Vacation Rentals By Owner In Islamorada, FL

$288.78

Beautiful Pool home in Islamorada

Islamorada, Florida, United States

PROPERTY NAME: The Bungalow Housebr32 Park Rd Islamorada, FloridabrbrLocation: Bayside Very close to the Publix Shopping CenterbrbrMINIMUM: 28 Days, All stays must be the whole month (s), No Partial Months AllowedbrbrMile Marker : 82brbrDetails: This home is absolutely beautiful with your own pool and Tranquil backyard - Bayside walking or biking distance to Downtown. The property is Private, plenty of parking for your vehicles and boat trailer if needed. It features a beautiful pool that is heated in the winter and chilled in the summer When you walk in you are at home, the house is beautifully decorated. The living room has a faux fire place and plenty of seating for the family, the kitchen is completely remodeled and fully stocked with everything you may need for your stay. You have 2 bedrooms and 2 baths there is a 3rd room that has a single pull out bed, with a desk and chair. There is a front porch to sit and enjoy the beautiful surrounding lush trees. You also have a Porch in the backyard to sit and enjoy the pool area. The backyard features beautiful trees and shrubs for privacy while enjoying the Pool. If you are looking for Private and Quiet, this is the house.brbrSleeping Arrangements: Sleeps 5 comfortablybrPrimary Bedroom: King Bed that is adjustablebrGuest Room: Queen BedbrbrAmenities Include: Heated Pool, Outdoor Seating, BBQ Grill, Private BackyardbrbrActivities: Beach, Swimming, Boating, Offshore Fishing, On shore fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours

3

Bed

2

Bath

6

Sleeps

$534.74

/ Nightly

Private Vacation Home

Canal front home in Venetian Shores. Perfect for families. A boater's paradise!

Islamorada, Florida, United States

This canal front home is located in the prestigious Venetian Shores neighborhood. The perfect location right off of Snake Creek, which gives you fast access to both Ocean & Bay, fuel, bait, and provisions.brbrThis beautiful, updated canal home has two bedrooms, two baths upstairs and a one-bath studio apartment downstairs. It offers various sleeping arrangements. 8 people can be accommodated upstairs and 4 people downstairs.brbrThe House:brUpstairs has Two Bedrooms, a king-size bed in the Master with en-suite bathroom, a twin/full/twin bunk bed in the other guest suite. There is also a nice size guest bathroom upstairs. The couch upstairs has a large pull out couch and there is a day bed in the sunroom area with 2 twin beds.brbrDownstairs has a queen size hide-a-bed, as well as a large pull-out couch. Enjoy the convenience of a first-floor bathroom and a full, updated kitchen. Perfect for entertaining!brbrThe home is fully stocked with all kitchen supplies and upscale appliances (Cuisinart toaster oven/airfryer, convection oven, espresso machine, coffee maker, Ninja blender, all new knives and pots/pans). New washer/dryer in laundry room, games for family fun including: ping-pong table, corn hole set, darts, 3 cruiser bikes, and 2 kayaks). Pool is maintained each week has a cooler and heater and is lit at night. Outdoor table converts to a fire pit. Traeger grill is also provided.brbrThe Dock: Your 35-foot private dock with a boat lift provides instant access to fun – whether boating, fishing, swimming, or relaxing. Boatlift can accommodate up to 14,000 lbs. Have your boats or yacht waiting just outside your door. Large, deep-draft sailboats or yachts are easily accommodated with a waterway 20 ft deep and 100 feet wide. Even tall vessels travel quickly between the Ocean and Florida Bay using the drawbridge just 1000 yards from the dock. With gas, bait, and tackle shops located before the bridge, your convenience is assured.

