72,107 properties available

Located in Siesta Key, Florida, United States. Villa 3 - Standard Plus - Aloha Kai Vacation Villas Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States.Known for its bright white quartz beaches and emerald green waters, Siesta Key is one of Florida’s top vacation destinations.The stunning sands of Crescent Beach and clear water of the Gulf of Mexico impress even the most seasoned travelers. Over 3-miles long, Crescent Beach is the perfect place to go on soul soothing walks and take in the most magnificent sunsets you will ever see.Aloha Kai is the perfect location for a laid-back vacation at the beach. We invite you to lounge under one of our shaded beach pavilions or at our pool, which happens to be the largest on Siesta Key.

Located in Siesta Key, Florida, United States. Villa 42 - Standard Plus - Aloha Kai Vacation Villas Comfortable coastal decor welcomes you to relax and enjoy your beach getaway. Stainless steel appliances enhance the kitchen. There is a walk in shower for your convenience. Don't overlook the front porch and back patio for areas to expand your living space. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States.Known for its bright white quartz beaches and emerald green waters, Siesta Key is one of Florida’s top vacation destinations.The stunning sands of Crescent Beach and clear water of the Gulf of Mexico impress even the most seasoned travelers. Over 3-miles long, Crescent Beach is the perfect place to go on soul soothing walks and take in the most magnificent sunsets you will ever see.Aloha Kai is the perfect location for a laid-back vacation at the beach. We

Located in Siesta Key, Florida, United States. Siesta Key Beachfront, Updated 2 BR, 2 BA Condo, Sunset Views; Peppertree Bay! **PLEASE NOTE: I rent to guests only through VRBO. If you've received a quote or information from any other site, it is not legitimate. Please feel to reach out to me through this site with questions.**Experience Siesta Key resort living at its best at Peppertree Bay! The condo:• Is located directly on the beach, with gorgeous views of the beach and Gulf of Mexico,• Has two bedrooms and two full baths on the second floor of a two-story building, and• Provides a large, screened lanai to enjoy the beach even when you’re in the home.The layout of the home and privacy provided by bedroom separation makes it ideal for couples, a guys' or girls' trip, or families with children. Anyone who wants quality time beach- or poolside—or to simply relax and just gaze out on the Gulf view—will enjoy time here. **Please note that there is a 28-night minimum stay requirement, which the HOA put in place and enforces.**BEA

Located in Siesta Key, Florida, United States. Gulf side, spacious 1 bedroom, 1 bath, 200 steps to Crescent Beach Large one bedroom, one bath, walk up on the second floor, sleeps 4. Beach access approx. 200 steps from the white powdery sands on Crescent Beach on Siesta Key. Spacious 900 sq. ft, is your vacation paradise. Gulf and beach side bask in its beauty as you gaze upon the aqua green waters and watch spectacular sunsets. A private outside balcony extends the length of the unit for dining, reading, or relaxing in the sun. The one bedroom features a King size bed that overlooks the balcony. The updated bathroom is a tub and shower combination. In the living room you will find a Queen size sleeper sofa and TV. The kitchen is well equipped with appliances such as stovetop/oven, microwave, dishwasher, refrigerator including kitchen tools and accessories for cooking and baking. Two beach chairs and towels are provided for your trips to the beach. A BBQ gas grill and patio table seating is provided at the entryway for you to enjoy

Located in Siesta Key, Florida, United States. Ocean View 1 Bedroom Condo on Siesta Key! Condo #424 is located on the 4th floor at Harbor Towers Yacht & Racquet Club with a gulf view! This unit is recently renovated, upgraded kitchen that is well-equipped. There is a walk-in shower, the condo comes fully stocked with all your towel needs. In the bedroom, you will find a king-size bed with new linens. Outdoor balcony off the living room and bedroom where you can enjoy an afternoon cocktail while watching the sunset. Lovely view of the lush landscape and waterfall, partial view of the gulf. Cable and hi-speed WIFI included. The unit has a pull-out sofa in the living room. We supply Beach Chairs, Umbrella, and rolling cooler for beach use.Unit Amenities:Fully equipped kitchen with dishes, silverware, cooking utensils, microwave, refrigerator, coffee maker, and stove.Cable TVLinens and towels providedFully enclosed lanaiOn-site laundry facilities on each FloorFront entrance security gatesElectronic key card entry locks at all exte

