Delray Beach Listings

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Monthly Rent $2,300

AVAILABILITY FOR WINTER 2026 Beautiful Remodeled Villa in 55+ Community in Delray Beach Delray Beach, Florida, Listing ID: 31974

Completely remodeled(2023), Fully Furnished 1 Bedroom 1 Bath villa in Highpoint Section 3, a 55+ Community. 800 sq ft open concept living space with Kitchen, Dining, Breakfast & Adult beverage bar and additional Florida Room with pull-down Murphy Bed for your visitors. Relax on...

  • Villa
  • 800+
  •  1
  •  1

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Monthly Rent $1,000 - $1,500

Lakefront Cabin with private beach in Central FL. Babson Park, Florida, Listing ID: 22493

Winter 2026 contract fell through! Considering offers! Enjoy gorgeous lakeside sunrises year round from our comfy guest cottage on 7,000-acre Crooked Lake. Nestled quietly among citrus groves in a safe, semi-rural neighborhood, you'll be minutes from town with restaurants,...

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Details No Image Available

$Multi-Month Discount!

Monthly Rent $2,300 - $3,250

Beautiful Lakefront Condo. Beach, Pool, BBQ, and Spa steps from your balcony. Winter in Paradise. Nightly Sunsets from your balc Sebring, Florida, Listing ID: 25161

Beautifully Furnished Condo. Master B/R - King Bed, Walkin closet, tv, prvt entrance to Lakefront Balcony, modern design, desk, prvt bath with dual vanity, granite counters, travertine floor, garden spa tub and separate walk in travertine tile shower. 2nd B/R, king bed or owner...

  • Condo
  • 1200-1400
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Monthly Rent $1,600

Beautiful lakefront living from this 2nd story apartment. Fishing, boat launch and sunsets! Four month rental minimum. Winter Haven, Florida, Listing ID: 26290

This property is in a very quiet 55+ community and located on a paved street that dead ends into Lake Hartridge. Lake Hartridge is the northern most lake in Winter Haven, on the Chain of Lakes, which is popular to navigate from one lake to another via boat. The community has a...

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  • 1500
  •  2
  •  2
Details No Image Available

$Multi-Month Discount!

Monthly Rent $1,700

Central Florida, The Best For Winter Guests!! Avon Park, Florida, Listing ID: 26488

The map of this property in the satellite view is extremely old. The road was paved years ago and there is landscaping and grass and hedges. Unfortunately, that is what it shows. This mobile home is located just down a path from peaceful Lake Glenada. This home is not in a...

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Details No Image Available

$Multi-Month Discount!

Monthly Rent $7,500

Spectacular Lake House Oasis on Gorgeous Lake June in Lake Placid Florida - 4 Bedroom 3 Bath Lake Placid, Florida, Listing ID: 26610

This amazing home is just what you are looking for if you want to relax in warm weather and enjoy beautiful sunsets! Enjoy your sipping your morning coffee while sitting on our amazing dock watching the sunrise. Enjoy all that lake life has to offer such as boating, fishing,...

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Charming lakeside living. Our house is in a 3/2 in a prime lakefront location in the heart of Florida, on Crooked Lake. Babson Park, Florida, Listing ID: 27254

Currently available for winter 2026! Only an hour from Orlando and 1.5 hours from Tampa, it’s the perfect hub from which to explore Florida, invite guests for a weekend, or to just enjoy the tranquility of lakefront life. The 100-year-old house needs some minor cosmetic work;...

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$Multi-Month Discount!

Monthly Rent $1,900

Tired of snow, ice, wind, shoveling and freezing temperatures? Come to beautiful Lake Byrd in Avon Park, Florida. Avon park, Florida, Listing ID: 27797

. This roomy home overlooks a serene lake with access for fishing. Walk around the lake morning and evening to enjoy the sunrise and sunset. House is fully furnished, clean, smoke free, 2 bedrooms, office, 3 baths, laundry room, garage, ceiling fans, air-conditioning, heat,...

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Spacious 4bd/3 bath ranch home that sleeps 8-10 in Babcock Ranch golf community, resort style pools, and more! Punta Gorda, Florida, Listing ID: 28370

Spacious 4 bedroom, 3 bath, 3 car garage ranch home. Easy access to I-75. Perfect for Snowbirds! 2 king beds, 1 queen, two single beds in this spacious ranch home. Screened in Lanai and golf cart available for use. All kitchen items included, handicap accessible, Full size...

