TOP 10 Best Upscale vacation rentals in Pensacola, Florida

Spanish Key by Luxury Gulf Rentals is a luxurious lodging institution located on Perdido Key Drive in Pensacola, Florida. This elegant establishment offers a range of upscale accommodations with breathtaking views of the Gulf of Mexico. Guests can enjoy spacious, beautifully furnished condos with top-of-the-line amenities and access to a variety of on-site facilities, including a swimming pool, fitness center, and private beach access. Whether you're looking for a relaxing getaway or a fun-filled vacation, Spanish Key by Luxury Gulf Rentals provides the perfect setting for an unforgettable experience on the Florida coast.

Welcome to Anchor Realty Florida, your premier destination for luxury beachfront real estate in Northwest Florida since 1962. Located at 225 North Pace Boulevard, Suite 111, Pensacola, FL 32505, our agency specializes in connecting you with the finest properties across the region. Whether you're seeking a stunning home along the pristine shores of St. George Island, the vibrant communities of Santa Rosa Beach (30A), the bustling locale of Destin, or the serene landscapes of Port St. Joe, Cape San Blas, and beyond, we have you covered. Our expertise extends throughout Escambia and Santa Rosa Counties, as well as the picturesque areas of Apalachicola, Carrabelle, and Mexico Beach. We also serve the broader Tallahassee region, including Southwood and Crawfordville. At Anchor Realty Florida, we cater to diverse real estate needs, offering a wide array of properties such as hotels, strip malls, single stores, apartments, and industrial properties.

Windward Condominiums is a luxurious beachfront property located at 16777 Perdido Key Drive in Pensacola, Florida. With stunning views of the Gulf of Mexico, this upscale condominium complex offers a range of amenities including a pool, fitness center, and private beach access. Each unit is beautifully appointed with modern furnishings and spacious layouts, perfect for a relaxing getaway or a permanent residence. The convenient location allows residents to enjoy all that Pensacola has to offer, from pristine beaches to vibrant nightlife and delicious dining options. With impeccable service and top-notch facilities, Windward Condominiums is the ideal choice for those seeking a sophisticated coastal lifestyle in the Sunshine State."

Grand Lagoon Yacht Club is a prestigious institution located at 10653 Gulf Beach Highway in Pensacola, Florida. This exclusive club offers a luxurious and sophisticated environment for yacht owners and enthusiasts to gather and socialize. With stunning views of the Gulf of Mexico, members can enjoy a wide range of amenities including a marina, fine dining restaurant, and event spaces for special occasions. Whether you are a seasoned sailor or simply appreciate the beauty of the sea, Grand Lagoon Yacht Club provides a unique and upscale experience for all who visit.

The Beach Club Resort & Spa is a luxurious lodging destination located at 18 Via De Luna Drive in the beautiful Pensacola Beach, Florida. This resort offers stunning ocean views, upscale accommodations, and a range of amenities to ensure a relaxing and enjoyable stay for guests. The on-site spa provides a range of rejuvenating treatments, while the beach club offers access to pristine sandy beaches and sparkling waters. Whether you're looking to unwind by the pool, indulge in gourmet dining, or explore the local attractions, the Beach Club Resort & Spa is the perfect choice for a memorable beach getaway.

Windemere Condominium is a luxurious oceanfront property located at 14511 Perdido Key Drive in Pensacola, Florida. Boasting stunning views of the Gulf of Mexico, this upscale condominium offers spacious and beautifully appointed units for both short-term rentals and long-term stays. Guests can enjoy a range of amenities including a beachfront pool, fitness center, and direct access to the pristine white sandy beaches. With its convenient location near local attractions, restaurants, and shopping, Windemere Condominium is the perfect destination for a relaxing beach getaway in the United States.

Harbour Point-Perdido Condo is a luxurious waterfront condo located at 154 Ethel Wingate Drive in Pensacola, Florida. This stunning property offers breathtaking views of the harbor and is just steps away from the pristine beaches of the Gulf Coast. The condo features spacious and elegantly furnished units, complete with modern amenities and upscale finishes. Residents can enjoy a range of on-site facilities including a swimming pool, fitness center, and private beach access. With its prime location and upscale accommodations, Harbour Point-Perdido Condo is the perfect destination for a relaxing beach getaway in the Sunshine State.

Arena Villas at Blue Angel is a luxurious residential community located in the heart of Pensacola, Florida. Situated at 7137 North Blue Angel Parkway, this stunning property offers a perfect blend of comfort and convenience. The spacious villas are designed with modern amenities and stylish finishes, providing residents with a truly upscale living experience. With easy access to shopping, dining, and entertainment options, as well as beautiful beaches and outdoor recreational activities, Arena Villas at Blue Angel is the ideal place to call home. Experience the best of Florida living at this prestigious address.

