Vacation Rentals By Owner In Islamorada, FL

Welcome to your slice of the Florida Keys at the Bay Harbour Condominium Complex in Islamorada. This bright and spacious 2-bedroom, 2.5-bath condo offers the perfect mix of comfort, style, and laid-back island living—ideal for a relaxing getaway with friends or family.brTucked inside a quiet, gated community, you’ll feel away from it all while still being close to everything that makes the Keys special.brThe kitchen is fully equipped with granite countertops and stainless steel appliances, making it easy to cook up your fresh catch or a casual dinner at home.brInside, the condo is bright, spacious, and thoughtfully designed with a clean coastal aesthetic. The open living area is filled with natural light and flows seamlessly onto a private screened-in balcony—ideal for morning coffee, evening cocktails, or simply enjoying the warm ocean breeze.brThe fully equipped kitchen features granite countertops and stainless steel appliances, making it easy to prepare anything from a quick breakfast to a full seafood dinner after a successful day on the water.brBoth bedrooms offer privacy and comfort, each with its own en-suite bathroom. The primary suite includes a king bed, balcony access, a large walk-in closet, and a spa-style bathroom with soaking tub, walk-in shower, and double vanity. The guest suite features a queen bed, pool views, and plenty of storage—perfect for couples or friends traveling together.brStep outside and enjoy beautifully maintained tropical grounds, a large resort-style pool, hot tub, and plenty of space to relax in the sun. Start your day with a workout in the fitness center or a match on the tennis courts, then cool off poolside.brBringing a boat You’re in the right place. Your private boat slip (with power & water) is just steps away, with quick access to both the bay and ocean—perfect for fishing, sandbars, or sunset cruises. Fish cleaning stations and grilling areas make it easy to enjoy your catch at the end of the day.br Resort-Style AmenitiesbrBay Harbour offers a full suite of amenities designed to enhance your stay:br• Heated/chilled pool & jetted hot tub br• Tennis courts & fitness center br• Clubhouse & beautifully maintained grounds br• Outdoor grills & fish cleaning stations br• Covered parking plus guest parking brAfter a day of fishing or exploring, clean your catch and enjoy a relaxed evening grilling by the pool as the sun sets over the water.

Condo

Just a Few Friends - Ocean View and Bring your Boat!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1118.27

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 shared pool is available, opened from 8:00AM to 10:00PM.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 $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Bayside Tranquility: 2 Spacious Villa w/ Private Patio | Onsite Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1409.6

This listing is for 3 separate rooms within a hotel. The price shown in the listing covers all 3 rooms.brbr✦ Each room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $300 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Bayside Tranquility: 3 Relaxing Villa w/ Spacious Living Area & Kitchen

Islamorada, Florida, United States

Bed

3

Bath

18

Sleeps

$1492.82

This listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Rooms are not adjoining and possibly not next to each other. Spaces are assigned upon arrival based on availability.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 shared pool is available, opened from 8:00AM to 10:00PM.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 $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

