58,368 properties available

Located in Islamorada, Florida, United States. Relaxing waterfront retreat with boat dock & amazing ocean views Paradise BeachOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'*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.Enjoy 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.Situated 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 Ke

Located in Islamorada, Florida, United States. Beautiful Islamorada Vacation rental pool home with private beach!!! Beautiful 5 bedroom, 3 bath pool home with 70 foot of dockage at mile marker 74.5 on the bay side. The first floor is a private apartment with two bedrooms, one has a queen and the other two queens. Has a full kitchen, living room, dining area and full bathroom. The second floor has three bedrooms, two with queens and the master has a king. we also have access to a private beach (white marlin beach) and we are just 4 houses and 3 lots down from open bay water. Great for paddle boarding or kayaking. Immediate access to bay and ocean via channel two bridge.So if you are going to visit the keys you must pick islamorada!!!  We have absolutely amazing restaurants most with amazing views.  The sunsets are amazing, we even get green flashes.  Islamorada is very narrow so almost where ever you are at you will be seeing the gorgeous water.  The colors are compared to the bahamas, trust me, living here can make traveling diffic

Located in Islamorada, Florida, United States. 3 BR 2 Bath Islamorada home with Private Beach Access Vacation in this cozy canal front home in the heart of Islamorada, midpoint between Miami and Key West. Large upstairs balcony with dining table and hammocks . Relax downstairs in sunroom or in breezy open carport with grill. Enjoy access to homeowners’ private beach in the community of Port Antigua . Restaurants and shopping minutes away .

Located in Islamorada, Florida, United States. Port Antigua Home in a Private Beach & Golf Cart Community Our relaxing 3 STORY, 4 bedroom, 3.5 bathroom home is located in Islamorada, Florida within the Private Beach community of Port Antigua. Conveniently situated at Mile Marker 74.5, near the world famous Tiki Bar, Theater of the Sea and you can even feed the tarpons at Robbie’s! There is easy ocean access from the 90’ concrete dock with wide canals. Water, shore power, and fish cleaning station are all conveniently located at the home’s dock. This home will accommodate up to 12 guests in beds and its open floor plan makes it easy for everyone to move around. There is a great downstairs terrace for entertaining, fishing, Barbecuing, or just hanging around. Updated kitchen with all modern appliances, two dining tables and a bar provides seating space for all guest and more. Two separate family rooms provide entertainment for all. This home has Vaulted ceilings, an outdoor shower, and a Refrigerator / freezer downstairs to store you

Located in Islamorada, Florida, United States. Fantastic Home in the Fishing Capital of the World! This is a custom-built Mediterranean style home located in an exclusive community with a private beach for owners and residents. The house has three stories, a master suite on the third floor with and office and an immense beautiful marble bath. There are two large bedrooms on the second floor, a full bath, living and dining area and an open French style exquisite kichen. Also, a large open porch.The first floor has independent in-laws' quarters with full bath in addition to the expansive lockable storage, gorgeous wet bar, huge freezer, covered parking area and large ice maker and fridge. There is a cargo lift from the ground to the second floor. There is room for 2 large boats to dock at the 175 feet corner dock area with davits, covered hot tub, 2 kayaks, 3 adult bikes, and golf cart. Seasonal rental from November 1st thru March 31st. Minimum rental 60 days, offered at $230.00 daily. Keywords: Three story corner home with

Located in Islamorada, Florida, United States. Beautiful 2/2 Florida keys home rental Beautiful 2/2 fully equipped Islamorda premier private neighborhood florida keys home . Private community with private beach , golf cart allowed on public road ,community access to private boat ramp. Will rent 3 month minimum to snowbirds From the month of November through April .Preferably to adults with no children and no pets. Access to 25' of rear dock space Beautiful views from terrace Please contact me for further details and information. Bill Dominguez 305 796 6526

Located in Santa Rosa Beach, Florida, United States. Seaside Cottage "SEA SHACK" * Adorable Tupelo Street, * Sleeps 4 * Dune Vacation Rentals presents "Sea Shack " a beautifully remodeled home from top to bottom and is the perfect location for your Seaside getaway! This quaint and luxurious guest cottage is located on peaceful Tupelo street and is a quick walk to the adult pool, fitness center, family pool and tennis facility. The guest cottage is decorated in a coastal luxury style, featuring creamy white walls, wood floors and brand new, vintage-style appliances in the kitchen.The living space of Sea Shack is on the first floor and features a flat screen TV, comfortable seating and a convertible sofa that pulls out to sleep one person. The kitchen features all new, vintage-style appliances surrounded by creamy white cabinets. The dining area that seats five is just off of the kitchen area and is surrounded by windows to provide plenty of natural light. One of your favorite places to spend time is sure to be the spacious, deck area. Th

