean Views\nNeighborhood jetty & tiki -sunsets\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Islamorada- Windley Key ,affordable 2 / 2 bath new 2023 Steps away from the gorgeous turquoise ocean. Bayside is also v ...
From $134 per night (USD)VRBO
- From $675 per night (USD)
VRBO
☀️Luxury 3 BR Remodeled! Ocean View PoolSpa, MarinaBikes Boat Slip Tennis\/Pickle
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Boat Slip is available for a small weekly fee of $150 Come enjoy relaxing or being active at luxurious Bay Harbour - a ...
From $675 per night (USD)VRBO
- From $723 per night (USD)
VRBO
Beautiful New Island Home for 2 Small Families
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Plan your vacation getaway in paradise at this amazing new canal-front home with all the comforts of home in a quiet nei ...
From $723 per night (USD)VRBO
- From $295 per night (USD)
VRBO
Tropical Paradise at Futura Yacht Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Futura Yacht Club is a private 70 unit community with a 53 slip marina. Easy access to the ocean through Snake Creek or ...
From $295 per night (USD)VRBO
- From $566 per night (USD)
VRBO
Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour C-312 - Beautiful three bedroom two and a half bath luxury condo at mile maker 74.5. Complex comes complete ...
From $566 per night (USD)VRBO
- From $1290 per night (USD)
VRBO
Alligator Reef Conch & Lobster Homes, a special slice of paradise
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Conch & Lobster Homes - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a priva ...
From $1290 per night (USD)VRBO
- From $373 per night (USD)
VRBO
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef (Unit # 114) at mile marker 85 in Isl ...
From $373 per night (USD)VRBO
- From $278 per night (USD)
VRBO
Canal front Oasis with Pool and Tiki Hut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
128 Tequesta Street - The perfect vacation home! This charming three-bedroom two bath home has everything you need for t ...
From $278 per night (USD)VRBO
- From $1246 per night (USD)
VRBO
Seaside Sanctuary 5 bed, 5 bath pool home
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This impressive home is located in Islamorada on a private lagoon with quick direct access to the Florida Bay. Featurin ...
From $1246 per night (USD)VRBO
- From $314 per night (USD)
VRBO
Waterfront Pool Home with great dockage!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Adorable waterfront pool home in Tavernier! Great dockage close to Tavernier Creek for easy bay and ocean access. Cozy c ...
From $314 per night (USD)VRBO
- From $411 per night (USD)
VRBO
Paradise Retreat
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful tranquil private beach is just the beginning of what awaits you in our completely renovated beach house. Port ...
From $411 per night (USD)VRBO
- From $677 per night (USD)
VRBO
Front Row, DIRECT Ocean\/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Paradise is only a click away. Our 2 BR/2.5 BA conch style townhouse is available for weekly and monthly vacation renta ...
From $677 per night (USD)VRBO
- From $624 per night (USD)
VRBO
Cute Canal front Venetian Shores Weekly Rental!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
107 San Remo Drive - Comfortable Venetian Shores canal home that has two-bedroom one bath upstairs and a one bedroom one ...
From $624 per night (USD)VRBO
- From $239 per night (USD)
VRBO
Bay Views from this Charming 3 Bedroom Canal Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
186 Airstream Lane - Located on a quiet street in Islamorada, this home offers you the best of both worlds. Fantastic, p ...
From $239 per night (USD)VRBO
- From $557 per night (USD)
VRBO
Panoramic Ocean Views from this 3 Bedroom Islamorada Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
137 LeSerra Lane - Beautiful designer appointed Oceanside canal home located at the mile marker 76.5 in Lower Matecumbe ...
From $557 per night (USD)VRBO
- From $347 per night (USD)
VRBO
Home in Islamorada Florida
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Water Front modern home perfectly situated on the Bay side. Located on a deep-water canal that offers all sorts of enjoy ...
From $347 per night (USD)VRBO
- Click For Pricing
VRBO
Little Piece of Paradise (AVAIL Oct-Dec)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Our Little Piece of Paradise is a relaxing place to enjoy with family and friends. We look forward to making it your hom ...
