Islamorada Rentals
From $857 per night (USD)VRBO
Port Antigua South Islamorada Canal Front Home with Pool Dock & Private Beach
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
SANCTUARY FOUND… At the intersection of two very wide sparkling canals sits this lovely, four bedroom, two and a half ba ...
From $857 per night (USD)VRBO
From $762 per night (USD)VRBO
Oceanfront, Pool, Dock... Checks all the boxes!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
141 LeSerra Lane - Freewheeler Vacations newest weekly rental is now available for your next Islamorada Vacation! Locate ...
From $762 per night (USD)VRBO
From $463 per night (USD)VRBO
Stunning Keys home w\/pool, jetted tub, elevator & more!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Paradise. Come and relax in our Bayside home and enjoy the coastal breeze and rustling palms in your own pri ...
From $463 per night (USD)VRBO
From $853 per night (USD)VRBO
Large Caribbean-Style Home w\/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $853 per night (USD)VRBO
From $1384 per night (USD)VRBO
Beautifully Renovated Home w\/ Custom Furnishings, Chef's Kitchen, & Veranda
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Welcome to the Jamaican Palm. Our most recently renovated home is a sight to behold. Every detail and fixture was handpi ...
From $1384 per night (USD)VRBO
From $609 per night (USD)VRBO
Oceanfront Home w\/ Patio, Kitchen, & WiFi - Steps to Marina & Activity Center
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to The Bird of Paradise. This Oceanfront home has everything you need for a relaxing getaway. Custom High ceilin ...
From $609 per night (USD)VRBO
From $896 per night (USD)VRBO
Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Grill, & Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $896 per night (USD)VRBO
From $522 per night (USD)VRBO
Cozy Caribbean-Style Home w\/ Outdoor Veranda - Steps to Beach-Entry Pool
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $522 per night (USD)VRBO
From $731 per night (USD)VRBO
Caribbean-Style Family Home w\/ Kitchen, WiFi, Outdoor Veranda, & Washer-Dryer
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $731 per night (USD)VRBO
From $1923 per night (USD)VRBO
Custom-Built Oceanfront Caribbean Home w\/ Gorgeous Ocean & Sunrise Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Carib ...
From $1923 per night (USD)VRBO
From $853 per night (USD)VRBO
Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Veranda, & Full Washer-Dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $853 per night (USD)VRBO
From $974 per night (USD)VRBO
Spacious Caribbean-Style Home w\/ Kitchen, WiFi, Grill, & Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $974 per night (USD)VRBO
From $804 per night (USD)VRBO
Breezy Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $804 per night (USD)VRBO
From $1923 per night (USD)VRBO
Custom-Built Oceanfront Caribbean Home w\/ Incredible Ocean & Sunrise Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Custom designed and built from the ground up by resort owner Phil Sena – with nothing compromised – this luxurious Carib ...
From $1923 per night (USD)VRBO
From $669 per night (USD)VRBO
Bright Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $669 per night (USD)VRBO
From $853 per night (USD)VRBO
Caribbean-Style Family Home w\/ Full Kitchen, WiFi, Veranda, & Washer-Dryer
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $853 per night (USD)VRBO
From $792 per night (USD)VRBO
Spacious Caribbean-Style Home w\/ Kitchen, WiFi, & Wraparound Outdoor Veranda
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Resort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all p ...
From $792 per night (USD)VRBO
From $890 per night (USD)VRBO
The Beach House-Luxury Oceanfront Home, Unobstructed Views, Pool, Sandy Beach
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
‘The Beach House’ at Tarpon Point in Islamorada-OWNER DIRECT RENTAL WITH NO ADMIN OR CC FEES ‘The Beach House’ is a lux ...
From $890 per night (USD)VRBO
From $1872 per night (USD)VRBO
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Spectacular property - two stories of true keys paradise in a relaxed basin-front setting. Newly renovated, the proper ...