Located in Santa Rosa Beach, Florida, United States. PRIME SEASIDE LOCATION 59 FT TO BEACH ACESS, 2 MINS TO AMPHITHEATER, Seasuite 1 QUEEN, 1 QUEEN SLEEPER SOFA - sleeps fourWelcome to the guest cottage Seasuite- located directly across from the beach in Seaside, Florida. This modern guest cottage has a prime Seaside location only 59 feet to the beach access at East Ruskin Pavilion and only a 2 minute walk to the Seaside, Florida. Park and walk to over 35 shops, restaurants, dining, and a gourmet grocery all within minutes from your cottage. Seasuite can be rented alone or in conjunction with the main house, SloMocean. Seasuite is the perfect couples escape or great for young families given its proximity to the beach and dining. At Seasuite you have a private beach escape for two close to all things Seaside, Florida. This newer construction guest cottage has been thoughtfully designed and furnished throughout. The first floor features a queen bedroom with an adjacent marble bathroom. The bathroom has a marble single vanity and a glass

Located in Santa Rosa Beach, Florida, United States. GUEST COTTAGE W/KING MASTER IN SEAIDE AND STEPS TO BEACH, Honahlea KING, 2 TWINS (sleeps four total)Perfectly situated just one block from the beach and steps away from the Westside pool in Seaside, ‘Honahlea’, the guest house of ‘Midsummer Night’s Dream’, is ready to host your next Seaside beach vacation. Arrive and make your way to the cottage by meandering down a tranquil sandy footpath and be warmly greeted by a white picket fence and an inviting open-air front porch, featuring outdoor fans and comfortable chaise lounge seating that overlooks the private front yard. What a fantastic spot to kick back and relax for morning coffee or after a day at the beach! This beach bungalow provides its guests with a master bedroom, featuring a king-size bed and jacuzzi tub. Also on the first floor, guests can enjoy a living/dining area, a fireplace, and a fully equipped kitchen. Off the living area is a bonus loft space (best for children) with a ship's ladder and features a futon sleeping twin

Located in Santa Rosa Beach, Florida, United States. LUXURY RENOVATED CONDO W/STUNNING GULF VIEWS IN SEASIDE, Musician KING, QUEEN SLEEPER SOFAPicture yourself in a recently renovated to the studs penthouse that overlooks Central Square and the Gulf of Mexico located directly across from the beach in Seaside, Florida. ‘Musician’ is situated in the middle of all things Seaside, can bring this vision to reality with incredible roof top gulf and sunset views!Ideally situated on the back side of the Dreamland Heights Building on the 3rd and 4th floor, this designer penthouse will serve as the perfect coastal hideaway. On arrival you’re greeted by a spacious outdoor common area featuring ample seating and gulf views! Step inside to the first level and to the left is a completely renovated kitchen with all new top of the line stainless steel appliances and a small dining area with bistro seating for two. Off the kitchen and before the king master bedroom is the one fully renovated marble bathroom with a single vanity and a glass enclosed wal

Located in Santa Rosa Beach, Florida, United States. Better Days in Seaside A quaint one bedroom, one bath cottage in the heart of Seaside, FL.Upon entering Better Days, you are welcomed in to the first floor hall that leads to the queen bedroom, full bath and laundry. The queen bedroom offers plenty of storage and a flat 24 in screen cable TV (not smart TV). There is a full bath with shower stall and a washer & dryer for your convenience.Head upstairs to the living area and enjoy the 39" flat screen smart TV and new futon sofa that can lay flat as small bed for a small child. The kitchen boasts all stainless steel appliances and a dining table for three. There is also a balcony off the living room for enjoying your morning cup of coffee or your evening glass of wine.* 3 night minimum Spring, Spring Break, Summer, and Fall; 2 night minimum Winter. Must be 25 years of age to rent and sign the registration.FEATURES:* Features 504 square feet* Seaside Private Beach at Pensacola Pavilion* 1-minute walk, 121 feet to beach access* Located on W