Click For PricingVRBO
- From $705 per night (USD)
Expedia
TikiBar with TV &Stereo, PrivateSpa, Heated Pool, Hammock,SUP’s, Kayaks,Bikes,FP
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
We are proud to announce- Castaway Island has been named for 2024’s KW people’s choice awards as a FINALIST for Best Va ...
From $705 per night (USD)Expedia
- From $477 per night (USD)
VRBO
Unique 2 Bedroom Bay Front Home with Roof Top Terrace
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
75130 Overseas Highway - Great house in Lower Matecumbe (south side of Islamorada) at the 75-mile marker on the bayside. ...
From $477 per night (USD)VRBO
- From $276 per night (USD)
Expedia
Amazing Sunsets+Sandy Beach+Pier+Heated Pool+Bikes+Kayak+2 Offices Quiet Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Time to change your latitude, attitude and immerse your body and mind in the calming, soothing waters that surround our ...
From $276 per night (USD)Expedia
- From $916 per night (USD)
VRBO
Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! A tropical palmy dream and playground for ocean lovers. Minutes on boat from the best san ...
From $916 per night (USD)VRBO
- From $242 per night (USD)
Expedia
Work remote, or not at all, in paradise at this cozy, beachy condo!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $242 per night (USD)Expedia
- From $375 per night (USD)
VRBO
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Enjoy the spirit of the Florida Keys in this 'keysey' furnished condo with everything provided. All you have to do is s ...
From $375 per night (USD)VRBO
- From $426 per night (USD)
Expedia
Islamorada Luxury Waterfront Condo with Boat Slip
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in ...
From $426 per night (USD)Expedia
- From $378 per night (USD)
VRBO
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much mor ...
From $378 per night (USD)VRBO
- From $398 per night (USD)
Expedia
Oceanfront! Oceanfront! Oceanfront!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
License # 25-0123 - Completely Renovated - 2 Bedroom, 2 Bath, condominium unit. Just steps from the elevator on the 5th ...
From $398 per night (USD)Expedia
- From $323 per night (USD)
VRBO
Discover the Charm of Island Living
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Privately owned condominium unit at the Futura Yacht Club in the Village of Islamorada. Futura is located on the Gulf o ...
From $323 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Penthouse view - Futura Yacht Club #604
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Condo #604, 3 Bedrooms, 2.0 Baths, (Sleeps 6) Enjoy penthouse views of the fabulous blue waters of the Atlantic and Flo ...
From $184 per night (USD)Expedia
- From $217 per night (USD)
VRBO
Executive Bay Club Condo (2 bds + loft & 3 full baths)
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 9
Come stay and watch the sunsets at our beautifully updated Keys townhouse at Executive Bay Club located in Islamorada on ...
From $217 per night (USD)VRBO
- Click For Pricing
Expedia
A great place to relax, fish, or even work from. 2\/2 , 66 ft
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
2 Master suites with great screened in porch overlooking Bayside canal. 66 dock, fully furnished. Large family room with ...
Click For PricingExpedia
- From $483 per night (USD)
VRBO
Keys Paradise with Private Beach and Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
NOTE: --PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE. --DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT N ...
From $483 per night (USD)VRBO
- From $819 per night (USD)
VRBO
Beautiful Bayfront Home with Amazing Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This Property has a large kitchen and living area open to amazing views of the bay with 4 bedrooms and 3 full baths. Yo ...
From $819 per night (USD)VRBO
- From $187 per night (USD)
VRBO
Spectacular Top Floor Oceanfront View Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Do everything or nothing at all - the heart of the Florida Keys on Plantation Key, FL - sport fishing and diving capital ...
From $187 per night (USD)VRBO
- From $685 per night (USD)
VRBO
Private Pool, Completely Renovated Lovely Cottage Home in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful 4 bedroom, 3 bathroom pool home in lovely White Marlin beach, Islamorada, FL. Home has been completely renova ...