3

Bed

3

Bath

10

Sleeps

$744.8

/ Nightly

Hotel

2 Guest Room, 2 Queens, Balcony, Free Parking, 3 Pools & Pet Friendly

Islamorada, Florida, United States

Set on 15 oceanfront acres in Islamorada, Three Waters Resort & Marina features island-inspired rooms. Guests enjoy three pools, beach and marina access, on-site dining, a water taxi to sister properties, and guided fishing or water sports for a full Keys experience.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 338 sq. ft, equipped with complimentary toiletries, TV.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services included in the nightly price.brbrThere are a few additional details to know before you book:brbr✦ The minimum age required for check-in is 21 years old.brbr✦ Please ensure you have a valid ID for check-in, as it is mandatory for entry.brbr———————————————brbrGuest Access:brDuring your stay, you will have access to the property and amenities according to the following schedule:brbr✦ Check-in is available from 04:00 pm.brbr✦ Fitness center is available.brbr✦ Outdoor pool available all year.brbr✦ Free parking lot – 1 space(s).brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $200 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $150 USD non-refundable pet fee per room per staybrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Please note that a fee will apply for smoking in guest rooms.br✦ Pack and Play subject to availability at time or request, free.br✦ Get 10% off + $40 daily breakfast credit (2 guests) on 4+ night stays. Stay: Apr 7–Dec 23, 2026. Book by Jun 30, 2026.

Bed

Bath

Sleeps

$610.02

/ Nightly

Private Vacation Home

Islamorada-Anglers Reef-LARGE/updated/Views DOCKAGE AVAILABLE

Islamorada, Florida, United States

Village of Islamorada license #24-0370br138 Anglers Way and boat slip #1 for 26' max boat length for this slip (extra fee)brCall me for more information 305-240-0592br2 large bedrooms amd 2.5 bathrooms. largest floorplan of two bedroom in Anglers.br Community kayaks and paddleboards are avail to use (just have to sign a waiver)brThis large Oceanfront Villa has 2 bedrooms (one with king bed and the other with One QUEEN SIZE BED and twin bunk beds) and 2 full bathrooms located on the 2nd floor, both with private balcony's. Down stairs there is a half bath, a full kitchen with stainless steel appliances, granite counters, living/dining room, wood floors, cable TV, Wi-Fi and 2 open porches with seating.This oceanfront resort is a boutique complex of 52 homes inspired by Key West architecture that was built in 2007. Gate community, located off the Old Hwy at MM 86 in Islamorada. Amenities include a community pool overlooking the Atlantic Ocean and 500ft of private beach. The home’s boat slip is available for rent with a deep channel out to the Atlantic. Be at Alligator Light house or the Famous Islamorada (Holiday Isle) sandbar in minutes. Launch your kayak or paddle board from the private beachbrbrKayaks are now available to all homes (provided by the community) on a first come, first serve basis. A waiver needs to be signed (attached to welcome email) in order to be able to use them.brbrPlease note, as of Aug 1, 2024. you will no longer be able to store a trailer outside the gate on the grass any longer. Trailers fitting under the carport are able to be stored there. Otherwise, we can recommend local storage lots you can contact.brbrCome on down and put your toes in the sand. It's always better in the Florida Keys.Angler’s Reef is the perfect place for all fishing and diving enthusiasts. Islamorada is known as “The Sport fishing Capital of the World”. Water activities abound including: diving, snorkeling, Para sailing, kiteboarding, paddle boarding, kayaking, and more. You may even spot manatees at the Dock. Fine dining and unique shops are within walking distance: Island Grill (Famous for their tuna nachos) serving breakfast, lunch and dinner oceanfront with live music. For late night entertainment, walk on over to Hog Heaven for a fun night of dancing. Also, within in walking distance is Theatre of the Sea, where you can watch a live dolphin show or even swim with the dolphins!brbrBring your boat (up to 26') max. If you have a larger boat, I will need to put it in another slip and there is an additional fee.

