Islamorada Rentals
From $320 per night (USD)VRBO
BOOK YOUR DREAM VACATION at BEACON REEF
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
JANUARY just opened up, book TODAY! (Jan 2026 only 30 days 10% discount) World Famous Beacon Reef Condo (a gated commun ...
From $320 per night (USD)VRBO
From $176 per night (USD)VRBO
Waterfront Paradise with Free Dockage - Contact us to price your stay!!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Please contact us for all of our rates for different length of stays! For shorter stays, make sure you have a minimum of ...
From $176 per night (USD)VRBO
From $627 per night (USD)VRBO
Elegant Bay Harbor Condo with 50 Foot Boat Slip, Heated Pool, Hot Tub, and Gym
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedr ...
From $627 per night (USD)VRBO
From $683 per night (USD)VRBO
Truly OceanFRONT-PanoramicOceanViews-WraparoundDecks-QuietLocation-AvailableSlip
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Uniquely designed 3 bedoom 2 1/2 bath OceanFRONT home! THERE ARE SOME HOMES WITH OCEAN PEEKS OR PARTIAL VIEWS THRU THE T ...
From $683 per night (USD)VRBO
From $287 per night (USD)VRBO
Executive Bay Club Bayfront/Beachfront paradise
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Watch the sunset from your private balcony from this bay front , beach front townhouse/condo. Recently remodeled and ful ...
From $287 per night (USD)VRBO
From $1337 per night (USD)Expedia
Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Sunset Reef is professionally cleaned including all linens and towels. The owners or property manager do not do the clea ...
From $1337 per night (USD)Expedia
From $253 per night (USD)VRBO
Beautiful 2/2 Islamorada Home Directly on Florida Bay (28 Day Minimum Rental)
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Our home is in Islamorada, in the middle Florida Keys. To be more specific, we are on Lower Matecumbe Key, which is the ...
From $253 per night (USD)VRBO
From $342 per night (USD)VRBO
*WINTER SPECIAL* 2 BR Waterfront Pool Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
“A Little Slice of Heaven”- completely renovated and updated in December 2020 waterfront pool home in paradise. This is ...
From $342 per night (USD)VRBO
From $550 per night (USD)VRBO
Charming 2 Bedroom Ground Level Home with Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Little Bay Lower Level - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a pri ...
From $550 per night (USD)VRBO
From $1362 per night (USD)VRBO
All the feels... tranquility and relaxation
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
75731 Overseas Highway - You are overcome with tranquility and relaxation as you pass through the gates of this oceanfro ...
From $1362 per night (USD)VRBO
From $138 per night (USD)VRBO
Beautiful 1 bedroom apartment with a Phenomenal direct bay view 312
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This apartment has a million dollar view, the kind you have always dreamed of for a vacation of a lifetime! The apartmen ...
From $138 per night (USD)VRBO
From $771 per night (USD)VRBO
Islamorada Island Getaway
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Relax and enjoy the Florida Keys lifestyle and outdoor living with full wrap around terraces. PLEASE NOTE: 28 night min ...
From $771 per night (USD)VRBO
From $289 per night (USD)VRBO
Coral Cove Resort - ‘A Fisherman’s Dream’
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy camaraderie with family and friends in this well-appointed, three-bedroom, ranch-style house in a lovely, private, ...
From $289 per night (USD)VRBO
From $319 per night (USD)VRBO
Islamorada cottage on deep water canal
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Our cottage is set in a quiet neighborhood on a deep, clear, wide canal. Situated bayside at mile marker 89, there is a ...
From $319 per night (USD)VRBO
From $687 per night (USD)VRBO
Latitude Adjustment FLKeys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Latitude Adjustment, Islamorada, Florida This home is our families' paradise in the Florida Keys and we want to share it ...
From $687 per night (USD)VRBO
From $177 per night (USD)VRBO
Sunsets at Islamorada, Florida Keys. 2/2 Townho
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Completely renovated with Mom' touch, 2 story with spiral staircase bayside townhome at Executive Bay Club. Mile Marker ...
