Vacation Rentals By Owner In Islamorada, FL

$375.64

Discover comfort at Alligator Reef - Lobster Home in Islamorada, perfect for families.

Islamorada, Florida, United States

The Lobster Home is a charming 2 bedroom, 2 bathroom oceanfront home located on the gated Alligator Reef property in Islamorada. Set just steps from the water, this home offers a relaxed Keys atmosphere perfect for a peaceful getaway.brbrGuests staying at Lobster enjoy access to the beautiful shared oceanfront grounds, including a sandy lounging area with a fire pit, an observation dock, and kayaks and paddleboards for exploring the clear waters.brbrComfortable and inviting, the Lobster House is ideal for a small family or couple looking to enjoy the beauty of the Florida Keys in a quiet waterfront setting.brbrFor larger groups or extended families, the nearby Conch House (3 bedroom, 2 bath) on the same property can also be reserved, allowing both homes to be booked together for a private oceanfront compound experience.brbrEnjoy the laid-back island lifestyle, ocean breezes, and endless views that make this special property a true Keys escape.brVACATION RENTAL LICENSE: 24-0389 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 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.

2

Bed

2

Bath

6

Sleeps

$455.63

/ Nightly

Private Vacation Home

Exclusive White Marlin Beach Retreat - Private Beach Access & Dock

Islamorada, Florida, United States

Your Islamorada waterfront getaway awaits at this charming three-bedroom home, offering comfortable accommodations with two queen beds, one full bed, and one twin bed. The home is fully air-conditioned and designed for relaxing after days spent on the water or exploring the Keys. Enjoy direct canal access with dockage for fishing boats, paddleboards, and kayaks, plus quick access to both the Atlantic Ocean and Florida Bay. A rare private sandy beach access adds an exceptional touch to this Islamorada property. Located in the heart of the Sportfishing Capital of the World, you’re just minutes from world-class offshore and backcountry fishing, snorkeling, diving, and renowned waterfront dining. Whether you’re planning a fishing trip, island escape, or laid-back beach vacation, this waterfront rental offers the ideal blend of comfort, convenience, and coastal beauty.

Bed

Bath

Sleeps

$393.76

/ Nightly

Apartment

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Islamorada, Florida, United States

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 559 sq. ft, equipped with complimentary toiletries, TV.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 18 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✦ Pool is available.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 $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Bed

Bath

Sleeps

$387.0

/ Nightly

Private Vacation Home

Bungalow #5 - 2 Bed/1 Bath & Pool in Islamorada

Islamorada, Florida, United States

Tucked away in the vibrant Florida Keys, is our pristine Bungalow paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing getaway, look no further. Relax with the family in this cozy Island retreat. Completely remodeled! Come enjoy the community heated pool and a morning bike run. Enjoy the Florida Keys with your own private backyard and private parking.

Bed

Bath

Sleeps

$659.01

/ Nightly

Private Vacation Home

Morada Zen - 4BR/3Bath Waterfront Ocean & Bay Access, Pool, Tiki, Dockage

Islamorada, Florida, United States

Islamorada Florida - Fishing Capital of the World!! Beautiful 4 bedroom, 3 bath home available for monthly rental (28 day minimum with 2 month minimum January 2026 to April 2026). Located on a wide harbor with quick access to the Atlantic Ocean and Florida Bay. Decorated in the Keys Cottage Style, you'll be impressed by the interior and absolutely WOWED by the exterior! Heated pool, hot tub, tiki hut, dockage, boat lift, covered dining area with a 10 person teak table, grills, bicycles, paddle boards, and the Zen Lounge. This is a 2 story home - Upstairs offers 1 King en suite bedroom, 2 Queen Br's and Guest Bath, Living Room, full Kitchen, dining area, screened porch. Downstairs has private access to 1 King Bedroom, Bath, Living Room and kitchenette. Plenty of sunning area around the pool, pool toys, and a SWAT misting system to keep the bugs away! Wifi and 5 tv's with streaming. Across the highway and a 5 minute walk away is Founder's Park with walking trails, exercise stations, volleyball court, pickleball and tennis courts, beach, pool, boat ramp. Islamorada offers quite a few options for fine dining, boutique and gallery shopping, several breweries, eateries within walking distance. Boat rentals available across the harbor. There's no better place to escape to than Morada Zen!