Bed

Bath

Sleeps

$402.48

/ Nightly

Apartment

Hidden Gem Islamorada | 1st Floor

Islamorada, Florida, United States

Summary:brThis newly renovated unit is truly is a Hidden Gem in the heart of Islamorada! This duplex is nestled in the trees just a few steps from one of the most amazing sunsets in the Upper Keys. Walking distance to all the wonderful shops, restaurants and breweries that Islamorada has to offer. Bikes and Kayaks can be rented steps away from the front door of this unit. Want to find a place that you'll want to return year after year Look no further! brbrThis unique property was originally built as motel in the 1950's. We have taken it upon ourselves to give it a facelift! Expects new bathrooms, flooring, beds, windows, and new split AC units in every room! Cool down when you get inside from that Florida heat! BrrrrrbrbrThe Space:brThis unit is 620 sq. ft. located on the first floor. Its two bedroom/two bath with a small kitchen and living room. brbrThe master bedroom has a Queen mattress with an en suite bathroom. brThe guest bedroom has a King memory foam mattress and an unattached bathroom.brThere are no dressers or closets in the units. We provide luggage racks, and places to hang clothing.brbrThis unit is part or a very unique and private wooded property that spans over the bay of the Florida Keys. This unit does has a courtyard view NOT a bay/ocean view. All staying guests have complete access to all the property has to offer. It’s a two minute walk to the boat basin and the most incredible sunset view in Islamorada!brbrMARINA/BOAT BASIN INFORMATION: br- You are allowed one 24’ vessels MAX WITH ENGINE to keep in the boat basin. The basin is too small to accommodate larger boats.br- BOATS EXCEEDING LENGTH OF 24' WILL BE MOVED OR SUBJECT REMOVAL AT OWNERS EXPENSE. BOATS MAY BE MOVED TO ACCOMMODATE OTHER BOATS.br- Holiday House Mariana waiver must be signed before boat can be on premise.br- Boat ramp is for max 20' vessels.br- You will have also have access to parking trailer on property for no addition fee.br- NO JETSKISbrbrGuest Access:brThe property is accessed via self check in with a key pad.brbrThe Neighborhood:brLocated at Mile Market 82.5 in the heart of Islamorada this unit is central to many shops, restaurants, and bars! Its right across the street from several shops, walking distance to several restaurants, and the famous Islamorada Beer Company! brbrWe provide a detailed GUESTBOOK with many great recommendations for food, drinks, and activities!!brbrOther Things to Note:br● Maximum 4 guests br● Laundry/courtyard/grill is SHARED with guests upstairsbr● Unit has a courtyard view NO OCEAN VIEWbrbrCancellation Policy br● 100% refund if you cancel at least 60 days before check-in. br● 50% refund (minus service fee) if you cancel at least 30 days before check-in. br● No refund if you cancel less than 30 days before check-in. brbrWe strongly recommend purchasing a separate travel protection policy to cover any refund requests outside the above cancellation rules.brbrMARINA/BOAT BASIN INFORMATION: br- You are allowed one 24’ vessel MAX WITH ENGINE to keep in the boat basin. The basin is too small to accommodate larger boats.br- BOATS EXCEEDING LENGTH OF 24' WILL BE MOVED OR SUBJECT REMOVAL AT OWNERS EXPENSE. BOATS MAY BE MOVED TO ACCOMMODATE OTHER BOATS.br- Holiday House Mariana waiver must be signed before boat can be on premise.br- Boat ramp is for max 20' vessels.br- You will have also have access to parking trailer on property for no addition fee.br- NO JETSKISbrbrInteraction with Guests:brHello and welcome, we try meet and greet all of our guests! Making sure you have a great vacation experience is my passion! We live her locally so will be available for any questions you may have throughout your stay. - Sean

2

Bed

2

Bath

4

Sleeps

$2915.75

/ Nightly

Apartment

Ocean View Two Duplex Penthouses / Retreat amenities: tennis court, heated Pool | Vista Key

