What are the top rated Cottage Rentals in Diamond Isle?

There are a lot of options in Diamond Isle. If you plan on staying in the Diamond Isle area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Diamond Isle: <a href="/property/1br-1ba-new-coastal-boutique-cottage-hgtv-worthy-sleeps-4-steps-to-beach/HA-321884439" class="class="static-page-link"">1BR/1BA NEW Coastal Boutique Cottage. HGTV Worthy! Sleeps 4. Steps to Beach!</a> <a href="/property/walkable-dog-friendly-cottage-downtown/HA-321961381" class="class="static-page-link"">Walkable Dog Friendly Cottage Downtown</a> <a href="/property/charming-3-bedroom-2-bath-cottage-with-hot-tub-downtown-dunedin/HA-3214535178" class="class="static-page-link"">Charming 3-bedroom/2-bath Cottage with Hot Tub Downtown Dunedin</a> <a href="/property/casita-verde-secluded-cottage-2-houses-from-pinellas-trail-and-3-blocks-to-gulf/HA-3214205741" class="class="static-page-link"">Casita Verde, Secluded Cottage 2 houses from Pinellas Trail and 3 Blocks to Gulf</a> <a href="/property/the-purple-flower-30-second-walk-to-the-beach-free-parking/HA-1214786620" class="class="static-page-link"">The Purple Flower - 30 Second walk to the Beach. Free parking.</a> <a href="/property/cute-and-cozy-beach-bungalow-steps-to-the-beach-free-off-street-parking/HA-1219386771" class="class="static-page-link"">Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!</a> <a href="/property/the-cottage-32-steps-to-the-beach-sleeps-2-drive-to-your-door-wifi-grill/HA-321664187" class="class="static-page-link"">THE COTTAGE - 32 Steps to the Beach - Sleeps 2, drive to your door, Wifi, Grill.</a> <a href="/property/white-beaches-walk-to-restaurants-and-shops-family-vacation-romantic-getaway/HA-1213015603" class="class="static-page-link"">White beaches, walk to restaurants and shops! Family vacation/Romantic getaway!</a> <a href="/property/the-lazy-lemon-cottage-steps-from-the-beach-frenchys-and-palm-pavilion/HA-3212839533" class="class="static-page-link"">The Lazy Lemon Cottage Steps From the Beach, Frenchys and Palm Pavilion.</a> <a href="/property/keylime-cottage-heated-pools-steps-from-the-beach-perfect-location/HA-3212839751" class="class="static-page-link"">KEYLIME COTTAGE Heated Pools, steps from the beach perfect location</a>

How much does it cost to rent a cottage in Diamond Isle?

The average cost for a cottage rental in Diamond Isle is $308 per night. Mauidreamwedding has a wide list of great cottages near Diamond Isle that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Diamond Isle that allow pets?

Yes, here are the top cottage rentals in Diamond Isle that allow you to bring your pet: White beaches, walk to restaurants and shops! Family vacation/Romantic getaway! 1000 Oaks Cottage Downtown Dunedin Cottage Walk to Restaurants Frenchy's Cottage 482 <a href="/all/usa/florida/clearwater-beach/diamond-isle" class="class="static-page-link"">See all pet-friendly vacation rentals in Diamond Isle on Mauidreamwedding</a>

Do you have any rental cottages in Diamond Isle that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Diamond Isle to find one that works for you.

Are there quality cottages in Diamond Isle that have indoor swimming pools?

As of 2026, the data from Mauidreamwedding shows that there are Over 105 private swimming pools or cottages with indoor pools in the Diamond Isle area along with other great amenities.

Diamond Isle Cottage Rentals By Owner

White beaches, walk to restaurants and shops! Family vacation/Romantic getaway!

From US $467

9.6 (109 Reviews)

Cottage

White beaches, walk to restaurants and shops! Family vacation/Romantic getaway!

Air Conditioner
Parking
Pet Friendly

Diamond Isle Cottage Rentals & Holiday Homes

Find the best cottages in Diamond Isle - We found 105 exact matches

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