Top Boutique Hotels in Osprey (2026)

Located on the bay in central Sarasota, the resort offers a spa center and access to a nearby private beach and outdoor pool. All rooms feature private balconies. All rooms at the The Ritz-Carlton, Sarasota are spacious and air-conditioned. They come equipped with a marble-trimmed bathroom and private balcony overlooking the bay or city. Each guestroom also has a work desk. Guests have access to the exclusive Ritz-Carlton Beach Club located just 3 miles from the hotel on the white sandy beaches of Lido Key. It features a private beach, comfortable lounge chairs, a gulf-front zero-entry heated swimming pool, hot tub and elevated Ladies and Gentlemen's changing facilities. Free shuttle service is provided to and from the Beach Club for resort guests. Guests will also have access to The Ritz-Carlton Golf Club, an award-winning, Tom Fazio designed par-72 golf course. Also available to guests is the newly renovated Ritz-Carlton Spa, harnessing the power of its lush Floridian surrounds to offer a revitalizing escape. Discover the soothing ways marine ingredients can remineralize the skin or how lavender crystals can encourage inner tranquility. Locally sourced ingredients, innovative techniques, and luxurious treatment rooms facilitate the restoration of mind and body. Guest can choose from an extensive menu of body treatments, facials, massages and beauty services. The Ritz-Carlton, Sarasota features an array of in-house dining options. Restaurants include Jack Dusty, Ridley’s Porch, The Lido Key Tiki Bar, and The Golf Club Grille. The hotel is just 4 miles from the Sarasota/Bradenton International Airport.

- "A beautiful hotel. We loved the spacious, clean hotel room with a luxurious bathroom. We also enjoyed using the nice gym, drinks at the pool and a trip to the private beach club." - "Everything was perfect." - "Reception staff fantastic All staff excellent" - "The convenience of the location to all the shops and restaurants in walking distances. I like the architecture and roman style of the building." - "This is a really fantastic hotel. A beautiful location and great facilities, especially the beach club. Service throughout the hotel was impeccable. This is a great resort with something for all the family. Shout out to Rachel and her club lounge team, including Ben and Tony. Their excellent hospitality and service made our time at the Ritz-Carlton a really special one."

Located in Sarasota, this Florida Hyatt Regency features an outdoor pool with waterfalls and a hot tub, a private 32-slip marina with boat docking facilities, and free WiFi. Breakfast is available for an additional fee. A work desk, laptop safe, 47-inch flat-screen TV, and iHome® docking station are included in all Hyatt Regency Sarasota rooms. Each private bathroom is tiled and equipped with a hairdryer and free toiletries. The Sarasota Hyatt Regency offers sailing, fishing, kayaking and biking. An airport transfer service is available for a surcharge. A 24-hour StayFit™ fitness center and in-room Yoga Away™ program are also offered. Currents Restaurant serves American fare with a view of the bay for breakfast, lunch, and dinner. Hurricane Hut offers tropical cocktails by the lagoon-style pool, and Currents Bar is a waterfront cocktail lounge near the lobby. Sarasota-Bradenton International Airport is 12 minutes’ drive from this hotel. Guests will be 3.1 mi from Ringling Museum and 2.1 mi from Sarasota Jungle Gardens.

- "Pleasant rooms. Clean pool area. Friendly and helpful staff." - "Everything" - "The property was exceptionally clean and was up to date." - "Clean, great location." - "The atmosphere, it was really nice and very tropical. Our room had a balcony and was a great place to read. The staff was helpful and attentive." - "Perfect" - "We enjoyed our stay." - "the location, the view, the pool! unfortunately, we read that the ritz residences will be taking over the Hyatt!"