From $685 per night (USD)VRBO
- From $288 per night (USD)
VRBO
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches ...
From $288 per night (USD)VRBO
- From $2109 per night (USD)
VRBO
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 12
Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features ...
From $2109 per night (USD)VRBO
- From $2137 per night (USD)
VRBO
Charming Ocean Front Pool Home with dockage & pool
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Step out the door to your private oceanfront beach with pool and dock at Midnight Runner. The property features two livi ...
From $2137 per night (USD)VRBO
- From $259 per night (USD)
Expedia
Beautiful Townhouse in the heart of the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
SNOW BIRD.. COME TO PARADISE. 2/2 with a Loft (can be a 3rd bedroom) beautifully located in the heart of the Florida Key ...
From $259 per night (USD)Expedia
- From $177 per night (USD)
VRBO
Pineapple Point pet friendly paradise Islamorada\n\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Pineapple Point, where the quiet peaceful setting will entice you to relax and enjoy Keys living. Our 2 bedro ...
From $177 per night (USD)VRBO
- From $353 per night (USD)
VRBO
Islamorada 3\/2 condo. Futura Yacht Club Dockage, swimming pool, sunsets
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay in idyllic Islamorada. Futura Yacht Club is a 70 unit c ...
From $353 per night (USD)VRBO
- From $388 per night (USD)
VRBO
Incredible Bayside Home in the Florida Keys!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
**To our guests** Nautilus Getaway has always been proud to utilize a contact-less check in process. We use CDC recommen ...
From $388 per night (USD)VRBO
- From $548 per night (USD)
VRBO
Family\/Pet Friendly Venetian Shores Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful Venetian Shores pool home with plenty of space to relax and play. Situated on a deep water canal with qui ...
From $548 per night (USD)VRBO
- From $575 per night (USD)
VRBO
Bright & Cheery Pool Front Home w\/ Optional Boat Slip at Anglers Reef Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths w ...
From $575 per night (USD)VRBO
- From $735 per night (USD)
VRBO
Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
*****New Owners/Listing so you may not see reviews yet for that reason****** ***** Please email and I will answer any q ...
From $735 per night (USD)VRBO
- From $391 per night (USD)
VRBO
Just a Few Friends - Ocean View and Bring your Boat!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Experience all the Florida Keys has to offer in this stunning 2 bed/ 2 ½ bath condominium with an Ocean View, located in ...
From $391 per night (USD)VRBO
- From $1042 per night (USD)
VRBO
Waterfront Oasis Legal weekly rental*Mins2Beach*Tons of dockage
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
I am a legal weekly rental in Islamorada!!! Commercial Ice Machine, bait freezer, and fish cleaning station!! SUPER PRI ...
From $1042 per night (USD)VRBO
- From $1153 per night (USD)
VRBO
BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into ou ...
From $1153 per night (USD)VRBO
- From $205 per night (USD)
VRBO
Indian Mound - Islamorada Keys Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Indian Mound is the ultimate family getaway! Relax in this three bedroom / two bathroom home that has recently been fur ...
From $205 per night (USD)VRBO
- From $199 per night (USD)
VRBO
Charming 2 Bedroom Condo in Wonderful Beacon Reef
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beacon Reef 404 - Beautiful two-bedroom two baths, condo with everything that you need for a perfect relaxing vacation. ...
From $199 per night (USD)VRBO
- From $506 per night (USD)
Expedia
Aqua Lodge Houseboat \"The Grey Lady\"
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This houseboat has 2 Queen beds, 1 Double bed and 1 Twin bed. The houseboat has a flat-screen TV with cable in the livin ...
From $506 per night (USD)Expedia
- From $354 per night (USD)
VRBO
Aqua Lodge Houseboat \"Sea Turtle\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to The Aqua Villas at Mangrove Marina Resorts “Sea Turtle” houseboat, located between Key Largo and Islamorada i ...
