Vacation Rentals By Owner In Islamorada, FL

Escape to a tropical paradise at this villa at Topsider Resort in Islamorada. Nestled among lush gardens, this private octagon-shaped stilt house offers a large balcony, a fully equipped kitchen, cozy living spaces, and complimentary amenities like WiFi and cable TV. Guests can enjoy a heated pool, private beach, Jacuzzi, and the famous 180' T-shaped pier stretching into the bay. The villa blends comfort with the vibrant island atmosphere of the Florida Keys.brbr• Oceanfront Private Beachbr• Heated Outdoor Poolbr• 180' T-shaped Pierbr• Spacious Private Balconybr• Fully Equipped Kitchenbr• In-Suite Washer and Dryerbr• Complimentary Boat Docking (up to 23')brbrWelcome to this charming 2 Bedroom Condo, perfect for families or couples seeking an unforgettable retreat in the Florida Keys.brbr• Master Bedroom: Queen-size bed, en-suite bathroom, closetbr• Second Bedroom: Two twin beds, closetbr• Bathrooms: Bathtub/shower combos, towels, essentialsbr• Living Area: Queen sleeper sofa, cable TV, access to balconybr• Kitchen: Full-size fridge/freezer, stove, oven, microwave, dishwasher, coffeemakerbr• Dining Area: Seating for 4br• Private Balcony: Views of lush tropical surroundingsbrbrOther amenities available at Topsider Resort include (but are not limited to):brbr• Jacuzzibr• Shuffleboard Courtsbr• Tennis Courtsbr• Bicycles and Kayaksbr• Charcoal Grills and Picnic AreasbrbrLOCAL FAVORITESbrbrFood & Drinkbrbr• Lazy Days South: Fresh seafood and tropical drinks with ocean views – 1.2 mibr• Hog Heaven: A laid-back BBQ joint famous for its smoked meats and casual island vibe – 2.5 mibr• The Fish House: Popular seafood restaurant offering local specialties and a relaxed atmosphere – 6.1 mibrbrOutdoor Activitiesbrbr• Alligator Reef Lighthouse: Snorkel among colorful coral reefs and tropical fish – 7.8 mibr• Florida Keys Overseas Heritage Trail: Scenic biking and hiking trail – 2.2 mibr• Robbie's of Islamorada: Feed tarpon, rent paddleboards, and enjoy waterfront dining – 5.4 mibrbrRecreational Activitiesbrbr• Theater of the Sea: Interactive marine park featuring dolphins and sea lions – 3.0 mibr• History of Diving Museum: Fascinating exhibits on diving history – 4.1 mibr• Islamorada Seafood Festival: Annual event celebrating fresh local seafood and live music – 6.0 mibrbrOTHER THINGS TO NOTE:br• Parking: Parking available for 2 vehicles per reservation at the resort.br• Pet Policy: Sorry, this is not a pet-friendly property.br• Smoking: No smoking permitted; fines up to $1000 apply for violations.br• Other Notes: Condo assignments are made at check-in; views and layouts may vary. Hair dryers available upon request. Quiet hours are from 10 PM to 7 AM (Sun–Thu) and 11 PM to 7 AM (Fri–Sat).br• Room assignments may differ from the photos, as each unit is unique.br

Condo

Beachfront Villa w/ Pier & Pool

Islamorada, Florida, United States

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Bath

Sleeps

$273.38

The Perfect Natural Light Island House.brbrYour Islamorada adventure begins at this 2-bedroom house. Inside, guests find a welcoming space featuring one king bed and one queen bed, perfect for a restful night. Two bathrooms add convenience, while air conditioning and heating keep the temperature just right. Whether you’re relaxing indoors or planning your next outing, this wonderful house offers a comfortable retreat. Guests will enjoy an enjoyable stay that feels like a true home away from home. Our place will help you feel at home while you're traveling in Islamorada.brThis Tommy Bahama Inspired Home Located at Mile Marker 81. Restaurants, Bars, Shops, and Beach all Walkable in this location. Located in the Heart of Downtown IslamoradabrbrThe Home features all Tommy Bahama Furniture, New Tempur-Pedic Breeze Mattresses. brbrIf you need specific dates please reach out to us.brbrRoom for Boat / Trailer StoragebrbrPerfect Biking LocationbrbrNew Bathrooms & Full KitchenbrWasher / Dryerbr65 Inch TV in Living RoombrWifibrIf you love Natural Light this is the house for you.

