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The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool

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A sign for 'The Radewinds Resort' with a white pergola structure, surrounded by lush tropical plants. - The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool (Bradenton Beach)
Room - The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool (Bradenton Beach)
Beach - The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool (Bradenton Beach)
Private kitchen - The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool (Bradenton Beach)
Terrace/patio - The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool (Bradenton Beach)
The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool provides a water park and more. Stay connected with free in-room WiFi.

Popular amenities

  • Pool
  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
  • Parking available

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About this property

The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool

  • The Gypsea Jewel | Tradewinds Cottage #22 | Unobstructed Sarasota Bay water views on Bradenton Beach!

    1 Bedroom | 1 Bathroom | Sleeps 4 | Charming Deluxe North Cottage - East-facing cottage

    Welcome to The Gypsea Jewel, a charming coastal retreat where beautiful bayfront views, warm Florida sunshine, and the laid-back lifestyle of Bradenton Beach are right outside your door. Located within the beloved Tradewinds Beach Resort, this Deluxe North Cottage offers the perfect combination of coastal comfort, convenient resort amenities, and easy access to the beautiful Gulf beaches. Whether you're planning a romantic getaway, a family beach vacation, or simply looking for a peaceful place to unwind, The Gypsea Jewel is a wonderful place to settle in and experience the charm of Bradenton Beach.

    The Gypsea Jewel is thoughtfully arranged to accommodate up to four guests. The private bedroom features a comfortable king-size bed, while the living area includes a queen sleeper sofa, providing additional sleeping accommodations for two guests. The fully equipped kitchen makes preparing everything from a quick breakfast to a home-cooked dinner convenient, while the regular drip coffee maker is ready for those slow coastal mornings. The Gypsea Jewel is equipped with central air conditioning and heating, complimentary Wi-Fi, and cable television provide the everyday comforts you need to relax and feel right at home. Step outside and enjoy the cottage's outdoor seating area overlooking the beautiful waters of Sarasota Bay. It's a wonderful spot to start your morning with a cup of coffee, catch the coastal breeze, or simply slow down and enjoy the peaceful waterfront atmosphere.

    BEACH DAYS & BAYFRONT MORNINGS

    One of the best things about staying at The Gypsea Jewel is having access to both the beautiful Gulf beaches and the peaceful waters of Sarasota Bay. Start your morning with a short one-minute stroll to Tradewinds' deeded beach access, where the soft white sands and sparkling turquoise waters of the Gulf await. Prefer a relaxing afternoon by the pool? The seasonally heated community swimming pool is approximately a 15-second walk from the cottage, making it easy to enjoy a refreshing swim or spend the afternoon soaking up the Florida sunshine. On the bay side of the resort, the community fishing pier offers a beautiful setting to enjoy the waterfront scenery, cast a fishing line, or watch the boats passing through Sarasota Bay. As the day winds down, head back to the Gulf to experience one of Bradenton Beach's unforgettable sunsets.

    SLEEPING ARRANGEMENTS - Maximum Occupancy: 4 Guests
    Primary Bedroom: King Bed – Sleeps 2
    Living Room: Queen Sleeper Sofa – Sleeps 2
    Bathroom: 1 Full Bathroom with Large Walk-In Shower

    TOP REASONS TO BOOK THE GYPSEA JEWEL
    Charming Deluxe North Cottage - East-facing cottage
    Unobstructed Sarasota Bay water views
    Approximately 5-second walk to the seasonally heated community pool
    Deeded Gulf beach access approximately one minute away
    Comfortable king-size bedroom and queen sleeper sofa
    Fully equipped kitchen with regular drip coffee maker
    Central air conditioning and heating
    Semi-private outdoor porch with seating overlooking Sarasota Bay, shared with neighboring cottages
    Complimentary Wi-Fi and cable television
    Bayfront fishing pier and community grilling areas
    Convenient Bradenton Beach location near dining and shopping
    Professionally managed by Anna Maria Rental Properties

    TRADEWINDS COTTAGE #22 AMENITIES

    Deeded Gulf beach access approximately a one-minute walk away
    Seasonally heated community swimming pool overlooking Sarasota Bay
    Bayfront fishing pier and community dock
    Complimentary self-service beach chairs
    Community picnic tables and charcoal grilling stations
    Beautifully maintained tropical resort grounds
    Convenient access to nearby restaurants, shopping, and local attractions
    Please note that the community dock is available for sightseeing and fishing but does not provide guest boat docking or boat access.

    Located at 1603 Gulf Drive North #22 Bradenton Beach, Florida 34217, The Gypsea Jewel puts you in a wonderful location for experiencing everything that makes Bradenton Beach such a special destination.