Located in Siesta Key, Florida, United States. Villa 12 - Premium Plus - Aloha Kai Vacation Villas This beautifully updated villa is just waiting to provide the perfect beach getaway. Stroll the beach with your morning coffee and return for sunset. It's only steps way from this villa. The screened porch will provide a nice spot for enjoy the balmy afternoon breezes. Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States.Known for its bright white quartz beaches and emerald green waters, Siesta Key is one of Florida’s top vacation destinations.The stunning sands of Crescent Beach and clear water of the Gulf of Mexico impress even the most seasoned travelers. Over 3-miles long, Crescent Beach is the perfect place to go on soul soothing walks and take in the most magnificent sunsets you will ever see.Aloha Kai is the perfect location for a laid-back vacation at the

Located in Siesta Key, Florida, United States. Siesta Key 3bdr Luxury - END UNIT RIGHT ON BEACH! - Gulf & Bay Club Amazing, large, almost 3,000 sq. ft. 3bdr 4 bath property with 180 degree water views perched right over the #1 rated beach in the U.S., - Siesta Key. 4th floor end unit closest to water. Windows galore, beautiful new updated renovations: All new wood floors, new marble kitchen, four new renovated bathrooms, and huge outdoor, screened, Lanai balcony located in the prestigious Gulf & Bay Club, Siesta Key's premier luxury complex. Stocked kitchen and amenities for your arrival. Enjoy complimentary local fine restaurant experience packages for longer term renters. Property features Tennis, an Olympic sized Pool located 20ft from beach edge, two other pools on property, flawless grounds, lagoons, outdoor grills, wet & dry saunas, hot-tub, basketball court, shuffleboard, clubhouse with recreation center, fitness facility, state of the art security, fob access, guard gate, blink outdoor doorbell camera, private beach with b

Located in Siesta Key, Florida, United States. Villa 37 - Standard Plus - Aloha Kai Vacation Villas Located on Siesta Key, a popular barrier island on Florida’s West Coast, Aloha Kai is a family friendly gated resort community nestled in the heart of Crescent Beach, the number one rated beach in the continental United States.Known for its bright white quartz beaches and emerald green waters, Siesta Key is one of Florida’s top vacation destinations.The stunning sands of Crescent Beach and clear water of the Gulf of Mexico impress even the most seasoned travelers. Over 3-miles long, Crescent Beach is the perfect place to go on soul soothing walks and take in the most magnificent sunsets you will ever see.Aloha Kai is the perfect location for a laid-back vacation at the beach. We invite you to lounge under one of our shaded beach pavilions or at our pool, which happens to be the largest on Siesta Key.

Located in Siesta Key, Florida, United States. Beachaven-Beautiful, Peaceful, Relaxing "Diamond on the Gulf" Remodeled and updated with stainless steel appliances and a full-size washer and dryer. The cathedral ceiling and numerous windows create a bright and vibrant ambiance. Two full-size beds are furnished in the bedroom. Relax, enjoy, and dine out on your private patio. Park your car in the adjoining carport.We look forward to hearing from you! Our private beach and heated pool overlooking the Gulf, are just a short walk down the esplanade between the north and south rows of condos. Beachaven provides chairs and chaise lounges at the pool and beach, and also tables and umbrellas at the pool. The pool complex has restrooms and showers, and a fantastic clubhouse that can be reserved for special occasions.Monthly rentals January - AprilTwo-week rentals May - December Thank you.

Located in Siesta Key, Florida, United States. New Rental on the Gulf, Private Beachfront Complex, 3 Pools, BBQ Grills New rental condo in Jamaica Royale, an oceanfront complex including a private beach! One bedroom condo in a complex with 3 heated swimming pools, one of which is facing the gulf. one free covered parking spot, community BBQ grills all on Famous Siesta Key with its soft, cool, powdery quartz sand..... walk the beach to pick-up shells, play in the soft gentle waves of the Gulf of Mexico, book a charter fishing expedition, rent jet skis or rent a sail boat for the day.....it's all here waiting for you! This is an adorable 1 bedroom, one bath villa that sleeps 6....with two queen beds and a queen sofa sleeper in the living room.Highlights: End UnitBEACHFRONT COMPLEX - NO WATER VIEWS FROM INSIDE.Steps Away From Community BBQ GrillsCourtyard Views from InsideTwo Queen Beds, Queen Sofa SleeperTwo Baths (powder & full bath)Full Stainless/Granite Counter KitchenTwo TV's, Cable/WiFi IncludedPrivate Full Size W/DOutdoor

