58,368 properties available

Located in Siesta Key, Florida, United States. Remodeled Townhome with Private Pool, Spa, and Ping Pong! Island Time East Island Time East by Siesta Key Luxury Rental PropertiesHome in Sarasota, FL 34242Siesta Key Luxury Rental Properties - The Best Homes, Location, and Vacation Experience on Siesta Key!Enjoy a beautiful coastal vacation at Island Time East, a three-bedroom and three-and-a-half bathroom getaway located just a short walk away from Florida's most stunning beach and the vibrant Siesta Key village. Island Time East boasts an amazing backyard with a sparkling pool, an in-ground spa, and a stunning waterfall. At A Glance• Private Pool and In-Ground Spa• Less than a 5-minute walk to the beach• Game Room• Dog Friendly• Covered PatioThe living area features a beach-themed decor complete with a cozy sofa, two comfortable side chairs, and an HDTV. The stunning kitchen with stainless steel appliances is perfect for preparing your favorite meals. The primary bedroom has a king-size bed and a balcony with comfortable seating, wh

Located in Siesta Key, Florida, United States. Large unit across from beach, walk to village, fully renovated & partial view. This unit is directly across from Beach Access 10 and is fully renovated and this is the first time on the market. There is a spacious king bedroom with tv, dresser and spacious closet with twin sleeping accommodations. The full bathroom has been fully renovated with tub and large single vanity. Dining area seats 4 and the kitchen is upgraded and well appointed with everything you should need to cook with. There is a living room with couch, seating area (with a small gulf view), tv and console and rollaway bed. The porch has glass windows that can be opened or closed, the area is air conditioned. There is a dining table for 2, rocking chair and two arm chairs with coffee table.

Located in Siesta Key, Florida, United States. The Village Breeze 6BR with heated Pool, near Beach, 250ft to Siesta Key Village! This is The Village Breeze 6BR, a Gertrude Rentals property. No car required! Three 2BR units, two units are side by side, and the 3rd is directly across the pool. Enviable location on quiet street, with heated Pool, near Beach, but just 250ft to the world famous Siesta Key Village. A true favorite of initiated guests, and sure to provide a combination of fun and rejuvenation you won't find in other getaways.The Location – The possibilities are endless! Enjoy the best Beaches, Seafood, Drinks, Ice-Cream, Shopping, Oysters, Live-Entertainment, fresh-Donuts, Daiquiris, big-Breakfast, and the Coldest-Beer on the Island. Rare secluded street in the heart of Siesta Keys world famous Village. Just a short walk to two of the best beaches on the planet and only 250 feet to all the best of the Village. One of only four units in this building. The beaches at this location are the widest and have panoramic views

Located in Siesta Key, Florida, United States. GROUND FLOOR CONDO DIRECTLY ON SIESTA BEACH! Only 3 blocks to Siesta Village Walk 50 ft. out your lanai door and you are on the white sands of Siesta Beach. Walk 3 blocks out your front door and you are in the heart of Siesta Village, dining and shopping area. No Car Required. This 2 BD/2 BA ground floor condo, corner unit, gives you direct access to 1,100 feet of PRIVATE sugar white sand of Siesta Beach (3.5 mi. long.) The views of the Gulf of Mexico, Big Pass and South Lido Beach are extraordinary. There are 2 pools in the complex. The one overlooking the Gulf of Mexico, is right on the beach just outside your lanai door about 40 ft. The condo's 26 foot expanse of tinted, hurricane poof glass doors on the lanai offer ever-present views of the beach and Gulf of Mexico from the Living Rm., Dinning Rm. and Primary Bedroom. This Beach home is 1440 sq. ft. which includes the 6'x26' lanai; The perfect place to enjoy cocktails and Siesta Keys beautiful sunsets. The home has been totally ref

Located in Siesta Key, Florida, United States. Modern 3 Bed/2.5 bath Gulf Side Condo Steps from Siesta Key Village and Beach! This updated, relaxing, modern, beachfront condo, offers partial beach views and a straight walk to the sugary white sand and crystal-clear water! With 3 bedrooms, 2.5 bathrooms, this home comfortably sleeps 8. Wake in the master bedroom’s king size bed to enjoy the Gulf of Mexico views from your own private balcony. In the second bedroom, is a queen size bed with another balcony and in the third bedroom is a full-over-queen size bunk bed, featuring a large walk-in closet. Perfectly located for a trip to the beach or a short walking into the Siesta Key Village, this lovely vacation home is sure to provide plenty of wonderful memories that will have you coming back year after year!*Stairs only. All guests must have the ability to use stairs.Master: KingBedroom 2: QueenBedroom 3: Bunk Bed (Full/ Queen)Included in your stay:Complimentary Bicycles,Wifi,Parking,Private Beach Access,Beach Chairs,Beach Towels,Beach

