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Welcome to ‘The Beach House’ at Tarpon Point in Islamorada – This luxurious oceanfront home is in a private gated enclave of 12 houses. This home sits directly on ‘The Beach’. Being the end home, it is nestled next to lush mangroves and the ocean offering a lot more privacy....
Featured review
This unit on Islamorada provides wonderful oceanfront views. Our group included five retired women who all worked together in the past. We try to make a reunion vacation happen once a year. This is the...
Distance to beach: 4 miles to Founders Park
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Welcome to Island Time!This newly constructed canal front residence located in the heart of Plantation Key is sure to help boost your serotonin and ensure complete relaxation. This impressive home can comfortably accommodate eight adults with four bedrooms and three bathrooms.The main living...
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Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9AM . If other times are required \ requested , please inquire. This house is usually not available from the end of...
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Skip the resorts!See why we have ALL 5-star reviews. It's named The Oasis for good reason! Located in the HEART of Islamorada on Upper Matecumbe, so you are a block or two from several restaurants and breweries you will fall in love with. The homes are well-apportioned for the discerning traveler.The...
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This unique home is situated on a quiet street, with a desirable corner canal location in Port Pine Heights, Big Pine Key. Bringing your boat along? No problem, plenty of dock space here! And quick and easy access to Pine Channel for excellent boating, fishing, diving and snorkeling!The exterior has...
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Summer never ends in the Florida Keys! Endless Summer is located on Summerland Key in the very desirable Summerland Cove neighborhood. This is a two bedroom, two bathroom comfortable home with additional and very accommodating living space on the lower level.Upstairs is open concept living with a...
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1440 sf - Sleeps 4 adults (also includes xtra bed in guest room plus EZ-Bed electric queen Bed and large sectional couch with chaise lounge and cuddler for larger families). Fully renovated and updated in 2021. 70ft foot dock and cleaning table. Great ambience, quiet home like feel. Private community...
Featured review
Here is the review I am trying to post via for our March 2024 stay.Wonderful! Fantastic! Amazing!Wonderful Hosts!!! Jay and Sharon are so welcoming and supportive! We felt at home before we...
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Adorable historical conch house 2 bdrm, 2 full bath on quiet street with all the modern day amenities & decor in convenient location, relax by your private heated/chilled pool surrounded by decking and palm trees. Enjoy your morning sitting on the front porch watching the breeze travel through the...
Featured review
Beautiful home on a quiet street and close to everything. No need for a car. You can walk or ride bikes to anywhere on the island. Outdoor area is just right for a group of six. Totally enjoyed the...
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"Wow beyond wow! This place had everything we needed and more. We like to rent a house where we can spend most of our time there enjoying family time. The pool and all the games with the game room and infinity table and the dining turned ping pong was amazing. Eric was very responsive..." -...
Featured review
Eric was the perfect host. We escaped a cold and snowy winter for Marathon and this home offered us the perfect get away! It included everything we could have needed…games, pool, grill, plenty of space...
Distance to beach: 3 miles to Founders Park
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Welcome to the Conch & Lobster Homes, a rare dual-home getaway located in the heart of Islamorada, just minutes from iconic Alligator Reef. Perfect for large families, multi-generational vacations, or group getaways, this tropical property comfortably sleeps up to 14 guests across two coastal designed...
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2/2 Main House, 1/1 Bunglow, Large Pool And Hot Tub On Beautiful Old Town LaneMulti-month Discounts availableHidden at the end of one of the most beautiful lanes in Old Town, Casa Escondida awaits you with its tropical seclusion and quiet serenity. Nestled amongst mature tropical landscaping,...
Featured review
The location is perfect - about 3 blocks from Duval, and 3 blocks from Truman, and a short bike ride to Ft. Zachary beach. We did not have a car, and did two Uber runs for groceries at Publix, then used...
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BOAT RENTAL: We offer to rent our personal boats to our guests, only. We own: Flats Boat - 17 ft Ranger with E Tech 75 Bay Boat - 24 ft Bay Scout with 225 HP Yamaha Open Fisherman - 29-ft Ocean Runner with twin 300 HP Verrado's These boats are set up with everything you need to fish the Keys,...
Featured review
The location of Southern Sunset couldn't be more perfect. Only 25 minutes to Key West, 5 min to a great little grocery store called Murrays (and maybe 15 min to Winn Dixie), a short drive to Capt Hooks...
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We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom...
Featured review
We had a wonderful month in Islamorada at this outstanding waterfront condo with pool and sauna, dock etc. The views were gorgeous from the 3 decks in this corner unit. The area is exciting and near both...
Distance to beach: 0.0 miles to Inch Beach - Just a 3 minute walk
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Note!! ALL Reservations are accepted on a "Saturday to Saturday" check in/Check out basis.Casa Mar Azul II is a charming 2 Bedroom, 2 Bath 1/2 Duplex (Sleeps 2-5) located at 12 7th Street directly across from the Key Colony Beach Golf Course with a great view out back of a 200 foot canal....