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Timber Creek will feature resort-style amenities and a full portfolio of stylish homes, villas and Townhomes Fort Myers, Florida, Listing ID: 28440

**Snowbirds, Monthly and Long-Term Guests Welcome! Please contact the owner if interested in renting on a monthly or annual basis and we can discuss the home being furnished.** Brand new construction, also available for annual rental at Timber Creek. Property is located on...

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Monthly Rent $5,000

Peaceful tranquility one block from the beach Vero Beach, Florida, Listing ID: 29080

Exciting architecture, vaulted beamed wood ceilings, cozy fireplace, numerous decks, wet bar, wood floors! Oversized windows let in tons of natural light & frame the surrounding ancient oaks making it feel like you're living in a peaceful tree house. Grand master suite w/sitting...

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Details No Image Available

$Multi-Month Discount!

Monthly Rent $6,000 - $10,000

Spacious 5 Bedroom, 3 bath House with Private Pool, Large Lanai and Lake Exposure at Glen Eagle Golf and Country Club. Naples, Florida, Listing ID: 29339

Welcome to a stunning, pet-friendly oasis in the Glen Eagle Golf and Country Club, Naples, Florida. This spacious 5-bedroom, 3-bathroom home is a perfect blend of comfort, luxury, and convenience, set within a secure gated community. Step into your own private retreat...

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  • 3100
  •  5
  •  3
Details No Image Available

$Multi-Month Discount!

Monthly Rent $8,500 - $9,999

Beautiful home in the heart of the Florida Keys. Located in sought-after neighborhood near prime dining and attractions. Islamorada, Florida, Listing ID: 29352

Beautiful home in the heart of the Florida Keys for your winter escape. There are many prime restaurants and attractions just a short drive away. The home is situated in one of the most sought-after, family oriented neighborhood in the Keys. Relax and talk the night away on the...

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Monthly Rent $6,000

Spend the winter in style in South Palm Beach. Recently renovated townhouse with every upgrade possible. South Palm Beach, Florida, Listing ID: 30093

This season, spend your time on the Island in style. Come see this never before listed 3 Bedroom Townhouse that has been completely renovated from the studs up. The First Floor features a 1/2 bathroom, a chef's kitchen (with Quartz countertop and Fisher & Paykel appliances),...

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  • 2400
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Monthly Rent $4,195

Live in Elegance & Convenience Near The Best of Boynton Beach. Three Secluded Pools. Indoor Parking Same Level. Boynton Beach, Florida, Listing ID: 30419

SPECIAL - Luxury condo for rent/lease. Incredible & Elegant Living !! Indoor parking garage space included, Three pools/hot tub, 24 hour fitness room. Walking distance to great restaurants and entertainment. 12 minute ride to the most beautiful beaches! ...

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  • 1460
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Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,500

Rate Reduced! Unused brand new apartment, everything is new. It is located on the lower floor of new house, canal front. KEY LARGO, Florida, Listing ID: 30742

The apartment is brand new including unused furniture. First time offered to rent apartment. Place to have jet ski or canoe in front of the house or a small boat under 18 feet. the community is well maintained and safe.

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Monthly Rent $2,800

A Hidden slice of paradise, with a water view from every angle. Your just steps to a heated pool or the saltwater. Boynton Beach, Florida, Listing ID: 30756

6 MONTH RENTAL INQUIRIES ONLY. There is no better place to spend the cold winter months than in this cozy waterside hide-away. Never before have you experienced the beautiful Florida winter living so close to the water that you inadvertently learn the daily tide schedule while...

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GREAT LOCATION! Near Hutchinson Island (Jensen Beach) - Savannah Preserve State Park ..Clover Park (MET Spring Training) Port St Lucie, Florida, Listing ID: 31868

Gorgeous Ranch home! 3BD 2BA, fenced backyard ..just minutes away from Hutchinson Island (Jensen Beach).. Savannah Preserve State Park.. Clover Park (Mets spring training).. shopping and great restaurants!

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Comfortable luxury home in peaceful neighborhood close to the beach, restaurants, malls and entertainment Hallandale Beach, Florida, Listing ID: 31940

Create unforgettable memories staying at this modern tropical vacation home. Centrally located close to sandy beaches of Sunny Isles, Hallandale, Hollywood, great restaurants, bars, water sports, recreational areas and malls. 30 min away from Wynwood, Design District and...

