Holiday Isle, Destin, FL Vacation Rentals: Price, Pool & Pet-Friendly Options

Key Takeaways

• Holiday Isle is a residential peninsula in Destin, Florida, between Destin Harbor and the Gulf of Mexico, known for its quieter beach atmosphere and canal-front homes.

• Now or Never 9117 is a pet-friendly 2-bedroom Sandpiper Cove condo for 6 guests, and Holiday House is a 5-bedroom Holiday Isle home sleeping up to 14.

• New Kids on the Dock is a canal-front 4-bedroom for 10 with a private pool and a 40-foot boat slip, and The Beach Won is a pet-friendly waterfront townhouse for 10.

• Nightly rates typically start from around $200 for smaller units, with premium waterfront properties costing more. 

• At Emerald Coast by Owner, you can book Holiday Isle, Destin, Florida vacation rentals directly through hosts, at transparent rates and no third-party guest service fees.

What Makes Holiday Isle One of Destin's Top Rental Communities?

Holiday Isle earns its reputation because it sits away from Highway 98 traffic on a quiet residential peninsula, yet still puts guests minutes from HarborWalk Village, Destin Harbor charters, and the city's best dining. That combination of peace and proximity is hard to find elsewhere in Destin.

What really separates it, though, is the water access. Destin Harbor and a network of finger canals wrap around the back of the peninsula, so several properties come with private docks and boat slips alongside the expected beach access. Guests get the Gulf out front and the harbor behind them.

Four properties cover the range: Now or Never 9117 for couples and small families, Holiday House for groups up to 14, New Kids on the Dock for boaters who want a private pool, and The Beach Won for pet owners who need a waterfront slip. All four are bookable directly through hosts on Emerald Coast by Owner, with no guest service fees.

Pool & Pet-Friendly Holiday Isle Vacation Rental Options 

1. Now or Never 9117 

Now or Never 9117 is an excellent pick for couples or small families who want comfort and convenience without needing a massive amount of space.

Now or Never 9117 is a 2-bedroom, 2-bathroom condo spanning 1,132 square feet inside the Sandpiper Cove Resort on Holiday Isle. It comfortably sleeps 6 guests and is designed for travelers who want a private, resort-style experience without the chaos of a crowded hotel.

It's close to Destin's best restaurants, outlet shopping, and waterfront attractions, yet tucked into a quiet, well-maintained resort setting. Guests at Now or Never have access to the resort's pools, tennis courts, and lush landscaping, which gives the property a secluded, tropical feel.

The condo is dog-friendly for one dog up to 30 pounds. A non-refundable pet fee of $150 applies, plus a $10 per pet fee collected on-site by Sandpiper Cove. Pets are not permitted on any beaches, so plan walks around the resort grounds rather than the sand.

2. Holiday House 

Holiday House is designed with large groups in mind, with 5 full bedrooms and enough common area to gather comfortably. 

Holiday House is a 5-bedroom home that sleeps up to 14 guests, making it a top choice for large families or multi-family group trips on Holiday Isle. Every bedroom has a smart TV loaded with streaming apps, so even the kids are entertained after a long beach day. 

Out back, a private boat dock gives the group direct harbor access, perfect for a morning cruise to Crab Island or an afternoon of fishing.  

3. New Kids on the Dock 

Te layout includes a downstairs apartment-style setup with its own kitchenette, a fenced yard, private gas grill, and bikes included with the stay. 

New Kids on the Dock is a 4-bedroom, 3-bathroom Holiday Isle house with a private pool, a 40-foot boat slip, and gated beach access just 300 steps from a private stretch of sand and other activities. 

Bedding includes 1 king, 1 queen, 3 doubles, plus a futon and sofa bed. This property is not pet-friendly, so travelers bringing pets will need to look elsewhere.

4. The Beach Won

Beach Won is a pet-friendly townhome with standard amenities and a private outdoor space.

The Beach Won is a pet-friendly waterfront townhouse in Holiday Isle, sleeping up to 10 guests across 4 bedrooms and 3.5 bathrooms, with a private boat dock and boat slip included. The property sits directly on the water with front-row views from a private outdoor patio, and it is minutes from Destin's white-sand beaches, dining, and shopping. 

Interior amenities include a wet bar, walk-in shower, crib, and water filter, and the bedding setup accommodates larger groups with 2 queens, 1 king, 1 double, and a bunk bed.