Featured review
We were looking for a place in the keys to dock our boat while enjoying all the Keys has to offer. The casa was well appointed for anything you might need in the kitchen including crock pot and blender....
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Family House in Big Pine Key, Fl on the water. Bring your Boat and have easy access to the most beautiful waters of the Keys. Boat dock on the back of the house, and house comes with everything, it will make you feel at home.Welcome to your Ultimate Luxury Island Escape! This beautiful waterfront...
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Welcome to Key West Getaway in Old Town!In the heart of Old Town, Southard Square Condominiums is an award-winning condo development with stunning gardens, a clubhouse with changing rooms/baths, seating area, kitchenette and one of the largest private community swimming pools in Key West. Staying...
Featured review
Thank you for you help in researching a vacation rental . We love key west an we will be inquiring with you in the future
Distance to beach: 3 miles to Anne's Beach State Park
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This 3-bedroom bayfront property is located on Lower Matecumbe in Islamorada. The view is spectacular with sunsets on the water most of the year. There is plenty of room for boat trailers, RVs and other toys inside the fence. There is covered parking for your vehicles and a seawall out front to tie your...
Featured review
All I can say is that this place never fails to impress! The views from every inch of the property are the best in all of the keys! Great communication with Rich and his office. Would recommend every...
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Tony's Conch Retreat is a spacious updated condo is located in a historic home on William Street that was converted into 5 condo units. Tony's Conch Retreat, unit 5, is on the 2nd floor, at the top of the stairs, and encompasses the rear of the home from end to end. It has a lovely view of the...
Distance to beach: 100 yards to Sombrero Beach
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Seaside Sandpiper is truly a unique property that can accommodate as few guests as you want and up to 30! Rent the 6 bedroom main house by itself or rent the entire 14 Bedroom Main house and Addition! Weddings, family reunions and business retreats are all possible at our home! Our pet friendly home...
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1st I want to thank all our past guests for their great reviews. Bay Harbour Starfish is a luxury condo overlooking a large boat basin with views of the Atlantic Ocean. Situated in Lower Matecumbe Key, Islamorada, the Sport Fishing Capital of the World. This very spacious 3 bedroom, 2 and half bath condo...
Featured review
Bay Harbor was delightful, from the condo unit to the grounds and amenities. We used the hot tub, exercise room and swimming pool, When we left there was 76 degrees, returned to 20 degrees in Pennsylvania.
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Welcome to our waterfront family home located in a quiet, yet friendly gated community in Marathon, Florida! If you’re looking for a relaxing and low-energy getaway for your family, you’ve found the perfect place.Consider a 14-day stay and receive an 8% discount OR 28-day stay and receive...
Featured review
The property was amazing the views of the water were fantastic. The dock area was super great for fishing off of every day. The elevator was a life savior for getting suit cases and groceries up stairs....
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Hidden in the heart of Islamorada, this oceanfront villa offers an unmatched privilege of a secluded private beach—an experience few can claim. Expansive terraces stretch across both levels, framing ocean views. This haven's open design and spacious rooms blend seamlessly with serene surroundings....
Distance to beach: 900 yards to Sombrero Beach
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"BELLA VISTA" - a Spectacular Oceanfront home in Marathon, Fla. with an Invisible-edge heated salt water pool that overlooks the Atlantic Ocean. Open Water Unobstructed VIEWS. VERY PRIVATE. Newly renovated! This 4 bedroom/3.5 bath home can comfortably sleep 8 people. Three bedrooms have King...
Featured review
Don’t think twice about booking this slice of heaven. My family of seven stayed at this glorious home. Absolutely spotless and very well stocked with everything you need. The views are amazing!! 5...
Distance to beach: 0.5 miles to South Beach
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This Studio is a lovely charmer nestled in a 6 unit compound in a residential neighborhood in the center of Old Town Key West. * Pet Friendly for flat fee of $90 * King size bed * WiFi included * check-out cleaning is an additional fee of $70 * 2 wall AC units * flat screen TV * Shared gas grill...
Featured review
This small unit had everything we needed. Very clean and convenient to everything we wanted to do. Will rent again! Pam was so easy to work with.
Distance to beach: 40 feet to Across the street
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FAMILY FRIENDLY GORGEOUS HOME WITH DIRECT WATER VIEW OF LARGO SOUND! WATCH THE SUN RISE FROM THE COMFORT OF YOUR LIVING ROOM! 3 BEDROOMS 2 BATHROOMS BEACH AND BOAT LAUNCH INCLUDED IN RATE! THIS IS THE OPPORTUNITY OF A LIFETIME! KING SIZE BED IN MASTER BEDROOM, Queen bed in 2ND BEDROOM AND TWIN...
