Islamorada Rentals
From $558 per night (USD)VRBO
☀️Luxury 3 BR Remodeled! Ocean View PoolSpa, MarinaBikes Boat Slip Tennis/Pickle
- Bedrooms:
- 2
- 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 $558 per night (USD)VRBO
From $506 per night (USD)VRBO
Beautiful 3 Bedroom Condo with Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 2
- 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 $506 per night (USD)VRBO
From $1156 per night (USD)VRBO
Alligator Reef Conch & Lobster Homes, a special slice of paradise
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Conch & Lobster Homes - Alligator Reef is a truly special slice of paradise with two individual homes nestled on a priva ...
From $1156 per night (USD)VRBO
From $500 per night (USD)VRBO
Gorgeous Anglers Reef Islamorada Florida Keys Oceanfront Pool
- Bedrooms:
- 1
- 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 $500 per night (USD)VRBO
From $1206 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 $1206 per night (USD)VRBO
From $516 per night (USD)Expedia
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 $516 per night (USD)Expedia
From $705 per night (USD)VRBO
Front Row, DIRECT Ocean/Pool Views, Anglers Reef, Islamorada. Boat Dock, Beach
- Bedrooms:
- 2
- 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 $705 per night (USD)VRBO
From $579 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 $579 per night (USD)VRBO
From $492 per night (USD)VRBO
Panoramic Ocean Views from this 3 Bedroom Islamorada Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
137 LeSerra Lane - Beautiful designer appointed Oceanside canal home located at the mile marker 76.5 in Lower Matecumbe ...
From $492 per night (USD)VRBO
From $347 per night (USD)VRBO
Home in Islamorada Florida
- Bedrooms:
- 3
- Bathrooms:
- 4
- 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 PricingVRBO
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 $665 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 $665 per night (USD)Expedia
From $454 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 $454 per night (USD)VRBO
From $349 per night (USD)Expedia
3-Bedrooms Private Sandy Beach Sunsets+Pier+Heated Pool+Bike+Kayak+Founders Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover a breathtaking three-bedroom getaway by the scenic bay in Islamorada. On our private white sandy beach, you’ll ...
From $349 per night (USD)Expedia
From $967 per night (USD)VRBO
Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location, location, location! A tropical palmy dream and playground for ocean lovers. Minutes on boat from the best san ...
From $967 per night (USD)VRBO
From $270 per night (USD)Expedia
Work remote, or not at all, in paradise at this cozy, beachy condo!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Flexible cancellation policy. Futura Yacht Club is an exclusive private, gated resort community. Not like a hotel, FYC ...
From $270 per night (USD)Expedia
From $384 per night (USD)VRBO
Beautiful 'Keysey' Condo in Bay Harbour Gated Community 24-0169
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $384 per night (USD)VRBO
From $388 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 $388 per night (USD)Expedia
From $395 per night (USD)VRBO
Beautiful Condominium with with Ocean view, Protected Boat Slip, Tennis,
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
“Ocean Breeze” – This Beautiful Condominium Features an Ocean view, Protected Boat Slip, Tennis, Gym, and much, much mor ...
From $395 per night (USD)VRBO
From $394 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 $394 per night (USD)Expedia
From $256 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 $256 per night (USD)VRBO
From $217 per night (USD)VRBO
Executive Bay Club Condo (2 bds + loft & 3 full baths)
- Bedrooms:
- 3
- Bathrooms:
- 2
- 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 PricingVRBO
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 PricingVRBO
From $519 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 $519 per night (USD)VRBO
From $831 per night (USD)VRBO
Beautiful Bayfront Home with Amazing Sunsets
- Bedrooms:
- 2
- 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 $831 per night (USD)VRBO
From $187 per night (USD)VRBO
Spectacular Top Floor Oceanfront View Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $279 per night (USD)VRBO
OPEN -Endless Bay Views... Sues Promise private villas, beach, dock, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches ...
From $279 per night (USD)VRBO
From $2145 per night (USD)VRBO
Luxury Waterfront Home with Sandy Beach, Hot Tub and Theater
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Enjoy all the beauty of Islamorada's clear blue waters from your private beachfront estate. Turtle Nest Estate features ...