2 Relaxing Bayfront Villa w/ Private Patio | Scenic Bayside Resort

Islamorada, Florida, United States

Bed

Bath

Sleeps

$583.76

Welcome to Angler’s Reef Villas & Marina, a stunning Islamorada vacation destination. Quaint streets and walking paths wind through this Caribbean fishing village-styled retreat, dotted with 52 cottages inspired by Native Conch and British West Indies themes adorned with metal roofs and gingerbread trim. More than five hundred feet of oceanfront and mangroves frame 36 protected, optional deep-water boat docks, perfectly poised for aquatic excursions.brbr*****ALL rentals must be from Saturday to Saturday. No Midweek rentals*********br*****Optional Dock is available to rent - Weekly Rates will Vary Slip 19**brbrLush, tropical landscape adorns this property. Find your home away from home in this two-bedroom, two and a half bath conch-style townhouse overlooking the resort style swimming pool. Our home has ocean views, 2 spacious decks, full kitchen, and other inspired amenities for your best vacation yet.br br****Optional Dock space is available to rent - Weekly Rates Vary Slip 19**br- 1 KING bed in the master bedroom with flat screen TV; br- 2 Queen with guest bedroombr- 2 FULL Bathrooms with SHOWERS and blow dryers + 1/2 Bathbr- LIVING ROOM with 2 SEPARATE SEATING areas with TV;br- DINING AREA for 6: with a table for 4 and 2 counter seatsbr- In-unit WASHER/DRYER;br- Fully equipped KITCHEN with appliances, KEURIG coffee maker, toaster;br- 2 BALCONIES with seating; br- All linens, beach and bath towels, bathroom essentials, kitchen utensils, plates, cookware, glasses are provided. brYou don’t need to bring a thing! This home is great for a family vacation. There is also a beach and kayaks available. brbrReserve your stay today!brbrOffshore, three miles south, is the famed Alligator Reef while just east lays the only living coral barrier reef in the Continental United States. Islamorada, located in the heart of the Florida Keys also teems with sailfish, tuna and dolphin in the Atlantic Ocean and tarpon and elusive bonefish in Florida Bay, and is known as the “Sport Fishing Capital of the World.”brbr*** All rentals must be from Saturday to Saturday. No Midweek rentalsbr*Dock space is available to rent - Weekly Rates Vary Slip 19**br*Please check slip availability prior to booking. br*Moored vessels may not exceed a maximum bridge height of 9 Feet, total length of 31 feet, or draft of 3.5 feet.br*Available for weekly and monthly vacation rentals.

Pool Front Home with Ocean Views at Anglers Reef in Islamorada and Slip.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$365.63

Beautiful bayside villa in Islamorada. Sandy beach, fishing dock, pool, tennis court and boat slip for up to 25 ft boat included. Bicycles available. Close to many restaurants, bars and places of interest.

Villa

Tropical Paradise

Islamorada, Florida, United States

Bed

Bath

Sleeps

$328.5

Perched on the second floor with partial side views, this charming studio is perfect for a cozy getaway in the heart of Islamorada. Designed to sleep up to 3 guests, the suite features a comfortable queen-size bed, a twin sleeper sofa, and a full bathroom for your convenience.brbrYour stay comes with access to the exceptional amenities at Caloosa Cove Resort and Marina. Relax by the heated pool, bask in the sun on the beach. Stock up on essentials at the General Store, or stay connected with complimentary Wi-Fi. Feeling adventurous Head to the on-site marina for Charter Boats or boat slip rentals and experience some of the worlds best sport fishing right at your doorstep.brbrExploring the area is a breeze with Caloosas free transportation app, and dont forget to take advantage of the Caloosa KeyCard, which grants you free access to Founders Park. This 25-acre haven features sandy beaches, a saltwater swimming area, and plenty of space to relax and unwind. Please Note: Guest passes to Founders Park do not include pool use.brDisclaimer: Photos represent typical units. Views and layouts may vary; furnishings are consistent throughout.brWhile we strive to maintain excellent amenities, occasional maintenance or unforeseen issues may arise.

Apartment

Coastal Studio Getaway – Second Floor with Partial Water Views

Islamorada, Florida, United States

Bed

Bath

Sleeps

$433.92

This Property is fully insured for rentals and licensed by the Village of Islamorada, license #24-0318.brbrWelcome to 134 Anglers, a luxurious escape for your vacation needs. Perfect for families, couples, or a friends getaway. Located in Anglers Reef, a gated community with heated swimming pool and two private beaches. Our availability calendar is always up to date and current.brbrOur beautiful house has 2 Bedrooms, 2.5 Bathrooms, A/C, Quartz counter tops, modern stainless steel appliances, SMART Tv's. Open porches and balconies, rich hard wood floors, dining room seating for 6, coastal décor. A truly unique place to stay in the keys, with a boutique – style feel.brbrAnglers Reef is one of the Florida Keys most luxurious developments with 52 villas and 30 boat slips. Set in meticulously landscaped gardens, overlooking a private heated 75 ft. swimming pool, private beach and the magnificent Atlantic Ocean. brbrAnglers Reef is the perfect home for fishing and diving enthusiasts, foodies, and anyone who enjoys beautiful sunrises and sunsets, the wonderful Florida sun, kayaking, paddle boarding, jet skiing, snorkelling – the list is endless. You may even spot Manatees in the Dock.brbrFor your convenience, we provide complimentary Wifi, Beach towels (as well as house towels), bed linens, washer, dryer, dishwasher, BBQ, books and lots of information about where to eat/what to do. 2 designated parking stalls, with single covered carport. Boat launch at neighboring Snake Creek Marina. The perfect Vacation Rental at Mile Marker 85.brbrIf you like staying in luxury accommodation with all the amenities you could possibly want or need then this is the house for you! Please call or email for a quote or for more information. brbrPets are not allowed