Located in Siesta Key, Florida, United States. Beach Road Condo - Private Deck - Siesta Key Village & Beach Walkable! Known for its quartz sand and crystal clear waters, the beaches of Siesta Keys are ranked No. 2 in the U.S. and No. 9 globally as one of the best travel destinations in 2024. Siesta Key, a barrier island in the Gulf of Mexico, is less than a 30 min drive from SRQ Airport. This vacation rental is one of a few hand-selected options brought to you by Siesta Key Dreams. With Beach and Village walkability, we are confident that this space will cultivate unforgettable memories.In addition to the stunning, white quartz sand, the beaches of Siesta Keys offer picnic areas, concession stands, and volleyball courts. The shallow, crystal water and year-round lifeguard protection makes each beach a safe and relaxing escape. Having your property mere minutes away from the ocean means that you will certainly witness breathtaking sunsets. A 3-minute walk from the beach reveals Siesta Village, which offers a wide-range of dining and

Located in Siesta Key, Florida, United States. Siesta Sea Life | Walking Distance to Siesta Key Beach & Village w/ Private Heated Pool! Welcome to Siesta Sea Life, a coastal villa that offers the perfect blend of luxury, convenience, and relaxation. This remarkable duplex property can be rented as a whole, known as Siesta Sea Life, or separately as Sea la Vie and Sea Esta, allowing you to choose the ideal accommodation to suit your needs. With a private heated pool, an unbeatable location just a 3-minute walk from Siesta Key Village, and a mere 1-minute walk to the pristine Siesta Key Beach, Siesta Sea Life is your ultimate gateway to an unforgettable vacation.Featuring 6 bedrooms and 4 full baths, including 2 master bedrooms, Siesta Sea Life provides ample space to comfortably accommodate up to 16 guests. The sleeping arrangements consist of 2 king beds and 6 queen beds, all equipped with high-quality linens to ensure a restful night's sleep.To ensure a seamless start to your vacation, we provide a starter pack of toiletry essenti

Located in Siesta Key, Florida, United States. Huge Yard, Heated Pool & Tiki Hut, Steps to Beach - The Pool House The Pool House by Siesta Key Luxury Rental PropertiesHome in Siesta Key, Florida Welcome to The Pool House, a gorgeous Sunset Pointe home where you can lounge by the sparkling pool in year-round sunshine, enjoy easy access to Siesta Beach, and dine in Siesta Village steps away. With five bedrooms and four bathrooms, there is plenty of space for your beach-loving crew to unwind and enjoy paradise. Pack your sunglasses and flip-flops and get ready for fun. Highlights• Less than 5-minute walk to Siesta Beach• Private heated pool with spa• Outdoor seating• Tiki hut• Ping Pong table• Dog friendly with approval and additional fee• Near restaurants and shopsWhen you enter the home, you'll notice the luxe coastal decor and open and airy spacious feel. There is a vibrant seating area with two sofas and a TV. Cooking is a breeze in the chef's kitchen with stainless steel appliances, a large island with countertop seating, and an

Located in Siesta Key, Florida, United States. Perfect location Walk to the village and beach Private Balcony Facing a stretch of Siesta Key’s Grand Canal, this 3-bedroom home is within strolling distance of the island’s best beaches, dining, shopping, and entertainment. Vaulted ceilings, an open multilevel floor plan, and breezy beach décor contribute to the space’s fresh, serene feel.Upon entry, immediately ascend to the main (second) floor. In the master bedroom, located on this main floor, you will find a king-sized bed with quality linens. An updated full bath is conveniently situated next to the master bedroom. Also on the main floor, the kitchen is equipped with modern cabinets, granite countertops with a sleek tile backsplash, and stainless steel appliances. Adjoining the kitchen is the dining area, which comfortably seats six and opens up to the great room. This spacious living area features sliding glass doors that open up to the balcony and 20-foot ceilings with ceiling fans. The flatscreen TV features cable with upgrad