Featured review
This place is amazing, beautiful beach right out the front door is why we come here. The host is the best, Nancy catered to all our needs. The home is nicely decorated, it had everything we needed. We will...
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3 bedroom 3 bathroom home on canal with room for a 25' boatThis home is having a pool installed and will be completed in the Fall of 2021Master Bedroom: King bed with TV, private bathGuest Bedroom: Queen Bed with TV3rd Bedroom: Queen bed , sleeper sofa, Tv mini kitchenHall...
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2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys and 15 minutes to Key West. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants...
Featured review
This is the perfect place for a Florida vacation. It has everything we were looking for and more. Private beach, quiet location, mature trees with coconuts and bananas. Tiki hut with a wet bar and comfy...
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The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views.The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge.Fishing and diving just steps outside your door. Then at night, Key West is just...
Featured review
This is our 2nd stay at this vacation rental. We love the view, pool, dock, house, privacy and the owners. A must for anyone vacationing in the Keys!!
Distance to beach: 3 miles to Sombrero
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Plan your Marathon Trip - Stay at Manatee Cove-4BR/2BA vacation home. Pool with Spa, Tiki, Quick Atlantic access!Escape to the Florida Keys ~ Gorgeous 4BR/2BA Home on the Atlantic side of the canal in Marathon. Our home offers the best pool in our area; who can say no to a hot tub, pool, and bar stools...
Featured review
My family and I had a wonderful week here. The owner and property manager were both a pleasure to work with. Our favorite amenity was the pool and hot tub. We had plenty of space and all of the beds were...
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Bitter End Vacation Rental –This Summerland Key beauty is the one you have been looking for. Located on Summerland Key with superb boating and access to deep water. Just the perfect spot to see sunset views and peaceful water vistas. Feel free to bring your pet along too!!The interior is...
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Canal front, Dock, Hot Tub and Cabana Club AccessWelcome to Orchid House, a lushly landscaped canal front home located on the beautiful island of Key Colony Beach. This property comes with boat dockage , private hot tub and access to the Cabana Club pool and beach.When you first drive up to the...
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This charming family-friendly residence in Duck Key presents a spacious and inviting environment, featuring three comfortably appointed bedrooms and three modern bathrooms, making it an ideal choice for a memorable getaway. Each bedroom is thoughtfully furnished with a plush king-sized bed, ensuring restful...
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Indulge in the epitome of coastal living in this expansive duplex penthouse boasting ocean views in Islamorada. Relish captivating tranquility with a grand open-concept layout seamlessly blending living, dining, and a wet bar, all framed by panoramic seascapes, a chef's kitchen and access to top-tier...
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You and your family will feel right at home in this charming Big Pine Key home. The Owners have totally refurbished this 2 bedroom plus den, 2 bath property in 2020. Soft sea colors and coastal décor make this a totally comfortable home away from home.Large and spacious living room, kitchen and...
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SALT & SKY has 4 bedrooms and 3 full bathrooms, sleeps 10 (including infants and children) - Upstairs Master w/ king & en suite bathroom - 1 guest room downstairs w/ queen size bed - A full bath is located on the first floor. Perfect for individuals who have trouble navigating stairs. - 2...
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Lady Grace will not be in Florida for the 2025-2026 season. Come visit her in the BAHAMAS!Bahama Cruise with exploration in the Exuma IslandsFor guests who want to enjoy a vacation on the move, our cruise aboard Lady Grace is for you. Nassau, Bahamas is the center of our winter cruise program,...
Featured review
The Lady Grace was awesome and Kelly and Capt Jamie were phenomenal. Everyone loved the yacht and everything she had. Plenty of beds bathrooms and gathering places. The sunset cruise was excellent and so...
Distance to beach: 3 miles to Sombrero Beach
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This charming oceanfront property is the perfect getaway for your next vacation. Located just steps away from the ocean, this cozy retreat features stunning views, modern amenities, and a spacious deck for outdoor relaxation. Enjoy the convenience of nearby shops, restaurants, and attractions. Book your...
Featured review
Newer, modern, comfortable, and well decorated oceanfront property. Had everything we needed and more. Beautiful views from the deck and very nice outside area. We appreciated that there were great...
Distance to beach: 3 miles to Sombrero Beach
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Start planning your perfect escape to the Florida Keys! Blue Ocean Bungalow is ideally located on a wide, deep-water canal with easy access to world-class fishing in the Atlantic and the Gulf. Enjoy all the amenities needed for a perfect island vacation: airy open living areas with canal views, cozy sunroom...
Featured review
Thank you . We had a great time..we fished, snorkeled and spent a wonderful time with family and friends.. we all highly recommend!!