From $1872 per night (USD)VRBO
From $550 per night (USD)VRBO
Cozy Cottage in the Heart of Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Little Bay Cottage - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private ...
From $550 per night (USD)VRBO
From $458 per night (USD)VRBO
A Piece of Paradise Islamorada, Fl. On the water 3\/2, 90 Ft of dock New Pool
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
''BEAUTIFUL BAY-FRONT PROPERTY!!!!'' NEW POOL Fully furnished, 1 story offering 3bd/2ba. The house can sleep up to 10. T ...
From $458 per night (USD)VRBO
From $2042 per night (USD)VRBO
This is The Oasis, YOUR private Oasis!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
The Oasis - This majestic property is over 2.75 acres of landscaped beauty. There is more white sand on this lot than an ...
From $2042 per night (USD)VRBO
From $344 per night (USD)VRBO
Expansive Ocean views!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour K-35 - This newly renovated unit is located in Ocean Harbor, one of the most exclusive condominiums in Isl ...
From $344 per night (USD)VRBO
From $901 per night (USD)VRBO
Beautiful Maison #307
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Maison Matecumbe #307 - Maison Matecumbe is an exclusive gated and private boutique complex comprised of 9 units. Centra ...
From $901 per night (USD)VRBO
From $1032 per night (USD)VRBO
You will never want to leave
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This Ocean Retreat offers breathtaking views from every room, with a 60' covered balcony that overlooks the 32' Pool/Spa ...
From $1032 per night (USD)VRBO
From $233 per night (USD)VRBO
Your Keys Getaway - A
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A beautiful home on the bay, in sunny Islamorada, Florida. You have access to one of the only beaches in Islamorada, whi ...
From $233 per night (USD)VRBO
From $442 per night (USD)VRBO
Cute & Cozy 3 Bedroom Canalfront Pool Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
137 Cortez Drive - The dream home away from home. The upstairs main floor offers two large bedrooms with cozy king beds, ...
From $442 per night (USD)VRBO
From $274 per night (USD)VRBO
Sunset from our own Private Balcony Directly over the Bay
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 7
Paradise in the Upper Keys. Just under 1 1/2 hrs. from Miami you can rent a piece of Heaven this Winter Season. Prime co ...
From $274 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 $330 per night (USD)Expedia
Casa Mia 7862778706
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Absolutely comfortable keys Home , great location to restaurants and activities, two bedroom and two full bath upstairs ...
From $330 per night (USD)Expedia
From $404 per night (USD)VRBO
AQUAMARINE OCEANVIEW “FLASH SALE 5\/1-5\/10\/25+DOCK+POOL+GYM+”150” 5 STAR REVIEWS!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE EMAIL US WITH ANY QUESTIONS??? WE ARE HAPPY TO PROVIDE THE ANSWERS ABOUT OUR PROPERTY, OUR RESORT, RESTAURANTS, ...
From $404 per night (USD)VRBO
From $240 per night (USD)Expedia
Tropical Escape | Sea Gulls 407 ~ Weekly Rental
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Located right on the Atlantic Ocean, in the heart of the Florida Keys on Plantation Key - the sport fishing and ...
From $240 per night (USD)Expedia
From $2183 per night (USD)VRBO
Private Tropical Oceanfront Estate with Pool and Beach
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
Last Resort Too - Welcome to Last Resort Too. This private hidden gem is situated on two prime oceanfront acres with a s ...
From $2183 per night (USD)VRBO
From $170 per night (USD)VRBO
STUNNING CONDO with BALCONY\/POOL in Oceanfront Building in beautiful Islamorada!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Gorgeous 2 bedroom 2 bath condo all on one floor with HEATED POOL, DOCK FOR FISHING, AND OUTDOOR BALCONY. Gated commun ...
From $170 per night (USD)VRBO
From $1453 per night (USD)VRBO
Waterfront... The Sapodilla House... Islamorada Family Estate Home...
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The Sapodilla House - The Sapodilla House is one of Islamorada’s gems. This tropical, sprawling estate has every amenity ...