Located in Siesta Key, Florida, United States. Upgraded Modern Condo on Beautiful Siesta Key! This unit (405) is located on the East corridor on the fourth floor, it faces east/south with plenty of sunlight throughout the year.There are two bedrooms in this unit, each located on the opposite sides of the living/dining room. Each bedroom has its own updated full bathrooms, king sized beds, and flat-screen TVs. Both bedrooms have views of the water so you can wake up to glimpses of sparkling water in the morning. The master bedroom features a dresser, a sitting area, and a walk-in closet. The second bedroom offers a workstation with spacious storage and a comfortable office chair.The living room is bright and sunny, with unobstructed views from the 4th floor. The room is decorated in cheerful and welcoming colors with a couch for relaxation, armchairs, and a flat-screen TV. You can enjoy coffee every morning or have a drink in the evening on the shady screened-in balcony with a beautiful view of the Intracoastal! The dining table can

Located in Siesta Key, Florida, United States. Renovated 1 BR/1 Bath, New Furniture & Appliances. White Sands Village Condominium is the ideal place to enjoy your stay on tropical Siesta Key, Florida. Situated just a short walk from the world-renowned Siesta Key Public Beach, it’s a great place for a two-week vacation or for an extended stay.Please note: THE MINIMUM RENTAL PERIOD IS 14 DAYS.Our condominium is privately owned and decorated, unique and beautifully maintained. Check out the amenities and photos!Our unit has an assigned carport. Why just go to Florida when you can visit the #1 Beach in the USA! White Sands Village is a short 0.3 mile from Siesta Public Beach. No need to worry about Beach Parking while staying here at White Sands Village.Siesta Beach: Rated 2021 #1 beach in Florida by Holidu https://www.bizjournals.com/tampabay/news/2021/06/23/siesta-key-beach-named-no-1-beach-in-the-state.html, 2020 Tripadvisor #1 beach in the USA https://www.sarasotamagazine.com/news-and-profiles/2020/08/siesta-key-beach-named-no-1-i

Located in Siesta Key, Florida, United States. Beach Access, Pools, Tennis & Pickleball - 1225 Gulf & Bayside 1225 Gulf and Bay Bayside by Tropical Sands Accommodations Condo in Siesta Key, FloridaWelcome to your dream Siesta Key getaway! This three-level vacation rental features three bedrooms and two baths, making it perfect for friends and family. Enjoy exclusive private beach access just a 5-minute walk away, along with community amenities like two heated community pools, a fitness center, tennis and pickleball courts, a fishing dock, and a scenic walking path to enhance your stay.Highlights • Private Beach Access • 5-minute walk to the beach • Two Heated Community Pools • Community Fitness Center, Fishing Dock, and Picnic Area• Community Tennis and Pickleball Court • Scenic Walking path Step into the tropical-inspired living space on the main floor, where you’ll find a cozy seating area, a fully equipped kitchen, and a stylish dining table. The screened-in balcony offers additional dining for al fresco meals. With th

Located in Siesta Key, Florida, United States. Harbor-view condo with pool, sports courts & fitness room - snowbirds welcome Midnight Cove II 823Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Located within the amenity-rich Midnight Cove II oceanfront complex, this second-story harbor-view condo is sure to delight guests of all ages for your next visit to Siesta Key! The open and sunlit layout of this vacation rental includes a well-equipped, full kitchen, a dining area with a table for four, and a living area with matching sofas - all illuminated by floor-to-ceiling sliding glass doors overlooking the marina.On-site, take a relaxing stroll through the property's 11 acres and then indulge in a variety of resort amenities, including a sparkling, outdoor pool, hot tub, sports courts, and a picnic area with gas grills for perfect cookouts in the abundant Florida sunshine.RESORT AMENITIES- Outdoor pool- Hot tub- Tennis courts- Basketball court- Pic