Anglers Reef- Family Friendly Community at a Fraction of the Cost.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$916.88

Come enjoy the beautiful Florida Keys in this new build stylish villa located in Islamorada close to shopping & restaurants but private and secluded perfect for a short term retreat to live a real island life! Welcoming seasonal snowbirds as well as short term group trips. Entire home completely stocked with all linens/supplies for ease, comfort and finished with immaculate decor. 5 bedrooms, 3 full bathrooms, private outdoor shower and private outdoor bath tub, 2 family private setup with each floor boasting its own living room, kitchen, coffee bars, ocean front master on each as well as private entrances per floor. Upstairs kitchen decked w/ Italian Bertazzoni appliances, 4 seat island with bar sink & wine fridge. Each bedroom equipped with smart TV's, balconies with outdoor furniture to sip sunset cocktails or enjoy nespresso watching the phenomenal sunrise each morning. Each bedroom has a walk-in or expansive closet equipped with everything needed for your stay. Weekly cleaning hotel-like services available . Fully equipped laundry room on each floor and garage full of beach games, rafts, bikes, paddle boards, kayaks, professional ping pong table, massive rafts that float 10 people that you can pull right into the ocean in footsteps . Parking available for up to 10 cars as well as plenty of room for water toys/boats. Access to boat ramp or potential space at a marina. Top floor terrace boasts a mini outdoor kitchen/BBQ and dining table with lounge chairs. First floor terrace boasts a brand new fully equipped kitchen with 2 fridges, BBQ, cooktop, sink, icemaker and plenty of lounge furniture. Look no further, this villa will be a special place to create your island memories. Sleeps 14 privately and comfortably. Need more space. ..my next door neighbor has her 2 bedroom/2bathroom beach home for rent ! Host your entire family with 2 villas on the ocean with huge stretches of sand and ocean! Discount possible with more than a 2 month stay.

Villa

Ocean Front Villa, 3/4's acre of private beach! Serenity, Retreat, Island Life!