From $1453 per night (USD)VRBO
From $889 per night (USD)VRBO
Ultimate luxury vacation home in Islamorada, Florida!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
SPECTACULAR HOME AND FISHERMAN'S PARADISE IN VENETIAN SHORES! This home is located in close proximity to many shopping ...
From $889 per night (USD)VRBO
From $567 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 $567 per night (USD)VRBO
From $171 per night (USD)VRBO
Oceanside townhome 2\/2 with boat ramp and dockage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This beautiful newly renovated townhouse is the prefect vacation home for you and your family. The third floor has a mas ...
From $171 per night (USD)VRBO
From $174 per night (USD)VRBO
Beautiful sunsets & water views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Bayfront Sand Pebbles #304 - A desirable Islamorada condo complex with a total of only 16 units. This two-bedroom two ba ...
From $174 per night (USD)VRBO
From $702 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 $702 per night (USD)VRBO
From $627 per night (USD)VRBO
Beautiful 3 Bedroom Condo - Bay Harbour A101
- Bedrooms:
- 3
- 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 $627 per night (USD)VRBO
From $478 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 $478 per night (USD)Expedia
From $188 per night (USD)VRBO
Executive Bay - Next to Beach and Pool!
- Bedrooms:
- 2
- 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 $437 per night (USD)VRBO
Great Townhome with Basin & Bay Views
- Bedrooms:
- 3
- 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 $437 per night (USD)VRBO
From $1614 per night (USD)VRBO
Beautiful Oceanfront Oasis with Pool
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Sea Ranch - Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marke ...
From $1614 per night (USD)VRBO
From $166 per night (USD)VRBO
Summer Special! Stunning 1st floor 2 bedroom Condo at Summer Sea
- Bedrooms:
- 2
- 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 $630 per night (USD)VRBO
Bay Harbour Islamorada Oceanfront Views 3\/2.5 UPDATED condo DOCK
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful views from this condo dock 32 available- Unit C109 License Number: VR-194 Bay Harbour is a gated community l ...
From $630 per night (USD)VRBO
From $441 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 $441 per night (USD)Expedia
From $1069 per night (USD)VRBO
4 Bedroom home w\/ pool, DOCKAGE, beach access & more in Islamorada
- Bedrooms:
- 3
- 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 $1936 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 $1936 per night (USD)Expedia
From $373 per night (USD)VRBO
Islamorada Bay Harbour 2\/2.5 Condo Free DOCK included -Rate Specials!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Unit B106 Village of Islamorada: License Number: 24-0368. Bay Harbour is a gated community located at MM 75 bayside i ...
From $373 per night (USD)VRBO
From $177 per night (USD)VRBO
Stunning 2-Bedroom with a million-dollar Bay View!!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This Fantastic Condo is just steps away from the fabulous turquoise waters of Florida Bay! Enjoy spectacular sunsets and ...
From $177 per night (USD)VRBO
From $566 per night (USD)VRBO
Stunning 3 Bedroom Condo with Basin & Ocean Views Located in Lower Matecumbe
- Bedrooms:
- 3
- 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 $566 per night (USD)VRBO
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 $332 per night (USD)VRBO
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 $332 per night (USD)VRBO
From $385 per night (USD)Expedia
Tarpon Bend ocean view with boat lifts
- Bedrooms:
- 3
- 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)Expedia
From $963 per night (USD)VRBO
Islamorada Penthouse with Private Beach & Pool!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: This brand new, three bedrooms, three-and-a-half-bathroom penthouse unit is located within a luxury beachfront ...
From $963 per night (USD)VRBO
From $743 per night (USD)VRBO
Beautiful Home On The Bay
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Large Home on Florida Bay, wonderful sunsets, great fishing, diving, kayaking etc.. This home could accommodate two fam ...