Located in Siesta Key, Florida, United States. Walk to Beach, 2nd Story, 2 En-Suite Bedrooms Bay Oaks Complex is a premier complex with every amenity you could want and need!! It's located across and down the street from the Beach and sits next to the Bay where you can walk to the water and enjoy an amazing sunrise every morning during your stay.This is a beautiful, updated and modern two level condo located on the second floor with 2 en-suite bedrooms upstairs, 2.5 baths updated and beautifully furnished in the very popular Bay Oaks on Siesta Key, Florida. The amazing amenities include access to a private fishing pier, private tennis court, billiard room, clubhouse, BBQ area, a heated swimming pool, plus it is a short distance from world renowned Siesta Beach with its white, powder sand. Free shuttle available (tips encouraged). This amazing complex was featured on HGTV at one point. The unit is located on the second floor, accessible by stairs (no elevator)This beautifully renovated condo has over 1,190 heated sqft, 1,390 to

Located in Siesta Key, Florida, United States. Renovated 3 bed & 2.5 bath condo across the street from private Siesta Key beach Stunning Siesta Key Condo Steps from the BeachWelcome to our completely remodeled, 1600 sq. ft. condo nestled just a few steps away from America’s best beach on scenic Siesta Key. With three bedrooms and two-and-a-half baths, this stylish retreat offers a perfect blend of comfort and convenience.Key Features:- Masterful Remodel: Immerse yourself in modern luxury. Our condo boasts all-new glassed-in shower installations, pristine toilets, elegant counters, and sleek sinks.- Gourmet Kitchen: The remodeled kitchen features stainless steel appliances, quartzite countertops, and ample cabinet space.- Bright and Airy: Fresh tile and paint adorn both floors, seamlessly connected by a charming spiral staircase.- Main Bedroom: The master bedroom suite is a sanctuary. Enjoy a king-size bed, dressing area, walk-in closet, and a spacious master bathroom with a dual-head shower enclosure.- Accessibility: We’ve widened

Located in Siesta Key, Florida, United States. Jamaica Royale 006 close to the beach! Delightfully updated one bedroom one bath. This is a garden view unit located in the garden/pool area of our beautifully landscaped property. Enjoy any of the three heated pools, shuffleboard and BBQ after a day of relaxing on our famous sandy white beach RATED #1 in the WORLD by Dr. Beach in 2011 and 2017. Delight in sunset evenings or relax on your back patio. you will love this unit! This unit has a 7 night minimum Saturday to Saturday rental policy, but can be booked for less to fill gaps. We will do our best to accommodate any request.

Located in Siesta Key, Florida, United States. Just Listed w/ Dock Views, Walk to Private Beach, Heated Pools Welcome to your perfect getaway in Siesta Bayside on the Bay, a beautiful 3-bedroom, 2-bathroom townhome offering stunning bay views and a short walk to Siesta Key Beach via private access. This updated, two-story residence features modern decor and resort-style amenities, making it ideal for a luxurious beach vacation.KEY FEATURES:Location & Access: Enjoy a 10-12 minute walk to Siesta Key Beach via private access. Siesta Key Village is just 1.7 miles away, providing a variety of dining and shopping options. A free shuttle stop is nearby for added convenience.Amenities: The community boasts two heated pools, tennis and pickleball courts, a fitness center, and a fishing dock. Beautifully maintained grounds include walking paths.Interior Highlights: The townhome includes a large, stainless steel kitchen with solid stone countertops, a breakfast bar, and a dining table for 6. The living room features a new 65" Smart TV, comfor

Located in Siesta Key, Florida, United States. Siesta Beach House #312 Minute Walk to Beach If you're looking for a great vacation location on beautiful Siesta Key, then look no further. This people friendly complex is the perfect place to bring the family for a true holiday get-away at the beach! You can enjoy swimming in the heated pool, take up a game of shuffleboard, stroll along gorgeous white sandy beaches, or swim in the crystal clear waters of the Gulf of Mexico. Come join us for the perfect vacation.