Located in Santa Rosa Beach, Florida, United States. BEACHFRONT ONE BED COTTAGE IN SEASIDE, AMAZING GULF VIEWS! Beachfront 7! KING, QUEEN SLEEPER SOFAWelcome to Beachfront Cottage 7- perfectly situated on the beach in Seaside, Florida! Offering stunning views of the Gulf and sunsets, this elegant and classic beach home is the ultimate relaxing getaway. With its prime location and brand-new furnishings in a timeless coastal style, this unique Seaside, FL retreat will have guests eager to return year after year.Guests can stroll down a charming, shaded footpath in Seaside, FL to reach the entrance of this delightful escape. Step inside to the first floor, where you'll find a spacious king primary suite filled with natural light, a flat-screen TV, a full bathroom (shower only), and a private screened-in porch with a soaking tub and privacy curtains. It doesn’t get any better than this!Head upstairs to the open and airy second story, which features a combined floor plan with a newly furnished living room, updated kitchenette, and a large ope

Located in Santa Rosa Beach, Florida, United States. RENOVATED & DIRECTLY ACROSS FROM THE BEACH IN SEASIDE, Mis B' Haven Pretty in Pink! Mis B’Haven is tucked away on the secret gem in Seaside called Rosewalk. Rosewalk in Seaside is a cluster of quaint cottages with a pedestrian footpath meandering through a thick grove of oak trees on the East side, directly across from Tupelo Pavilion. This just-renovated-in-2020 cottage features the classic Seaside tongue and groove walls throughout in an adorable shade of pink. The home has undergone a major renovation and remodel with new furniture, new stainless steel kitchen appliances, countertops, bathroom renovations, not to mention the new dining table and fresh paint inside and out. The first floor includes a bedroom with a double bed, and a second bedroom with one twin bed and a full bath. The living room features new furniture throughout, a flat screen mounted TV, and has an updated dining area with a custom built in dining bench adjacent to the living room. The renovated kitchen is full si

Located in Santa Rosa Beach, Florida, United States. Seaside "Phenomenon"| 3 BR| Sleeps 8| 2 KINGS| Newly renovated! |Bikes Home Highlights:- 2 Private Parking Spots plus 2 Additional Seaside Parking Passes- Short walk to the private Seaside beach with access via Savannah or Tupelo pavilions-2 King bedrooms and a Bunk Room-TVs in all bedrooms with cable -Great Room TV cable + streaming available-Up to 8 Wrist Bands TOTAL for private beach access (per Seaside guidelines they will not provide us with more bands than the home sleeps)- Walking/biking distance to Seaside, shops and restaurants- Fully stocked kitchen- Two beach cruiser bikes included- Sandpiper Linen Program Participant: All linen, bedding and bath, are the highest quality. 450 thread count sheets for each bed and oversized towels in each bathroom are provided.Home Details: This cozy (hypo allergenic) cottage is decorated in classic and breezy colors. The downstairs open floor plan offers a living room with a flat screen TV, Apple TV and Wi-Fi, a modern well-equipped kitchen

Located in Santa Rosa Beach, Florida, United States. In Seaside, Across From West Side Pool, Guest House, Great Location! 1 QUEEN, 1 SLEEPER SOFA"Time Out of Time" is a delightfully appointed guest house tucked away in the pines on quiet Forest Street. Minutes away from the Gulf and just a few steps from the West side Pool, this one-bedroom hideaway is a perfect Seaside spot!The first floor includes a queen bed and bath (shower only), as well as a stackable washer/dryer in the closet. A spiral staircase leads to the second floor where there is a living area that opens to a small balcony where you will enjoy the Gulf breeze. There is also a dining area for two and a fully-equipped kitchen with access to the landing area that connects to the main house.For your convenience, there is an outdoor shower. For additional options, the main house, "Timeless", may be rented as a 4-bedroom cottage. Due to safety of spiral staircase, not suitable for children under five.* 3 night minimum Spring, Spring Break, Summer, and Fall | 2 night minimum Winte