From $2145 per night (USD)VRBO
From $2066 per night (USD)VRBO
Charming Ocean Front Pool Home with dockage & pool
- Bedrooms:
- 4
- 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 $2066 per night (USD)VRBO
From $276 per night (USD)VRBO
A piece of Paradise in the Keys.
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 5
Beautiful Canal Home in Florida Keys Islamorada. Amazing sunsets at our private beach just few blocks away. We have the ...
From $276 per night (USD)VRBO
From $152 per night (USD)Expedia
Beautiful Townhouse in the heart of the Florida Keys
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $152 per night (USD)Expedia
From $329 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 $329 per night (USD)VRBO
From $388 per night (USD)Expedia
Incredible Bayside Home in the Florida Keys!
- Bedrooms:
- 3
- Bathrooms:
- 3
- 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)Expedia
From $496 per night (USD)VRBO
Bright & Cheery Pool Front Home w/ Optional Boat Slip at Anglers Reef Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths w ...
From $496 per night (USD)VRBO
From $930 per night (USD)VRBO
Anglers Reef Direct Ocean, 4 bedroom, Dock, Comm Pool & Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Direct OCEANFRONT home with HEATED POOL, BOAT SLIP, & BEACHES in the desirable Anglers Reef Community. This 4 bedroom, 3 ...
From $930 per night (USD)VRBO
From $333 per night (USD)VRBO
Just a Few Friends - Ocean View and Bring your Boat!
- Bedrooms:
- 2
- 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 $333 per night (USD)VRBO
From $806 per night (USD)VRBO
Waterfront Oasis 2Mins2BeachTons dockage VERY Private Immediate ocean/bay access
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious five bedroom home on huge canal. Commercial Ice Machine, bait freezer, and fish cleaning station!! SUPER PRIV ...
From $806 per night (USD)VRBO
From $1041 per night (USD)VRBO
BAYSIDE PARADISE ~ Heart of Islamorada ~ Private Boat Dockage
- Bedrooms:
- 3
- 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 $1041 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 $486 per night (USD)VRBO
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)VRBO
From $441 per night (USD)Expedia
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)Expedia
From $515 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 $515 per night (USD)VRBO
From $380 per night (USD)Expedia
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)Expedia
From $133 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 $133 per night (USD)VRBO
From $201 per night (USD)VRBO
Ocean Views from Balcony, Living Room and Bedroom. Islamorada License 24-0380
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The major reconstruction projects are finally complete. The game room, gym, pool, lobby, elevators and grounds are built ...
From $201 per night (USD)VRBO
From $561 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 $561 per night (USD)VRBO
From $380 per night (USD)Expedia
Waterfront Sunset View Aqua Villa Dolphin @ Mangrove Marina Resort
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $380 per night (USD)Expedia
From $1012 per night (USD)VRBO
To Paradise \nBook our website fishing & excursions bigdavechartersandtours.com\n
- Bedrooms:
- 1
- 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 $1012 per night (USD)VRBO
From $224 per night (USD)VRBO
Beautifully Renovated 2 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Yacht Club #205 - This charming condo is located in the Futura Yacht Club community, located at mile marker 88.5 ...
From $224 per night (USD)VRBO
From $1767 per night (USD)VRBO
4 bedroom, Ocean front,Top tier Condo in Islamorada, Florida Keys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing Maison Residences Unit 204, Poolside... — UP TO 32’ BOAT SLIP MAY BE AVAILABLE, CALL FOR DETAILS — A world- ...
From $1767 per night (USD)VRBO
From $254 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 $254 per night (USD)VRBO
From $515 per night (USD)VRBO
Ocean Views for DAYS!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
132 Columbus Drive - Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in t ...
From $515 per night (USD)VRBO
Click For PricingExpedia
Venetian 4/4 Waterfront Canal Home W/Pool, 70' Dock w/access to ocean and bay
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This beautiful deep saltwater canal front 3 bedroom 3 bathroom pool home with an additional one bedroom one bath "in-law ...
