Islamorada, Florida Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Islamorada, Florida on RentalSaver.com!

Islamorada Rentals

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)
Expedia
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)
Expedia
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)
Expedia
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)
Expedia
From $153 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 $153 per night (USD)
VRBO
From $354 per night (USD)
Expedia
Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC
Bedrooms:
1
Bathrooms:
3
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)
Expedia
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)
Expedia
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)
Expedia
$Remodeled Townhome at EBC w\/ Beach, Pool and more - 20% OFF FOR THE SUMMER!$
From $210 per night (USD)
VRBO
Remodeled Townhome at EBC w\/ Beach, Pool and more - 20% OFF FOR THE SUMMER!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Newly renovated and remodeled 1,359sf townhome at EXECUTIVE BAY CLUB in the heart of Islamorada REDUCED 20% MAY-AUGUST 2 ...
From $210 per night (USD)
VRBO
From $406 per night (USD)
Expedia
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 $406 per night (USD)
Expedia
$Venetian Tropics weekly Pvt home w\/heated Pool, 3 bedroom \/70ft dock w\/canal$
From $786 per night (USD)
VRBO
Venetian Tropics weekly Pvt home w\/heated Pool, 3 bedroom \/70ft dock w\/canal
Bedrooms:
4
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 $786 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 $952 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 $952 per night (USD)
VRBO
From $743 per night (USD)
Expedia
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)
Expedia
$3\/2 condo Futura Yacht Club Pool, Dockage, Wifi, dockage, beach$
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 $258 per night (USD)
Expedia
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)
Expedia
From $308 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 $308 per night (USD)
VRBO
Click For Pricing
Expedia
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 Pricing
Expedia
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
$2BR\/1BA Serene Cozy Cottage of Shady Palms in Islamorada With Heated Pool$
From $339 per night (USD)
Expedia
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 $339 per night (USD)
Expedia
From $1872 per night (USD)
VRBO
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 $1872 per night (USD)
VRBO
$Islamorada Bay Harbour 2\/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!$
From $373 per night (USD)
Expedia
Islamorada Bay Harbour 2\/2.5 Condo Free DOCK included MONTHLY DISCOUNTS!
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
Unit B106 Village of Islamorada: License Number: 24-0368. BOOK MONTHLY AND SAVE $$$$ Bay Harbour is a gated community ...
From $373 per night (USD)
Expedia
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)
Expedia
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)
Expedia
From $450 per night (USD)
VRBO
Spectacular Ocean Front Home In Beautiful Islamorada!Slip,Com Pool, & Prv Bch
Bedrooms:
3
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 $450 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Breezy Beach Waterfront home in Port Antigua
Bedrooms:
4
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)
Expedia
From $194 per night (USD)
VRBO
Captain's Quarters Piece of Peace
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy, quaint, and peaceful townhouse with Best Location in Islamorada, Florida. Close enough yet not too far from the To ...
From $194 per night (USD)
VRBO
$A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included$
From $536 per night (USD)
Expedia
A Pirates Great Escape ~ 3bed\/2baths Ocean View Boat Slip included
Bedrooms:
2
Bathrooms:
4
Sleeps:
6
Oceanfront Penthouse Condo with a Private Boat slip. Small Gated Community on the southern tip of Islamorada. The condo ...
From $536 per night (USD)
Expedia
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
$Bay Harbour Islamorada Oceanfront Views 3\/2.5 UPDATED condo DOCK$
From $610 per night (USD)
Expedia
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 $610 per night (USD)
Expedia
From $443 per night (USD)
VRBO
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 $443 per night (USD)
VRBO
$4 Bedroom home w\/ pool, DOCKAGE, beach access & more in Islamorada$
From $1069 per night (USD)
Expedia
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)
Expedia
From $416 per night (USD)
VRBO
Anglers Reef Islamorada home with ocean views, private marina, beach & pool
Bedrooms:
3
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 $416 per night (USD)
VRBO
$Luxury waterfront Islamorada Retreat w\/private pool, hot tub, lanai bar& firepit$
From $779 per night (USD)
Expedia
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 $779 per night (USD)
Expedia
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 $388 per night (USD)
Expedia
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Bedrooms:
3
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 $388 per night (USD)
Expedia
From $478 per night (USD)
VRBO
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)
VRBO
From $188 per night (USD)
Expedia
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)
Expedia
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)
Expedia
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)
Expedia
From $672 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 $672 per night (USD)
VRBO
From $702 per night (USD)
Expedia
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)
Expedia
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)
Expedia
Gorgeous Canalfront, Ocean View 3 Bedroom 3.5 Bath Home- Water Enthusiasts Dream
Bedrooms:
4
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)
Expedia
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 $250 per night (USD)
Expedia
RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Huge terrace- accessible from every room! Spacious and clean. Peaceful and away from the highway, yet near everything! S ...
