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The Round Up: Gorgeous 5 Bedroom House Rental in Rosemary Beach, FL for Your Dream Vacation

Home Rental in Rosemary Beach Florida

Welcome to The Round Up, your dream vacation oasis in Rosemary Beach, FL. Immerse yourself in luxury and relaxation in this 5 bedroom house rental, perfect for accommodating large groups. Explore the community pool, enjoy modern amenities.

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Rental overview

Why You'll Love This Rental

The Round Up is a 5-bedroom, 4.5-bath home in Rosemary Beach, Florida, with 2,440 square feet and sleeping for up to 12 guests. Set near the water and near a beach, it also includes private beach access and access to a community pool. A complimentary tram service to the beach is provided seasonally (March–October), and bikes are included for getting around locally.

Inside, the home is arranged with two primary king bedrooms—one on the first floor and one upstairs—plus additional guest rooms that include a queen room, a room with two twins, and a bunk room with four twin beds. The kitchen and dining setup includes an 8-person dining table with additional seating for four at the breakfast bar. Everyday conveniences include Wi‑Fi, washer/dryer, towels and linens, and a full kitchen with major appliances. Outdoor features include a gas grill and an outdoor shower, along with parking for two vehicles in front and additional first-come, first-served spaces beside the home.

Good fit for
Family Vacations Group and Reunion
Private Beach Access Near a beach with private beach access.
Community Pool Access Includes access to a community pool.
Seasonal Beach Tram Complimentary tram to the beach runs March–October.
Two King Primaries Two primary bedrooms include king beds, one on each floor.
Outdoor Shower Outdoor shower available for rinsing off after the beach.
At a glance

Property Highlights

Waterfront - NearbyLocation Setting
Near a BeachBeach Access
5 BedroomsBedrooms
4 Full, 1 Half BathroomsBathrooms
Sleeps 12Guest Capacity
2440 sq. ft.Living Space
Pool (Community)Pool
Internet AccessInternet
TelevisionTelevision
YesAir Conditioning
YesWasher / Dryer
Location & nearby Explore the Area

Located in Rosemary Beach, Florida, The Round Up is listed as waterfront nearby and near a beach, with private beach access. The home also provides access to a community pool and offers a complimentary seasonal tram service to the beach (March–October). Bikes are included, supporting local exploring by bike. Parking is available for two vehicles in front of the home, with additional first-come, first-served spaces on the side.

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Availability Calendar

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About this rental

About This Rental

The Round Up is a 2,440-square-foot home in Rosemary Beach with 5 bedrooms and 4.5 bathrooms, accommodating up to 12 guests. The setting is listed as waterfront nearby and near a beach, with private beach access. Guests also have access to a community pool, and a complimentary tram to the beach operates seasonally from March through October.

The sleeping plan is spread across two floors, including a first-floor primary bedroom with a king bed. Upstairs, a second primary bedroom includes a king bed and a bathroom with a walk-in shower and soaking tub, plus a private balcony. Additional upstairs bedrooms include a bunk room with four twin beds, a guest room with a queen bed, and a guest room with two twin beds. In total, the home provides 2 king beds, 1 queen bed, 2 single beds, and 2 bunk beds.

For meals and downtime, the home includes a full kitchen with a refrigerator, stove, oven, microwave, dishwasher, toaster, and standard coffee maker, along with dishes and silverware. Dining is arranged with an 8-person table and extra seating for four at the breakfast bar. Living spaces include a living room and an upstairs loft/landing seating area with a TV.

Outdoor and practical amenities include a gas grill, an outdoor shower, air conditioning and heating, Wi‑Fi, and a washer/dryer. Parking includes space for two vehicles in front, plus additional first-come, first-served spaces on the side of the home. Check-in is 4:00 PM CST and checkout is 10:00 AM CST.

The Round Up by Oversee 30A | Perfect in Walton County Awards – Three-Time Diamond Winner – Best Rental Mgmt. 2026, 2025, 2024

Introducing "The Round Up", your ultimate beach getaway. With 2,440 square feet of luxury living space, this stunning 5 BDRM, 4.5 BTH home sleeps up to 12 guests.

Highlights:
Seacrest
.4 mile to beach (private access)
1 block to Florida's 2nd largest community pool!
️ Complimentary tram to beach and back
Near Rosemary Beach and Alys Beach
4 bikes!
Outdoor shower
4-star restaurants
️ Boutiques

Staying between Alys Beach and Rosemary Beach? My goodness, what a great spot! With 3 complimentary bikes, you and your crew will have a blast cruising to 30A’s best shopping and dining. Also, the beach tram stop is right outside the home, providing a convenient shuttle to the shore, just minutes away.