Click For PricingExpedia
From $653 per night (USD)VRBO
Sunrise Haven - Maison 306 - Beach, Pool, Hot Tub, Kayaks, SUPs & Day Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Sunrise Haven is professionally cleaned including all linens and towels. The owners or property manager do not do the c ...
From $653 per night (USD)VRBO
From $159 per night (USD)Expedia
Spring & summer dates available licensed rental vr #25-0235 NO BOATS
- Bedrooms:
- 1
- 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 $159 per night (USD)Expedia
From $266 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 $266 per night (USD)VRBO
From $144 per night (USD)VRBO
Charming and Cozy Townhouse in the Fl Keys with Pool and Beach Access
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $144 per night (USD)VRBO
Click For PricingVRBO
5 bedrooms, Heated/Chilled Pool, Open Water Views, Boat Dockage, Sleeps 13--15,
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 15
This owner operated property is the vacation spot for you and your Family. Located on Grassy Key just one hour from the ...
Click For PricingVRBO
From $629 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 $629 per night (USD)VRBO
From $1125 per night (USD)VRBO
Sanctuary In Paradise Featured on H G T V
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Open Ocean on “Millionaire’s Row” Unique property featuring separate: ~1BR 1BA Upstairs Suite ~2BR 2BA Downstairs Apt. ...
From $1125 per night (USD)VRBO
From $333 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 $333 per night (USD)VRBO
From $1119 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 $1119 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 $1084 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 $1084 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:
- 7
- 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 $380 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 $380 per night (USD)VRBO
From $279 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 $279 per night (USD)VRBO
From $672 per night (USD)VRBO
Islamorada Oceanfront Home with Ocean View, Dock, Comm Pool & Beach
- Bedrooms:
- 2
- 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 $672 per night (USD)VRBO
From $523 per night (USD)VRBO
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 $523 per night (USD)VRBO
From $731 per night (USD)VRBO
Charming Beach Front Home in Lower Matecumbe
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
113 Sunset Drive - Come and stay in this adorable "beachy backyard" home located on the crystal-clear Atlantic Ocean! Th ...
From $731 per night (USD)VRBO
From $474 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 $474 per night (USD)VRBO
From $1587 per night (USD)VRBO
Ultra Luxurious 4 Bedroom ocean front Rental home in Islamorada, Florida Keys
- Bedrooms:
- 4
- 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 $1587 per night (USD)VRBO
From $356 per night (USD)Expedia
WOW! WATERFRONT CANAL HOME-RELAXING, FRESH & CLEAN-FISH, SWIM, SNORKEL CLOSE BY!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
WATER FRONT CANAL HOME 3 BEDROOM/ 3 BATH COTTAGE. BRING YOUR BOAT, LOTS OF PROTECTED DOCKAGE. FULLY UPDATED HOME. Up ...
From $356 per night (USD)Expedia
From $319 per night (USD)VRBO
Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 3
Oceanfront property offering a unique experience for your tropical escape with views of both Islamorada Sandbar and Alli ...
From $319 per night (USD)VRBO
Click For PricingExpedia
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 $488 per night (USD)VRBO
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)VRBO
From $412 per night (USD)Expedia
ISLAMORADA WATERFRONT HOME, SPECTACULAR VIEW-GREAT DOCKAGE-WiFi-CONTACT OWNER
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
***Contact owner with description of group. *** Reach out to owner (from the contact owner section), to quickly get the ...
From $412 per night (USD)Expedia
From $245 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 $245 per night (USD)VRBO
From $2281 per night (USD)VRBO
Southern Diversion Estate Islamorada
- Bedrooms:
- 3
- 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 $2281 per night (USD)VRBO
From $212 per night (USD)VRBO
A Great Place! Spacious 2/2 retreat with ocean views in the heart of the Keys.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Coral Harbor is the best kept secret in Islamorada. Quiet, gated community with ocean views, clubhouse, pool and a salt ...
From $212 per night (USD)VRBO
From $274 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 $274 per night (USD)Expedia
From $1864 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 $1864 per night (USD)VRBO
From $249 per night (USD)VRBO
A little Piece of Heaven to wash your worries away
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
A fully furnished two bedroom, two bath townhouse located in Islamorada, also known as the "Fishing Capital of the World ...