2 Bedroom Island Inspired Luxury house in Downtown Islamorada

Islamorada, Florida, United States

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Bath

4

Sleeps

$485.98

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 a room within a hotel.brbr✦ Your room is 388 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✦ 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 $100 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.

The Cove, Age 21 Plus, Guest room, 1 King, Ocean view, Balcony

Islamorada, Florida, United States

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Bath

Sleeps

$1074.39

Villa by the Bay – Your Islamorada Escape for Sunsets, Fishing & Island LivingbrbrBring your heart, your family, and your fishing gear to Villa by the Bay, a charming island retreat tucked inside the quaint gated community of Coral Cove in the heart of Islamorada. With just eight homes in the community, this peaceful getaway offers the perfect blend of privacy, comfort, and easy access to everything that makes the Florida Keys unforgettable.brbrWhether you're planning a world-class fishing adventure, a relaxing family getaway, or a romantic escape, Villa by the Bay is your ideal home base.brbr Breathtaking Bayfront SunsetsbrbrEnd every day the way island life was meant to be enjoyed—watching the sun melt into the bay from the dock area. Gentle ocean breezes and vibrant sunset colors create a relaxing atmosphere you’ll look forward to every evening.brbr A Fisherman’s ParadisebrbrIslamorada is known as the “Sport Fishing Capital of the World,” and Villa by the Bay puts you right where you want to be.brbrDirect ocean accessbrbrPrivate dockage available (upon request and fee)brbrEasy access to deep-sea fishing, backcountry fishing, and sandbarsbrbrPerfect for bringing your own boat or chartering a local guidebrbrSpend the day chasing sailfish, mahi, snapper, or tarpon, then return home to relax by the pool and relive the day’s best catches.brbr Private Heated Saltwater Plunge PoolbrbrAfter a day on the water or exploring the Keys, unwind in your private heated saltwater plunge pool. The soothing waterfalls and tranquil sounds create a relaxing oasis perfect for evening cocktails, family time, or a quiet morning coffee.brbr Community AmenitiesbrbrCoral Cove is a quiet gated enclave designed for peaceful island living. Guests enjoy access to:brbrCommunity swimming poolbrbrCommunity dockbrbrGated privacybrbrBeautiful bay views throughout the propertybrbrWith only eight homes, the atmosphere remains calm, welcoming, and uncrowded.brbr Walk to Islamorada’s Best Restaurants & BarsbrbrOne of the best parts of staying at Villa by the Bay is the central location. Many of Islamorada’s favorite spots are within walking distance.brbrEnjoy fresh seafood, tropical cocktails, and live music at nearby local favorites. Whether you're craving sunset dining, casual tiki bars, or a lively night out, it’s all just steps away.brbrNo long drives—just pure island convenience.brbr Relaxed Island LivingbrbrVilla by the Bay was designed for easy, comfortable stays where you can truly unwind.brbrWake up to warm tropical breezes.brSpend afternoons fishing, boating, snorkeling, or paddleboarding.brReturn home for a refreshing swim in the plunge pool.brThen end the day watching spectacular Florida Keys sunsets over the bay.brbrThis is the laid-back Keys lifestyle people come back for year after year.brbr Thoughtful Guest AmenitiesbrbrTo help you settle in comfortably, we provide initial starter supplies, including:brbrCoffeebrbrPaper towelsbrbrBasic toiletries for each guestbrbrFor longer stays, additional supplies can easily be purchased locally and are the responsibility of the guest.brbr Optional Private DockagebrbrBringing your boat Private dockage may be available upon request for an additional fee. Please inquire ahead of your stay to confirm availability and details. (Up to a 42 ft boat)brbr Why Guests Love This Homebrbr✔ Private heated saltwater plunge pool with waterfallsbr✔ Beautiful sunset views from the dock areabr✔ Gated community with only 8 homesbr✔ Walkable location to restaurants and nightlifebr✔ Community pool and dockbr✔ Optional private dockage for boatersbr✔ Centrally located in Islamoradabr✔ Perfect for fishing trips, couples, or family vacationsbrbr Your Keys Adventure Starts HerebrbrWhether you’re casting lines at sunrise, exploring the turquoise waters of the Keys, or enjoying sunset drinks on the balcony, Villa by the Bay delivers the authentic Islamorada experience.brbrRelax. Fish. Explore. Repeat.brbrReady, set… book your unforgettable stay at Villa by the Bay today!brbrLicense #26-0059

