Cottage vacation rentals in Hillsborough County
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Hillsborough County
Guests agree: these cottages are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Hillsborough County cottage rentals
Cottage rentals with a hot tub
Cottage in Dunedin
4.9 out of 5 average rating, 72 reviewsSunny - Key West Vibe Cottage - Pool - Walkable
Cottage in Tampa
4.95 out of 5 average rating, 99 reviewsHot tub, 2 floors riverfront, Bush Gardens, kajaks
Cottage in Safety Harbor
4.9 out of 5 average rating, 68 reviewsDowntown Luxe Comfort Cottage with Hot Tub!
Cottage in Dunedin
5 out of 5 average rating, 11 reviews1000 Oaks Cottage 3bed/2bath with hot tub
Cottage in Palm Harbor
4.83 out of 5 average rating, 90 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
Cottage in Largo
5 out of 5 average rating, 34 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
Cottage in Saint Petersburg
4.99 out of 5 average rating, 72 reviews"TROPI COTTAGE"
Cottage in Largo
4.96 out of 5 average rating, 80 reviewsHidden Oasis #1, high&dry near the beach
Pet-friendly cottage rentals
Cottage in Tampa
4.96 out of 5 average rating, 80 reviewsRiver adjacent, Quiet neighborhood, King bed
Cottage in Clearwater
4.73 out of 5 average rating, 263 reviewsClearwater cottage
Cottage in Dunedin
4.99 out of 5 average rating, 305 reviewsPrivate Yard Walk to Downtown Dunedin & Waterfront
Cottage in Clearwater
4.84 out of 5 average rating, 122 reviewsBeach Guest Cottage. Gulf Semi Private Area.
Cottage in Gulfport
4.73 out of 5 average rating, 45 reviewsThe Cottage at Wishing Well, Gulfport
Cottage in Riverview
4.95 out of 5 average rating, 76 reviewsAlafia River Cottage
Cottage in Gulfport
4.99 out of 5 average rating, 263 reviewsGulfport Art District - One Block From Beach!
Cottage in Thonotosassa
4.96 out of 5 average rating, 24 reviewsTampa-Retreat I Homestead with 5th Gen Floridians
Private cottage rentals
Cottage in Largo
4.78 out of 5 average rating, 60 reviewsCottage by the Coast 2 bd - Pet Friendly
Cottage in Dunedin
4.97 out of 5 average rating, 73 reviewsPrivate and Romantic I The Highland Hideaway
Cottage in St. Petersburg
4.94 out of 5 average rating, 17 reviewsModern Cottage
Cottage in Dunedin
4.84 out of 5 average rating, 57 reviewsCozy Cottage in the Heart of Dunedin
Cottage in Palm Harbor
4.69 out of 5 average rating, 70 reviewsCrystal Beach Yellow Cottage
Cottage in St. Petersburg
4.93 out of 5 average rating, 14 reviewsBeach Cottage- Pass a Grille- Steps to beach
Cottage in St. Petersburg
4.99 out of 5 average rating, 90 reviewsSt Petersburg Cottage- Beaches, Downtown & Trail
Cottage in Tarpon Springs
4.85 out of 5 average rating, 98 reviewsPalm Cottage * King Bed * Tropical Yard
Destinations to explore
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- Family travel hub Tips and inspiration
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