Located in Siesta Key, Florida, United States. Stunning 3 Bedroom / 2.5 Bath Condo Steps from Siesta Key Beach! This must-see, beautiful home on Siesta Key offers a much sought after modern and contemporary design. This unit, located on the 2nd floor above the garage, has 3-bedroom, 2.5-bathrooms and can sleep up to 6 guests. Enjoy the fresh island breeze from your balcony, or step outside and relax in the warm sun by the pool, private to the Ocean Vue units. Less than 300 feet from beach access #11, this home offers quick access to the #1 rated Siesta Beach! You can even take the short walk into the Siesta Key Village where you can experience the many great shops, restaurants, and live entertainment the island has to offer. *This property is stairs only; all guest must have the ability to climb stairs.*No garage parking. Driveway parking only.Bedroom 1: QueenBedroom 2: KingBedroom 3: Queen Sleeper SofaIncluded in your stay:Complimentary Bicycles,Wifi,Parking,Beach Chairs,Beach Towels,Beach Wagon,Beach Cooler,Free-Rides Around Sies

Located in Siesta Key, Florida, United States. Nook Cottage Across street from beach and Heated Pool This is a ground floor, one bedroom, one bath unit with King-size Serta ICOMFORT CF 3000 Memory Foam Gel Series bed in the master and full bath off of the bedroom, ensuite. Large walk-in tile shower with glass enclosure.The Nook features a fully equipped kitchen with granite counter tops and cozy dining area and beach chic laminate wood flooring throughout. This unit is naturally bright and spacious, with white-washed tongue and groove accent walls. Enjoy a flat screen, 55 inch TV in Living, DVD player and a flat-screen TV in master bedroom. Relax in the lovely outside garden area off the front entry, with table and chairs and extra seating for guests. This is a dog-friendly unit, but dogs must be approved by the office before booking. There is a dog fee placed on the reservation. (Maximum 2 Guests).

Located in Siesta Key, Florida, United States. Rooftop with Gulf Views, Heated Pool/Spa, and Games - Siesta Palooza Siesta Palooza by Siesta Key Luxury Rental Properties Home in Siesta Key, FL Resort island living awaits at Siesta Palooza! This eight-bedroom and eight-bath home is a true masterpiece with a picture-perfect backyard and marvelous amenities including, a sparkling pool, rooftop deck, ping pong table, washer and dryer, and loft area with video games. Highlights• Less than a 10-minute walk to the beach• Private pool and in-ground spa• Rooftop deck• Ping Pong table• ElevatorSiesta Key Luxury Rental Properties - The Best Homes, Location and Vacation Experience on Siesta Key! This home has four levels that can be easily accessed by using stairs or an elevator. The main living floor features a coastal seating area with a television and a fully-equipped kitchen with high-end appliances and essential amenities. Guests can choose to enjoy their meals at the kitchen island, in the formal dining room, or on the main deck that is

Located in Siesta Key, Florida, United States. Spacious Siesta Key Paradise-Canal front, private pool, walk to SK Beach/Village Beaches, Boating and Bistros! Live the island lifestyle in this spacious 5 bedroom, 4 bathroom house located on desirable Palm Island on Siesta Key. Lounge in the heated pool and spa or enjoy your favorite libation at your private Waterfront Tiki Bar. The best location on Siesta Key. 7 minute walk to Siesta Key Beach, 9 minute walk to Siesta Key Village. Large private heated pool with hot tub.House is located on the Grand Canal with access to the Intercostal Waterway, with private dock. Large private deck right on the canal for relaxing or entertaining. Also has Tiki Bar adjacent to pool and dock, with large fire pit area. Large heated pool has ample chase lounges, chairs and dinning area that seats 10. Pool area also has large spa whirlpool.The 5 bedrooms will accommodate 10 people. Master suite and 3 other bedrooms on main(second) floor, along with 3 full bathrooms. Master suite is equipped with

Located in Siesta Key, Florida, United States. 3-bedroom king bed, house in superb Siesta Key with WiFi, AC This 3-bedroom house is perfect for your escape to Siesta Key. With 1 king bed and 2 queen beds, guests can unwind in the wonderful bedrooms. The bathroom features a shower and a hair dryer for added convenience. In the cozy living room, there's an extra full bed for additional sleeping space. Enjoy the tranquil atmosphere of this quaint property, complete with amenities like a washing machine, AC, WiFi, and an iron. We hope you enjoy what our place and Siesta Key has to offer.