From $177 per night (USD)VRBO
From $205 per night (USD)VRBO
Exec Bay w/heated Pool, Marina, Beach, Pets ok, Tennis/Pickleball
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come and relax at our beautiful Executive Bay Club (EBC) townhouse T2 in the “T” building. EBC is located in Islamorada, ...
From $205 per night (USD)VRBO
From $239 per night (USD)VRBO
Bayside Waterfront Home with 40 ft Dock
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
28-day minimum rental Welcome to our paradise vacation home, away from home. This Florida Keys house has 3 bedrooms, 2. ...
From $239 per night (USD)VRBO
From $919 per night (USD)VRBO
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Located in prestigious Venetian Shores Islamorada's premier waterfront community! This home was completely remodeled... ...
From $919 per night (USD)VRBO
From $1139 per night (USD)VRBO
Private beach and dazzling bayside sunsets await you!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The home is located at mile marker 88.9 bayside in Islamorada. It's one of eight houses located on a mile long private ...
From $1139 per night (USD)VRBO
From $310 per night (USD)VRBO
Ocean Harbour Condominium is an Oceanfront Fisherman's Paradise in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This spacious two bedroom, two bath condominium overlooking the ocean is located on a quiet 12 acre private gated commun ...
From $310 per night (USD)VRBO
From $398 per night (USD)Expedia
Anglers Reef Islamorada - 2:2.5, Marina, Pool, Beach.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
- VR#258 - Saturday check-in. 2 bedroom and 2.5 bath at 117 Anglers Way. Awesome family get-a-away in beautiful Islamor ...
From $398 per night (USD)Expedia
From $572 per night (USD)VRBO
Islamorada-Anglers Reef-LARGE/updated/Views DOCKAGE AVAILABLE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Village of Islamorada license #24-0370 138 Anglers Way and boat slip #1 for 26' max boat length for this slip (extra fee ...
From $572 per night (USD)VRBO
From $417 per night (USD)VRBO
Paradise with surrounding beaches and amazing fishing!!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to paradise! This waterfront home is in the heart of the Florida Keys. This 3 bedroom 3 bath home comfortably sl ...
From $417 per night (USD)VRBO
From $1606 per night (USD)VRBO
A True Islamorada Oasis with Breathtaking Bay Views
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 18
Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a privat ...
From $1606 per night (USD)VRBO
From $571 per night (USD)VRBO
Lush Tropical Waterfront Oasis With Heated Pool, Dock And WiFi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This tropical oasis includes a heated pool and dock that reaches out onto a protected lagoon that opens into the Florida ...
From $571 per night (USD)VRBO
From $244 per night (USD)VRBO
Newly redone condo with spectacular 5th floor open bay view.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Clean contemporary condo, with very nice accommodations. 2 Bedrooms with 2 bathroom/Showers, and also murphy bed in out ...
From $244 per night (USD)VRBO
From $1325 per night (USD)Expedia
The Snook House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This impressive home is tastefully decorated and features an open floor plan, soaring ceilings, an unimpeded, nearly 180 ...
From $1325 per night (USD)Expedia
From $220 per night (USD)VRBO
Florida Keys' Jewel - Executive Bay Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
An ample 1,400 sq ft. town home in the heart of Islamorada. Updated in 2025. Two bedrooms and one bathroom upstairs. On ...
From $220 per night (USD)VRBO
From $223 per night (USD)Expedia
Deep Water Canalfront Home W / Boat Ramp
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Clean & updated oceanside canalfront home. Located at desirable Lower Matecumbe in the Village of Islamorada, M.M.74.B ...
From $223 per night (USD)Expedia
From $486 per night (USD)VRBO
Charming Islamorada Villa in Gated Anglers Reef – Pool & Kayaks
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*Boat Slip Available: August 25 - September 5, September 13-19, September 27 - October 10, November 8-22 Keezy Does ...
From $486 per night (USD)VRBO
From $245 per night (USD)VRBO
Executive Bay Club U2 ~ 3 bed / 3 bath + Loft Townhouse in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to Executive Bay Club U2! Located in the heart of Islamorada, this fully upgraded townhouse offers everything y ...