From $354 per night (USD)VRBO
- From $486 per night (USD)
Expedia
Aqua Lodge Houseboat \"Calypso\"
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
It doesn’t get much more unique than the Aqua Villas at Mangrove Marina. Come experience the adventure of living on the ...
From $486 per night (USD)Expedia
- From $441 per night (USD)
VRBO
Aqua Lodge Houseboat \"Captain's Quarters\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to The Aqua Villas at Mangrove Marina Resorts “Captain’s Quarters” houseboat, located between Key Largo and Isla ...
From $441 per night (USD)VRBO
- From $570 per night (USD)
VRBO
Venetian Shores Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Desirable Venetian Shores neighborhood. Newly renovated home with open concept kitchen, dining and living room. Convenie ...
From $570 per night (USD)VRBO
- From $380 per night (USD)
VRBO
Aqua Lodge Houseboat \"Yellow Tail \"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Are you ready to be adventurous , do something unique and fun? Well, it doesn’t get Yellow Tail houseboat, is a 1 bedro ...
From $380 per night (USD)VRBO
- From $380 per night (USD)
Expedia
Aqua Lodge Houseboat \"Tarpon\"
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This Aqua Lodge has a master bedroom with a queen-sized bed, equipped with TV and Air Conditioning unit. The cathedral c ...
From $380 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Beautifully Updated Studio Apartment, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautifully updated apartment is new to the rental market. Modern and clean with all the comforts of home, tropical ...
From $146 per night (USD)VRBO
- From $4489 per night (USD)
Expedia
Stunning Oceanfront Villa, Luxe Resort Perks at the Islands of Islamorada Resort
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Islands of Islamorada Resort: Your Luxury Oceanfront Retreat Awaits! Indulge in the epitome of coastal e ...
From $4489 per night (USD)Expedia
- From $1402 per night (USD)
VRBO
Romantic Oceanview Retreat with Beach Access at The Islands of Islamorada Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience Coastal Luxury at The Islands of Islamorada Resort Welcome to Your Perfect Oceanview Suite! Immerse yoursel ...
From $1402 per night (USD)VRBO
- From $3945 per night (USD)
Expedia
Stunning Accessible Oceanfront Villa, Luxe Perks at The Islands of Islamorada
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to The Islands of Islamorada Resort: Your Tropical Paradise Awaits! Experience the perfect blend of coastal cha ...
From $3945 per night (USD)Expedia
- From $547 per night (USD)
VRBO
San Remo Canal Front
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
San Remo Canalfront - Venetian Shores five bedroom and four bath home with 70 ft. dock just minutes to Snake Creek for i ...
From $547 per night (USD)VRBO
- From $202 per night (USD)
VRBO
Ocean Views from Balcony, Living Room and Bedroom. Islamorada License 24-0380
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
The major reconstruction projects are finally complete. The game room, gym, pool, lobby, elevators and grounds are built ...
From $202 per night (USD)VRBO
- From $688 per night (USD)
VRBO
THE premier gated oceanfront complex in the heart of Islamorada.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
May and June 2024 Special $3400 weekly!!....Oceanfront Maison Matecumbe #303 - Maison Matecumbe is a premier gated ocean ...
From $688 per night (USD)VRBO
- From $634 per night (USD)
VRBO
Paradise Found - Three Story Beach House w\/ private beach, dock and Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
28 Day Minimum Stay. Please contact us for specific dates of availability. 3 story bayside home with its own beach. G ...
From $634 per night (USD)VRBO
- From $422 per night (USD)
VRBO
Waterfront Sunset View Aqua Villa Dolphin @ Mangrove Marina Resort
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
The Dolphin houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-screen ...
From $422 per night (USD)VRBO
- From $994 per night (USD)
Expedia
To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Forget your worries in this spacious and serene space. Relax while sitting and watching TV or listening. . to music in ...
From $994 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Beautifully Renovated 2 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 ...
From $265 per night (USD)VRBO
- From $2217 per night (USD)
VRBO
4 bedroom, Ocean front,Top tier Condo in Islamorada, Florida Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 204, Poolside... — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world- ...