Bed

Bath

Sleeps

$805.58

/ Nightly

Private Vacation Home

Beach Dream House, relax and enjoy the clear waters of Islamorada FL

Islamorada, Florida, United States

Welcome to our Dream Beach House where you can enjoy the most panoramic views in Islamorada, Florida. Enjoy the sun rising over the Atlantic Ocean and superb views from every room in the house: 360 degrees of glass and a wraparound balcony . Pool and private sandy beach. Two spacious rooms and a very large loft. brThe loft is a great getaway for kids and young adults with spectacular views of the ocean, along with a pool table, queen bed and extra large brL shaped sofas along the windows, and smart TV. Kayaks and paddle boards are available for our guest to enjoy the clear waters of the Florida Keys. Pool is heated at 85 degrees year around. brSea turtle nests are in the area, if u get lucky u could see baby turtles hatching one day. brOur Dream House is near the best restaurants in Islamorada. Gated, very private 1/2 acre, slice of paradise. Special rate for monthly rentals.brbrPlease we really appreciate your reviews !!!! brWe Thank U and God bless U always. brbr

Bed

Bath

Sleeps

$550.01

/ Nightly

Private Vacation Home

Completely RENOVATED Water Front OASIS! ONE Story! NEW stunning POOL, MINI GOLF!

Islamorada, Florida, United States

We invite you to stay in our waterfront oasis! Relax in the stunning NEW pool or have fun playing mini golf just out back. This beautifully updated home features private dock access, a fully renovated outdoor space with a tiki area, and a fenced in yard for added privacy. Home offers a spacious floor plan with an additional den area. Home is immaculate with amazing views and an open floor plan.brbrThis gem offers many amenities including, washer, dryer, cable, high speed internet, barbecue. Enjoy paradise from the back yard, which offers waterfront tikki, above stunning NEW pool, mini golf, and spacious terrace with outdoor TV. Home offers over 60 feet of dockage, small boat ramp, and outdoor cleaning station. brbrHome is centrally located in Plantation Key Colony, Islamorada, a safe and quiet neighborhood. Home is less than a mile away from the grocery store, movies, hospitals, and some of the best dinning in all of Islamorada. Access to community boat ramp and Plantation Key Colony park with be granted. Property is located minutes from the renown Founders Park!brbrThis piece of paradise is located on a deep water canal. You have immediate Ocean access through Tavernier Creek. Minutes away from some of the World's best DIVE Spots and Sandbars!

Bed

Bath

Sleeps

$465.51

/ Nightly

Private Vacation Home

Beautiful Islamorada Waterfront Home

Islamorada, Florida, United States

Fully renovated 5-bedroom 3-bathroom vacation style home for rent in Islamorada on a canal. It is located near the white Marlin Beach. Comes completely furnished with a beautiful coastal design that will make you feel on vacation 24/7. 2 bedrooms are on the first floor with a bathroom and their own living room. It has an outside staircase access to the second floor where there is an open concept spacious kitchen and the other three bedrooms. This property also has a crystal-clear pool and a dock to park your boat. Property is being offered at $12,000 a month. 28 Night Minimum

5

Bed

3

Bath

8

Sleeps

$2493.63

/ Nightly

Private Vacation Home

Turtle Cove: Stunning 7-bedroom home in Islamorada with a private pool and open water views.

Islamorada, Florida, United States

Turtle Cove - Turtle Cove is a true hidden treasure in Islamorada. This oceanfront gated estate consists of an enclave of four charming cottages nestled in beautiful landscaping with a total of seven bedrooms and seven bathrooms. When entering through the gate you will feel a sense a tranquility that makes you realize your vacation has started. Each cottage has it's own personality with an array of unique, yet tasteful decor. The property offers a boat basin, tiki hut, oceanfront pool, outdoor showers, paddle boards, kayaks and bikes. All of this combined to make the perfect family retreat. Your own little oasis you'll never have to leave. brVR#24-0385, 24-0386, 24-0416, 24-0134brbrIf 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.

Bed

Bath

Sleeps

$630.38

/ Nightly

Private Vacation Home

GREAT LOCATION !!! White Marlin Beach House, Islamorada

Islamorada, Florida, United States

Contact owner for rates and availability (305-431-2006).brRelax in Islamorada, Florida Keys... 'Sport Fishing Capital of the World.' Enjoy deep blue water or back country fishing. Dive, snorkel, and swim on a clear, white, sandy beach (rare in the Keys!). Walk/jog among beautiful waterfront homes. Sip wine while gazing at glorious sunsets while surrounded by coconut palms.brbrManatees, tarpon, mangrove snappers, and other native fish species swim the waters off our dock. Beautiful tropical vegetation, shore birds, and other marine life are all around you. You will cherish the memories of your stay in this 'Island Paradise.' Islamorada is known as 'The Purple Isle' and is located in the heart of the Florida Keys - midway between bustling Miami and laid-back Key West.brbrThis charming island home on a deep-water canal features high-beamed ceilings and a 'loft.' The walk-around deck, open floor plan, and kitchen designed for entertaining make this home an excellent choice for a carefree vacation. The home is newly furnished and redecorated and has two spacious bedrooms each with a private bath. The home is equipped with High Speed Wireless Internet Access.brbrThe home's 70-foot boat dock gives easy bay and ocean access and the private beach is a few steps away with your own private access.brbrKeywords: Beach House