Villa

Islamorada Florida Bay Villa Plunge Pool, Boat Dock, Amazing Sunset Views

Islamorada, Florida, United States

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Select Dates for Price

Welcome to our beach house located in the heart of Islamorada. Just a short drive from the best restaurants, bars, state parks, dive boats, and fishing charters! This townhouse is the perfect destination for those who love the bounty and beauty of the ocean.brbrYou would be able to enjoy of the tennis court, pool, shuffle board, pickle ball, tiki hut with picnic area, charcoal grill, boat ramp, boat storage, dock, our 2 ocean kayaks, BBQ, and private ping-pong table!brbr*Boats must be 25' 00 feet or less* brbrFeel free to contract us with any questions about your stay. brbr

Beautiful Beach Home

Islamorada, Florida, United States

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Bath

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$574.52

Monthly rentals only, no split months, thank you.brDay 1, of the month , to end of the month.brbrWelcome to, GULFVIEW 150, ISLAMORADA, WHITE MARLIN BEACHbrSports Fishing Capital Of The World br3200 sq ft. home , with brand new private poolbrbr5 minute walk to White Marlin Beach, from home ! br Members only, private key fob entry, to access beach.brbrLower Matecumbe, White Marlin Beach, ISLAMORADA, brTri Level 4 Bedroom, 3 Bath home, sleeps 8 to 10,brwith pool.brYou will enjoy the beautiful spacious 800 sqf with 16.5 foot vaulted ceiling main room masterfully crafted by gifted carpenters with an open kitchen, newer appliances , induction Miele cooktop and *reverse osmosis drinking water filtration , complete with 70 TV internet, cable tv, a pool table, KMP L shape sofa, beautiful Tommy Bahama dining room table that expands to seat 8 - all opening up to 9'x50' , back veranda with plenty of seating for your whole group! brA wrap around walk way all on the 2nd level, of this beautiful 3200sq.ft under A/C. over 5200+sq ft. under roof including 900 sq ft garage and it's covered porches.brThe stunning 700sqft master bedroom suite, on the 3rd level, boasts its own balcony with seating. br brDock your boat, at the new 53' dock with multiple electrical outlets and 3 water hoses making boat maintenance easy . The property also has a natural gravel ramp for use of water toys - New Commercial Manitowac Ice machine and chest freezer, in the garage, to support your fishing needs - Outdoor shower at dock- New quality fish cleaning Station, with storage and shade. br*Weber gas grill and Blackstone grill 36 inches * Tournament rated Ping pong table- Security cameras protect dock & front parking.brNewly renovated downstairs apartment Mahi-Mahi Suite) with separate A/C, full kitchen. Living room, with Scan Design queen sleeper sofa- king size bed in bedroom, 55 TV and table for 4 . It's own patio with outside table and bar.brbrA short 3 minute boat ride, takes one into Florida Bay, another quick 3-5 min run and to the ocean and theSports Fishing Capital of the World via channel 5..brTake a 1.5 block stroll up Gulfview Drive, or ride any the 6 included bikes to private White White Marlin Beach(*best beach in the keys), have a Bar-b-que (grills, tables Adirondack chairs, all provided at the beach) go for a swim and catch the beautiful sunsets, not to be missed!brPlenty to do for the sports enthusiast, ecotourist, & the food enthusiast. The home is unique to the Florida Keys, with its 16.5' vaulted beamed ceilings in the main room with open and full wrap around balconies. 3rd floor features a massive 500 sg ft. master bedroom (20x25) with 14 ft beamed ceilings, a 65 TV and its own wrap around balcony. There is so much more we could list about this amazing home! brYou will love this home, that captures what the Florida Keys paradise living is all about. br We welcome you, to come and make beautiful long lasting memories.brbr*Close to Fine Dining br*The Best Sport Fishing in the KeysbrbrbrLocated between Miami & Key WestbrbrKey west Airport 1.5 hrs away, great day trip.brMiami Airport 1.5 hrsbrFort Lauderdale Airport 2 hrs

