58,368 properties available

Located in Islamorada, Florida, United States. Luxury Oceanfront Estate in Islamorada - Your Tropical Paradise Awaits! Welcome to Orchid Beach, your ultimate oceanside escape! Nestled directly on the beach, this gated estate greets you with vibrant orchids woven into tropical landscaping, leading to an impressive waterfront home. Offering a unique getaway, the estate provides the perfect blend of togetherness and privacy with living accommodations spread across three distinct pods.The main living pod serves as the estate's heart, featuring a spacious, beautifully appointed living area, a fully equipped gourmet kitchen, a dining space, and an office loft. Large windows and French doors offer stunning ocean views and seamless indoor-outdoor living. The master suite pod is a secluded haven with a king-sized bed, en-suite bathroom, and private terrace. Wake up to a sunrise view over the ocean without leaving your bed. For groups of friends or families, the guest pod includes three guest rooms, each with its own entrance and en-suite ba

Located in Islamorada, Florida, United States. Beautiful unit in one of the most prestigious Condo Complex in Islamorada PROPERTY NAME: Beacon Reef #30183201 Old Highway, Islamorada, FloridaLOCATION: Ocean side CondoMINIMUM STAY: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 83.2DETAILS: Fully renovated condo that offers inspiring tropical views including the ocean from the open-air balcony accessed from the main living area and the master bedroom suite. This charming, clean, spacious 2 bedroom 2 bath condo has all the comforts for a wonderful vacation. Furnishings have been updated and new items are being added frequently. This unit is located in one of the most desirable complexes in Islamorada. Its central location provides convenient access to everything Islamorada has to offer - world class diving, fishing, and restaurants. If you are feeling adventuresome, snorkel or scuba dive in the crystal clear sea or take a fishing charter to some of the best fishing spots in the world. If you

Located in Islamorada, Florida, United States. Sun, Sand, and Relaxation Awaits! Ocean View Accommodation w/ Private Patio! Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical reside

Located in Islamorada, Florida, United States. Canary Island Palm North Poolside,1 King Bed, 2 QueenBeds, 1 Pull Out Poolside,1 King Bed, 2 QueenBeds, 1 Pull OutResort guests stay in warm and inviting Caribbean-style homes. Rich mahoganies, teaks and Tommy Bahama furnishings all provide a unique experience.Many of the homes are named after one of the specimen palm trees on the property. Each home enjoys privacy among native gardens.Guests enjoy the beautiful Caribbean decor and high, open ceilings. Solid wood Anderson doors and windows, chiseled stone or tile flooring, open living and dining area all add to your tropical experience. Wrap-around outdoor verandas and comfortable lounging chairs create a seamless transition to outdoor living where you are just steps away from our one-of-a-kind tropical garden beach-entry pool.This home includes a full washer-dryer, Weber BBQ gas grill, wireless Internet, and cable TV.

Located in Islamorada, Florida, United States. Your Oceanfront Islamorada Retreat with Pool & Private Boat Basin! Oceanfront property offering a unique experience for your tropical escape with views of both Islamorada Sandbar and Alligator Lighthouse! This rental can be separated into two distinct units, each equipped with its own full kitchen, bedroom, and bathroom. Embrace the laid-back atmosphere as you lounge at this property's shared pool with your favorite book or sip on a cool drink.For those with a passion for boating, you'll love the private boat basin right on the property with space to accommodate a boat up to 24 feet. You can easily explore the crystal-clear waters of the surrounding area or embark on a fishing adventure or explore the famous Islamorada Sandbar. Whether you're grilling up fresh seafood on the outdoor barbecue grill, enjoying a family movie night in the living room, or savoring a meal together at the dining table, every moment spent here is sure to create lasting memories.

Located in Islamorada, Florida, United States. Remodeled Stilt home with Ocean Views PROPERTY NAME: Blue Water Retreat137 Ocean Lane, Islamorada, FloridaLOCATION: Oceanside Canal home located in Lower Matecumbe, IslamoradaMINIMUM: 28 Days, All stays must be the whole month(s), No Partial Months AllowedMILE MARKER: 76.3DETAILS: This home has it all - ocean side Lower Matecumbe location, remodeled in 2009 and 2022. Relax by the splash pool or sunbathe on the roof top and enjoy the spectacular views. There are blue water ocean views from almost every room in this home. This home is located on a canal front lot, offers dockage for a boat up to 30' with easy access to the ocean - a straight shot of about 200 yards to open water from the dock. The wrap-around screened balcony provides a respite after a day on the water. Take a dip in the pool and enjoy some afternoon refreshment. Grill your day's catch on the gas grill and dine at home or take it to one of our many fine local restaurants and let the chef cook it to your specificati