Bed

Bath

Sleeps

$393.46

/ Nightly

Private Vacation Home

LAST MINUTE MEMORIAL WEEK 300 a NIGHT SUMMER 2026 SPECIAL DISCOUNTED RATES

Islamorada, Florida, United States

Our house is located in Islamorada, FL, the fishing capital of the world. Our single-family, Key-style home is located in an exclusive gated community of 50 island homes called Angler's Reef. The community includes a beautiful oceanfront pool, a private marina, and two stunning man-made beaches, a rarity in the Florida Keys. A famous sandbar amid turquoise waters is located right in front of the community and can be reached by kayak or boat.brbrOur island home is cleaned professionally and we maintain a non-smoking pet-free environment. The house sleeps four and has a Master bedroom with an en-suite Master bathroom and a large private balcony. The large second bedroom is also a master suite featuring an en-suite bathroom with a tub and a small private balcony. The living area includes a formal dining room and living room, as well as a modern open kitchen. A large queen sofa bed can accommodate two if more sleeping space is needed. A large private porch amid lush tropical gardens with BBQ and white wood rocking chairs. The house is tastefully decorated and equipped for all your needs to enjoy a perfect vacation.brbrOur village offers restaurants for all tastes and prices as well as fun adventures for singles, couples and families. We have numerous unique boutiques and shops, where you can also find rare items. But most important is that you will have the time of your life in our beautiful place in Angler's Reef!brbrNote: Children welcome, non smoking only, pets not allowed, wheelchair inaccesible

2

Bed

2

Bath

6

Sleeps

$379.69

/ Nightly

Private Vacation Home

Escape to beautiful Islamorada!

Islamorada, Florida, United States

Located 90 minutes from Miami and 20 minutes to the world-famous Tiki Bar sandbar (dock to anchor) one of the best in the Keys. Enjoy easy and quick access to the bay or ocean via Snake Creek, excellent fishing/water activities, dining, and amazing sunsets. There is a marina located nearby that sells fuel, bait, ice and offers boat rentals.brbrThis is a 2 story property, 4 bedrooms and 2 bathrooms are on the 2nd floor, the first floor has a kitchen, living room and full bathroom. The deep water canal is double-wide and you have 70' of dock.brbrThere is 28 night minimum stay required and offered for rent October 1 - April 30.

4

Bed

3

Bath

10

Sleeps

$495.02

/ Nightly

Private Vacation Home

Best location in downtown Islamorada. 2 Houses with Beach access!

Islamorada, Florida, United States

Unbelievable location in Islamorada Florida Keys! You have beach access and boat trailer parking. This listing is for 2 houses - 1 property. The 2 homes are right next to each other offering plenty of space for your group getaway. Walk to the beach and walk or bike to great restaurants, marinas and shopping. The beach is a 2 minute walk down the street as well as the famous Islamorada Brewing Co! The home comfortably sleeps 10 people. We are a local family who is happy to help with your Island Getaway!

Bed

Bath

Sleeps

$630.38

/ Nightly

Private Vacation Home

GREAT LOCATION !!! ** White Marlin Beach House, Islamorada FLORIDA KEYS

Islamorada, Florida, United States

Contact owner for rates and availability at (305-431-2006).brRelax in Islamorada, Florida Keys... 'Sport Fishing Capital of the brWorld.' Enjoy deep blue water or back country fishing. Dive, brsnorkel, and swim on a clear, white, sandy beach (rare in the brKeys!). Walk/jog among beautiful waterfront homes. Sip wine while gazing at glorious sunsets while surrounded by coconut palms, Manatees, tarpon, mangrove snappers, and other native fish species. Swim the warm waters at our beach and fish off our dock. Beautiful tropical vegetation, shore brbirds, and other marine life are all around you. You will cherish brthe memories of your stay in this 'Island Paradise.' Islamorada Florida is known as 'The Purple Isle' and is located in the heart of the Florida Keys - midway between bustling Miami and laid-back Key West.brThis charming island home on a deep-water canal features high-beamed brceilings and a 'loft.' The walk-around deck, open floor plan, and brkitchen designed for entertaining make this home an excellent choice brfor a carefree vacation. The home is newly furnished and redecorated brand has two spacious bedrooms each with a private bath. The home is brequipped with High Speed Wireless Internet Access.brThe home's 70-foot boat dock gives easy bay and ocean access and the brprivate beach is a few steps away with its own private access.