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Beautiful, fully remodeled waterfront home with water on both sides! Ocean and lagoon views from bedrooms, dining room, balconies and kitchen. Cable TV with premium channels and wi-fi internet access. The home is in a quiet neighborhood on a cul-de- sac and very convenient to Tavernier or Islamorada...
Featured review
A well maintained home in a perfect quiet setting. The owner Patrick was outstanding to work with and made sure that all was in order. He is an excellent communicator. Welcome bottles of wine greeted us....
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One of the only white sandy beaches in the Fl Keys and 1 mile whole of it!Newly built,state of the art,beautifully done 5 bedroom home, 4 master suites w/ king beds and facing open water! Magnificent indoors and out! Each bathroom is exquisite,very large stone,glass and hand picked tiles. The...
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DOCKSIDE RETREAT is a 4 bedroom 3 bath canal front home that has a private pool, private dock, fish cleaning station, with a green light under the dock, two paddle boards, a kayak, four bikes, and a Tiki Hut for the ultimate Keys vacation! There are 4 parking spots for vehicles and one boat trailer (you...
Featured review
We had a fabulous stay in your property. We really appreciated all of your amenities. We love to cook some of our meals in and you had a great selection of pots and pans and dinnerware. We also like...
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Watch dolphins play in Shelter Cove while swimming in our oversized poolRelax in the private pool with the Spectacular Shelter Bay in the background...Our home is located directly on Shelter Bay in Key Colony Beach with some of the most spectacular views of open water a guest can ask for. We have...
Featured review
We enjoyed are stay at this well appointed and conveniently located vacation home. The setting is perfect and the home was loaded with every convenience you would need. Margie, the property owner, is...
Distance to beach: 3 miles to Bahia Honda Park
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Modern 4 bedroom 2 bath stilt home centrally located in Big Pine. Heated salt water swimming pool. Corner canal front lot with 120 ft of dockage. 5 min. to the Gulf and 10 min. to the Atlantic. Close to the Winn Dixie grocery store. Free public boat ramp 5 min away. Room on property to park 6+ cars...
Featured review
Well, we think the house is very nice and clean. Great location, lovely neighbors nice quiet place we have only positive things to say and nothing negative so have a great day
Distance to beach: 8 miles to Sombrero Beach
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Welcome to Marlin House – your perfect Keys getaway! This 2-bedroom, 2-bath coastal retreat offers the perfect balance of comfort and adventure. Relax in your own private plunge pool, enjoy fully stocked amenities for a stress-free stay, and make yourself at home with thoughtful touches throughout.Step...
Featured review
We had the most wonderful stay at Marlin House on Duck Key . Thank you Paola ! You were such an exceptional host !!!! The townhome is tastefully appointed , clean, great location, lovely patio with private...
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The apartment is in a house on the canal and across from the beach with beach access. It is situated on the ground floor of a two storey Keys house where you would be the only residents. All the amenities would be yours and you would have space, tranquility and privacy in the tropically planted landscape....
Featured review
This is the perfect apartment for one couple. Wonderful location on the oceanside with ocean views across the street. Has a great dock for your boat with great ocean access. Fish cleaning table is under...
Distance to beach: 1 miles to Sombrero Beach
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Weekly rentals in the Keys {and generally elsewhere } are based on a Saturday to Saturday occupancy. Check - in is on Saturday at 4:00 PM, and check - out is on the following Saturday at 9:00 AM. Check in directions are emailed to you the week prior to your arrival { please check "spam" } Pups...
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Meet your perfect vacation getaway, Maracaibo Manor! Located on Little Torch Key in the highly desirable Jolly Roger Estates neighborhood, with excellent deep water access for boating, diving, fishing and snorkeling at the famous Looe Key Reef.This roomy home has two bedrooms and two bathrooms upstairs,...
Distance to beach: 2 miles to Anne's Beach
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House, 3 Bedrooms, 2 Baths, (Sleeps 4-6)Spacious ground level home that will be easy on your legs--NO stairs to climb! The home is fully equipped with linens for the king, queen, and 2 double beds. The master bedroom has its own bath. A separate media room with a flat screen TV as well as a large...
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Pineapple Tides, located at "The Tides at Vaca Cut" (Unit #8), is a new 5 bedroom 4 bath home with a private pool and boat slip!Perfectly situated on the water with stunning views, sunrise and sunset colors, and direct quick access to both the Atlantic Ocean and the Gulf of Mexico via Vaca...
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Seaglass-Paradise on the Gulf is located in Marathon—the heart of the the beautiful Florida Keys. The Keys are a series of 40 islands connected by 40 bridges , off the southern most tip of Florida. The chain of islands extends 120 miles into the Atlantic Ocean and Gulf of Mexico. The area is famous...
Featured review
Really enjoyed our stay at Seaglass! Description was spot-on, lots of opportunity for fishing if that's your thing, unit was well stocked with cookware, kitchenware, supplies, etc. Lots of signage of what...
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