Located in Islamorada, Florida, United States. Your Islamorada Hideaway! Beachfront Accommodation. Onsite Pool, Parking Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residentia

Located in Islamorada, Florida, United States. Islamorada beach house - PRIVATE BEACH - KAYAKS - DOCK SPACE Enjoy the Florida Keys from our newly renovated home in a quaint neighborhood located in Islamorada. This 2 bedroom, 2 bathroom open concept home is spacious and serene. Enjoy the cross breeze from the balcony, bring down your boat using the private ramp or dock your boat on the 54 feet of dock space.Boat maintenance is made easy with fish cleaning station and water hose. Ice machine and freezer to support your fishing needs. Outdoor shower at dock. Gas grill and two fishing kayaks available. A short 3 minute boat ride, takes you into the Florida Bay, another quick 3-5 minute run to the ocean and "Sport Fishing Capital of the World" via channel 5. Take a stroll or ride a bike to the best private beach in the Keys. Kayak to the beach, watch beautiful sunsets, or grill on the beach.

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

Located in Islamorada, Florida, United States. Your Retreat in the Heart of Islamorada! Kitchenette, Outdoor Swimming Pool! Our furnished rooms, which draw inspiration from Islamorada's lush tropical surroundings, offer luxurious bedding and plenty of space to take in the tranquil ambiance. Each of the guest rooms and suites in our three-bedroom house is decorated in the light, natural colors of Islamorada and furnished with a remarkable range of facilities. They are also infused with the casual elegance of the tropics with our resort amenities. Guests have access to all the amenities they might possibly need right on the premises, including a restaurant, bar, swimming pool, and slips for those visiting with boats. But if you want to venture offsite, we have a shuttle service that can take you around.PLEASE NOTE:- The property requires a damage deposit of USD 100/night/unit on the credit/debit card provided. The deposit is required for EACH UNIT and is refunded IN FULL upon check-out.- Early check-in is subject to availability upon

Located in Islamorada, Florida, United States. Gated Estate Duplex on the Bay with dockage PROPERTY NAME: Little Bay Lower Duplex82246 Overseas Highway, Islamorada, FloridaLOCATION: Duplex located directly on the Florida BayMINIMUM STAY: Weekly or MonthlyMILE MARKER: 82.2DETAILS: - Located on a one-acre lush tropical setting in a gated compound directly on Florida Bay- One of 3 separate units for rent by the week or month, each sleeping up to 6 people- Protected dockage for up to a 34-foot boat- Sunning area with lounge chairs on the peninsula- Hammocks, pergola, and tiki for relaxing- Panoramic views of Florida Bay- Spacious interior with 2 bedrooms, 2 bathrooms, and a queen-size sleeper sofa- Updated kitchen with new appliances and granite countertopsThis vacation rental is the perfect place to relax and enjoy the beauty of Florida Keys. With its protected dockage, you can safely moor your boat and enjoy all the water activities the area has to offer. Or simply relax on the sunning area or in one of the hammocks and soak up the

Located in Islamorada, Florida, United States. Beach Bliss, Just Steps to the Ocean! Outdoor Pool, Near Coral Bay Marina Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical residenti

Located in Islamorada, Florida, United States. Dip Your Toes In The Sand! Beachfront, Pool, Near History of Diving Museum Step into our thoughtfully designed and spacious accommodations, featuring modern furnishings and luxurious amenities. Our well-maintained rooms offer comfort and tranquility, providing a peaceful haven to rest and rejuvenate after a day filled with adventure. Each room boasts a cozy ambiance, complete with plush bedding, elegant decor, and all the essentials you need to feel at home. With a private beach just steps away from your doorstep, you can enjoy the soothing sound of waves and the warm kiss of the sun, making your stay truly unforgettable. Whether you're lounging by the pool, exploring the nearby coral reefs, or indulging in fresh seafood at our waterfront restaurant, our property creates an idyllic retreat for an unforgettable escape in the heart of Islamorada's enchanting landscape.PLEASE NOTE:This listing is specifically for a hotel room located within a hotel, distinguishing it from typical resident

Located in Tierra Verde, Florida, United States. Waterfront Condo in island paradise! Spacious 2 bedroom waterfront condo in gated community on the beautiful upscale island of Tierra Verde. Fully furnished with fully equipped kitchen. 3 heated pools, 3 hot tubs, 3 tennis courts, clubhouse with fitness center, pool table, library and ample walking trails along the waters edge. Fort DeSoto Beach/State Park 5 minutes away with walking trails, bike and kayak rentals galore! St Pete Beach/Pass-a-Grille Beach close by as well 15 minute drive to downtown St Pete restaurants, farmers markets and night life. Active community for great Florida living! 3 month minimum stay.