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1991.73

/ Nightly

Private Vacation Home

Oceanfront Estate on Islamorada, Florida Keys - Ocean Oasis of Islamorada

Islamorada, Florida, United States

It's an Ocean Oasis here on this beautiful estate in Islamorada! Over one acre right in front of your PRIVATE beach on the Atlantic Ocean. No one bothering your sandy shoreline while you bask in the sun. Enjoy 5 bedrooms, 4 bathrooms and countless amenities. Two kitchens, ample living rooms, & two sets of washers and dryers are just some of our conveniences. Make your way outside, and you will not be disappointed with the extensive choice of complimentary entertainment. A large pool surrounded by chaise loungers sits relatively near our 10-person hot tub. Here you can also find ample Adirondack chairs with side tables surrounding the area. If you're more the physical type, get ready to have some fun! Head over to your personal paddle bar where you can find various water toys such as kayaks and paddleboards. Let's not forget our outdoor toy closet; here you can find several cornhole sets, life jackets, and other outdoor games like giant Jenga. brbrAs the sun comes down, get ready to enjoy some of the most magical skies you will ever see. Our sunsets here are world famous and you won't want to miss this! May we suggest; this is the perfect time to let the grill master in your group do their best work! Always cleaned and ready to go, our grill sits just alongside our 10-person teak bar. Equipped with a built-in cooler and bar lights, it sets quite the tone for a relaxing seaside night. Easily a great way to enjoy the locals catch. Something found on almost every corner here in Islamorada!brbrThe night is young, and you have some pretty great options to still enjoy on this property. Our hammock cove is a place many find themselves happily lost. With more stars in sight than you've probably ever seen, it's easy to see why people migrate here. The swaying palm trees are a welcomed sound as they support 3 double hammocks for your enjoyment. Still not ready to rest you say Great!!! Grab one of the many beach towels on premise and head back to the pool. A completely surreal experience awaits here at night. The market lights & perfectly placed landscape lighting pair perfectly with your choice of tunes on our Sonos surround speakers.br If true relaxation is what you're looking for, then you've found the perfect place!br

5

Bed

4

Bath

12

Sleeps

$1040.1

/ Nightly

Private Vacation Home

Relax in Sunset Cottage, bayfront 4BR pool home retreat in picturesque Islamorada.

Islamorada, Florida, United States

This stunning, fully renovated retreat checks every box for the perfect Keys escape—sweeping bay views, a private pool and spa, and all the outdoor living space you could dream of. Soak up the sun from your two-story tiki, gather around the fire pit for sunset cocktails, or fire up the grill in the outdoor kitchen for a laid-back dinner under the stars.brbrStep inside to find a beautifully designed interior with coastal-chic finishes, spacious living areas, and water views from nearly every room. With dockage for your boat, you're just minutes from world-class fishing, snorkeling, and sandbar adventures.brbrWhether you're floating in the pool, reeling in the catch of the day, or simply relaxing with a drink in hand—this bayfront beauty delivers the ultimate Islamorada vacation experience.

Bed

Bath

Sleeps

$461.44

/ Nightly

Private Vacation Home

Casa 157 @ White Marlin Beach

Islamorada, Florida, United States

*3 Bedrooms, 2 Baths, Single Story Charming Keys House, Washer /dryer, Wifi/cable, backyard is completely fenced inbrbr*strategically Located Between Miami and Key West( 2hrs from Ft Lauderdale International Airport & 1.5 Hrs from Miamibrbr60 Foot of Dock With Electric & Water ; no fish cleaning stationbrEasy access to both Bay Side & Ocean BoatingbrAmple Side yard parkingbrThere are many places around to put your boat in... most of our guest use Caloosa Cove Marina (ocean side)brbr*Private (key Required) White Sand Beach (dogs are not allowed)br2-man Ocean Kayak, 3 Bicycles, the Hammock for Two & Enjoy the Night Sky Full of the Constellations for You to Namebrbr*close to Fine Dining & the Best Sport Fishing in the Keysbr, 1.5hrs from Key Westbrbr Islamorada, 33036, aka White Marlin Beach, aka Lower Matecombe ... aka MM 74.5brbr

Bed

Bath

Sleeps

$258.94

/ Nightly

Apartment

Islamorada Escape - Executive Bay w/Pool, Fishing Dock, Beach, Tennis/Pickleball

Islamorada, Florida, United States

Located in Islamorada, mile marker 87 right in the middle of beautiful Florida Key's. This Executive Bay Club Condo provides full 3 bed 2 bath accommodations with community amenities that include an outdoor swimming pool, free private parking, multiple tennis and pickleball courts. Huge Dock to see most amazing sunsets as well as go fishing along with beach access is available (No Boats Allowed with Rental).

3

Bed

2

Bath

8

Sleeps

$210.49

/ Nightly

Private Vacation Home

Charming 2 bedroom townhome at Executive Bay Club!

Islamorada, Florida, United States

Your chance to experience one of Islamorada's most sought-after communities has arrived! Brand new to the rental pool, this beautifully renovated townhome in Executive Bay Club (Unit C3) is the perfect escape for the winter season.brThe Owners have recently purchased and are in the process of refurnishing with all-new coastal-chic décor — photos coming soon! You'll love the modern updates, bright open spaces, and resort-style amenities.brEBC has it all: a newly refreshed pool and lounge area (looking AMAZING!), tennis and pickleball courts, and a stunning clubhouse overlooking the bay.brNow booking for the winter season — come enjoy the relaxed, island lifestyle at Executive Bay Club, where every day feels like vacation.brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

Bed

Bath

Sleeps

$394.62

/ Nightly

Condo

Seagulls 701: A charming 3BR condo in Tavernier, FL, perfect for families.

