
Cottage holiday rentals in Hillsborough County
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Top-rated cottage rentals in Hillsborough County
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for cottage rentals in Hillsborough County
Cottage rentals with a hot tub

Cottage
4.96 out of 5 average rating, 176 reviewsHarbor Oasis with Hot Tub

Cottage
4.95 out of 5 average rating, 106 reviewsHot tub, 2 floors riverfront, Bush Gardens, kajaks

Cottage
4.91 out of 5 average rating, 75 reviewsDowntown Luxe Comfort Cottage with Hot Tub!

Cottage
5 out of 5 average rating, 14 reviews1000 Oaks Cottage 3bed/2bath with hot tub

Cottage
4.83 out of 5 average rating, 90 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub

Cottage
5 out of 5 average rating, 42 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail

Cottage
4.99 out of 5 average rating, 78 reviews"TROPI COTTAGE"

Cottage
4.95 out of 5 average rating, 86 reviewsHidden Oasis #1, hot tub near the beach
Pet-friendly cottage rentals

Cottage
4.96 out of 5 average rating, 153 reviewsThe Pelicans Roost / Gulfport

Cottage
4.86 out of 5 average rating, 36 reviewsLive Simply Cottage: Spacious 4-Bedroom Home!

Cottage
4.96 out of 5 average rating, 115 reviewsArtsy guest house; near downtown w/ private patio

Cottage
4.87 out of 5 average rating, 165 reviewsBEACH! Sunny Escape! Steps 2 Famous Beach w/2 Bike

Cottage
4.83 out of 5 average rating, 6 reviewsBeach front renovated cottage #8

Cottage
4.85 out of 5 average rating, 130 reviewsClose to Beach Guest Cottage in Semi Private area.

Cottage
4.99 out of 5 average rating, 263 reviewsGulfport Art District - One Block From Beach!

Cottage
4.79 out of 5 average rating, 47 reviewsThe Green Bench Cottage - Pet Friendly
Private cottage rentals

Cottage
4.98 out of 5 average rating, 80 reviewsPrivate and Romantic I The Highland Hideaway

Cottage
4.93 out of 5 average rating, 15 reviewsBeach Cottage- Pass a Grille- Steps to beach

Cottage
4.96 out of 5 average rating, 25 reviewsTampa-Retreat I Homestead with 5th Gen Floridians

Cottage
4.92 out of 5 average rating, 36 reviews🏡Cottage near Clearwater & Belleair Beaches🏖🌴☀️

Cottage
4.89 out of 5 average rating, 44 reviewsCozy Cottage - Nature Lovers Dream - Horses - Lake

Cottage
4.96 out of 5 average rating, 47 reviewsOld Florida Paradise Secret Lair Cottage

Cottage
4.94 out of 5 average rating, 31 reviewsElegant Crystal Beach cottage within sea glimpse

Cottage
4.96 out of 5 average rating, 50 reviewsThe Cook Cottage sleeps 4 in Dunedin
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