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1245.85

Sunset Reef is professionally cleaned including all linens and towels. The owners or property manager do not do the cleaning. and laundry.brbrIslamorada Florida is known as the Sports Fishing Capital of the Florida Keys. Our custom designed and built 5000 square foot home, “Sunset Reef,” is half way between Key West and mainland Florida. Our home is located on the calm bayside at Mile Marker 76 on the Historic Overseas Highway. The highway follows Henry Flagler’s famous railroad to Key West that was destroyed in the deadly Labor Day hurricane of 1935. Miami International Airport is a 90 minute drive without rush hour traffic. Fort Lauderdale International Airport is a 2 hour drive without rush hour traffic. From Sunset Reef a visit to Key West is an easy 75 mile, 90 minute drive. “Downtown Islamorada” is home to a number of great restaurants for casual waterside dining or more upscale seafood, chop or steak dinners. Whether you are coming to the Keys for a restful break from cold weather, to catch lobster and stone crabs, to go scuba diving, to spend your time fishing the back country for snook, redfish, bonefish and tarpon or to go off shore fishing for dolphin, wahoo, snapper and grouper, Sunset Reef in Islamorada can be your comfortable home away from home. Our Islamorada vacation rental license number is 25-0266. Maximum of 8 adults plus children under age 7 for a maximum of 10 people for Sunset Reef rentals. brbrSunset Reef is a private, gated, one and one quarter acre, bayside waterfront estate. From outside the reef scene gates on Overseas Highway, US 1, you have no idea what is located on the property. The “Keys” styled home is surrounded by manicured grounds. We are located on the calm bay side of Lower Matecumbe Key in Islamorada, Village of Islands, Florida. The property includes a pool and hot tub looking out over the bay and Matecumbe Bight. There is a 90 foot deep water dock with 50 Amp shore power and water available. The bayside deck area has Adirondack chairs and a wood burning fire pit. The pool area includes lounges, tables and umbrellas. Relax in the hammock or a lounge, read a book, snorkel and swim in the calm shallow bay water, have fun on a stand up paddle board or kayak south to the “hurricane hole” to look for Manatees. You can fish from the dock and walk into the water to snorkel for lobster. We never tire of the stunning sunset views from the bayside deck area and then enjoy an open fire sitting around the fire pit on cool evenings. brbrOur 4 bedroom, 4 ½ bath home is three stories with a roof top sundeck. The elevator can take you, your luggage and groceries to all indoor living levels of Sunset Reef. You will climb the spiral staircase from either the middle level or the upper level to the roof sundeck for views of not only the islands in Everglades National Park on the bayside, but of the Atlantic Ocean and the historic lighthouse on Alligator Reef. Walk the property through our shade garden, ring one of the peace bells, sit on a teak bench and relax amid the native and tropical landscaping. The spacious ground level covered patio facing the bay is perfect for entertaining and dining. The complete “outdoor kitchen” includes a large gas grill, burners and rotisserie. brbrThe entire home was designed to embrace the fabulous west facing bay views. The upper level contains the living/dining great room, large gourmet kitchen, powder room and master bedroom. The entertainment area has a wall mounted SMART HDTV, DVR, and a stereo system including speakers in the master bedroom, bathroom and on the outside deck. The master bedroom has a desk area, walk-in closet and bathroom with a double shower/steam room, separate jetted tub and double vanity. The entire west wall of the great room is sliding glass doors opening onto a covered deck for dining, lounging and relaxing. There is a built in gas BBQ, lounges, dining table and seating area. The all granite kitchen has an island with cook top, prep sink and eat-in area. There is a third prep/bar sink at the elevated bar/eat-in area. All of the stainless steel appliances, 48 inch refrigerator/freezer, double convection oven/microwave, warming drawer, dishwasher, ice maker and wine cooler are top of the line. The kitchen is completely stocked with all necessary small appliances including a Keurig beverage maker, drip coffee maker, electric kettle, cookware, serving pieces, platters, pizza pan, cookie sheets, cutlery, food processor, teapot, toaster, blender, waffle iron, etc.brbrThe middle level has three bedrooms with en-suite bathrooms. All bedrooms open onto outdoor covered deck areas with lounges, tables and chairs. There is another living area on this level with a desk area, wall mounted HDTV, DVD player and speakers on the outside deck and ground level outdoor kitchen area. The laundry room is also located on the middle level. brbrThe ground level has the entry area with the elevator and stairs to the middle and top levels. The storeroom has a refrigerator/freezer, a chest freezer, coolers, paddles, USCG life jackets, bicycle helmets and pool towels. 6 Kayaks, 4 SUPs and an assortment of bicycles are included for guest usage. The garage and motorized watercraft are not included with the rental of Sunset Reef. The house has the X-1 Comcast Cable TV and fast residential Internet available. Both hardwired and passphrase secured wireless Internet access is available on both living levels.brbrSunset Reef has immediate access to Everglades National Park and back country fishing. Atlantic Ocean access is 2.5 miles SW to Channel 2 and 3.5 miles to Channel 5 for larger boats. Robbie's marina and Atlantic Ocean access is 2 miles NE through a mangrove channel.brbrIf you zoom in on the map, the icon will come down on the exact location of Sunset Reef.brbrNeed baby gear during your stay We have some baby gear that is available to our guests. This includes a full sized crib, high chair, and a couple of pack-n-plays. We do not have enough to supply both of our vacation rental properties in Islamorada, so check with us first We have set up an account with BabyQuip to help our guests with obtaining baby stuff to make their vacation easier and safer.brbrRent cribs, car seats, strollers, toys and more from BabyQuip! As seen on Shark Tank, BabyQuip offers clean, sanitized, and safe baby gear in Islamorada. Visit Sunset Reef’s unique link https://www.babyquip.com/a/ky6u1w to make a reservation.brbrIf you are looking for another weekly Islamorada vacation rental property, please look at our Atlantic side, beach front 3 bd, 3 full ba condo at MM 80.6, www.vrbo.com/1174114 or www.HomeAway.com/1174114. We also have a Park City/Deer Valley, Utah 4 bd, 4 1/2 ba vacation rental home. www.vrbo.com/206330 or www.HomeAway.com/206330.