Located in Santa Rosa Beach, Florida, United States. Seaside " Golden Lady" |2BR with Loft |Sleeps 6-8 | Next to West Family Pool! Home Highlights:- Located in Seaside with access to the private beach at the Natchez Pavilion-30 Second walk to the largest, family pool-2 Queen suites with cable TV access plus additional sleeping spaces- Walking/biking distance to Seaside, shops and restaurants- Spacious outdoor patios- Fully stocked kitchen- Two adult beach cruiser bikes-Up to 8 Wrist Bands TOTAL for private beach access (per Seaside guidelines they will not provide us with more bands than the home sleeps)- Sandpiper Linen Program Participant: All linen, bedding and bath, are the highest quality. 450 thread count sheets for each bed and oversized towels in each bathroom are provided.Home Details: Upon entering Golden Lady, you'll enjoy the Seaside popular designed "flip flop" floor plan with the 2 main sleeping areas on the first floor and the living/dining space upstairs. Each of the 2 guestrooms offers a queen bed with private on-suite

Located in Santa Rosa Beach, Florida, United States. BEACHFRONT HONEYMOON COTTAGE, RENOVATED IN SEASIDE! GULF VIEWS, - Sanctuary Sanctuary is a 1 bedroom, 1 bath honeymoon cottage on the beach offering romantic accommodations for you and your significant other with panoramic ocean views from your private balcony. Sanctuary underwent a complete renovation Spring of 2020 with a kitchen renovation, master bath renovation, and all new designer furniture throughout. The main level boasts a king bedroom with flat screen TV, private bath with tile shower, and private lower screened in porch with a deep soaker tub. Upstairs is a spacious living room with wrap around sofa, flat screen TV, complete with views of the gulf from the living room. The kitchen has been recently renovated with all new top of the line stainless steel appliances and a large farmhouse sink. Just off the living room is your private balcony. Enjoy your morning coffee overlooking the gulf or watch the sun set over cocktails at your private outdoor dining table. We hope you

Located in Santa Rosa Beach, Florida, United States. DIRECTLY ACROSS FROM BEACH with gulf views in Seaside, FL! Sip N Dip KING, QUEEN, QUEEN SLEEPER SOFALocated directly across from the beach in Seaside, this recently updated cottage conveniently opens onto both 30A and Tupelo Street. Once the residence of The Modica's, (of Modica Market), “Sip 'n Dip” is a timeless Seaside updated cottage with a prime Seaside location just 72 steps to the beach access and a 4 minute walk to the Seaside Amphitheater. This cottage is perfect for young families looking for a beach vacation and located within walking distance to all things Seaside, with over 35 shops and restaurants just steps from your front door. Guests will enter through the side exterior, onto a large screened-in furnished front porch surrounded by lush landscaping providing plenty of privacy. The front porch has a picnic table and adjacent outdoor lounge area perfect for dining Al Fresco or an evening glass of wine. From the front steps you will find and an additional open-air porch

Located in Santa Rosa Beach, Florida, United States. Beach House - Short Walk to Seaside & Beach! - Sleeps 10 Comfortably Come and enjoy the white sand and crystal blue beaches of 30A! The location of "Ellesmere" is ideal, located on picturesque Forest Street only 2 blocks from both the beach and Seaside. "Ellesmere" is nestled under a canopy of magnolia and live oak trees which provides a special feel of seclusion and privacy, while being only a short walk to Seaside and to public beach accesses. After you’ve finished lounging at the beach and enjoying all that Seaside has to offer, escape the commotion and return to the property to take a dip in the heated pool. Upon arriving at the property, park your car and walk or bike to Seaside to enjoy all the galleries, fine cuisine, antiques, live theatre, outdoor bazaars and entertainment. On your first day take a short stroll to the stunning beach and soak up the sun, grab a bite to eat at the Seagrove Market Cafe, try the shaved ice at Frostbites and then end your perfect day with fine di

Located in Santa Rosa Beach, Florida, United States. Ocean Blue - New Luxury Cottage in SEASIDE FL OCEANBLUE, 2 BR/2.5BA Brand New Cottage, 35 Tupelo St., Seaside, FL 32459The best luxury cottage in Seaside for your vacation get away. It's the newest cottage, just finished consruction 2/2019. What could be better than being in the town of "Seaside Florida" and being 150 feet from the private beach walkover. Less than 1 minute walk to the beach and 3 minute walk to center of town. Ocean Blue is a newly constructed 2 BR/2.5BA Cottage in Seaside FL community, just 150 ft to the Tupelo Beach Walkover. Just a 1 min. walk, as the 3rd house from Hwy 30A to the beach. 2 Free Adult Bikes, 4 Free Beach chairs and 2 umbrellas to take to the beach, and wagon with beach toys. Commercial carrier to carry the beach chairs and umbrellas.Ocean Blue is pure and total luxury with the highest end finishes and amenities. It is 800 square feet of living. 1st floor has white shell stone floors. Granite countertops. Custom made spiral staircase made of Hickory