Located in Siesta Key, Florida, United States. Beautiful 2 Bedroom Lake View Home on Siesta Key! Beautiful lake view, 2-bedroom, 2-bath home on Siesta Key! This home is a spacious unit, featuring a king bed in the master and 2 twin beds in the second bedroom. This home sleep up to 4 guests. Outside your living room is a 20 ft long deck with a stunning full-length view of the lake! A brief walk from the condo to sand, is the beautiful Siesta Key Beach! This location has something for everyone, Our House at the Beach offers guests a heated pool, tennis courts and a covered pavilion with grilling area. The community is complete with a heated pool, pavilion, and tennis courts. Relax on our world-famous Siesta Beach, or take a trip to Siesta Key Village, which offers endless boutique shopping, live entertainment, and dining, making this condo the perfect place for you to enjoy your island getaway vacation! Bedroom 1- KingBedroom 2- 2 twin bedsLiving Room - Sleeper SofaAdded Amenities Included in Your Stay:Complimentary Bicycles,Wifi,P

Located in Siesta Key, Florida, United States. BH · 2/2 Beach House Apt on Siesta Key Welcome to the Beach House Suite Apartment at Solitude Suites on Siesta Key. This spacious split plan 2 bedroom, 2 bathroom suite was remodeled in 2021. New luxury vinyl floors, furniture & more!Sleeps upto 6 people. Master Bedroom offers a king bed & en suite bathroom with walk in closet. 2nd Bedroom offers a queen bed. 2nd Bathroom is off the living area, also with a shower. The “Beach House” also has a full granite kitchen, french door style stainless steel refrigerator, and plenty of space! There is a private screened lanai overlooking the pool and mostly the canal out to Sarasota Bay. Outdoor seating for 4 people with views over the boat dock, canal and heated pool. The living room boasts a huge 75” wall mounted smart TV (apps and cable). There is a dining table with 4 chairs as well as a breakfast bar onto the kitchen with another 4 chairs. Long private screened lanai connects from the master bedroom, living room and 2nd bedroom. This Beach

Located in Siesta Key, Florida, United States. Midnight Cove II 940B - Breathtaking Views! Welcome to Midnight Cove II and thanks for checking us out! We think we are quite spectacular if we must say so ourselves! Siesta Key and our local community are brimming with shopping, dining, art and culture. Ride the Siesta Key Breeze Trolley “ it's FREE and find relief knowing you won™t be driving around the village searching for a parking spot. Take a stroll to the beach via our dedicated beach access and enjoy a little sand-in-your-toes experience. Our Bayside property provides views of the Intracostal waterway while also being within walking distance to the Gulf of Mexico. Our property offers a heated swimming pool with a large pool deck complete with lounge chairs and seating with sun shade, 2 tennis courts with 1 of them having pickle ball lines, basketball court, club house, barbecue grilling area, a beautiful observation deck at the end of our property and even private docks available to rent for your boat. During season (Febru

Located in Siesta Key, Florida, United States. Our House at the Beach C-225 Warm and Inviting Townhouse! Lake houses offer a generous bi-level layout that includes separate dining and living rooms spaces. The eat-in kitchen is fully stocked with pots, pans, dishware, flatware, and has full-sized appliances including a dishwasher, microwave and washer and dryer for your convenience. Off the large living room there is a balcony overlooking the Lake. The master bedroom suite also opens onto a balcony and has an en-suite bathroom with closets and dressing area. The second bedroom has an adjacent full second bathroom. Each Lake House offers central A/C, ample closet and storage space, cable TV in each bedroom and garage parking for one car. The development includes a private pool, covered pavilion area with a BBQ, a picnic area and tennis courts.

Located in Siesta Key, Florida, United States. Heron Lagoon, dock, pool, the Pineapple at Siesta Key Bungalows The Siesta Key Bungalows offer a heated pool, courtyard and a dock on Heron Lagoon. This is a resort that has something for everyone. The Pineapple Bungalow features a bright and airy one bedroom space; experience an open floor plan connecting a welcoming living room and full-kitchen. With a queen-size bed and private bathroom you'll feel at home. The Bungalow is fully stocked with linens, care essentials, plus eating and cooking utensils. An additional single-roll-away-bed allows accommodations for three guests.We are happy to provide free, high-speed internet, Wi-Fi, HD Television equipped with live sports & extensive channel options via complementary streaming services, also included are electric appliances so you will not miss a beat. You have your own private veranda, great for lounging. Take a few steps further and you can enjoy the private dock on Heron Lagoon. The resort's private dock allows for lounging, fishing,