Located in Siesta Key, Florida, United States. The Little Salty - Siesta Key Cottage Live the Siesta Key lifestyle: • Short walk to the beautiful white sand beaches • Linger in the vibrant cafes and shops of The Village • Kayak along the key’s Grand Canal • Spend afternoons relaxing in the pool • Enjoy Siesta’s famous sunsets on your private dockThe houseNestled beneath the majestic southern live oaks and native palms, this is a two bedroom, two bath home with a 1 bedroom, 1 bath attached apartment. Both are fully furnished with everything you need for an amazing retreat. It is located on quiet and charming Palm Island, the “heart of Siesta Key”. The main cottage has an updated eat-in kitchen with everything you could want and overlooks the screened pool where you can cool off from long days at the beach. The large living and dining areas are perfect for entertaining and look out onto a covered patio just steps from your private dock and the famous Siesta Key Sunsets. The apartment offers a fully equipped galley kitchen overlooki

Located in Siesta Key, Florida, United States. Tivoli by the Sea-Unit 701 - Stunning & Spacious one bedroom wit Your Ultimate Vacation Getaway Awaits Here! This beautifully decorated 1 bedroom/1 bath condo has all the comforts of home. This unit does not have a balcony, but does have plenty of natural light from the wall length windows in the living area. There is a gorgeous partial view of the Gulf of Mexico from each room. This unit features a queen size bed and sleeps 4. *Note: This unit does not have an outside balcony, view looks past the rooftop on the 7th floor. *No Washer/Dryer in unit , coin laundry in common areas on each floor.* Minimum 1 week rental.

Located in Miramar Beach, Florida, United States. FALL DATES AVAIL! Pet-Friendly 3BR Luxury Home walk to beach! This Tuscan stunner is the definition of luxury and comfort. Bel Sol is located within walking distance of beach, shopping, restaurants, and is the perfect spot for your vacation. Now Pet Friendly! (additional fee applies) One of the prettiest neighborhoods in all of Destin. A gated community with only a few homes make this vacation rental a must! No large crowds, and noise here and the tropical pool is truly an oasis!This unique home is simply stunning! Bel Sol is a Luxury Tuscan style home located in the upscale gated community of St. Tropez., a low density community with only 29 homes. Very quiet and private and the tropical pool is only about 25 steps from your backdoor! It includes deeded beach access & is located in the heart of Miramar Beach. This home's oversized balcony off the kitchen and den overlooks the stunning tropical lagoon style pool and hot tub and is surrounded by lush landscaping. Everything about th

Located in Miramar Beach, Florida, United States. GULF FRONT***Beach Service & Wi-Fi Included*** Looking to get away from the hustle and bustle? HAVE WE GOT A PLACE FOR YOU! As you walk into our unit you will be tranquilled by the warm, inviting, and relaxing colors and furnishings as well as the magnificent views. The living room is furnished with an elegant sofa and chair for you to relax in while watching your favorite program on the 32'flat screen TV. Meals can be prepared in our fully equipped kitchen and then enjoyed at the beautiful raised dining table and chairs or at the kitchen counter/bar. The full sized refrigerator will certainly come in handy for all your perishables.Enjoy the comforts of home when you enter the master bedroom. You will be welcomed by the soothing colors and furnishings of this elegantly decorated room. We have provided a TV which is placed in an armoire for comfortable viewing. Our unit is also furnished with full sized twin bunk beds as well as a queen size pullout sofa bed.A washer & dryer is a

Located in Miramar Beach, Florida, United States. Free Beach SRVC!!Direct VIEWS! Free Beach Bonfires M/F nts! Pickleball Courts 2nd floor and direct ocean views! Want to avoid the elevator? Take the stairs to the 2nd floor! Recent guest, Sharon H. had this to say...'Absolutely Beautiful!"We stayed at this awesome condo for our Anniversary in April. It was absolutely perfect!!! The condo is so fresh and clean with everything you need for a getaway!! It is beautifully decorated and the view from the balcony is spectacular!! We hope to book this place again soon!! A huge thanks to Julie for being so easy to work with!"This 1 bedroom/ 1 bath Gulf front efficiency is renovated and fabulous! Don't worry about carrying your chairs and an umbrella to the beach, because this unit comes with free beach service (March -Oct). Gorgeous and ocean front!Free Beach Bonfires on Monday and Friday nightsNew granite, new cabinetsLarge walk-in showerDirect ocean facing balconyNew King mattressAll New FurnitureWell Equipped Kitchen area has: toaster oven,