How Much Are Holiday Isle Vacation Rentals?

Holiday Isle vacation rental pricing varies significantly by property size, waterfront proximity, season, and rental platform, so there isn't a single flat rate for the community. 

Holiday Isle vacation rentals start at about  $200 per night, with a four-bedroom starting at about $286 per night. 

Typical additional fees on Destin-area rentals include cleaning fees of $175 to $450 depending on property size, a damage waiver of $69 to $109 (or a refundable deposit), combined sales and lodging tax of approximately 12% to 13%, and pet fees of $150 to $350 per stay for pet-friendly properties.

Holiday Isle Vacation Rentals: Comparison at a Glance

Save Costs When You Book Holiday Isle Rentals at ECBYO

The right Holiday Isle vacation rental depends on how many people you're traveling with, whether a boat matters to you, and whether pets are joining. Small families and couples often land on Now or Never 9117 for the resort amenities and low-friction ground-floor entry. Large groups look at Holiday House for its capacity, while boating families gravitate toward New Kids on the Dock or The Beach Won for the private slip and canal or waterfront frontage.

The savings come from cutting out the layers between you and the property manager. Emerald Coast by Owner lists several Holiday Isle properties directly with hosts, so what you see on the listing is closer to what you actually pay at checkout. Visit our platform to compare Holiday Isle, Destin, Florida vacation rentals, filter for private pool or pet-friendly stays, and lock in a rate without a platform markup.  

Frequently Asked Questions (FAQs)

What is the average cost of a Destin vacation rental?

The average cost of a Destin vacation rental depends heavily on size, season, and location within the city. Shoulder season months like May, September, and early October offer the most competitive rates without sacrificing beach weather. Peak summer months typically push rates higher than the annual average, with premium waterfront properties commanding significantly more.

What are some pet-friendly beachfront rentals in Destin, Florida?

At Emerald Coast by Owner, our platform lists a substantial inventory of pet-friendly Destin rentals across beachfront and near-beach communities. Properties like Now or Never 9117 (Sandpiper Cove), Holiday House, and The Beach Won on Holiday Isle all welcome pets, though policies vary by unit. 

Where is Holiday Isle in Destin, Florida?

Holiday Isle is a residential peninsula community located in Destin, Florida. Destin Harbor and a network of finger canals wrap around the back of many properties, meaning several rentals come with direct water access or a dock. It sits off Gulf Shore Drive, the peninsula's only access road, which contributes to the quieter, more private atmosphere that sets it apart from the busier stretches of Destin along Highway 98. 

How close is Destin to Miami?

Destin is about 640 miles from Miami by car, which is roughly 9 to 10 hours of driving, depending on traffic and route. Most travelers from South Florida fly into either Destin-Fort Walton Beach Airport (VPS) or Northwest Florida Beaches International Airport (ECP) near Panama City. VPS is the closer of the two at roughly 20 miles from Holiday Isle; ECP is about 50 miles east and closer to an hour's drive. 

How do I avoid service fees when booking a Holiday Isle rental?

The most straightforward way to avoid service fees is to book Holiday Isle, Destin, Florida vacation rentals directly through an owner platform like Emerald Coast By Owner (ECBYO), which connects travelers directly with hosts rather than routing bookings through a third-party marketplace. Direct booking also gives you a direct line of communication with the owner, which means faster responses to questions, more flexibility on check-in and check-out times, and a clearer understanding of exactly what's included in the rental.

 

*Disclaimer: Rental rates, fees, availability, and policies are subject to change and vary by property, season, and host. Always confirm current details directly with the property owner before booking. For more information, visit Emerald Coast by Owner (ECBYO).

About the Author

Joe Godar of the Emerald Coast by Owner Editorial Team creates destination guides, vacation-planning resources, and local travel content focused exclusively on Gulf Coast vacation rentals.

Our team researches beach communities, vacation rental trends, family travel planning, local attractions, and direct-booking best practices across Florida, Alabama, Mississippi, Louisiana, and Texas. Every guide is written to help travelers make more informed booking decisions while avoiding unnecessary third-party guest service fees.

Since launching in 2016, Emerald Coast by Owner has helped connect travelers directly with verified vacation rental hosts across the Gulf Coast.

This article was reviewed for accuracy and updated using local destination research and current vacation rental market insights.