3200sqft Masterpiece Home, Fishing Paradise ,Waterfront, Beach, Pool, Islamorada

Islamorada, Florida, United States

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Bath

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$354.38

This single-story canal front home located in the heart of Islamorada (MM86) in the Florida Keys-fishing capital of the world. Home is on the bayside in the upscale community of Venetian Shores. This spacious split floor plan home features 3 bedrooms and 2 bathrooms, open floor plan living area, screened in patio and large outdoor deck for your enjoyment. Home is equipped with all comforts of home.brEnjoy the canal view from almost every room in this immaculate home! Open floor plan includes the living room with quad-reclining sofa, a large screen TV, fully equipped kitchen, dining area and eat in counter with bar stools.brThe large master bedroom offers serene canal views with a king-sized bed, an over-sized en-suite bathroom which includes a jetted tub & separate shower. Bedrooms 2 and 3 both feature queen-sized beds with a shared bathroom. brRelax and enjoy your morning coffee or favorite cocktail in the private fully screened patio or enjoy sitting under the stars as you barbecue on the gas grill on the large outdoor deck all while enjoying a view of the canal surrounded by mangroves offering a tropical atmosphere. brOther amenities include high speed WIFI, smart TV’s and large washer and dryer.brThis home is centrally located where you will not have to go far to enjoy the best that Islamorada has to offer. Founders' Park is one mile north where you can enjoy access to many amenities such as: a sandy beach, Olympic-sized pool, walking and bicycle paths as well as volleyball, baseball and softball fields, basketball, tennis, soccer, doggie park, kids' playground, marina, boat ramp and much more. (Some additional fees may apply at Founder's Park). Nearby Snake Creek Marina offers boat slip, boat & kayak rentals. Fine dining restaurants such as Chef Michael’s, Ziggie Mad Dogs, Pierre’s, MM88 restaurants are nearby as well as casual dining restaurants such as Island Grill, Lorelei, Islamorada Fish Company and the historical Green Turtle Inn. brShopping is also conveniently nearby with grocery stores and many other retailers in proximity.brbrMINIMUM 28 DAYS RENTAL

Beautiful, Spacious, Single Story Home - Islamorada

Islamorada, Florida, United States

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Bath

Sleeps

$464.12

Escape to Islamorada’s Finest Oceanfront Gated Community brbrSoak up the sun and enjoy the ocean breeze from this charming 2 bedroom, 2 bath Key West style villa located in the exclusive community of Angler’s Reef. Accommodating up to six people, this exquisite home makes it easy to both entertain and relax with its open floor plan, private balconies, and abundance of on-site amenities. brbrOn the ground level of your island home, you will find a charming dining room, fully equipped kitchen, and spacious living area complete with a large sectional sofa, stainless steel appliances, bar seating, and a convenient half bath. No detail was left undone with granite countertops, hardwood floors and crown molding. French doors leading to a tranquil back porch with comfortable lounge furniture make this a perfect place to unwind with a pre-dinner cocktail or to dine alfresco. brbrUpstairs you will find two spacious master suites complete with private balconies, flat screen TV’s with Netflix capabilities, and clean ensuite bathrooms. The second floor also features laundry facilities and a futon for guest use. brbrFor your convenience, the home is equipped with complimentary WiFi, Netflix, beach towels hair dryers, pool floats, beach chairs, two 2 man kayaks, games, BBQ grill, coozies and whatever else you may need for the perfect Florida Keys Vacation.brbrThe grounds of this luxurious oceanfront resort are perfectly decorated with lush tropical landscaping and quaint streets filled with bright Caribbean-inspired homes. Enjoy all the wonders of this highly sought after community including a heated oceanfront pool, private marina with deep-water dockage and two white sandy beaches with kayaks for your own use. brbrLooking to explore further Perfectly located on the oceanside of Windley Key, you can hop in your boat easily access some of the best fishing spots in the Atlantic or launch a kayak from the beach and visit the world-famous Islamorada sandbar. brbrAnglers Reef is located at mile marker 84 and is one of the best kept secrets in the Florida Keys. You are only minutes away from downtown Islamorada or Tavernier with great restaurants, boutiques, grocery stores and local attractions. brbrPlease inquire for boat slip availability. brbr7 night minimum. Saturday to Saturday rentals are preferred. Please inquire for rates and availability.brbrAngler's Reef 105 ~ MM84.5 Oceanside brbrVR: 24-0236