Located in Tierra Verde, Florida, United States. Stunning Remodel & Kitchen, On the Bay, Close to Beach, available January 2025 Beautifully Remodeled Condo with Waterfront Views of Tampa Bay located on the island of Tierra Verde. Close to everything and only a few minutes drive to the beautiful white sand beaches of St Pete. Enjoy miles of Bike Paths through Ft Desoto Park right outside the complex. We provide everything you need to start your stay! Beautiful waterfront pool and hot tub, tennis courts, small marina, deck with communal grills overlooking the bay - this place is a wow! It's a friendly, quiet small community. Condo is convenient to Tampa, Clearwater and Sarasota and only10 minutes to downtown St. Pete with lots of restaurants, museums, music venues and more.IF days are blocked that you are interested in staying ...please message me!!

Located in Tierra Verde, Florida, United States. Renovated 6/2023 Top Floor Balcony Water View 2B/2B, Pool, Hot Tub, Grill, WIFI Gorgeous Water View!! - Completely Renovated JUNE 2023!!BALCONY WATER VIEW OF TAMPA BAY AND POOL at Holiday Island Resort! Escape to this recently renovated condo!! Non-smoking, no pets allowed. This condo complex was built on the narrow island of Tierra Verde which is surrounded by the Gulf of Mexico on the west side and Tampa Bay on the east side. The property is 3 miles from Fort Desoto, which was rated #1 beach in the United States in 2005. Bring your own bicycles to enjoy the bike path which is accessible from our property into Fort DeSoto which is a Pinellas County Park. The park has miles of beautiful beaches where you can purchase refreshments, roller blade, fish off the pier, rent camp sites, launch boats or have any kind of fun in the sun you can imagine! Easy access to interstate highways. Tampa International Airport is a quick 25 minute drive. Beaches and restaurants are 5 minute drive. This i

Located in St. Petersburg, Florida, United States. Tierra Verde Sunset Point Waterfront Mansion This waterfront mansion has unobstructed views of the Gulf of Mexico. This exquisite estate also affords nice views of shell key and pass -a -grille. Watch the dolphins play while sunning pool side.

Located in Tierra Verde, Florida, United States. Ft.Desoto/St. Pete Beach UPDATED, PEACEFUL, WONDERFUL.Tired of "fees"? Not here! Besides an incredible experience and a fantastic condo at a great location we offer BY OWNER pricing that is simple and not gouging.For a MONTHLY rate for the months of May through December we will also give 37% off which should basically bring you down to about $3,000 baseWe charge only for the condo, a legitimate cleaning fee which is not padded, and the legitimate lodging tax.Take a break and unwind at this peaceful oasis. The CLOSEST building to the water, the A building and our wonderfully updated condo is the closest to the large heated, waterview pool and hot tub. Literally 6 steps!King bed in master and and look at the pics to see how wonderfully updated the unit is.Also the 3rd closest resort to the incredible beaches and bike trails of Ft. DeSoto. Literally 1.9 miles to the beginning of the park and 3.4 miles to the park entry booth, So 5 minutes to the incredible and typically lightly attended

Located in Tierra Verde, Florida, United States. From serene morning sunrises to exciting nearby attractions, Immerse yourself Breathtaking Sunrises and Serene MorningsStart your day with the stunning sight of the sun rising over Tampa Bay from your private waterfront balcony. Enjoy a cup of coffee while surrounded by lush tropical landscaping, creating a perfect peaceful retreat.Immerse yourself in the island lifestyle at Wander Residences. Whether you're seeking relaxation or adventure, our waterfront complex provides the perfect setting for a memorable vacation. Book your stay today and discover the tranquility and charm at Wander Residences! Nestled on the picturesque waterfront of Tampa Bay, Wander Residences offers a serene and relaxing escape for your next vacation. This fully furnished rental in Building F provides stunning waterfront views and is ready for you to bask in the Florida sunshine, explore the sandy beaches, and indulge in a variety of activities. Resort Amenities At Wander Residences, you can enjoy a range of ame