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Monthly Rent $2,175

Nestled in the park-like community of Golden Gate, Aqua Bay Apartments is conveniently located minutes to I-75, Naples, Florida, Listing ID: 33637

Nestled in the park-like community of Golden Gate, Aqua Bay Apartments is conveniently located minutes to I-75, just 7 miles from the world famous beaches of Naples and a short drive to the best shopping and dining on the west coast of Florida. Aqua Bay is an apartment...

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Details No Image Available

$Multi-Month Discount!

Monthly Rent $15,500

This stunning oceanfront 2-bedroom, 2.5-bathroom condo is designed to offer you a luxurious and unforgettable stay! Riviera Beach, Florida, Listing ID: 34128

The following is a detailed description of all of the rooms in the unit and the amenities found within… Master Bedroom Retreat: Indulge in the comfort of a Split-King bed with dual-adjustable Tempur-Pedic pillow top mattresses, ensuring independent, personalized...

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  • 1600
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Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,750

Two bedroom/two bath condo on the 10th hole (1st floor) of the Jack Nicklaus Design Golf Course! Punta Gorda, Florida, Listing ID: 34210

A Golfer's Vacation Paradise at Webbs Reserve in Babcock Ranch! New, professionally decorated, 1st floor condo overlooking the Jack Nicklaus 10th hole golf course! This Terrace Style Condo has been beautifully Designed & Furnished. Guests love the openness of the kitchen,...

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Details No Image Available

$Multi-Month Discount!

Welcome to Casa Catalina – Your Private Lakefront Getaway in the Heart of Miami! Miami, Florida, Listing ID: 34221

Welcome to Casa Catalina – Your Private Lakefront Getaway in the Heart of Miami! Nestled just blocks from Tropical Park and minutes from Historic Coral Gables, Coconut Grove, Miami Beach, Pinecrest and the airport! Casa Catalina offers a serene lakeside escape perfect...

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  • 3300
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Details No Image Available

$Multi-Month Discount!

Monthly Rent $6,500 - $20,000

Beachfront Bliss at Vesper Dunes – Private Beach Emerald Coast Retreat, 3 King Suites, Bunk Room, Sleeps 14 Miramar, Florida, Listing ID: 34252

Welcome to Vesper Dunes, your beachfront paradise in Miramar Beach, Florida. This spacious 4-bedroom, 3.5-bath townhome comfortably accommodates up to 14 guests with three private king suites and a large bunk room perfect for families or friends. Spread across three levels,...

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Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,600 - $5,700

Only March Left - Luxury Naples Golf & Country Club Condo – 2BR/2BA with Lanai Views, Resort Amenities Naples, Florida, Listing ID: 34286

ESCAPE TO LUXURY, LEISURE, AND FLORIDA SUNSHINE IN A FULLY RENOVATED GOLF & COUNTRY CLUB COMMUNITY — LOCATED IN NAPLES, RECENTLY VOTED THE #1 BEST PLACE TO LIVE IN THE U.S. (U.S. NEWS & WORLD REPORT). The newly reimagined Countryside Golf & Country Club offers snowbirds an...

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  • 1200
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Details No Image Available

$Multi-Month Discount!

Monthly Rent $3,195

90 DAY min. rental. AVAILABLE NOV 15, 2025. Fully furnished charming cottage nestled in Lake Placid, FL. Lake Placid, Florida, Listing ID: 34331

This charming cottage in Country Walk, a community nestled in Lake Placid, Florida, a true winterless paradise, is perfect for relaxation and privacy. Located in a cul-de-sac on a quiet street within the complex, and resting in approx., half an acre lot, offers all the comforts...

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Monthly Rent $2,250

Aqua Villa #405 Fort Walton Beach, Florida, Listing ID: 34480

Welcome to Aqua Villa 405—a comfortable, no-nonsense beachfront condo on beautiful Okaloosa Island that offers everything you need for a classic beach vacation, including space for up to 8 guests. Located directly on the Gulf of Mexico, this 2-bedroom, 2-bath condo features...

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Monthly Rent $4,350

Azure #115 4BR/3BA Condo Fort Walton Beach, Florida, Listing ID: 34481

*** There will be ongoing building construction at this location between 8/4/2025 – 3/16/2026. During this prolonged construction period, there will be construction noise (grinding, banging), dust, etc. about the property. There will be no heavy noise before 7am or after 5pm....