Sunset Reef - Bayside Gated Estate, Pool, Spa, Deep Water Dock, Kayaks & SUPs

Islamorada, Florida, United States

Bed

Bath

10

Sleeps

$795.0

Escape to paradise in the heart of Islamorada, the fishing capital of the world! This stunning 4 bedroom home sleeps 8 and offers a tranquil retreat in a quiet, secluded, private community. Enjoy the heated community pool, boat dock, and private boat ramp. This home has plenty of parking and its own commercial ice machine, and is a boaters dream. Indulge in great shopping and restaurants nearby, and don’t miss the chance to snorkel or paddle board in the natural aquarium just off the dock. Unwind on one of the beautiful porches surrounded by nature and watch the birds dance across the sky. Your island paradise awaits!brbr

Beautiful Islamorada Home in he heart of the keys, boat-slip, pool, and gated.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$562.17

NOTE:br--PLEASE SEND AN INQUIRY TO BE SURE YOUR DATES ARE AVAILABLE. br--DOCKAGE AVAILABLE AT FOUNDERS PARK MARINA RIGHT NEXT DOOR FOR A FEE. NO DOCKAGE AND NO TRAILERS ALLOWED ON PROPERTY. (Condo rules, not ours!!)brbrLuxury resort amenities with all the comforts of home! brGorgeous, spacious condo with modern updates just steps from the crystalline waters of the Florida Bay. Updated kitchen appliances, granite counter tops and fully equipped with all the extras you might imagine make the kitchen a gourmet cook's delight. Breakfast bar and large wooden table accommodate up to 10 comfortably in the adjoined dining area. The open floor plan makes it a great space to sit with your family and friends while others are preparing food in the kitchen in one of three couches and three comfy chairs. You'll find one full bath downstairs and another upstairs, both completely remodeled this year with tile and luxury finish.brbrEnjoy sitting under the stars or making your favorite barbecue foods on the private outdoor patio equipped with large gas grill, surrounded by greenery and shaded by palms. Just off the patio, but hidden by the greenery is one of the complex's two tennis courts. And only a few steps away is the pool and club house where you can swim in the large, heated pool or just relax in the shade in one of the many lounge chairs. brbrThe enormous master bedroom hosts a dreamy king bed with orthopedic mattress and memory foam top and is decorated with classy Keys style, and a Queen bed up in the loft space, as well as plenty of room for a queen air mattress down below if you need it. brThe second bedroom has a Queen beds, and two twin (bunk) beds. Wooden ceilings with inset lights are a highlight of the high-end updates made in the recent remodel. There's plenty of space for everyone to relax and enjoy the escape to paradise.brbrMarvel at the most spectacular sunsets on the planet from our private beach, just a minute walk from the front door. Jump from the wooden dock to swim in the clear blue water, or just enjoy watching the variety of colorful reef fish, rays, nurse sharks, and even frequent visits from manatees! Fishing is great right off the dock, too.brbrYou won't ever have to go far to enjoy the best that Islamorada has to offer. Walk easily to nearby Founders Park, where you will find a large sandy beach with beach volleyball, a play ground, an olympic sized pool, a walking/ running path, an outdoor gym, soccer and baseball fields, and a marina. Various restaurants are within a mile of the property and the heart of downtown Islamorada is 4 miles to the south. brbrOther amenities include parking for up to 2 vehicles, high speed WIFI, smart TV, and a large washer and dryer onsite so you can pack light.brbrNote: The bed configuration is different than the photos but the same beds are all there, as follows: Large bedroom with King bed and a Queen bed up in the loft. Space for queen air mattress if needed. Second bedroom has a queen and two twin bunks.