Islamorada, Florida, United States

Welcome to our penthouse condo, a stunning vacation rental with breathtaking ocean views. This modern and tastefully furnished space offers a seamless blend of comfort and luxury. The open layout maximizes natural light, highlighting the panoramic vistas of the sparkling ocean. Enjoy the convenience of a fully equipped kitchen, spacious bedrooms, and contemporary amenities. Immerse yourself in relaxation on the private balcony, where you can savor morning coffee or evening cocktails while taking in the mesmerizing sunset over the water. Ideal for those seeking a serene and upscale retreat, this penthouse promises an unforgettable coastal getaway. VR#-24-3171brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

3

Bed

2

Bath

6

Sleeps

$1416.61

/ Nightly

Private Vacation Home

Islamorada Palm Cove - Private Waterfront Home

Islamorada, Florida, United States

Welcome to Islamorada Palm Cove, a private four-bedroom retreat tucked inside a gated enclave in the heart of Islamorada, the Sport Fishing Capital of the World. Set along a protected lagoon with direct access to both Florida Bay and the Atlantic Ocean, this exceptional home offers private boat dockage and a ramp, making it ideal for anglers, divers and boaters alike. Spend your days on the water and your evenings unwinding in the heated and chilled pool, surrounded by lush tropical calm. Inside, the home features impeccable finishes, thoughtful design, and modern-day comforts throughout. The main living areas are bright and inviting, perfect for gathering after a day of adventure. Two of the four bedrooms are privately located downstairs and accessed separately from the main living space, offering added privacy for guests, extended family, or couples traveling together. Though peaceful and secluded, Islamorada Palm Cove is just minutes from downtown, where you’ll find renowned restaurants, local shops, and island culture. World-class sport fishing, fly-fishing, diving, snorkeling, and boating are right at your doorstep, with the coral reef and historic Alligator Lighthouse just offshore. Perfectly positioned for exploring the Keys, the home is approximately 1.5 hours from Miami and 2 hours from Key West, offering easy access while still feeling worlds away.brWhether you’re here for adventure or pure relaxation, Islamorada Palm Cove delivers the best of the Florida Keys—privacy, water access, luxury, and tranquility—all in one unforgettable setting.

Bed

Bath

Sleeps

$159.35

/ Nightly

Condo

Stunning view from this beautiful 1 bedroom condominium-Summer Sea, Islamorada

Islamorada, Florida, United States

Premier 1 bedroom unit with both a stunning bay view and a view of the pool off the private balcony. Fully updated with the open concept kitchen open to the dinning and living room. Stunning white cabinets and modern bathroom, Tile floors and granite countertops through out the apartment. Comfortable queen size bed with a pull out couch in the Livingroom. brThe perfect place to lounge and enjoy your days! brbrThe SpacebrThe condominium is right on the bay with two pools (one heated), a beautiful beach area, Marina with a new composite Dock, Fish cleaning stations, Tiki huts with BBQ grills and pick neck tables, Remodeled workout room and game room, community room, fabulous sunsets and friendly residential atmosphere. Safe and secure gated community with 2 brand new elevator. brbrFeatures/Location DescriptionbrSummer Sea is a multi-story residential waterfront condominium with a friendly atmosphere with on-site management. The perfect place to spend your vacation. This condominium is on Plantation Key just north of the famous Marker 88 Restaurant, a 5-star gourmet restaurant with outside bar. Four restaurants within walking distance. The complex is located at mile marker 88.5 which is within The Village of Islamorada. With an abundance of community areas such as a beautiful sandy area and lots of space to stretch, large, shared kitchen/entertaining area, game rooms, a gym, beach, 2 pools (one heated), laundry rooms etc. br28-day minimum, Minimum rental of 2 months when renting February. No Pets, No Smoking.brFlorida Lease required. application and background check performed by the condominium is required. Summer Sea Condominium requires a 5-day notice, and their $200 fee is nonrefundable. Please note that a $1,500 security deposit will be HELD against your credit card three days before your arrival and released after departure. This is not a charge, just a hold until it can be verified that there is no damage. If you cancel your reservation, a cancellation fee of 3% will be charged to cover costs. Summer Sea Condominium requires a 5 day notice. Feel free to inquire for all details.brOffered through Blue 9 Realty Inc., DBA Keys Vacation Brokers, Jonelle Kop, Tavernier, FL