Charming Angler's Reef Home with Pool, Dock, Beach & Ocean View

Islamorada, Florida, United States

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Bath

Sleeps

$286.88

Video of inside, outside, surrounding areas and waterways available upon request.br* Each level is a (3/2) for a small group br* Both levels (6/4) for a larger group.br* Rates are per Levelbr* Perfect for sharing with family and friends in total privacy and comfort with separate entrances and amenities from level to level and on the best location for all you came to find in our Beautiful Florida Keys! br* Fully furnished, beautifully decorated and equipped with all the comforts of home away from home.br* Each Separate Level has 3 Bedrooms with plush bedding and 2 Full Bathrooms, Fully Stocked including all Towels and Linen, brModern Kitchen with Granite Counter Tops, Stainless Steel Small and Large Appliances, separate central air units, fans in every room, cable TV, WiFi, washer and dryer. brbrIt’s perfect for a Small Group or large families or Groups to share in privacy and comfort!brAlso Great for Family Reunions, Holidays and Special Occasions. br brFrom our Upstairs unit enjoy the breezes and view of the water in a nicely furnished and private wraparound terrace. brThe lower unit enjoys a fenced Tropical back yard, with a relaxing hammock, a large Jacuzzi and Tiki Bar by the Pool.brbrOur 75' Dock is Equipped with Water, Electricity, and Hands Free Fish Cleaning Station. Ample space for two boats comfortably.brOur Deep and Wide Canal provides Immediate Access to the Bay, and Tavernier Creek provides Access to the Ocean in Just Minutes. brThere are Many Well Known Reefs Close By making it The Best Location for All Water Sports and Great Fishing! brLet Us Reserve Our Home to Celebrate Your Special Occasions and Holidays with Your Family and Friends and Do It All On Your Next Vacation In 'Parroteyes'. brbrOur Rates:br- During Summer Months: May/June/July/August, September, October and November, our rate for the house is $3,800.00 per month Per Level.br-Winter Months: December/January/February/March/April, Our Rate is $4,200.00 per month, Per Level.brOur rates includes all Utilities, Internet, Cable, WiFl, Netflix, Hulu, Maintenance of Jacuzzi, Pool and Grounds.

Apartment

Fabulous Waterfront Pool Two Level Home

Islamorada, Florida, United States

Bed

Bath

Sleeps

$1490.6

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 4 separate rooms within a hotel. The price shown in the listing covers all 4 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 $400 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.

4 Guest Room, 2 Queens, Balcony, Free Parking & Pet Friendly

Islamorada, Florida, United States

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Bath

Sleeps

$742.85

126 Palermo DrivebrCheck out this new to the Vacation Rental Market home in Venetian Shores on canal with 70' dock, pool, tiki hut and hot tub.brbrCall Jennifer for more information 305-240-0592.brbrCompletely remodeled in 2021, this concrete home has very spacious bedrooms (each with a KING bed), beautifully appointed with all new furniture, new gourmet kitchens and new bathrooms.brbr70’ of Deep Water dockage included in rate. Bring your big boat(s)! Large, deep canals with Drawbridge out to ocean via Snake Creek! Parking for one trailer on lot.brbrTwo Bedrooms and Two full Bathrooms upstairs with large kitchen and open living floor plan. There is also a full sized washer and dryer and large closets. Wonderful screened porch for your morning coffee where you will be sure to see some great wildlife (tarpon rolling, birds and an occasional dolphin or turtle)!brDownstairs (separate) you will find a Large ONE King Bedroom and Full Bathroom with full kitchen and large living room. Walk out the sliders to the pool deck, and amazing view of the canal.brbrOur on site care taker is in a separate apartment (ground level street side) and is there to help with maintaining the property and is a great resource for local fishing spots!brCome enjoy your next vacation in the best neighborhood in the Keys! Close to restaurants, parks/beach, the famous Islamorada Sand Bar and so much more!