From $245 per night (USD)VRBO
From $181 per night (USD)VRBO
Fabulous \" Sea Breeze 41 \", 3 / 2 Condo & 33' Boat Slip- Oceanside in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Luxury Island Retreat w/ Boat Slip, Pool, Marina & Private Balcony – “Sea Breeze 41” | Coral Harbour Club, Islamorada W ...
From $181 per night (USD)VRBO
From $405 per night (USD)VRBO
Key Lime Cottage in Islamorada
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Relax, Recharge & Explore – Detached Islamorada Cottage w/ Pool, Paddleboards & Fire Pit ☀️ Welcome to your own private ...
From $405 per night (USD)VRBO
From $232 per night (USD)VRBO
Keys Cozy Townhouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Enjoy breathtaking sunset from your own private beach. Cottage nautical townhouse with your outside terrace. Best r ...
From $232 per night (USD)VRBO
From $281 per night (USD)VRBO
Islamorada Bayfront Townhouse in Executive Bay Club
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Bayfront beautiful double townhouse with stunning bay views. Watch the sunsets from your balcony or from the beach right ...
From $281 per night (USD)VRBO
From $547 per night (USD)VRBO
Luxury Islamorada Oasis: Pool, Dock, Fire Pit, King Beds & Canal Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover Your Slice of Islamorada Paradise! Contact Us Directly for Availability Welcome to our newly remodeled, canal ...
From $547 per night (USD)VRBO
From $354 per night (USD)Expedia
Waterfront Sunset View Aqua Villa at Conch Shell @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Conch Shell houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $354 per night (USD)Expedia
From $478 per night (USD)VRBO
Gorgeous 3/2 plus loft Islamorada next to Marina, Pool, Dock & Beach
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Townhome with all extras. Keys style with beautiful new furnishings, newly remodeled with three bedrooms plus oversized ...
From $478 per night (USD)VRBO
From $419 per night (USD)Expedia
Sunsets on the bay at Villa Mia
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come and enjoy sunsets on the bay at Villa Mia! We created a peaceful retreat for our family and friends to enjoy. It is ...
From $419 per night (USD)Expedia
From $461 per night (USD)VRBO
🌴 Casa 157 @ White Marlin Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
*3 Bedrooms, 2 Baths, Single Story Charming Keys House, Washer /dryer, Wifi/cable, backyard is completely fenced in * ...
From $461 per night (USD)VRBO
From $1075 per night (USD)Expedia
The Bonefish House at Tarpon Point ~ 4 Bed/4 Bath Oceanfront Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Introducing the "Bonefish House," at Tarpon Point! This opulent, luxury, home is equipped to accommodate eight adults w ...
From $1075 per night (USD)Expedia
From $111 per night (USD)VRBO
Beautiful, sunlit home with pool, tennis court & beach access - near the marina
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Executive Bay Club Condo M-1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply ...
From $111 per night (USD)VRBO
From $409 per night (USD)Expedia
Gulf View Retreat @ Bay Harbor
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: 2/2 Bay harbor condo with stunning Marina and Ocean views! The Space: Escape to the breathtaking Gulf View Ret ...
From $409 per night (USD)Expedia
From $172 per night (USD)VRBO
Keys Life Cottage ~ Downtown Islamorada Cottage with Pool Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to the Keys Life Cottage! This coastal inspired two-bedroom, one-bath home is tucked away on a large landscaped ...
From $172 per night (USD)VRBO
From $1872 per night (USD)VRBO
Ocean & beachfront 4 bedroom, dockage, luxury residence, Islamorada, FL Keys
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Florida Keys Beachfront Vacations at Maison Residences Maison Residences offers world-class oceanfront residences in th ...
From $1872 per night (USD)VRBO
From $135 per night (USD)VRBO
Tropical Condo On The Ocean 1 BR/1 BA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Please note: We require a 28 day minimum rental. Located on the Ocean at mile marker 90 on Plantation Key, in Islamor ...
From $135 per night (USD)VRBO
From $303 per night (USD)Expedia
Ocean & Bay Views. Welcome To Paradise!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Sleeps 4, 1 Bedroom - King Bed, 2 Full Bathrooms, Queen Sleeper Sofa, 2 TVs, Balcony, fully stocked kitchen, towels & l ...