    Spend your days enjoying the beautiful Gulf beaches, exploring charming coastal neighborhoods, browsing local boutiques, or discovering the area's fantastic waterfront restaurants. Nearby dining favorites include Beach House Waterfront Restaurant, SALT Bar & Table, Island Time Bar and Grill, The Kokonut Hut, and Tide Tables Restaurant and Marina. Take advantage of the complimentary island trolley service and explore popular destinations such as historic Bridge Street, Holmes Beach, and the City of Anna Maria. Whether you're looking for fresh seafood, live music, boutique shopping, or simply another beautiful stretch of beach, there's always something to discover. And when you're ready to escape the activity, your comfortable Bradenton Beach cottage will be waiting.

    GOOD TO KNOW BEFORE BOOKING

    Maximum occupancy is four (4) guests.
    Primary booking guest must be at least 25 years old and remain onsite throughout the reservation.
    Check-in begins at 4:00 PM local time
    Check-out is by 10:00 AM local time
    No pets are permitted.
    No smoking or vaping.
    Parties, events, and spring break groups are prohibited.
    No street parking.
    RVs, trailers, boats, and watercraft may not be parked at the property.
    Guests must comply with all condominium association rules and local noise ordinances.
    A signed rental agreement is required within 72 hours of booking.
    Pool heating is seasonal and subject to community operation.
    Children must be supervised by an adult when using the swimming pool and community amenities.
    Rates, availability, and minimum stay requirements are subject to change without notice.

    OUR COMPLETE CLEAN LINEN PROMISE

    At Anna Maria Rental Properties, your comfort and peace of mind are important to us. Every reservation includes our Complete Clean Linen Promise, ensuring all bed linens, comforters, and bath towels are professionally laundered between guest stays and freshly prepared for your arrival.

    PROFESSIONALLY MANAGED BY ANNA MARIA RENTAL PROPERTIES

    The Gypsea Jewel is proudly managed by Anna Maria Rental Properties, a locally owned and personally managed vacation rental company dedicated to providing exceptional guest experiences throughout Bradenton Beach and the surrounding island communities. From the moment you book until the day you depart, our local team is here to help make your beach vacation as comfortable and enjoyable as possible. Come experience beautiful bayfront mornings, relaxing beach days, and the easygoing coastal charm of Bradenton Beach.

    ANNA MARIA RENTAL PROPERTIES | RENTAL AGREEMENT & BOOKING TERMS
    By submitting payment for your reservation, you acknowledge that you have read, understood, and agree to comply with the terms and conditions of the Anna Maria Rental Properties Rental Agreement. Your reservation is subject to these terms, which constitute a legally binding agreement. Guests are responsible for any damages to the property, its furnishings, or amenities caused by themselves or members of their reservation during their stay. Travel Insurance: Anna Maria Rental Properties and our property owners strongly encourage all guests to purchase travel insurance to protect against unexpected cancellations, travel interruptions, emergencies, and other unforeseen circumstances. Once the applicable cancellation and refund period has expired, no refunds will be issued except as otherwise required by law or expressly provided in the Rental Agreement. Compliance with Rental Terms: All guests are expected to respect the property, surrounding community, and applicable condominium association rules. Violations of the Rental Agreement may result in termination of the reservation and removal from the property, subject to applicable law and the terms of the agreement. At Anna Maria Rental Properties, we maintain these standards to protect our homeowners' investments, preserve the quality of our vacation rentals, and ensure an enjoyable experience for all guests. If you have any questions regarding the Rental Agreement or reservation terms, please contact Anna Maria Rental Properties before completing your booking.

About the area

Located in Bradenton Beach, this condo is on the waterfront. The area's natural beauty can be seen at Bradenton Beach and Coquina Beach. Fish Hole Adventure Golf and Florida Maritime Museum at Cortez are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with horse riding and ecotours nearby. Visit our Bradenton Beach travel guide
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Bradenton Beach, FL

What's nearby

  • A coastal town with a long sandy beach, clear blue ocean, and residential buildings along the shore.
    Bradenton Beach
    5 min walk - 0.4 km
  • A waterfront scene with a clock tower, palm trees, and a pier extending into the water.
    Historic Bridge Street Pier
    20 min walk - 1.7 km
  • A sandy beach with people sunbathing and swimming, a clear blue sky, and buildings in the background.
    Cortez Beach
    2 min drive - 1.4 km
  • Anna Maria Sound
    1 min walk - 0.0 km
  • Aluna Wellness Center & Spa
    8 min walk - 0.7 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    24 min drive

Restaurants

  • Anna Maria Oyster Bar on the Pier
    17 min walk
  • Daquiri Deck Bradenton Beach
    15 min walk
  • Anna Maria Island Beach Cafe
    4 min drive
  • Circle K
    14 min walk
  • Beach House Waterfront Restaurant
    12 min walk

Frequently asked questions

Does The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool?

On-site parking is available at the property.

What time is check-in at The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool?

Check-in begins at 4:00 PM.

What time is check-out at The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool?

Checkout is at 10:00 AM.

Where is The Gypsea Jewel - Tradewinds Cottage #22 | Beach Access & Bayfront Pool located?

Situated on the waterfront, this condo building is steps away from Anna Maria Sound and Bradenton Beach. Aluna Wellness Center & Spa and Bradenton Beach Marina are also within 15 minutes.

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