Bed

Bath

Sleeps

$1113.75

/ Nightly

Private Vacation Home

3 Bedroom Private Oceanfront House - Sol

Islamorada, Florida, United States

Nestled in the tropical setting of La Jolla Resort in Islamorada, Florida, this 3 bedroom private oceanfront house overlooks the bay, with unparalleled privacy and nearly 2 acres of tropical trees, private boat docks and some of the best unobstructed sunset views the keys have to offer. Complete with fire pits, private outdoor seating, chaise lounges and plenty of room to unwind and relax.brbr*Guests can use all the amenities offered at La Jolla Resort including the pool and beach area.

3

Bed

3

Bath

8

Sleeps

$281.26

/ Nightly

Hotel

Comfort and Convenience! Free Onsite Parking, Pets Allowed, Free Breakfast

Islamorada, Florida, United States

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 495 sq. ft, equipped with complimentary toiletries, TV.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 18 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✦ Pool is available.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 $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Bed

Bath

Sleeps

$393.76

/ Nightly

Apartment

Your Home Away From Home! Onsite Pool, Free Breakfast, Free Parking

Islamorada, Florida, United States

Take a break and experience the laid-back lifestyle in the beautiful Islamorada!brbrThis listing is for a room within a hotel.brbr✦ Your room is 559 sq. ft, equipped with complimentary toiletries, TV.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 18 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✦ Pool is available.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 $50 refundable deposit, returned after check-out if no damages occur.brbr✦ Pets are welcome with an additional charge of $50.00 (per pet per night). per pet, per night. Up to 2 dogs, max 50lbsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ A mandatory resort fee applies per unit, per night, plus applicable taxes.

Bed

Bath

Sleeps

Select Dates for Price

Hotel Resort

Keys Villa

Islamorada, Florida, United States

Two bedroom gem in the Florida Keys!! Enjoy our sand beach, beautiful sunsets, fish from our docks, swim in our pool, relax in our hot tub or explore in our kayaks. Private boat ramp and boat slip!!

2

Bed

2

Bath

6

Sleeps

$229.5

/ Nightly

Private Vacation Home

Charming 2-bedroom house in welcoming Islamorada with WiFi, AC

Islamorada, Florida, United States

This brilliant house in Islamorada is a wonderful choice for guests seeking a cozy retreat. With 2 bedrooms, 2 bathrooms, pool, and essential amenities like WiFi and AC, this home offers everything you need for a comfortable stay. Whether you're relaxing in the living room or enjoying the outdoor space, you'll feel right at home here. You're sure to make fantastic memories with a stay at our place.

Bed

Bath

Sleeps

$394.13

/ Nightly

Private Vacation Home

Islamorada's Anglers Reef- Extra special June rates

Islamorada, Florida, United States

Welcome to 128 Anglers Way: Morada Daydreaming. Our home away from home in the Angler's Reef exclusive gated community is calling you. This house has 2 bedrooms upstairs, each with it's own full bath and private balcony. Washer and dryer combo is conveniently located upstairs near the bedrooms. The house is family friendly and includes a pack and play.brbrThe main level open floor plan features peek a boo ocean views. It also contains a half bath, a full kitchen with stainless steel appliances (including a double oven), granite countertops, Brazilian cherry hardwood floors, and a living/dining combo. A brand new washer and dryer was installed in January. A cozy outdoor seating area and gas grill is provided off the back porch.brbrAngler's Reef is a premier resort style complex at MM 85 with only 52 houses. The neighborhood includes a heated community pool that overlooks the ocean, complimentary kayaks and paddle boards (first come, first served upon signing a waiver), private marina, and a private 500 foot beach. If a boat slip is required, we can assist you in renting one for boats up to 31' in length. The neighborhood is lushly landscaped and our unit comes with two assigned parking spaces. The location is ideal with many wonderful restaurants and attractions nearby - several within walking distance.

2

Bed

2

Bath

6

Sleeps

Vacation Rentals By Owner In Islamorada, FL

$375.64

$455.63

$393.76

$387.0

$659.01

$805.58

$550.01

$465.51

$2493.63

$630.38

$393.46

$379.69

$495.02

$630.38

$1113.75

$281.26

$393.76

$229.5

$394.13

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