Venetian Shores Home -DOCK remodeled 3/3 POOL/Hot Tub! Deep water Dockage

Islamorada, Florida, United States

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Bath

Sleeps

$341.25

This opulent condo is located within Ocean Harbour which is one of Islamorada’s most sought after gated communities featuring 12 acres of lushly landscaped grounds, oceanfront pool & spa, club house, gym, tiki huts with a grilling area, lighted tennis court, and a marina with a boat ramp. This luxurious corner unit offers expansive panoramic ocean views, impressive custom kitchen & bathrooms, oversized screened-in porch and the finest furnishings that other units can’t offer. With a 50’ boat slip available upon request, you can enjoy the convenience of easy and quick access to world class fishing, diving, and snorkeling right out of your backyard. Head just a few miles south and travel through Snake Creek to access the Florida Keys Bay and Everglades National Park. Fish the flats for snook, redfish, bonefish, tarpon and permit or head offshore for sailfish, mahi-mahi, snapper, wahoo and more.brbrNot a fisherman No problem! This home is located only 1 mile from Founders Park and features a bayfront beach, olympic size swimming pool, kids splash pad, picnic areas, playgrounds, fitness and walking trails, basketball court, soccer field, baseball field, pickle ball court, and a golf driving cage (Park entry fee required). A 5-10 minute drive north or south will take you to Key Largo or downtown Islamorada, both offering endless restaurants, breweries, shopping, and activities. Key West is a scenic 2 hour drive south. brbrHave any questions Feel free to ask away! Coastal Vacation Rentals of the Florida Keys is located in the heart of Islamorada and has a full office staff to ensure you have the best vacation possible.brbrReservation Deposit & Cancellations: A reservation deposit equal to one-half (50%) of the total reservation amount is due at the time of booking. TENANT shall be entitled to a refund of the one-half (50%) reservation deposit, less any non-refundable fees, if the reservation is cancelled at least 60 days prior to the occupancy date. The remaining balance, including any required security deposit, is due no later than 60 days prior to the occupancy date. If the cancellation occurs within 60 days of the occupancy date, the full reservation amount shall be non-refundable. If the booking is made less than 60 days prior to the occupancy date, the full reservation amount shall be due at the time of booking, and TENANT shall not be entitled to a refund of any amounts paid in the event of cancellation. As an exception to the foregoing, TENANT shall be entitled to a refund of all amounts paid if COASTAL re-rents the property for the same amount and for the full rental period. If the property is re-rented for fewer days or at a lower rate, COASTAL may deduct from the refund the difference between the total amount due under TENANT’s original reservation (including all taxes and fees) and the amount received from the subsequent rental. brbrInstant quote prices and calendar availability are subject to change without notice and are not guaranteed. Please contact Coastal Vacation Rentals of the Florida Keys to speak to one of our associates to confirm pricing and availability.

Condo

Ocean Harbour P21 ~ Modern Oceanfront Islamorada Condo with Boat Slip

Islamorada, Florida, United States

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Bath

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$122.65

Whether you spend your next Florida vacation playing in the cool surf or hanging out with good friends on the private patio, you will love staying in this gorgeous retreat. Guests will be delighted by the fantastic location of this condo, offering a large pool, 2 tennis courts, a furnished clubhouse, first-come-first-serve dockage, and a bayfront beach ideal for kayaking and paddleboarding. Whether you're looking to relax by the pool or explore the water, this condo has everything you need for a memorable vacation. brbrInside, an open and spacious living area features comfortable furniture, attractive wall art, and a large TV. The full kitchen is loaded with stainless steel appliances and enough counter space and cookware to inspire any family chef. Serve your dinner guests at the handsome wood dining table while the kids swing their feet from the barstools of the breakfast bar. You can take your breakfasts outside as alfresco meals to enjoy the gardens and walkways while you eat under the table umbrella. Use the free WiFi to research your next adventure or download an excellent playlist to your device for a trip to the shared tennis court. You'll love streaming your favorite Netflix movies with the kids and lots of hot buttered popcorn. The shared pool is a great way to cool off after a hot-weather hike on one of the many nearby trails. One of the guest bedrooms has access to a private balcony.brbrYou'll have many great restaurants nearby whenever you need a break from the kitchen. Book a trip through Capt. Easy Charters, one and a half miles southwest, to reel in today's limit of saltwater fish! Ready to crash some waves You can rent equipment and find all kinds of swimwear and accessories when you visit Otherside Boardsports, less than five miles south.brbrTHINGS TO KNOW brThis home does not have any ground-floor bedrooms.brThis property is managed by Vacasa Florida LLC.