From $2217 per night (USD)VRBO
- From $270 per night (USD)
VRBO
Florida Keys Plantation Key Colony on Canal with Boat lift, 7K month + Taxes
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Canal side Retreat in the Colony 28 day minimum no pets! You won't believe your eyes! It looks like a cozy conch cottag ...
From $270 per night (USD)VRBO
- From $606 per night (USD)
Expedia
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
COVID-19 Update: Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manag ...
From $606 per night (USD)Expedia
- From $225 per night (USD)
VRBO
Spring & summer dates available licensed rental vr #25-0235 NO BOATS
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is a legally licensed rental in the Village of Islamorada license # vr 131 The entire condo has been updated ...
From $225 per night (USD)VRBO
- From $253 per night (USD)
VRBO
Beautiful Cottage in Islamorada on canal front! Wifi, Smart TVs and No Stairs!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated and decorated CBS home on bay side with charming details throughout. Wifi, smart TV and no stairs! ...
From $253 per night (USD)VRBO
- From $199 per night (USD)
VRBO
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Drive down south to enjoy the tranquil and beautiful Florida Keys. Enjoy a cozy and spacious townhome in the heart of I ...
From $199 per night (USD)VRBO
- From $3109 per night (USD)
Expedia
9 bedrooms, Heated Pool, Open Water Views, Boat Dockage, Sleeps 24
- Bedrooms:
- 3
- Bathrooms:
- 9
- Sleeps:
- 10
This owner operated property is the vacation spot for you and your Family. Located on Grassy Key just one hour from the ...
From $3109 per night (USD)Expedia
- From $618 per night (USD)
VRBO
COASTAL ELEGANCE FOR RENT IN ISLAMORADA !!! PARADISE FOUND ON DEEP WATER
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This designer REMODELED IN JULY 2021 3bdr, 2bath home is located on a 60 foot deep water dock in quiet Plantation Key, F ...
From $618 per night (USD)VRBO
- From $1117 per night (USD)
Expedia
Sanctuary In Paradise Featured On H G T V
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Open Ocean on “Millionaire’s Row” Unique property featuring separate: ~1BR 1BA Upstairs Suite ~2BR 2BA Downstairs Apt. ...
From $1117 per night (USD)Expedia
- From $570 per night (USD)
VRBO
Relax in Islamorada-Canal Front 3 Bedroom \/ 2 Bath Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax in Islamorada Canal Front 3 Bedroom/2 Bath Home Spacious Keys style 3 bedroom / 2 bath home located on deep cana ...
From $570 per night (USD)VRBO
- From $298 per night (USD)
VRBO
WATERFRONT FISHING COTTAGE\/ DOCKAGE + Walking distance to world famous Lorelei
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
1940s Old Keys Fishing Cottage with dockage available. Large Waterfront property and walking distance to world famous L ...
From $298 per night (USD)VRBO
- From $1132 per night (USD)
VRBO
Egret House @ Tarpon Point
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Indulge in breathtaking ocean vistas from every living level, complemented by an inviting waterfront pool! The ...
From $1132 per night (USD)VRBO
- From $1584 per night (USD)
Expedia
Iconic Ted Williams Estate. Bayfront, Heated Infinity Pool & Hot Tub, Dockage.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
TED’S PLACE License # VR052 - Minimum Stay 1 Week, Saturday thru Saturday – Unbeatable Location - 1.5 acres – Bayfront ...
From $1584 per night (USD)Expedia
- From $1151 per night (USD)
VRBO
Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Islamorada- the Fishing Capital of the World. Oceanfront living doesn't get better than this. In the heart o ...
From $1151 per night (USD)VRBO
- From $1559 per night (USD)
VRBO
Large bay-front home with dockage, pool and beach in the heart of Islamorada
- Bedrooms:
- 8
- Bathrooms:
- 4
- Sleeps:
- 10
The Dock View House is one of three private homes located at Mermaid's Bay Boutique Estate. Located in the heart of Isla ...