From $303 per night (USD)Expedia
From $361 per night (USD)VRBO
Ocean front paradise, 6th story balcony ocean view
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Islamorada is the fishing capital of the world, and home to the famous Islamorada sandbar. 🏖️ This condo is a 6th floor ...
From $361 per night (USD)VRBO
Click For PricingExpedia
JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Boat ramp and boat slip available for your stay!! I only have June 28-July 5 available for rent this year. You will LOVE ...
Click For PricingExpedia
From $339 per night (USD)VRBO
Beachfront Islamorada Villa with Dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The perfect Islamorada getaway awaits. Sandy Pointe Villa provides panoramic water views overlooking the Florida Bay, ...
From $339 per night (USD)VRBO
From $354 per night (USD)VRBO
Bayfront Islamorada Townhome with Dock & Beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy all the wonders Sandy Pointe Townhome has to offer. With breathtaking bay views, deep water dockage and a private ...
From $354 per night (USD)VRBO
From $518 per night (USD)VRBO
Islamorada's Finest Canal Front 'One Story' Vacation Home WiFi-HDTV-NO STAIRS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Islamorada is considered the fishing capitol of the world!You can do deep sea,offshore game and back country fishing!It ...
From $518 per night (USD)VRBO
From $134 per night (USD)VRBO
Beautiful Modern Studio, recently remodeled, new to the market, Summer Sea 405
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This beautiful modern Studio apartment has just been completely remodeled and new to the rental market. Every detail has ...
From $134 per night (USD)VRBO
From $146 per night (USD)VRBO
Wake up in Paradise. Islamorada Florida - 6-month minimum without boat lift.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
(6 month minimum rental) - $4,800 per month (boat slip not included). Conveniently located on a quiet street in Port An ...
From $146 per night (USD)VRBO
From $549 per night (USD)VRBO
Luxury, Elegant, Water Front Home, Heated Pool, Plantation Key, Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
VILLAGE. RENTAL LICENSE # VR-007 Please always send email request with dates desired , as sometimes the dates on the ca ...
From $549 per night (USD)VRBO
From $208 per night (USD)VRBO
Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And ...
From $208 per night (USD)VRBO
From $135 per night (USD)VRBO
Beautiful 1 bedroom apartment, king size bed, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This is a beautiful, recently renovated, one bedroom apartment at Summer Sea Condo. A wonderful garden view with a side ...
From $135 per night (USD)VRBO
From $354 per night (USD)VRBO
Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Sea Biscuit houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each houseboat has flat-scr ...
From $354 per night (USD)VRBO
From $423 per night (USD)VRBO
POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your own tropical paradise in Islamorada overlooking the fabulous Florida Bay - this family favorite is just 67 miles s ...
From $423 per night (USD)VRBO
From $269 per night (USD)VRBO
Oceanfront Private Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to Paradise Cottage!! This downstairs portion of a dual family dwelling is fully renovated a 1/1 cottage with ...
From $269 per night (USD)VRBO
From $405 per night (USD)VRBO
Large Waterfront Home with 80 ft Dockage and Boat Lift with Pool In Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
80ft Dock and Boat Lift very close to Islamorada Sandbar and Alligator Reef. Great fishing, diving, snorkeling and boat ...
From $405 per night (USD)VRBO
From $332 per night (USD)VRBO
Beautiful Vacation Home in Islamorada with Pool
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
*****28 Day Minimum Rental***** Spacious 3/3 canal front home in Lower Matecumbe. Heated pool to refresh after a long ...
From $332 per night (USD)VRBO
From $758 per night (USD)Expedia
Venetian Shores Escape! Heated Pool, 3BR, 70ft Dock, Dog-Friendly!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Vacation Rental License No VR-001 WEEKLY RENTAL Located on the peaceful upper Keys, in Islamorada, this home is situat ...
From $758 per night (USD)Expedia
From $385 per night (USD)VRBO
Tarpon Bend ocean view with boat lifts
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
3/2 Waterfront Home in Lower Matecumbe Key in Islamorada, Florida. Featuring a 70' ft private dock with 2 boatlifts (1- ...