Condo

Beautiful, sunlit home with pool, tennis court & beach access - near the marina

Islamorada, Florida, United States

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Bath

Sleeps

$504.64

We have recently completed an inside and outside renovation. The Bayview Villa is a private, secluded villa facing Florida Bay and in view of the fabulous Everglades and gorgeous sunsets. Quick access to offshore fishing. Located in a lush tropical hammock in a quiet, one acre residential area (rare). The villa is approx. 30 feet from the water. The property contains a wading beach and a free marina with night lights, power and water. An enclosed patio offers private outdoor grill and dining.brbrThe villa itself comes with a fully-equipped new stainless kitchen, full size LG washer and dryer, linens, two queen and one king beds, Cable TV, and a dining room. French doors in the dining area face the bay, spacious 700 square foot patio,and marina giving the feeling of the outdoors being in. Beautiful glass block showers with pebble floors are in both baths. brbrIslamorada proudly calls itself the 'Fishing Capital of the World' but there is so much more to do

Bayview Villa- Pet-Friendly Waterfront Paradise. A fisherman's dream!

Islamorada, Florida, United States

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Sleeps

$216.74

Step into your own slice of paradise at this sunlit, open-concept home overlooking the turquoise waters of the Florida Keys. With enchanting views from nearly every room, Tollgate Tides is the perfect retreat for a surf trip with friends, a romantic couples' getaway, or a family vacation by the shore.brbr⭐ Location Highlightsbr • Robbie's of Islamorada (10 miles): Feed the famous tarpon, book a fishing charter, or browse local artisan shops.br • Long Key State Park (10 miles): A must for kayaking, snorkeling, and beach picnics.br • Windley Key Fossil Reef Geological State Park: Walk through ancient coral trails and enjoy prime birding.br • Local seafood dining: Savor the catch of the day at waterfront restaurants or take a sunset cruise for unforgettable views.brbr Why You'll Love Itbr • Outdoor living: Spacious waterfront patio for grilling your fresh catch, alfresco dining, or simply soaking in the coastal breeze.br • Gourmet kitchen: Fully equipped with stainless steel appliances, a wine fridge, and bar/island seating perfect for gathering.br • Relaxation: End your day with a soak in the jetted tub or stream your favorite movies with HBO and Netflix.br • Activities for all: Sneak in a tennis match on the shared courts, explore nearby state parks, or enjoy family time with games in the living area.br • Everyday comforts: Private washer/dryer, central AC, and wide-clearance access for ease of mobility.brbr Amenities at a Glancebr • High-speed internet + streaming (HBO & Netflix)br • Oceanfront views from balcony, deck & patiobr • Shared tennis courtsbr • Jetted tub for ultimate relaxationbr • Fully equipped kitchen with wine fridgebr • Private washer/dryer & central ACbr • Snowbird-friendly for extended staysbrbr✨ Tollgate Tides blends comfort and adventure in one perfect waterfront escape. Whether you're here for fishing, snorkeling, sunset cruises, or simply soaking up the tropical vibe, you'll find everything you need to make unforgettable Florida Keys memories.brbrThings to KnowbrCheck-in time: 4:00 PMbrCheck-out time: 10:00 AMbrAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AMbrNo smoking is permitted anywhere on the premises.

Radiant waterfront retreat with remarkable views, patio, tennis court, & grill

Islamorada, Florida, United States

Bed

Bath

Sleeps

$465.11

Your Waterfront Escape in the Heart of Islamorada Awaits!brbrWelcome to your dream getaway in the Florida Keys—where turquoise waters, tropical breezes, and that unmistakable “island time” feeling set the tone for an unforgettable stay. Nestled right on the water in beautiful Islamorada, this spacious 3-bedroom home offers the perfect blend of relaxation, adventure, and true Keys lifestyle.brbrStep outside to your private waterfront deck, thoughtfully furnished for lounging, sipping morning coffee, & beginning the day with one of Islamorada's famous sunrises. Gather for meals in the outdoor dining area, where warm breezes and water views create the perfect backdrop for unforgettable moments.brbrEnjoy exclusive key-card entry to Port Antigua's resident access beach and 50 foot boat ramp, giving you the true Florida Keys experience. Spend your days lounging on the sugar-soft sandbar, relaxing under tiki huts, grilling at the charcoal BBQ stations, or enjoying a picnic at the waterfront tables. When you get home, cool off in the sparkling private pool, unwind in the hot tub after a day of exploring the islands, or challenge your crew to a friendly match at the ping-pong table. Whether you're soaking up the sun or slowing down under the stars, this home is built for relaxation.brbrIslamorada—known as the “Sport Fishing Capital of the World”—offers endless opportunities to enjoy the ocean. Spend your days snorkeling vibrant reefs, chartering a fishing boat, kayaking through mangroves, or simply embracing the laid-back island lifestyle that makes the Keys so special. Delicious seafood restaurants, waterfront bars, boutiques, and local attractions are just minutes away.brbrWith three comfortable bedrooms and an inviting open layout, there's plenty of space for families or groups to unwind. Large windows highlight the water views, while coastal-inspired décor brings the beauty of the Keys indoors.brbrWhether you're here for adventure, relaxation, or a little of both, this Islamorada retreat gives you the best of waterfront living in one of the most iconic destinations in the Florida Keys. Your island escape starts here!