1

Bed

1

Bath

4

Sleeps

$675.0

/ Nightly

Private Vacation Home

Ocean Front House: 3-bedroom house in fantastic Islamorada with cool AC

Islamorada, Florida, United States

This house is the perfect home base for your trip to Islamorada. With three cozy bedrooms, including a king bed and four twin beds, guests will find plenty of space to relax. Two bathrooms add convenience for everyone in your group. You can enjoy the amenities of a full kitchen. The house stays comfortable year-round thanks to air conditioning. We hope you enjoy what our place and Islamorada has to offer.

Bed

Bath

Sleeps

$1065.1

/ Nightly

Private Vacation Home

Coastal Retreat ~ Brand New 4-Bedroom Home in the Heart of Islamorada

Islamorada, Florida, United States

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, including a fully equipped kitchen and an outdoor grilling area. Enjoy the privacy of your own pool and patio that extend from the living area. Located in the very heart of Islamorada, where you can explore its vibrant culinary scene with some of the best restaurants, breweries and live music in town. Choose from Square Grouper, Pierre's and Morada Bay to Green Turtle Inn, Florida Keys Brewery or Islamorada Beer Company. To experience more of what Islamorada has to offer, take part in various activities, such as visiting the Theater of the Sea or Founders Park, kayaking or paddle boarding, or even chartering a boat for deep sea fishing or diving at one of many marinas around town. brGolf cart rental available at daily or weekly rates.brbrPlease note, this property is located in a brand new development with ongoing construction on the houses closest to the water. Our house is situated in the center of the development, therefore, the construction should not interfere with the vacation experience.

Bed

Bath

Sleeps

$1595.07

/ Nightly

Private Vacation Home

Experience luxury at Little Bay Compound in Islamorada with stunning views.

Islamorada, Florida, United States

Little Bay Compound - Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. brbrThe Upper & Lower Duplex are each 1,500 sq ft units, each with two bedrooms, two full baths, full modern kitchen, laundry, family room, and 10' x 40' porch overlooking the bay. Each unit accommodates 6 people (upper master bedroom: king and twin murphy, Guest bedroom: two twins, sofa sleeper) (lower master bedroom: queen and twin murphy, guest bedroom: two twins, sofa sleeper)brbrThe Cottage is a bright and airy 1,250 sq ft unit with a huge master bedroom (king & sofa bed), 2nd sunroom with sofa bed and twin murphy bed, two full baths, laundry room, and combined family room, kitchen, & great room. The Cottage accommodates 6 people. brAll units come equipped with central a/c and ceiling fans, loads of outdoor furniture and BBQs for each unit, large private boat basin with 12' X 25' Chickee hut and 12' X 25' Pergola, bait prep station, freshwater shower and power on the dock. The spacious front yard is enhanced by Tropical Landscaping and offers a large circular driveway with plenty of parking for cars and trailers. Located in the heart of Islamorada within walking distance to water & land activities, restaurants, shops, and more! brIf booking more than a year in advance current prices may not reflect annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brbrPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.brVR#- 24-0336, 24-0334, 24-0335 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.