From $385 per night (USD)VRBO
From $1214 per night (USD)Expedia
Islamorada Penthouse with Private Beach & Pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: This brand new, three bedrooms, three-and-a-half-bathroom penthouse unit is located within a luxury beachfront ...
From $1214 per night (USD)Expedia
From $755 per night (USD)VRBO
Beautiful Home On The Bay
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Large Home on Florida Bay, wonderful sunsets, great fishing, diving, kayaking etc.. This home could accommodate two fam ...
From $755 per night (USD)VRBO
From $442 per night (USD)VRBO
3/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Your own tropical paradise overlooking the fabulous Florida Bay - this family favorite is just 67 miles south of Miami! ...
From $442 per night (USD)VRBO
From $258 per night (USD)VRBO
Winter Special - Beautiful Waterfront Pool Home
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
“A Little Slice of Heaven”- completely renovated and updated in December 2020 waterfront pool home in paradise. This is ...
From $258 per night (USD)VRBO
From $334 per night (USD)Expedia
Whispering Palms | Sea Gulls 210 ~ Weekly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: NEWLY UPDATED! A peaceful sweeping view of the Atlantic stretches the entire length of this oversized balcony. ...
From $334 per night (USD)Expedia
Click For PricingVRBO
Studio in the heart of the Florida Keys, snowbird community
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
400 sq ft fully equipped studio,full bathroom & kitchenette. Chase sofa with sleeper. On wide private canal to the Ocea ...
Click For PricingVRBO
From $579 per night (USD)VRBO
Holly’s Hideout (Fisherman's Dream)
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This amazing home is centrally located on a clean, clear canal with deep water access to either the bay or ocean via Tav ...
From $579 per night (USD)VRBO
From $351 per night (USD)VRBO
2BR/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy a unique and secluded vacation experience in the heart of Islamorada at Shady Palms! Our charming cottage features ...
From $351 per night (USD)VRBO
From $1727 per night (USD)Expedia
Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamor ...
From $1727 per night (USD)Expedia
From $353 per night (USD)VRBO
Islamorada Bay Harbour 2/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unit B106 Village of Islamorada: License Number: 24-0368. BOOK MONTHLY AND SAVE $$$$ Bay Harbour is a gated community ...
From $353 per night (USD)VRBO
From $136 per night (USD)VRBO
Stunning 2-Bedroom with a million-dollar Bay View!!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This Fantastic Condo is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacular sunsets and ...
From $136 per night (USD)VRBO
From $499 per night (USD)VRBO
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour A-304 – Beautiful three bedroom two and a half bath luxury penthouse condo located at mile marker 74.5 baysi ...
From $499 per night (USD)VRBO
From $453 per night (USD)Expedia
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
VRL# 25-0132 we are one of Islamorada’s limited number of licensed weekly vacation homes. This magnificent home with di ...
From $453 per night (USD)Expedia
From $420 per night (USD)VRBO
Breezy Beach Waterfront home in Port Antigua
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Relax in this beautiful and comfortably updated bayside home in Port Antigua. Port Antigua is the Lower Keys best kept ...
From $420 per night (USD)VRBO
From $441 per night (USD)Expedia
A Pirates Great Escape ~ 3bed/2baths Ocean View B
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada.The condo h ...
From $441 per night (USD)Expedia
From $166 per night (USD)VRBO
Summer Special! Stunning 1st floor 2 bedroom Condo at Summer Sea
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Reduced price for summer of 2024. Summer Sea Condo #108: Newly remodeled and beautifully decorated 1st floor corner uni ...
From $166 per night (USD)VRBO
From $449 per night (USD)Expedia
3200 square ft. Masterpiece Home, Fishing Paradise Waterfront, Beach Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
"Monthly rentals only, no split months, thank you." Day 1, of the month , to end of the month. Welcome to, GULFVIEW 150 ...