Playa Esmeralda Vacation Home Up To 14 People is located in Bradenton Beach, just 14 miles from The John and Mable Ringling Museum of Art and 6 miles from Anna Maria City Pier. This property offers access to a patio and free private parking. Greens of Manatee Golf Club is 9 miles from the vacation home and Van Wezel Performing Arts Hall is 14 miles away. With free Wifi, this 5-bedroom vacation home provides a TV and a kitchen with a dishwasher and oven. Towels and bed linen are provided in the vacation home. The accommodation is non-smoking. Popular points of interest near the vacation home include Cortez Beach, Bradenton Beach, and Coquina Beach. The nearest airport is Sarasota Bradenton International Airport, 12 miles from Playa Esmeralda Vacation Home Up To 14 People.

- "loved everything about this Inn ! the house and decor is beautiful. loved the upstairs kitchen/playroom/sitting area. the whole inn was comfortable and immaculate. colors were soothing. loved the hot tub and the pool was beautiful. gym was very nice." - "The property was beautiful and very well kept." - "We loved the location. It was very clean and although our room was small it had everything we needed. It was also very quiet." - "Great location in Bradenton beach. Comfortable bed and bedding. Excellent shower with good pressure. Lots of outside spaces to sit and relax. Great communal living area with very good facilities."

Wyvern Hotel, Ascend Hotel Collection features views of the Punta Gorda city skyline, 2 on-site restaurants, and a poolside rooftop bar. Fisherman's Village marina and shopping center is 6 minutes' drive from the property. Complimentary WiFi is provided for all guests. A 32-inch flat-screen cable TV, and a seating area are featured in all rooms at this Wyvern Hotel, Ascend Hotel Collection. An iPod docking station is provided. Select rooms have a city or harbor view. Guest computers are available upon request at the Wyvern Hotel, Ascend Hotel Collection. Guests can consult concierge services regarding a local tour or dinner reservations. Free parking is offered on site as well. Perch 360 offers rooftop dining for lunch and dinner while 88 Keys Florida serves contemporary American fares for dinner. The full-service bar is located on the hotel roof and features nightly specialty cocktails. Guests will be 4 minutes’ walk from the Charlotte Harbor Event and Conference Center and 4.3 mi drive from the Punta Gorda Airport. Seminole Lakes Country Club golf course is 11 minutes' drive away.

- "They have a wonderful rooftop bar. Different activities on different days, we were lucky enough to experience a big band. Nice drinks and nice view of the town." - "Spacious, well appointed room and friendly efficient staff" - "I live in PGi and became homeless because Hurricane Milton flooded my house. I had no where to go so I appreciated the clean room and friendly staff. Thank you !" - "Very nice" - "Friendly staff, very clean & comfortable. Loved the oversize towels. Great location with rooftop bar, great views."

Located in St. Pete Beach, Florida, this Mediterranean-style hotel features an outdoor swimming pool, a 7-slip marina, and a rooftop bar. It is within walking distance of the white sand beaches of the Gulf of Mexico. Complimentary WiFi is offered in all rooms and suites Rooms at The Hotel Zamora feature a 42-inch flat-screen cable TV, coffee machine, iPod docking station, and Frette® bed linens. Guests can use the work desk with a cordless telephone. Free toiletries, bathrobes, and a walk-in shower are included in each private bathroom. A 24-hour fitness center, evening wine hour, hot tub, and beach amenities are offered to guests at the St. Pete Beach Hotel Zamora. Guests will enjoy the convenience of dry cleaning services, a 24-hour reception, and morning coffee and tea service. Gulf Beaches Historical Museum is 1.7 mi from this hotel, and Fort De Soto Park is 15 minutes' drive away. John's Pass Village and Boardwalk is 6.1 mi away, and guests will be 29 minutes’ drive from Tampa International Airport.