From $743 per night (USD)VRBO
From $348 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 $348 per night (USD)VRBO
From $449 per night (USD)VRBO
POPULAR BAYFRONT Townhouse Futura Yacht Club, Pool, Dockage
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Your own tropical paradise in Islamorada overlooking the fabulous Florida Bay - this family favorite is just 67 miles s ...
From $449 per night (USD)VRBO
From $277 per night (USD)VRBO
RELAX in your PRIVATE Oceanfront Cottage!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Due to COVID-19 and the precedented times we are living, our home will provide hand sanitizer and have the whole house s ...
From $277 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:
- 4
- 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 $505 per night (USD)VRBO
No shoes, No shirt, No problem!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
125 Porto Vista Ct - No shoes, No shirt, No problem! In this Pt Antigua Pool Home, you will need to go nowhere to have a ...
From $505 per night (USD)VRBO
From $138 per night (USD)VRBO
Beautiful 1 bedroom apartment, king size bed, Summer Sea Condo
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This is a beautiful, recently renovated, one bedroom apartment at Summer Sea Condo. A wonderful garden view with a side ...
From $138 per night (USD)VRBO
From $545 per night (USD)VRBO
Peaceful 2 Bedroom Oceanfront Cottage with Pool and Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Green Cottage - The Green Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their ...
From $545 per night (USD)VRBO
From $550 per night (USD)VRBO
Charming 2 Bedroom Upstairs Home with Bay Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Little Bay Upper 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 $222 per night (USD)VRBO
Beautifully Renovated 2 Bedroom Oceanfront Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
132 Atlantic Lane - Looking for your next home away from home You cannot go wrong with this recently renovated two-bedro ...
From $222 per night (USD)VRBO
From $328 per night (USD)VRBO
Beautiful 3 Bedroom Condo with Ocean Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Ocean Harbour K-21- Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from hom ...
From $328 per night (USD)VRBO
From $146 per night (USD)VRBO
Wake up in Paradise. Islamorada Florida - 6-month minimum without boat lift.
- Bedrooms:
- 3
- 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 $233 per night (USD)VRBO
Islamorada Paradise! Luxury Townhouse! Sleeps 4-6 Boat Slip And Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This Modern Upscale duplex Home Has All The Amenities For A Wonderful And Special Vacation. King Size Master Bedroom And ...
From $233 per night (USD)VRBO
From $289 per night (USD)VRBO
Ocean Views and Secure Dockage = Vacation
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
141 Ocean Lane - "The Beach Fixes Everything". That's the sign that greets visitors as they enter the living room of thi ...
From $289 per night (USD)VRBO
From $509 per night (USD)VRBO
Waterfront Paradise Found: Explore the Serene Beauty of Islamorada!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 6
179 Venetian Way - NEW POOL!!! Located in Venetian Shores, one of the premier Islamorada neighborhoods, this three-bedro ...
From $509 per night (USD)VRBO
From $1731 per night (USD)VRBO
Ocean & beachfront 4 bedroom, dockage, luxury residence, Islamorada, FL Keys
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Florida Keys Beachfront Vacations at Maison Residences Maison Residences offers world-class oceanfront residences in th ...
From $1731 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:
- 2
- 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 $675 per night (USD)VRBO
Beachy 3 Bedroom Condo with Ocean Views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Oceanview Maison Matecumbe #306 - Maison Matecumbe is an exclusive gated and private boutique townhome complex. This won ...
From $675 per night (USD)VRBO
From $442 per night (USD)VRBO
Tranquil Garden View One Bedroom Cottage with Pool and Boat Basin on a Beautiful Oceanfront Prope...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Hawksbill Cottage - The Hawksbill Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all wi ...
From $442 per night (USD)VRBO
From $787 per night (USD)VRBO
Charming 2 Bedroom Oceanfront Cottage with Pool and Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages al ...
From $787 per night (USD)VRBO
From $315 per night (USD)VRBO
Romantic Garden View Studio Cottage Nestled in Lush Landscaping with Pool and Dockage located on ...