Inside, the inviting coastal décor is adorable! And features soothing white and blue hues, beach glass accents, and pearlescent tile, creating a beachy atmosphere. You'll appreciate the convenience of the fully enclosed outdoor shower near the back door.

Relax and reconnect on the covered front porch, in the cozy living room, or in the loft, with a seating area and TV on the upstairs landing. Outside, unwind in the shade of the covered porch, which comfortably seats seven, or bask in the Florida sunshine on the expansive patio or gather around the fire pit.

The open galley kitchen features custom cabinets, marble countertops, and a spacious pantry. Enjoy the 8-person dining table, with additional seating for four at the breakfast bar.

A luxurious primary bedroom, king, is on the first floor, while another occupies the upstairs area, with a private deck and porch swing bed, and an in-room coffee maker. Additionally, the white marble bathroom includes a soaking tub. On the second floor is a bunk room with four twin beds, a guest room with two twin beds, and another guest room, queen.

Don't miss the chance to experience coastal living at its finest. Go on half-day bike adventures through gorgeous neighborhoods, over dune lakes, to faraway beaches! Pack for a wine-picnic, in the sand! There isn’t a single beach access, or eatery, or bar, that isn’t bike-friendly.

Book your luxurious stay at The Round Up today and create adventures, laughs, and lots of lasting memories.

Welcome! Our dedicated team at Oversee 30A, a local company, is committed to ensuring your stay is nothing short of exceptional. We strive for perfection and are just a stone's throw away should you require any assistance. Reach out to us anytime, seven days a week, with the added peace of a 24/7 emergency line.

Overview:
-.4 mile to beach (private access)
- 1 block to community pool and amphitheater
- Short walk or bike ride to Rosemary Beach and Alys Beach
- Complimentary tram service to beach and back (March-October)
- 5 bedrooms, 4.5 baths
- 2,440 sq. ft.
- Gas grill
- Outdoor shower
- Wi-Fi
- 4 bikes included
- Parking for 2 vehicles in front, plus spaces on first come, first serve basis on side of home

Overnight:
- King in 1st floor primary bedroom; walk-in shower; TV
- King in 2nd floor primary bedroom; walk-in shower, soaking tub; TV; private balcony
- Bunk room with 4 twin beds in 2nd floor guest room; shared bath
- Queen in 2nd floor guest room; shared bath
- Two twin beds in 2nd floor guest room; full bath

Check-in is 4:00 PM CST. Checkout is 10:00 AM CST.
Before you book

Vacation Rental Policies

Check In

4:00 PM

Check Out

10:00 AM

Things to enjoy

Activities and Special Interests

This property provides access to the following activities and special interests:

Boating
Biking
Fishing
Golfing
Hiking
Sailing
Surfing
Wind Surfing
Family Vacations
Group and Reunion
Canoeing
Fly Fishing
Kayaking
Beach
Deep Sea Fishing
Ocean
Scuba Diving

Other Activities and Special Interests

Marina
Water Parks
Zoo
Antiquing
Bird Watching
Eco Tourism
Outlet Shopping
Paddle Boating
Jet Skiing
Para-sailing
Snorkeling
Swimming
Water Tubing
Historic
Romantic
What's included

Property Amenities

Featured Amenities

Pool (Community)
Air Conditioning
Television
Internet Access
Dishwasher
Washer/Dryer
Grill

Property Features

Towels/Linens
Parking
Hair Dryer
Iron / Ironing Board
Microwave
Refrigerator
Toaster
Oven
Stove

Other Property Amenities

Free Parking, Street Parking, Resort, Private beach access, Community pool, Carbon monoxide detector, Standard coffee maker, Cleaning: Included, Marina, Water Parks, Zoo, Dishes & Silverware, Fire extinguisher, Living Room, Hangers, Heating, Hot Water, Long Term Stays Allowed, Private Entrance, Private Living Room, Shampoo, Smoke Detector, Antiquing, Bird Watching, Boating, Eco Tourism, Outlet Shopping, Paddle Boating, Shopping, Wildlife Viewing, Hospital, Near Ocean, Cycling, DeepSea Fishing, Fishing, Fishing - Bay, Fishing - Fly, Fishing - Freshwater, Fishing - Surf, Hiking, Jet Skiing, Para-sailing, Pier Fishing, Sailing, Snorkeling, Surfing, Swimming, Tennis - Community or Local, Water Tubing, Wind Surfing, Family, Meal delivery, Kitchen, Kitchen, Complimentary bikes, Kitchen Island, Dining table, 3 Oversee Bikes