Waterfront Escape Featuring Private Pool, Hot Tub & 50 ft. Boat Dock

Islamorada, Florida, United States

Bed

Bath

Sleeps

$345.15

*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.brbrEnjoy incredible beach and ocean views from this family-friendly, waterfront retreat. This home features a beautiful, sandy backyard that leads directly to the ocean, a private boat dock, four beach cruiser bikes, a hammock, beach chairs and umbrellas, and a screened and furnished back patio. With plenty of space for the entire family, this gorgeous home is ready-made for your next Florida Keys getaway.brbrSituated near the end of a private road, this home is tucked away from the hustle and bustle yet still close to all that Islamorada has to offer. Nearby attractions include the Theater of the Sea, the History of Diving Museum, the Keys History and Discovery Center, and Indian Key Historic State Park. Stop by a local charter company to enjoy guided tours on the water or visit one of the many nearby shops or restaurants. brbrTHINGS TO KNOWbrA Tesla EV charger is located onsite.brThis property is managed by Vacasa Florida LLC.

Relaxing waterfront retreat with boat dock & amazing ocean views

Islamorada, Florida, United States

Bed

Bath

Sleeps

$970.86

Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island setting. Unwind at the zero-entry pool, Tiki Bar, or private beach with hammocks. Guests enjoy kayaking, snorkeling, access to restaurants and services across sister resorts, plus convenient access to snorkeling and local culture.brbrThis listing is for 2 separate rooms within a hotel. The price shown in the listing covers all 2 rooms.brbr✦ Each room is 300 sq. ft, equipped with complimentary toiletries, standard quality 37-inch TV, available with Standard cable, and Premium cable.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✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 5:30PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 7:00AM and 11:00AM.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. $50 nonrefundable fee per pet per day/ max 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Refundable security deposit charged nightly. brbr✦ Complimentary shuttle within 4 miles. brbr✦ Early check-in & late check-out subject to availability for a fee.br br✦ Smoking prohibited indoors; designated smoking areas provided.

2 Rooms w/ Balcony, Courtyard View, Outdoor Pool, Free Parking & Pet Friendly

Islamorada, Florida, United States

Bed

Bath

Sleeps

$541.07

Located oceanfront in Islamorada, Amara Cay Resort features stylish rooms and suites with balconies in a boutique island setting. Unwind at the zero-entry pool, Tiki Bar, or private beach with hammocks. Guests enjoy kayaking, snorkeling, access to restaurants and services across sister resorts, plus convenient access to snorkeling and local culture.brbrThis listing is for a room within a hotel.brbr✦ Your room is 264 sq. ft, equipped with complimentary toiletries, standard quality 37-inch TV, available with Standard cable, and Premium cable.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✦ Public or shared fitness center open 24/7, available in the property.brbr✦ Outdoor shared pool available all year, opened from 8:00AM to 5:30PM.brAdditional features:br • Heated poolbrbr✦ Free parking lot – 1 space(s).brbr✦ Shuttle service is available upon reservation between 7:00AM and 11:00AM.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 $59.00 per night will be collected upon check-in, not included in the daily rate.brbr✦ Pets are welcome. $50 nonrefundable fee per pet per day/ max 2 petsbrbr✦ We use multi-unit listings, so rooms are similar but may have small differences.brbr✦ Refundable security deposit charged nightly. brbr✦ Complimentary shuttle within 4 miles. brbr✦ Early check-in & late check-out subject to availability for a fee.br br✦ Smoking prohibited indoors; designated smoking areas provided.

Courtyard View King Room w/ Balcony, Outdoor Pool & Free Parking

Islamorada, Florida, United States

1

Bed

1

Bath