From $250 per night (USD)
Expedia
From $890 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 $890 per night (USD)
VRBO
From $567 per night (USD)
Expedia
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)
Expedia
$Oceanside townhome 2\/2 with boat ramp and dockage$
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 $167 per night (USD)
Expedia
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 $167 per night (USD)
Expedia
From $278 per night (USD)
VRBO
Relax in this updated townhome while overlooking the sparkling Atlantic Ocean
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Windy Cove #3 - Relax in this great townhouse style condo, which overlooks the sparkling Atlantic Ocean. This condo feat ...
From $278 per night (USD)
VRBO
From $420 per night (USD)
Expedia
Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!
Bedrooms:
2
Bathrooms:
3
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:
3
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 $132 per night (USD)
Expedia
Oceanfront Luxury Condo
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 $132 per night (USD)
Expedia
From $602 per night (USD)
VRBO
Islamorada Waterfront Paradise with 5 Bedrooms, Pool and Dock
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Escape to your tropical island paradise in the heart of the Florida Keys! Nestled in cross keys location, to Tavernier C ...
From $602 per night (USD)
VRBO
From $449 per night (USD)
Expedia
Beautiful Harbor Front Oceanside Home on the Atlantic Ocean
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Oceanside 3/3 located on beautiful 10 acre harbor. Amazing natural surroundings, harbor & ocean views. New furnishings, ...
From $449 per night (USD)
Expedia
From $1441 per night (USD)
VRBO
Opulent waterfront estate with dock, pool, hot tub & rooftop view - dog-friendly
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Waterfront Wonder Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1441 per night (USD)
VRBO
From $388 per night (USD)
Expedia
Keys Villa - Secluded tropical paradise located on the water!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Private, secluded villa faces Florida Bay in view of the fabulous Everglades. Located in a lush tropical hammock in a q ...
From $388 per night (USD)
Expedia
From $940 per night (USD)
VRBO
Marlin House @ Tarpon Point
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
Summary: Stunning ocean views from all living levels & a waterfront pool! The Space: Welcome to the captivating Marlin ...
From $940 per night (USD)
VRBO
From $132 per night (USD)
Expedia
Beautiful Studio Apartment - Summer Sea Condo #230
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Summer Sea Condominium Unit 230 is a brilliant, clean and modern efficiency apartment, upgraded with tile throughout and ...
From $132 per night (USD)
Expedia
From $279 per night (USD)
VRBO
SPECTACULAR OCEANFRONT VIEWS , FREE WIFI, HD SMART TV'S, SUMMER SPECIAL RATES
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
OCEAN VIEWS EVERYWHERE in this Gorgeous 2 Bedroom/2bath Apartment overlooking the ATLANTIC OCEAN on next to top floor!! ...
From $279 per night (USD)
VRBO
$New 2\/1 Remodeled Cozy Home in Tavernier Key$
From $166 per night (USD)
Expedia
New 2\/1 Remodeled Cozy Home in Tavernier Key
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Relax at this peaceful and centrally-located 2/1 remodeled private home in Tavernier Key. Located near Tavernier Creek M ...
From $166 per night (USD)
Expedia
Click For Pricing
VRBO
Charming 2 bed, 2 bath cottage 100 feet from private sandy ocean beach
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Charming fully furnished 2 bedrooms each with a king bed, 2 bath cottage just 100 feet from shared private sandy beach o ...
Click For Pricing
VRBO
From $459 per night (USD)
Expedia
Luxury 3 bedroom condo overlooking harbor with ocean view, boat slip, amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a la ...
From $459 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
$STUNNING CONDO with BALCONY\/POOL in Oceanfront Building in beautiful Islamorada!$
From $170 per night (USD)
Expedia
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)
Expedia
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 $453 per night (USD)
Expedia
Anglers Reef Islamorada Ocean Views DOCK Beach Pool Boat Slip NO ROAD NOISE!
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
INTERIOR LOT—-NO ROAD NOISE—-BOAT SLIP AVAILABLE———Interior Painted Jan 2024---New Furniture in Family Room---Beautifull ...
From $453 per night (USD)
Expedia
$Anglers Reef Islamorada 2\/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool$
From $441 per night (USD)
VRBO
Anglers Reef Islamorada 2\/2.5 DOCK AVAILABLE Bikes, Kayak available, Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Village of Islamorada Vacation Rental license #24-0372. 113 Anglers Way Call Jennifer for more information 305-240-0592. ...
From $441 per night (USD)
VRBO
From $453 per night (USD)
Expedia
Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Come stay at the Tipsy Turtle in Angler's Reef! This magnificent home with ocean views from all 4 balconies is located ...
From $453 per night (USD)
Expedia
From $334 per night (USD)
VRBO
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 $334 per night (USD)
VRBO
From $276 per night (USD)
Expedia
3 BR 2 Bath Islamorada home with Private Beach Access
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Vacation in this cozy canal front home in the heart of Islamorada, midpoint between Miami and Key West. Large upstairs ...