5

Bed

6

Bath

18

Sleeps

$321.29

/ Nightly

Private Vacation Home

Deep Water Home located in White Marlin Beach Neighborhood

Islamorada, Florida, United States

PROPERTY NAME: Marlin Housebr156 Venetian Drive, Islamorada, FL 33036brbrLOCATION: Bayside Canal home located in the popular Islamorada neighborhood of White Marlin BeachbrbrMINIMUM STAY: 90 days, this is a 3 month minimum brbrMILE MARKER: 74.5brbrDETAILS: You will love this charming and cozy Keys Holiday Rentals home! There is a wonderful open concept floor plan with 2 nicely proportioned bedrooms and 1 bath. The kitchen is updated and user friendly. For the boaters in the family, you can dock up to a 38ft boat in the canal behind the house. This property has a private small boat ramp that can be used to launch a boat in the canal. The deep and wide canal with quick access to the bay will be a favorite. The Channel 5 Bridge is a short ride, and you can be in the Atlantic Ocean in no time. There's a gorgeous private sandy beach only available to residents of the White Marlin neighborhood. No Smoking Property.brbrSLEEPING ARRANGEMENTS: Sleeps 4 comfortablybrPrimary Bedroom: King Bed Private Bathroom with Shower and TubbrGuest Bedroom: Queen Bed Shared Bathroom with Shower/Tub CombobrbrAMENITIES INCLUDE: This home features dockage on a wide, deep-water canal. It can accommodate boats with maximum length of 38 Feet and only Minutes to the Bay.brbrACTIVITIES: Beach, Swimming, Boating, Offshore Fishing, On Shore Fishing, Paddle Boarding, Museums, Wildlife Reserves, Art, Shopping, Historic Tours and Culinary Adventures. If you run out of things to do, Miami is only 83 miles away. brbrENHANCED CLEANING, DISINFECTION AND SANITIZATION: Our number one priority is the wellbeing and safety of our guests. We have contactless check-ins and check-outs. Our properties are cleaned and sanitized by professionally trained and equipped housekeepers who provide quality service, security and personal accountability. We use CDC housekeeping protocols, approved disinfectants and personal protection equipment. Our properties are private, well maintained, hygienic and sanitized. A whole safe and private space just for you and your family.

2

Bed

1

Bath

4

Sleeps

$1175.49

/ Nightly

Private Vacation Home

Oceanfront 3 bedroom with dock

Islamorada, Florida, United States

Behold this exquisite oceanfront pool residence, which has been flawlessly renovated. Nestled in a remarkable location with direct access to a sandy beach and a private dock, this noteworthy home boasts two bedrooms and two baths on the upper level, while the lower level comprises a spacious entertainment area alongside a bedroom and a bath. Embracing an expansive half-acre lot with 100' ocean frontage, the property showcases breathtaking vistas across the majestic Atlantic Ocean. Prepare to be captivated--this residence cannot be missed!

Bed

Bath

Sleeps

$563.63

/ Nightly

Private Vacation Home

Enjoy a serene stay at 137 LeSerra Lane, a 3-bedroom canal retreat in Islamorada.

Islamorada, Florida, United States

Beautiful designer-appointed oceanside canal home located at Mile Marker 76.5 on Lower Matecumbe Key in Islamorada. Situated as the second home from the point, the property enjoys beautiful ocean views and a peaceful setting while still being close to everything Islamorada has to offer.brbrThe home features a bright, open layout with modern décor and water views from nearly every window. The fully equipped kitchen includes a dishwasher, microwave, coffeemaker, toaster, and blender—everything you need to prepare meals after a day on the water. The home also offers Wi-Fi and two flat-screen TVs for your comfort.brbrBoaters will appreciate the protected dockage for up to two boats, including 30 feet of dockage and a fish cleaning station, making it easy to enjoy Islamorada's world-class fishing.brbrThe location is ideal for exploring the area. Anne's Beach is just nearby, offering nature trails, boardwalks, picnic and BBQ areas, and sandy spots tucked into the mangroves. You're also just minutes from Robbie's Marina, Bud N' Mary's, and Caloosa Cove Marina, making it easy to book a fishing charter, rent a boat, or enjoy local dining.brbrDespite being close to everything, the home sits in a quiet part of town while still only minutes from “Downtown Islamorada,” including Worldwide Sportsman and the Islamorada Fish Company.brbrThis property has become a favorite for many guests, with visitors returning year after year to enjoy this special spot in the Keys.brbrPlease note: if booking more than one year in advance, pricing may be subject to annual cost-of-living adjustments. Reservations are confirmed after speaking directly with our team.brVACATION RENTAL LICENSE: 24-0300 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.brIf booking more than a year in advance current prices may not reflect the annual cost of living increase. brMany of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us. brPlease note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.

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Bed

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Bath

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Sleeps

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