Escape to the ultimate luxury getaway in Rosemary Beach, Florida with this exquisite 5-bedroom vacation home. Located at 102 Surfer Lane, the property boasts a blend of coastal decor and modern amenities, including custom furnishings and a cozy living space. Enjoy spacious bedrooms, a bunkroom for added flexibility, and easy access to the nearby beach. Situated close to Alys Beach and Rosemary Beach, you'll have convenient access to dining options, retail therapy, and nearby attractions. Find out more about this dream vacation rental and discover all the luxurious features awaiting you in this stunning beachside retreat.

Property Highlights

Situated in the charming coastal town of Rosemary Beach, Florida, the 5-bedroom vacation home at 102 Surfer Lane offers a tranquil retreat with elegant coastal decor and modern amenities. This property boasts a range of outdoor amenities, including an outdoor shower for rinsing off beach sand, a covered patio for relaxation, and a loft area for unwinding. Families will appreciate the family-friendly features such as the bunkroom with four twin beds, guest bedroom with two twin beds, and two luxurious bedrooms with king-sized beds. Additionally, the close proximity to Alys Beach and Rosemary Beach provides convenient access to retail and dining options, making it an ideal location for those seeking a peaceful getaway with the freedom to explore and enjoy the surroundings.

Interior Design Features

Enhancing the ambiance of the 5-bedroom vacation home in Rosemary Beach, FL, the interior design features a blend of coastal decor elements and modern amenities tailored for maximum comfort and style. The custom furnishings throughout the house add a touch of elegance and sophistication, perfectly complementing the coastal charm of the surroundings. From the open galley with custom cabinets and marble counters to the cozy living spaces adorned with a mix of white, pearlescent, and blue tiles, every corner exudes a sense of relaxation and luxury. Guests can unwind in style in the various relaxation areas, including a loft and covered patio, making this vacation home an ideal retreat for families or friends seeking a peaceful getaway by the beach.

Luxurious Bedrooms and Bunkroom

The 5-bedroom vacation home in Rosemary Beach, FL boasts two luxurious bedrooms with king-sized beds, a bunkroom featuring four twin beds, and a guest bedroom with two twin beds, offering a blend of comfort and style for guests seeking a luxurious retreat.

  1. Bedroom Decor: The bedrooms are elegantly decorated with coastal accents, creating a serene and beachy ambiance.
  2. Spacious Layout: Each bedroom is thoughtfully designed to provide ample space for relaxation and privacy.
  3. Beach Activities: Guests can easily access the nearby beach for a day of sun, sand, and water activities.
  4. Bunkroom Fun: The bunkroom is perfect for children or friends traveling together, adding a playful touch to the luxurious setting.

Location and Nearby Attractions

Situated between Alys Beach and Rosemary Beach, this 5-bedroom vacation home in Rosemary Beach, FL offers guests not only a luxurious retreat but also convenient access to a variety of nearby attractions and amenities. Guests can indulge in beach activities just 0.4 miles away, with a private entrance for a more secluded experience. For dining options, the property is close to various restaurants and cafes, allowing visitors to explore local cuisine. Additionally, within walking distance, guests can enjoy the convenience of an amphitheater and swimming pool for entertainment and relaxation. Trams are also available to connect guests to the nearby beaches, making it easy to explore the area's coastal beauty and enjoy a hassle-free vacation experience.

Booking Information and Inquiries

For efficient and tailored assistance regarding booking details and inquiries for the 5-bedroom vacation home in Rosemary Beach, FL, please do not hesitate to reach out to our property management team.

  1. Availability Inquiries: Contact us to check specific dates and availability for your desired stay.
  2. Property Management Services: Our team is dedicated to providing excellent service for all your booking needs.
  3. Rates and Reservations: Inquire about pricing, special offers, and secure your reservation with ease.
  4. Assistance and Questions: We are here to help with any queries you may have, ensuring a smooth booking process.
Helpful details

Frequently Asked Questions

The Round Up is located in Rosemary Beach, Florida.

The Round Up accommodates up to 12 guests.

5 Bedrooms and 4 Full, 1 Half Bathrooms.

The listed beach access for The Round Up is Near a Beach.

Yes. The property lists Pool (Community).

The Round Up is professionally managed by Oversee.
Local management

Professionally Managed By

Oversee
In business since 2011
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Property reference
#169579 · The Round Up
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