From $276 per night (USD)
Expedia
$AQUAMARINE OCEANVIEW “FLASH SALE”\n5\/1-5\/10\/25+DOCK+POOL+GYM+”150” 5 STAR REVIEWS$
From $404 per night (USD)
VRBO
AQUAMARINE OCEANVIEW “FLASH SALE”\n5\/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 $225 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 $225 per night (USD)
Expedia
Click For Pricing
VRBO
Aqua Villa Starfish @ Mangrove Marina Resort on the waterfront
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
The Starfish houseboat has 1 Queen bed, 2 Twin Beds . Each houseboat has flat-screen TVs with cable and complimentary Wi ...
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VRBO
From $233 per night (USD)
Expedia
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)
Expedia
From $740 per night (USD)
VRBO
Large Canal Front Family home in the heart of Islamorada
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
Make yourself at home at this beautiful stay in Islamorada. Minutes away from the open ocean and the bay, this home is o ...
From $740 per night (USD)
VRBO
From $442 per night (USD)
Expedia
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)
Expedia
From $525 per night (USD)
VRBO
Waterfront with a pool & private beach access.
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Waterfront with pool. Private beach access within a mile. All amenities needed to enjoy a fun and relaxing vacation. A f ...
From $525 per night (USD)
VRBO
From $1024 per night (USD)
Expedia
New~Pools~Dock~Bikes~3 King Beds~Kayaks~EV charger
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
There's a reason why we have ALL 5-star reviews! HeartofMorada is located in the HEART of Islamorada on Upper Matecumb ...
From $1024 per night (USD)
Expedia
From $273 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 $273 per night (USD)
VRBO
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Expedia
Beautiful oceanfront resort located at mile marker 73.8
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
We are committed to providing outstanding service and a great vacation experience to all of our guests. While Caloosa Co ...
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Expedia
From $313 per night (USD)
VRBO
Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
This opulent condo is located within Ocean Harbour which is one of Islamorada’s most sought after gated communities feat ...
From $313 per night (USD)
VRBO
From $2025 per night (USD)
Expedia
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 $2025 per night (USD)
Expedia
From $222 per night (USD)
VRBO
Beautiful centrally located home in the Florida keys<br>
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Centrally located in the Florida keys close to Islamorada where there are great restaraunts and shops.Park your boat in ...
From $222 per night (USD)
VRBO
$A Piece of Paradise Islamorada, Fl. On the water 3\/2, 90 Ft of dock New Pool$
From $458 per night (USD)
Expedia
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)
Expedia
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VRBO
Dog-friendly escape with private dock, porch, balcony, water view, & central AC
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Sun-kissed Bliss Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
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VRBO
From $340 per night (USD)
Expedia
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 $340 per night (USD)
Expedia
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)
Expedia
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)
Expedia
From $462 per night (USD)
VRBO
Anglers Reef Islamorada, Bikes,Kayak,Paddle Boards DOCK available-Pool
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
112 Anglers Way Islamorada Village vacation rental #24-0371 Call me for more information 305-240-0592. (2 houses side b ...
From $462 per night (USD)
VRBO
$3 bed \/ 2 bath in the heart of Tavernier$
From $182 per night (USD)
VRBO
3 bed \/ 2 bath in the heart of Tavernier
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
Welcome to the Cottage on Pearl! Escape the ordinary office routine and enjoy the freedom of working from our home! Wit ...
From $182 per night (USD)
VRBO
From $2061 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 $2061 per night (USD)
VRBO
From $550 per night (USD)
Expedia
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)
Expedia
From $633 per night (USD)
VRBO
Breathtaking Bay Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
76004 Overseas Highway - Enjoy spectacular sunsets while drinking an iced cold beverage on the observation deck of this ...
From $633 per night (USD)
VRBO
From $382 per night (USD)
Expedia
Oceanfront home ON Tavernier Creek
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
This home is a fisherman's dream come true. New dock right on Tavernier Creek. You will be in open ocean in minutes!! ...
From $382 per night (USD)
Expedia
From $868 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 $868 per night (USD)
VRBO
$Tavernier Keys Home w\/ 70’ Dock & 20k Boat Lift on Bayside! 3\/2.5 Plus Game Room$
From $462 per night (USD)
Expedia
Tavernier Keys Home w\/ 70’ Dock & 20k Boat Lift on Bayside! 3\/2.5 Plus Game Room
Bedrooms:
4
Bathrooms:
5
Sleeps:
8
Gorgeous and Spacious Bayside Tavernier Keys Home with a 70’ foot Dock for your Boat and 20,000 lb Boat Lift. Be in the ...
From $462 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Anglers Reef Islamorada
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
2 Bed & 2.5 Bath Villa in Anglers Reef .Upscale gated community with resort living in the Florida Keys. Everything you n ...
From $461 per night (USD)
VRBO
$Islamorada Anglers Reef! “Sandbar Bungalow Villa\ AMAZING! Middle row location!$
From $574 per night (USD)
Expedia
Islamorada Anglers Reef! “Sandbar Bungalow Villa\" AMAZING! Middle row location!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
AMAZING MIDDLE ROW! COMPLETELY UPDATED! BOAT SLIP AVAILABLE This oceanfront resort is a boutique complex of 52 homes ins ...
From $574 per night (USD)
Expedia

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