From $1559 per night (USD)VRBO
- From $401 per night (USD)
VRBO
3 bed 2 bath condo at Futura Yacht Club!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Completely remodeled 3 bedroom condo. Kitchen completely redone Spring of 2021 Sleeping accommodations: king bed in mas ...
From $401 per night (USD)VRBO
- From $327 per night (USD)
VRBO
Work from home in this slice of Islamorada paradise!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come visit this tropical, remodeled vacation home and get a taste of all Islamorada has to offer with cozy, modern and c ...
From $327 per night (USD)VRBO
- From $1445 per night (USD)
VRBO
OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
82754 Overseas Highway - OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Ke ...
From $1445 per night (USD)VRBO
- From $618 per night (USD)
Expedia
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come stay at the Salty Pelican in Angler's Reef! This magnificent home with amazing direct ocean views from the master b ...
From $618 per night (USD)Expedia
- From $515 per night (USD)
VRBO
Brand New \/ Totally Renovated Luxurious Home with POOL
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***POOL Built in July 2019; Tropical landscaping installed 2020/2021 with great privacy*** Located in Islamorada the pr ...
From $515 per night (USD)VRBO
- From $743 per night (USD)
VRBO
Charming Beach Front Home in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! Th ...
From $743 per night (USD)VRBO
- From $482 per night (USD)
VRBO
Relax in this beautiful townhome overlooking the sparkling Atlantic Ocean
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Windy Cove #1 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo feat ...
From $482 per night (USD)VRBO
- From $2082 per night (USD)
Expedia
Ultra Luxurious 4 Bedroom ocean front Rental home in Islamorada, Florida Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 202, Poolside… — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world-c ...
From $2082 per night (USD)Expedia
- From $446 per night (USD)
VRBO
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WATER FRONT CANAL HOME. BRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. All Systems, fully functional, ...
From $446 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful 2\/2 Florida keys home rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with privat ...
Click For PricingExpedia
- From $159 per night (USD)
VRBO
Beautiful home in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy all that Islamorada has to offer! Live the Keys life in this beautiful deep water canal front home. Lo ...
From $159 per night (USD)VRBO
- From $488 per night (USD)
Expedia
Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Cozy waterfront villa with heated pool and quick access to Ocean and Gulf fishing and diving. Laid back Tiki Hut great f ...
From $488 per night (USD)Expedia
- From $502 per night (USD)
VRBO
WOW!! WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CLEAN-CONTACT OWNER
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
***Contact owner with description of group. *** Reach out to owner (from the contact owner section), to quickly get the ...
From $502 per night (USD)VRBO
- From $263 per night (USD)
VRBO
Recently Renovated Luxury Townhome in Islamorada, Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Recently renovated! A beautiful 2 bedroom 2 full bath plus loft townhome located in Executive BayClub MM87, it is a priv ...
From $263 per night (USD)VRBO
- From $2185 per night (USD)
VRBO
Southern Diversion Estate Islamorada presidents week open
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Southern Diversion is located directly in the Village of Islamorada in the Florida Keys and walking distance to all the ...
From $2185 per night (USD)VRBO
- From $210 per night (USD)
Expedia
Paradise in Plantation Key\/Deep Water Canal House\/Boat Dock\/MM 89
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Paradise in Plantation Key. If you are looking to relax and learn about “Keys Time” you are looking in the right area! ...
From $210 per night (USD)Expedia
- From $462 per night (USD)
VRBO
Charming 2 Bedroom House with Peekaboo Views
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Angler's Reef #118 - Angler's Reef is a beautiful oceanfront gated community located in Islamorada. This modern updated ...
From $462 per night (USD)VRBO
- From $1863 per night (USD)
VRBO
Lush Garden Estate in Islamorada FL, W\/ Pool, Dockage, Ocean Front & great views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Island Villa Rental Properties offers this 3 bedroom home with a one bedroom guest house, rents all as one. Located on t ...
From $1863 per night (USD)VRBO