Located in Tierra Verde, Florida, United States. Quiet Tierra Verde Waterfront Condo Minutes from Saint Pete It only took one visit for us to fall in love with Tierra Verde, and I think it would be the same for YOU! Tierra Verde is quiet area just minutes away from Saint Pete Beach and Downtown. Cross over the bridge and enjoy the perks of Saint Pete while staying in the luxury that is the Tierra Verde community. Our condo is located right on a canal where you can watch boats pass by, or get lucky and see the manatees! The short travel down the canal opens up into the beautiful Tampa Bay - where you can see the Tampa Bay bridge that lights up in wondrous colors at night! Looking for a nice dinner & drinks? You don’t even have to leave Tierra Verde. Within a mile radius, you can walk or bike ride and find local spots for food, drinks, and even live music! The condo also features a well-kept pool, tennis courts, and a spot to store your recreational water toys (kayak, paddle board, etc).

Located in Tierra Verde, Florida, United States. Tierra Verde - St. Petersburg Waterfront Mansion Estate - Pool - Boat Dock This Single Family Home contains 7,719 sq ft of covered living space! This Exclusive Tierra Verde Homefront is located at the end of a Private Cul De Sac. The back Faces Boca Ciega Bay with an Extraordinary Pool & Outdoor Entertainment Area. The Pool is lined with Fountains, Topicals & offers a Boat Dock. The Guest Pool House is located in a separate building next to the Pool and includes an Ensuite Bath with Water Views from the Bedside. The Master Suite in the main house has a Private Entry and Sitting area Poolside. Signed Contract and Photo ID Required Before Check-InExterior Cameras Record Audio and Video 24/7With its 30ft high Sprawling Entry Ceilings, Chandeliers, Formal and Informal Dining Rooms, Fireplaces, Master Office Space and Uniquely Textured Walls it is Exquisite. The open Spacious Kitchen with Walk In Pantry, 6 Burner Gas Stove, 3 Ovens and an extra large Double Door Refrigerator/Freezer, is ope

Located in Tierra Verde, Florida, United States. Tierra Palms - Pool View, Garage, Nearby Beaches Beautifully decorated 2-bedroom condo in idyllic Tierra Verde. Experience life on "The Island" and live like a local, just minutes from the beautiful beaches of Fort De Soto Park and a quick drive to all St. Petersburg has to offer. Corner unit next to the pool with upper and lower screened-in patios. With an inviting open floor plan, well-appointed kitchen, and two-car garage - you'll have everything you need to feel like you are home. Monthly rental minimum with rental agreement required. NO MAIL MAY BE DELIVERED TO THE PROPERTY. PLEASE INQUIRE WITH THE LOCAL POST OFFICE TO SECURE A PO BOX DURING YOUR STAY IF YOU FEEL YOU MAY NEED MAIL DELIVERY. The spaceWelcome home to "Tierra Palms", a stylish and comfortable two-bedroom condo located in beautiful Tierra Verde, just over the bridge from St. Pete Beach. With a minimum 30-day rental policy, we are the perfect destination for those seeking warmer climates in cooler weather. Spend your w

Located in Tierra Verde, Florida, United States. TRANQUILITY ON TIERRA VERDE 3 BEDROOMS TOWNHOUSE - ALL EN SUITE MASTER IS A KING OTHER 2 ROOMS QUEENS SPACIOUS LIVING ROOM DINING ROOM KITCHEN OPEN PLAN BIG MASTER , NEWLEY RENOVATED & SOME MORE RENOVATION WILL BE DONE BY NOVEMBER , 2 NEW BEDS , NEW MASTER SHOWER ....THE BEST NEIGHBOURS , QUIET ...NO PETS - POSSIBLY 1 VERY SMALL DOG UNDER 15lb. FEE WOULD APPPLY APPROVAL NEEDED TO BOOK MUST BE OVER 40 NO KIDS , MIN AGE 25 for any guest THXS ANN

Located in Holmes Beach, Florida, United States. Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill Palm Oasis Villa West is a 2 bedroom, 1 bath ground level condo that is walking distance to pristine Gulf beaches. This duplex villa has lush tropical landscaping and the heated shared pool is surrounded by a privacy fence. It is located in a quiet and desirable part of the island. Relax in the chaise loungers before you fire up your own BBQ grill for your favorite grill specials. Each unit has its own private back yard with a 6 person dining table and grill. There is plenty of brick paver deck space to soak up the Florida sunshine! This property can be rented together with its neighboring Villa East property VRBO 1411133 to serve as a family retreat, providing a level of privacy that a single-family home does not offer. Also, this is a perfect Villa duplex for in-laws or grandparents.The master bedroom has a king-sized bed. The second bedroom has twin beds and one has a pullout trundle bed. This unit co