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Kemp Cottage - The Kemp Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their o ...
From $315 per night (USD)VRBO
From $343 per night (USD)VRBO
Cozy Treetop Studio on Oceanfront Property with Pool and Boat Basin
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Treehouse Cottage - The Treehouse is the upper level of Hawksbill Each cottage has it's own personality and characterist ...
From $343 per night (USD)VRBO
From $443 per night (USD)VRBO
Bayside Retreat - Adorable 3 Bedroom Bayfront Duplex with Dockage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Bayside Retreat - Completely renovated bayfront duplex home. This bayfront home consists of three bedrooms and three bat ...
From $443 per night (USD)VRBO
From $447 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 $447 per night (USD)VRBO
From $1078 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 $1078 per night (USD)Expedia
From $237 per night (USD)VRBO
Executive Bay Club U2 ~ 3 bed \/ 3 bath + Loft Townhouse in Islamorada
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Executive Bay Club ~ Islamorada’s Hidden Gem! This townhouse is located in the heart of Islamorada and offer ...
From $237 per night (USD)VRBO
From $1246 per night (USD)VRBO
Direct Ocean Front Estate, Private Beach, HUGE Salt Pool\/Hottub, Private Basin!!
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 14
Oceanfront Estate on 3.5 PRIVATE. Tropical Acres in the Heart Of Islamorada. Nothing like this rental in the Keys. Feat ...
From $1246 per night (USD)VRBO
From $202 per night (USD)VRBO
Fabulous \" Sea Breeze 41 \", 3 \/ 2 Condo & 33' Boat Slip- Oceanside in Islamorada
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Experience high-end coastal luxury while staying at “Sea Breeze 41” in the highly sought-after Coral Harbour Club Condom ...
From $202 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:
- 6
- 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 $362 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 $362 per night (USD)VRBO
From $1196 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 $1196 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. Two bedrooms and one bathroom upstairs. One bedroom has two ...
From $220 per night (USD)VRBO
From $118 per night (USD)VRBO
An adorable, decorated studio apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Summer Sea #333 - An adorable, decorated studio apartment that has everything you need for your stay in the keys. Summer ...
From $118 per night (USD)VRBO
From $262 per night (USD)VRBO
Oceanfront 2 Bedroom Condo with Contemporary Flair
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Ocean Harbour K-44 - Islamorada's Desirable Ocean Harbour Condominium Complex. Remodeled two-bedroom two bath unit with ...
From $262 per night (USD)VRBO
From $629 per night (USD)VRBO
Poolside Maison Matecumbe #302 - Great 3 Bedroom Condo
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Poolside Maison Matecumbe #302 - Islamorada oceanfront complex...Maison Matecumbe. The unit has one level living with th ...
From $629 per night (USD)VRBO
From $2586 per night (USD)VRBO
Key West Style Estate on Private Lush Beachfront Property
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 12
Kara Pan - Islamorada's Premier Oceanfront Estate Home... Kara Pan 1. Discreet Key West style home is situated on a four ...
From $2586 per night (USD)VRBO
From $202 per night (USD)Expedia
Deep Water Canalfront Home W \/ Boat Ramp
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Clean & updated oceanside canalfront home. Located at desirable Lower Matecumbe in the Village of Islamorada, M.M.74.B ...
From $202 per night (USD)Expedia
From $2071 per night (USD)VRBO
Your PRIVATE OCEANFRONT ESTATE awaits! Dive into the Infinity Pool & 150' Beach
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Exquisite Oceanfront - Luxury and tranquility await you at this elegant Islamorada oceanfront estate. Drive through a ga ...
From $2071 per night (USD)VRBO
From $214 per night (USD)VRBO
Serene Sunsets from Your 2 Bedroom Villa
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Serene Sunsets from your villa! Sandy Pointe is located in prestigious Port Antigua on Lower Matecumbe. This condo is a ...
From $214 per night (USD)VRBO