  • Condo
  • N/A
  •  4
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Monthly Rent $2,780

Azure #223 | Partial Views Of The Beach, Hot Tub, Pool & much more! Fort Walton Beach, Florida, Listing ID: 34482

*** There will be ongoing building construction at this location between 8/4/2025 – 3/16/2026. During this prolonged construction period, there will be construction noise (grinding, banging), dust, etc. about the property. There will be no heavy noise before 7am or after 5pm....

  • Condo
  • 0
  •  3
  •  2
Monthly Rent $3,885

Azure #307 | Panoramic Gulf Views, Community Pool & Much More! Fort Walton Beach, Florida, Listing ID: 34483

*** There will be ongoing building construction at this location between 8/4/2025 – 3/16/2026. During this prolonged construction period, there will be construction noise (grinding, banging), dust, etc. about the property. There will be no heavy noise before 7am or after 5pm....

  • Condo
  • 0
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Monthly Rent $2,780

Azure #319 | Unparalleled Views Fort Walton Beach, Florida, Listing ID: 34484

*** There will be ongoing building construction at this location between 8/4/2025 – 3/16/2026. During this prolonged construction period, there will be construction noise (grinding, banging), dust, etc. about the property. There will be no heavy noise before 7am or after 5pm....

  • Condo
  • 0
  •  3
  •  2
Monthly Rent $4,350

Azure #404 | Private Covered Balcony with Views of the Gulf! Fort Walton Beach, Florida, Listing ID: 34485

*** There will be ongoing building construction at this location between 8/4/2025 – 3/16/2026. During this prolonged construction period, there will be construction noise (grinding, banging), dust, etc. about the property. There will be no heavy noise before 7am or after 5pm....

  • Condo
  • 0
  •  4
  •  3
Monthly Rent $3,885

Azure #405 | New Coastal Glam Style with Views of The Gulf! Fort Walton Beach, Florida, Listing ID: 34486

*** There will be ongoing building construction at this location between 8/4/2025 – 3/16/2026. During this prolonged construction period, there will be construction noise (grinding, banging), dust, etc. about the property. There will be no heavy noise before 7am or after 5pm....

  • Condo
  • 0
  •  3
  •  3
Monthly Rent $3,885

Azure #410 | Comfort, Convenience, and Coastal Charm—designed to host unforgettable vacations! Fort Walton Beach, Florida, Listing ID: 34487

*** There will be ongoing building construction at this location between 8/4/2025 – 3/16/2026. During this prolonged construction period, there will be construction noise (grinding, banging), dust, etc. about the property. There will be no heavy noise before 7am or after 5pm....

  • Condo
  • 0
  •  3
  •  3
Monthly Rent $5,500

Bella Riva #209 | Beach Front & Private Beach Walk Fort Walton Beach, Florida, Listing ID: 34488

Your Luxurious Mediterranean inspired beach front condominium awaits you! Unit 209 is the largest floor plan in the building boasting over 2400 square feet, 4 bedrooms, 3 bathrooms and a huge 440sq ft. terrace w/ gas grill. This upscale condo is professionally decorated w/...

  • Condo
  • 0
  •  4
  •  3
Monthly Rent $4,515

BLU #200 | Gulf Front Swimming Pool & Barbecue Area! Fort Walton Beach, Florida, Listing ID: 34489

Discover a haven of elegance and comfort at our four-bedroom condo at Blu, a gated beachfront property on the pristine white sand shores of Okaloosa Island. Immerse yourself in the serene ambiance of the interior, adorned with tasteful décor in soft grays and whites,...

  • Condo
  • 0
  •  4
  •  3
Monthly Rent $2,250

Emerald Towers West #4001 | Gulf Views & A Spacious Balcony. Fort Walton Beach, Florida, Listing ID: 34490

This beautiful 2-bedroom, 2-bath condo is located on the 4th floor and offers breathtaking, direct views of the Gulf and sugar-white beaches from its spacious private balcony. Enjoy a fully equipped kitchen, in-unit washer and dryer, four flat-screen TVs, DVD player, and...