Keys Paradise with Private Beach and Pool

Islamorada, Florida, United States

Bed

Bath

8

Sleeps

$466.83

Located on a private beach and close to Indian Key Historic State Park.brbrThis listing is for a room within a hotel.brbr✦ Your room is 370 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 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✦ Outdoor shared pool available all year, opened from 10:00AM to 10:00PM.brbr✦ Free parking lot.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $150 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). Max 2 pets/room; pet form due at check-inbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Steps Away from Coral Bay Marina! Pool, Beachfront, Free Parking, Pets Allowed

Islamorada, Florida, United States

1

Bed

1

Bath

Sleeps

$736.91

This listing is for a room within a hotel.brbr✦ Your room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Breathtaking Bayfront Villa w/ Private Patio & Living Area, Perfect For Couple

Islamorada, Florida, United States

Bed

1

Bath

Sleeps

$627.79

This listing is for a room within a hotel.brbr✦ Your room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Stunning Bay View Villa in Florida Keys | Beach Getaway w/ Scenic Outdoor Pool

Islamorada, Florida, United States

Bed

Bath

Sleeps

$473.56

This listing is for a room within a hotel.brbr✦ Your room is 1042 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Picture-Perfect Villas Offering Pool Relaxation & Ocean Adventures Nearby

Islamorada, Florida, United States

Bed

Bath

Sleeps

$414.0

This listing is for a room within a hotel.brbr✦ Your room is 950 sq. ft, equipped with complimentary toiletries, kitchen with basic amenities, TV, ensuring cleanliness and comfort throughout your stay.brbr✦ Cleaning services availability and frequency vary by staybrbrThere 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 shared pool is available, opened from 8:00AM to 10:00PM.brbr———————————————brbrOther Things to Note:brThere are several additional things to note:brbr✦ A credit/debit card is required at check-in for a $100 per night refundable deposit, returned after check-out if no damages occur.brbr✦ A mandatory resort fee of $60.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome with an additional charge of $100.00 (per night). $100 per night. Up to two pets/roombrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.

Waterfront Escape: Bayfront Accommodation w/ Kitchen, Onsite Pool, Free Parking

Islamorada, Florida, United States

Bed

Bath

Sleeps

$522.66

Little Bay Cottage - 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. brbrAll 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! brbrIf 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.brbrVR-24-0336 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.

Cottage

Relax at Little Bay Cottage in Islamorada, a cozy retreat.

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1433.51

Welcome to your dream getaway at Coastal Cove Villa! Nestled in the heart of downtown Islamorada, this spacious 4-bedroom, 4-and-a-half-bathroom abode offers the perfect blend of comfort and luxury for your vacation retreat.brbrAs you step through the front door, you'll be greeted by a warm and inviting atmosphere, where relaxation meets style. The open-concept living area boasts plush sofas and modern decor, providing an ideal space for lounging and catching up with loved ones. Whip up your favorite meals in the fully equipped kitchen, complete with stainless steel appliances and ample counter space, perfect for preparing delicious feasts.brbrWhen it's time to unwind, retreat to one of the four cozy bedrooms, each thoughtfully appointed with comfortable furnishings and soft linens to ensure a restful night's sleep. With 4 and a half bathrooms, there's no need to worry about sharing space – everyone can enjoy their own private oasis.brbrStep outside to the private patio area and soak up the sunshine as you sip your morning coffee or enjoy a leisurely al fresco dinner under the stars. And if you're looking to explore the area, you're in luck – Maison Residence is conveniently located near a plethora of attractions, from stunning beaches to vibrant shopping and dining destinations.brbrWhether you're seeking a relaxing retreat or an adventure-filled escape ,this is the perfect home base for your next vacation. Book your stay today and start making memories that will last a lifetime!

Condo

Experience luxury at Coastal Cove Villa, a 4-bedroom retreat in beautiful Islamorada!

Islamorada, Florida, United States

Bed