- "The location , it was peaceful , clean and staff was pleasant . Restaurant was great ." - "Beautiful location and hospitality." - "Very clean and friendly service." - "Wonderful building and location. Hotel Zamora is a feeling." - "Very clean, quite, and friendly staff . Very nice hotel close to beach and other attractions" - "Staff was great and did everything they were suppose to" - "Everything was perfect" - "Love everything about The Zamora. Beautiful, Clean, Friendly staff"

Nestled in the heart of Gulfport, Florida, a charming waterfront community adorned with artists, writers, musicians, and small businesses, The Peninsula Bed & Cocktails stands as a testament to history and innovation. As a historic boutique hotel under new ownership, we've curated a revolutionary concept where mixology meets hospitality, delivering a unique experience where the art of cocktails will enhance your stay. Step into our veranda, exuding Old South Florida charm, and walk through our French doors into our lively and picturesque Lobby Bar. Here, skilled mixologists await, ready to guide you on a tantalizing journey of flavors. Each room within our establishment is a tasteful homage to iconic cocktails from around the globe. As you enter your room, You'll be embraced by the essence and ambiance of your chosen cocktail, creating a sensory experience like no other.Welcome to Gulfport, where Peninsula Bed & Cocktails invites you to savor the art of fine living.

- "Staff" - "Very unique. Centrally located, all within walking distance, restaurants, stores and such." - "It was very nice and comfortable" - "So cute and clean. Wonderful staff. Everyone helpful and engaging. Loved the tote with towels in o take to the beach with us." - "The hotel is extremely welcoming, and well located. Breaskfast and complimentary snacks were very Nice. I'd 100% recommend." - "Real quirky property that is designed beautifully. The rooms were super clean and the welcome snacks and drinks were fantastic."

Island Grand at TradeWinds is located on 28 acres, directly on a Gulf of Mexico beach in Saint Pete Beach. The hotel offers 5 outdoor swimming pools, 8 restaurants and bars. Guest rooms at the Island Grand are equipped with a microwave, coffee machine, toaster, small refrigerator, and kitchenware. A flat-screen cable TV is also included. Some rooms offer views of the Gulf of Mexico. Island Grand at TradeWinds features 2 hot tubs and a variety of water sports, or stand up paddle boards, floating loungers, mini golf. Guests can enjoy paddle boats, beach volleyball, a water slide, and beach cabanas. Themed drop-off camps are available for an additional fee. Water sport activities include water slide rides and parasailing. Dining options at the Island Grand at TradeWinds include the Palm Court Italian, Flying Bridge.Casual dining includes a poolside beach bar and grab-and-go options. Fort De Soto Park is 16 minutes' drive from Island Grand at TradeWinds, while Central St. Petersburg is 10 mi away. The Dali Museum is just 11 mi from the hotel. Our new kids club is called Shelldon's Adventure Club. We offer kid's programs for a fee: Day Camp, and Kids Night Out

- "I just absolutely love this resort. It's my second time staying, and I'm never disappointed. There are plenty of amenities and lots to do for all ages." - "Everything and everyone were great. Happy staff and great people" - "Absolutely excellent stay, clean room, great staff, great location. Tradewinds Island Grand is a fantastic resort!" - "The location on the beach was perfect," - "Very clean and lots of things to do!" - "Location was great with a beautiful ocean view. Beach was close. Pools were awesome."

This Saint Petersburg, Florida hotel features 2 on-site restaurants and free property-wide Wi-Fi. Guests are a 15-minute walk from the shops and restaurants and Saint Petersburg Pier. A flat-screen cable TV is featured in all rooms at this Saint Petersburg Ponce De Leon Boutique Hotel. A microwave and refrigerator are available upon request. A business center with printer access is available at the Ponce De Leon Hotel. A 24-hour front desk and laundromat are available for added convenience. Guests can find Spanish tapas at Ceviche Tapas Restaurant for lunch and dinner. Pincho y Pincho and Flamenco Bar features live music on select nights. The property is a 10-minute walk from the Dali Museum. The Saint Petersburg Marina is a 5-minute walk away.

- "Perfect location! Quiet, felt very welcoming!" - "Great location, hotel has character, comfy bed, great shower." - ""I can't stop raving about the location, the staff, and the amazing service we received! It was an unforgettable experience, andlanning our next visit. I highlying it out for yourself!" we're already p recommend check" - "The corner room pier view was amazing" - "Nice" - "Perfect central location amazing price clean had everything we needed"