  • Condo
  • 0
  •  2
  •  2
Monthly Rent $3,465

Emerald Towers West #4002 | Uninterrupted Beach Views, A Private Balcony, and space for up to 8 guests! Fort Walton Beach, Florida, Listing ID: 34491

Emerald Towers West 4002 – Gulf-Front Comfort, Free Beach Service & Prime Island Location Treat yourself to a front-row seat to the stunning Emerald Coast at Emerald Towers West 4002, a spacious 3-bedroom, 3-bath beachfront condo on beautiful Okaloosa Island. Located...

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Monthly Rent $2,150

Welcome to Emerald Towers West 5003—your quiet Gulf-front escape on the west end of Okaloosa Island. Fort Walton Beach, Florida, Listing ID: 34492

Welcome to Emerald Towers West 5003—your quiet Gulf-front escape on the west end of Okaloosa Island. Locally managed by Legacy Vacations, this 5th floor one-bedroom condo is designed for families and small groups looking for a peaceful beachfront getaway with unforgettable...

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  • 0
  •  1
  •  1
Monthly Rent $2,570

Experience year-round bliss on the stunning Emerald Coast with a stay at Island Princess #114 in Fort Walton Beach Fort Walton Beach, Florida, Listing ID: 34493

Experience year-round bliss on the stunning Emerald Coast with a stay at Island Princess #114 in Fort Walton Beach. Situated on the sought-after Okaloosa Island, this 2-bedroom, 2-bathroom condo is your ideal beachfront retreat. Enjoy the perfect blend of convenience and luxury...

  • Condo
  • 0
  •  2
  •  2
Monthly Rent $2,940

Directly on the white sandy shore rests Island Princess 116, a three-bedroom Fort Walton Beach vacation condo. Fort Walton Beach, Florida, Listing ID: 34494

Directly on the white sandy shore rests Island Princess 116, a three-bedroom Fort Walton Beach vacation condo. On the ground level, the condo has such easy access to both pool and beach. Guests love being so close. This condo offers complimentary beach service (1 umbrella, 2...

  • Condo
  • 0
  •  3
  •  3
Monthly Rent $2,940

Looking for the ultimate beach escape? Look no further! This stunning 3-bedroom, 3-bathroom condo on Okaloosa Island! Fort Walton Beach, Florida, Listing ID: 34495

Looking for the ultimate beach escape? Look no further! This stunning 3-bedroom, 3-bathroom condo on Okaloosa Island is the perfect vacation spot for your next getaway. Just steps from the sugar-white sands and sparkling emerald waters of Fort Walton Beach, this spacious and...

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  •  3
  •  3
Monthly Rent $2,940

Welcome to Island Princess 700 – Your Budget Friendly Dream Beach Getaway! Fort Walton Beach, Florida, Listing ID: 34496

Welcome to Island Princess 700 – Your Budget Friendly Dream Beach Getaway! Perched on the top floor of the family-friendly Island Princess resort, this spacious 3-bedroom end unit offers breathtaking Gulf views right from your private balcony! Feel the ocean breeze, watch...

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  • 0
  •  3
  •  3
Monthly Rent $2,150

Island Sands #108 – Ground Floor Beachfront Getaway Fort Walton Beach, Florida, Listing ID: 34497

Island Sands #108 – Ground Floor Beachfront Getaway Step right onto the sand from this beautiful ground-floor condo on Okaloosa Island! Island Sands #108 is a spacious 1-bedroom, 1.5-bath retreat with easy beach access from the private patio. Inside, you’ll find a king...

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  • 0
  •  1
  •  1 1/2
Monthly Rent $2,250

Welcome to Islander Beach Resort #7005—your seventh-floor beachfront retreat on beautiful Okaloosa Island. Fort Walton Beach, Florida, Listing ID: 34498

Welcome to Islander Beach Resort #7005—your seventh-floor beachfront retreat on beautiful Okaloosa Island. Managed locally by Legacy Vacations, our team is close by, available, and committed to serving you with genuine hospitality throughout your stay. This bright and...

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  • 0
  •  2
  •  2
Monthly Rent $2,575

Unit 506 offers stunning views of the Santa Rosa Sound, modern coastal finishes, and a peaceful stroll of The Gulf! Fort Walton Beach, Florida, Listing ID: 34499

Welcome to our newly updated island getaway! Perched on the 5th floor of Palm Court Yacht Club, Unit 506 offers stunning views of the Santa Rosa Sound, modern coastal finishes, and a peaceful setting just a short stroll from the Gulf of Mexico. 2 Bedrooms | 2 Bathrooms |...

  • Condo
  • 0
  •  2
  •  2