From $249 per night (USD)VRBO
From $153 per night (USD)VRBO
Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Premier 1 bedroom unit with both that stunning bay view and a view of the pool off the balcony. Fully updated with the o ...
From $153 per night (USD)VRBO
From $178 per night (USD)VRBO
New- Stunning 1 B apartment with incredible view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This beautiful apartment is new to the rental market and recently fully remodeled. Modern, clean with a stunning direct ...
From $178 per night (USD)VRBO
From $157 per night (USD)VRBO
New -Beautiful modern 1 bedroom with peek-a-boo water view
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Quiet and serene, this beautiful one bedroom apartment is fully updated with all the comforts of home. Open concept kitc ...
From $157 per night (USD)VRBO
From $291 per night (USD)Expedia
Bayside: Bayfront villa W/ free onsite boat ramp marina & trailer parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Bayside is a first floor apartment overlooking the water. Bayside is located on a small resort property nestled in a nat ...
From $291 per night (USD)Expedia
From $1125 per night (USD)VRBO
5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Deep water dockage & heated pool! Modern, clean & fresh interiors make this rental perfect. Manatees visit the dock ...
From $1125 per night (USD)VRBO
From $689 per night (USD)Expedia
Private Bayside Waterfront Home 2 acres, Beach, Deep Water Boat Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private 2acre Single Family Home awaits! Just another day in Paradise. Located at 75.7MM! Cozy, quiet, 3 bedroom (1 K ...
From $689 per night (USD)Expedia
From $428 per night (USD)VRBO
BRAND NEW Island-design home located in Islamorada fishing capital of the world!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
The Pink Sands House is located in the beautiful Lower Matecumbe island in close proximity to all your Class-A shopping, ...
From $428 per night (USD)VRBO
From $338 per night (USD)Expedia
Paradise @ Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Sleeps 8, 2 Story Townhome On The Bayside, Mile Marker 87 Our Islamorada beach modern decorated townhome is waiting for ...
From $338 per night (USD)Expedia
From $393 per night (USD)VRBO
Bay Views from this Charming 2 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Townhome #708 - Enjoy the spectacular view of the Florida Bay from either one of two balconies in this 2-story to ...
From $393 per night (USD)VRBO
From $494 per night (USD)VRBO
Anglers Reef- Family Friendly Community at a Fraction of the Cost.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This Property is fully insured for rentals and licensed by the Village of Islamorada, license #24-0318. Welcome to 134 ...
From $494 per night (USD)VRBO
From $321 per night (USD)VRBO
Sea Gulls Oceanfront Condo with large heated oceanfront pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
About an hour and fifteen minute drive from Miami International Airport and about 90 minutes from Ft. Lauderdale to wil ...
From $321 per night (USD)VRBO
From $2162 per night (USD)VRBO
Brand New Unique Deep Water Gulf Front Estate. Beach, Pool, Hot tub and docks
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This is a brand new house. Just completed August 2014 This unique Gulf Front property is located among Gumbo Limbo, M ...
From $2162 per night (USD)VRBO
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Angler's Reef Resort by KeysCaribbean
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
<p>While you're here, you can enjoy all the comforts of home and more, including a full-sized refrigerator/freezer and a ...
Click For PricingVRBO
From $999 per night (USD)Expedia
Islamorada Boaters Paradise with 70' Dock and private beach access..
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Calling all boaters and anglers! You will love our home. Nestled on a canal only 3 minutes to the bay and 10 minutes to ...
From $999 per night (USD)Expedia
From $297 per night (USD)VRBO
Keys Kottage: Bayside villa W/ free onsite boat ramp marina & trailer parking.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Kottage is a free-standing 2 bedroom/2 bath villa located on a small resort property nestled in a native hammock on ...
From $297 per night (USD)VRBO
From $175 per night (USD)VRBO
Endless Paradise at Executive Bay Club in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
* Beautiful 3/2 townhome with tile and wood floors, close to pool and beach * 50' LCD TV with stereo system, DVD ...
From $175 per night (USD)VRBO