From $449 per night (USD)Expedia
From $1069 per night (USD)VRBO
4 Bedroom home w/ pool, DOCKAGE, beach access & more in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Island Villa Rental Properties offers this large, modern 4 bedroom canal front home with pool in Lower Matecumbe Key in ...
From $1069 per night (USD)VRBO
From $393 per night (USD)Expedia
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Angler's Retreat is a 2 bedroom, 2.5 bathroom single-family home with picturesque ocean views, privacy, and space. The p ...
From $393 per night (USD)Expedia
From $801 per night (USD)VRBO
Luxury waterfront Islamorada Retreat w/private pool, hot tub, lanai bar& firepit
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to "Casa de Karma", your own private, resort style paradise! Enjoy your large heated pool (with sun shelf and s ...
From $801 per night (USD)VRBO
From $666 per night (USD)VRBO
Beautiful 3 Bedroom Condo - Bay Harbour A101
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Bay Harbour A-101 - Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 ...
From $666 per night (USD)VRBO
From $354 per night (USD)VRBO
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This beautiful villa is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Mark ...
From $354 per night (USD)VRBO
From $465 per night (USD)Expedia
Breathtaking ocean views for your Paradise vacations
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house s ...
From $465 per night (USD)Expedia
From $188 per night (USD)VRBO
Executive Bay - Next to Beach and Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Come to Paradise and Enjoy it in comfort.! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), par ...
From $188 per night (USD)VRBO
From $386 per night (USD)VRBO
Great Townhome with Basin & Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Futura Townhome #731 - Enjoy the spectacular view of the Florida Bay from this beautiful townhome. This townhome is a tw ...
From $386 per night (USD)VRBO
From $670 per night (USD)VRBO
Waterfront beautifully renovated 6 Bedrooms 4 Bath , Gated Private Home
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
This Beautifully renovated Compound / Property Comes With A recently completed and Magnificent Landscape Oasis , That Be ...
From $670 per night (USD)VRBO
From $635 per night (USD)VRBO
The PERFECT ESCAPE with Private Pool and Dock
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful 4 bedroom/ 4 bathroom home has a 60' dock. Its canal leads straight out to Snake Creek and has immediate ...
From $635 per night (USD)VRBO
From $404 per night (USD)VRBO
Boater's Paradise
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
This incredible property in Islamorada is the ultimate getaway, offering a spacious and flexible layout with 9 beds—per ...
From $404 per night (USD)VRBO
From $525 per night (USD)VRBO
Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to Paradise! This fabulous Keys home with Tommy Bahama décor throughout is a Fisherman & Water Enthusiast's Dre ...
From $525 per night (USD)VRBO
From $210 per night (USD)VRBO
Islamorada Spectacular Vacation At Executive Bay Club
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Come, Enjoy and Relax in our beautiful piece of the paradise in the Florida Keys. The Executive Bay Club is located in I ...
From $210 per night (USD)VRBO
From $839 per night (USD)VRBO
Ultimate luxury vacation home in Islamorada, Florida!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
SPECTACULAR HOME AND FISHERMAN'S PARADISE IN VENETIAN SHORES! This home is located in close proximity to many shopping ...
From $839 per night (USD)VRBO
From $566 per night (USD)VRBO
Perfect Home for a get away! Private homeowners beach, enjoy Islamorada.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Perfect home for a get away! Home is located in Islamorada. 3 bedroom 3 bath gorgeous private homeowners beach and priv ...
From $566 per night (USD)VRBO
From $420 per night (USD)Expedia
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Flori ...
From $420 per night (USD)Expedia
From $354 per night (USD)VRBO
Waterfront Sunset View in the Aqua Villa Sand Dollar @ Mangrove Resort LLC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
The Sand Dollar houseboat has 1 Queen bed, 1 Queen sofa sleeper and 2 Twin beds in the loft. Each house boat has flat-sc ...
From $354 per night (USD)VRBO
From $124 per night (USD)VRBO
Oceanfront Luxury Condo\n\n28 night minimum. Book Jan 7-Feb4 for 600 discount.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Seagulls Condominiums Islamorada Tavernier Key Largo New Lazy Boy recliner added to our open concept living room. Uppe ...
From $124 per night (USD)VRBO