Located in Miramar Beach, Florida, United States. Coastal Bliss and Million Dollar Views Breathtaking Gulf View Condo with Luxurious AmenitiesWelcome to your slice of paradise at Surfside Condominiums, where every moment is a picturesque postcard of beachfront bliss. Nestled along the pristine shores of one of the world's most beautiful beaches, this stunning condo offers an unrivaled retreat for those seeking the ultimate getaway.Step inside to discover a haven of comfort and style, where panoramic Gulf views greet you at every turn. Whether you're savoring your morning coffee or toasting to another stunning sunset, the unobstructed vista from your private space promises moments of tranquility and awe.After a day of sun, sand, and surf, retreat to the embrace of your king-size Sleep Number bed, where plush linens and ocean breezes ensure a restful night's sleep. Catch up on your favorite shows or unwind with a movie on the large, flat-screen TV, or indulge in the array of amenities Surfside has to offer.From complimentary beach servi

Located in Miramar Beach, Florida, United States. Cozy Studio Just Steps From The Beach Cozy studio comfortably accommodates 4 people with two queen size beds. This year DAILY BEACH SERVICE is included in your rental. A daily set up of 2 chairs and an umbrella on the beach. A daily value of $50z This service is available March 1st to October 31st.This unit comes fully furnished with a mini fridge, microwave, toaster, Keurig coffeemaker, and all linens.* Complimentary high speed WI-FI* Flat screen TV with DVD player* Private balcony* Picnic area with barbecues (gas and charcoal)* Outdoor kitchen* Garage parking for 1 car24 Hour Security* Heated pool* 2 Hot Tubs* Beach BarAnd a host of other recently upgraded amenities.Surfside Resort boasts an onsite restaurant, The Royal Palm Grill, Surfside Spa, and Rogue and Pure beauty salon. There are also numerous sporting amenities at Surfside including tennis courts, basketball courts, pickle ball, shuffleboard and a complimentary fitness center. Surfside Resort is close to many shoppi

Located in Miramar Beach, Florida, United States. Magnificent Sixth-floor Oceanfront Condo with pool, Tennis & Gym Beach House B602Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Beach House 602B is a lovely condo boasting a casual coastal feel, breathtaking views of the Gulf of Mexico, and plenty of space for the whole family. With a king-size bed in the main bedroom, two twin-size beds in the guest bedroom, along with a queen-size sofa bed in the living room, Beach House 602B accommodates up to six guests comfortably. Whether you are taking a family beach vacation, going on a spontaneous trip with friends, attending a special event, or any occasion between, Beach House 602B offers a picturesque accommodation for your next beach vacation. Upon entering, you will be adorned with welcoming décor as well as gorgeous tile floors with carpeting in the bedrooms. You will find the guest bedroom on your left, featuring two twin-size beds with floral beddi

Located in Miramar Beach, Florida, United States. Updated Gulf view condo with resort pool, hot tub, gym & beach bar Surfside Resort 206Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'This elegant, recently updated condo at the Surfside Resort will truly check every box for your next escape to Miramar Beach! The open floor plan, the well-appointed kitchen, and the generous balcony space with views of the Gulf of Mexico are just what you need for quality family time. You'll also enjoy shared access to a swimming pool, a kiddie pool, a hot tub, a beach bar, a gym, and more - this resort has something for everyone!What's nearby:The central location of the Surfside Resort is sure to please any crowd. You'll be right across Scenic Gulf Drive from the white sand beach, and a short stroll from the Surf Hut (a local favorite for beachside dinners and games in the sand). This area is a shopper's haven, with Silver Sands Premium Outlets (two miles northeast)

Located in Miramar Beach, Florida, United States. The Crescent 107 - a premier condominium along Scenic Highway 98 Beach Set Up Included in Season!EV charging capabilitiesIf you’re looking for more than just a sunshine state of mind, look no further than The Crescent 107, a beautiful condo in Miramar Beach! Just steps from the beach and with two community pools, you’ll be soaking up the sun in no time. Our warm and friendly Scenic Stays team looks forward to welcoming you on your next coastal getaway!The Crescent 107 is a lovely condo with two bedrooms and two baths accommodating up to six. Coastal elegance permeates the open-concept living/dining space while large sliding glass doors invite the outdoors in. Cook and dine in relaxed luxury in the beautifully appointed kitchen, a lovely environment for serving up your favorite meals. Generous counters and cabinets are handy, particularly if you need additional room to store a few staples. The kitchen flows seamlessly into a spacious living room, with plush furnishings and a flat-scree