Located in Seaside, New York, United States. In Seaside Proper, 'Sealink', 4 Houses from Beach, Gulf View 'SEALINK' One of the BEST locations in Seaside! This wonderful home, in Seaside proper, is the third house on Odessa Street at the west end of Seaside. 'SEALINK' is only 4 houses north of the beach and 4 houses south of the swimming pool.With it's quaint picket fence and over-sized wrap around porch, 'SEALINK' offers so many places to relax and enjoy the gulf breezes. On the screened porch, you will find comfortable seating, swing, gas grill, and dining table for just kicking back after a day on the beach or entertaining your family and friends. Even the sound of the rain on the porch roof from an occasional summer shower makes reading a good book read better. As you enter the house, an expansive foyer with staircase leads to the second and third floors. Beautiful bright beach colors are incorporated into the furnishings and original works of art throughout the house. In addition to the porch, you will find there are man

Located in Santa Rosa Beach, Florida, United States. Hidden Gem in Old Seagrove with Gulf Views-Steps from Seaside and the Beach! Gardner's Eden is a family-owned and operated house located just off of 30-A in Old Seagrove Beach. Situated about120 yards from the beach, you can easily walk down to the water or to Seaside (literally 10-15 yards away). It is situated on a private, dead-end street with no through traffic. The house is 2 floors with 3 bedrooms, 3 full baths and sleeps up to 6 adults comfortably. The unbeatable location provides quick and easy access to the state park, local restaurants, shopping, and the neighboring communities (Seaside, Seagrove and Watercolor), yet provides an escape away from the hustle and bustle of the crowds.Gardner's Eden has an open floor plan, perfect for families or enjoying the company of friends. The large living and dining area flows into the well equipped kitchen. One of the first floor bedrooms contains a king bed, the other first floor bedroom contains two twin beds, each with an en sui

Located in Seaside, New York, United States. Beautiful original Seaside Cottage + Swim & Tennis Club: Sleeps 6 Bella Vista, an authentic Seaside cottage, holds the unique distinction of being the first building established in the Seaside area, originally constructed in 1981 on Tupelo Street. Originally serving as the sales office for Seaside, it has since been lovingly converted into a cherished home. The quaint beach décor, coupled with its expansive screen porch, makes it a timeless favorite for families seeking an authentic Seaside experience. Positioned just as the second house on Tupelo, it's mere steps away from the beach pavilion.The cottage sleeps up to 6 with 2 queen bedrooms (each with a full bathroom), living room, dining room, snack bar, and kitchen all on one level. Spend your day at the beach or enjoy Seaside's private pool and tennis facilities. * Sorry No Pets Allowed * Parking for 2 cars. * Rate (excluding monthly) includes up to 6 amenity passes to Swim & Tennis Club.If you need more room, add Margarita Days to

Located in Santa Rosa Beach, Florida, United States. INCREDIBLE GULF VIEWS FROM BALCONY, ACROSS FROM BEACH - Cork the Whine 1 KING, 1 QUEEN SLEEPER SOFA, sleeps 4Welcome to, 'Cork the Wine'- a stylish, one-bedroom unit, ideally located on the third floor of the Dreamland Heights building in Seaside's own, Central Square! This condo offers stunning, panoramic gulf and town views from a private balcony and a modern, yet coastal interior that promises the ultimate reset. Upon arrival, guests can make their way to the Dreamland Heights building and into an elevator to access the entry door. Pre-entry, a pleasant, spacious common deck area with seating, as well as town and gulf views, lives outside your entry door! Step into the unit to locate a ship’s ladder and spiral staircase, which carries guests upstairs into a second story, featuring an open living area with tall ceilings, large windows, slipcover seating, a queen-size sleeper sofa and access to a private balcony that overlooks the town and the gulf! This level also features a dining