What are the top rated Cottage Rentals in On Top of The World?

There are a lot of options in On Top of The World. If you plan on staying in the On Top of The World area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in On Top of The World: <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/jd-s-hideaway-by-the-sea-2-blocks-off-main/HA-1214826762" class="class="static-page-link"">JD&#39;s Hideaway By The Sea: 2 Blocks off Main!</a> <a href="/property/key-west-style-cottage-with-pool-hot-tub/HA-3213319486" class="class="static-page-link"">Key West Style Cottage - with pool/hot-tub</a> <a href="/property/key-west-style-cottage-with-pool-hot-tub/HA-3213325315" class="class="static-page-link"">Key West Style Cottage - with pool/hot-tub</a> <a href="/property/last-minute-discounts-for-fall-quaint-bungalow-just-off-main-street/HA-1219404921" class="class="static-page-link"">Last minute discounts for Fall - Quaint Bungalow just off Main Street!</a> <a href="/property/dunedin-cottage-close-to-clearwater-beach-honeymoon-island-blue-jays-stadium/HA-321780883" class="class="static-page-link"">Dunedin Cottage Close To Clearwater Beach, Honeymoon Island,Blue Jays Stadium.</a> <a href="/property/key-west-style-cottage-with-pool-hot-tub/HA-3213321871" class="class="static-page-link"">Key West Style Cottage - with pool/hot-tub</a> <a href="/property/charming-newly-reno-1-min-to-downtown-dunedin/HA-3213053928" class="class="static-page-link"">Charming Newly Reno 1 min to Downtown Dunedin</a>

How much does it cost to rent a cottage in On Top of The World?

The average cost for a cottage rental in On Top of The World is $279 per night. Chicagosbestvacationrentals has a wide list of great cottages near On Top of The World that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in On Top of The World that allow pets?

Yes, here are the top cottage rentals in On Top of The World that allow you to bring your pet: Downtown Dunedin Cottage Walk to Restaurants 1000 Oaks Cottage Cozy and roomy cottage Cozy Coastal Cottages of Dunedin 1 <a href="/all/usa/florida/clearwater/on-top-of-the-world" class="class="static-page-link"">See all pet-friendly vacation rentals in On Top of The World on Chicagosbestvacationrentals</a>

Do you have any rental cottages in On Top of The World that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in On Top of The World to find one that works for you.

Are there quality cottages in On Top of The World that have indoor swimming pools?

As of 2026, the data from Chicagosbestvacationrentals shows that there are Over 67 private swimming pools or cottages with indoor pools in the On Top of The World area along with other great amenities.