Perdido Towers is a prestigious institution located at 16785 Perdido Key Drive in Pensacola, Florida. Our luxurious towers offer breathtaking views of the Gulf of Mexico and white sandy beaches. With top-of-the-line amenities and world-class service, Perdido Towers is the perfect place for those seeking a sophisticated and elegant living experience. Whether you're looking for a vacation rental or a permanent residence, Perdido Towers provides a serene and upscale environment for all residents. Come and experience the ultimate in coastal living at Perdido Towers.

Baywatch Condominiums is a luxurious waterfront property located at 1150 Fort Pickens Road in Pensacola Beach, Florida. With stunning views of the Gulf of Mexico and white sandy beaches, this upscale condominium complex offers a relaxing and exclusive retreat for guests. The spacious units feature modern amenities and stylish decor, perfect for a comfortable stay. Guests can enjoy access to a variety of on-site facilities, including a swimming pool, fitness center, and private beach access. Whether you're looking for a romantic getaway or a fun family vacation, Baywatch Condominiums provides the perfect setting for a memorable stay in Pensacola Beach.

Sans Souci Condominiums is a luxurious beachfront property located at 999 Fort Pickens Road in Pensacola Beach, Florida. These stunning condominiums offer breathtaking views of the Gulf of Mexico and provide guests with a relaxing and upscale vacation experience. With spacious and beautifully decorated accommodations, guests can enjoy all the comforts of home while being just steps away from the pristine white sandy beaches. The property also features a pool, hot tub, and fitness center for guests to enjoy. Whether you're looking for a romantic getaway or a fun-filled family vacation, Sans Souci Condominiums is the perfect destination for your next trip to Pensacola Beach.

Welcome to Pfeiffer House, your premier destination for comfort and elegance in the heart of Pensacola, Florida. Nestled at 28 Zaragoza Street, our charming establishment combines historic charm with modern amenities, offering a unique and memorable experience for all our guests. At Pfeiffer House, we pride ourselves on providing exceptional service and a warm, inviting atmosphere. Whether you're visiting for business or pleasure, our beautifully appointed rooms and suites are designed to ensure a restful and rejuvenating stay. Each space is thoughtfully decorated, blending classic elements with contemporary touches to create a serene retreat.

Welcome to LaDonna Braidlow, Your Emerald Coast Realtor, where finding your perfect home is more than just a transaction—it's a journey we embark on together. Nestled in the picturesque Perdido Key, Florida, at 14112 Perdido Key Drive, our realty service is dedicated to making your home-buying experience as seamless and enjoyable as possible. LaDonna Braidlow is passionate about people and real estate, bringing a wealth of knowledge and an unwavering commitment to each client’s unique needs. Whether you're searching for a charming family home, an investment property, or a tranquil retreat near the beach, LaDonna is here to listen, guide, and work tirelessly to match you with a property that feels just right.

Welcome to Team Perdido - Pete King Realtor/Team Leader, your trusted real estate agency located at 13578 Perdido Key Drive, Pensacola, Florida. As part of the renowned Pointe South Real Estate, one of the most productive realty companies in the Pensacola/Alabama Beaches area, we pride ourselves on offering unparalleled service in the real estate market. Our dedicated team, led by one of the top agents on the “Key,” is committed to providing expert guidance and support whether you are buying or selling a property. At Team Perdido, we understand the importance of having a Realtor who comprehends the market dynamics and customer reactions to pricing and value. Our knowledgeable and high-energy team, along with our diligent administrative staff, works tirelessly to build strong relationships with our clients. For sellers, we ensure that all disclosures and paperwork are meticulously handled, allowing you to make informed decisions about listing your property. For buyers, we focus on matching you with properties that meet your needs and financial criteria, guiding you through the entire process from contract signing to closing.

Silurian Pond Apartment is a luxurious residential complex located at 3000 Hollywood Avenue in Pensacola, Florida. This modern and stylish apartment building offers a range of spacious and well-appointed units, perfect for individuals and families looking for a comfortable and convenient living space. The property features a serene pond on the premises, providing a peaceful and scenic backdrop for residents to enjoy. With easy access to local amenities, shopping, dining, and entertainment options, Silurian Pond Apartment is the ideal choice for those seeking a vibrant and modern lifestyle in the heart of Pensacola.

La Playa Condominiums is a luxurious beachfront property located at 13555 Sandy Key Drive in Pensacola, Florida. With stunning views of the Gulf of Mexico, this resort-style complex offers a range of amenities including a swimming pool, fitness center, and private beach access. The spacious condos feature modern furnishings, fully equipped kitchens, and private balconies overlooking the ocean. Perfect for a relaxing vacation or a permanent residence, La Playa Condominiums offers a serene and upscale living experience by the sea.

Chapins Landing is a premier waterfront institution located at 711 Underwood Avenue in Pensacola, Florida. This charming establishment offers a unique blend of luxury accommodations, stunning views, and top-notch amenities for guests to enjoy. Whether you're looking to relax by the pool, take a stroll along the beach, or indulge in fine dining at the on-site restaurant, Chapins Landing has something for everyone. With its convenient location and impeccable service, this institution is the perfect destination for a memorable getaway in the Sunshine State.