Cottage vacation 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.
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 Safety Harbor
4.96 out of 5 average rating, 158 reviewsHarbor Oasis with Hot Tub
Nov 6 – 13
Cottage in Tampa
5.0 out of 5 average rating, 5 reviewsTraveler's Sanctuary
Dec 31 – Jan 7
Cottage in Odessa
5.0 out of 5 average rating, 17 reviewsBreathtaking Lakefront Glass Cottage
Sep 8 – 15
Cottage in Palm Harbor
4.85 out of 5 average rating, 52 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
Feb 22 – Mar 1
Cottage in Largo
5.0 out of 5 average rating, 19 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
Nov 24 – Dec 1
Cottage in Largo
4.95 out of 5 average rating, 59 reviewsHidden Oasis #1, just a few minutes to the beaches
Jan 19 – 26
Cottage in Tampa
4.94 out of 5 average rating, 79 reviewsHot tub, riverfront, Bush Gardens, kajaks, 2floors
Apr 21 – 28
Cottage in Treasure Island
5.0 out of 5 average rating, 29 reviewsCasa Sunset by Agua Salá
Sep 30 – Oct 7
Pet-friendly cottage rentals
Cottage in Tampa
4.74 out of 5 average rating, 125 reviewsEclectic cottage nestled in million $ street
Jun 1 – 8
Cottage in Treasure Island
4.93 out of 5 average rating, 102 reviewsTreasure Island Beach Cottage
Aug 7 – 14
Cottage in Clearwater
4.84 out of 5 average rating, 118 reviewsBeach Guest Cottage. Gulf Semi Private Area.
Dec 12 – 19
Cottage in Dunedin
4.84 out of 5 average rating, 317 reviewsCozy up in a French Country nest NEAR EVERYTHING
Sep 6 – 13
Cottage in Tampa
4.96 out of 5 average rating, 25 reviewsCarriage House 1893
Apr 11 – 18
Cottage in St. Petersburg
4.96 out of 5 average rating, 95 reviewsArtsy guest house; near downtown w/ private patio
Mar 9 – 16
Cottage in Ruskin
4.92 out of 5 average rating, 91 reviewsLittle Manatee River Cottage
Apr 19 – 26
Cottage in Gulfport
5.0 out of 5 average rating, 8 reviewsGulfport Breezy Cottage KING - Outdoor living too!
May 8 – 15
Private cottage rentals
Cottage in Madeira Beach
4.8 out of 5 average rating, 163 reviewsQuaint Madeira Beach Cottage with Heated Pool
Nov 17 – 24
Cottage in Dunedin
4.92 out of 5 average rating, 167 reviewsDowntown Keylime Cottages 3
Oct 1 – 8
Cottage in Madeira Beach
4.96 out of 5 average rating, 135 reviewsBEACHFRONT FAIRWINDS Cottage Lower
Sep 19 – 26
Cottage in Treasure Island
4.9 out of 5 average rating, 115 reviewsHistoric Holly House on Treasure Island
Jan 1 – 8
Cottage in Tampa
4.96 out of 5 average rating, 55 reviewsTranquil Guesthouse Hideaway (Near MacDill AFB)
Jul 22 – 29
Cottage in Dunedin
4.95 out of 5 average rating, 97 reviewsBeachBunkies Cottage 2. Four miles to the beach!
Jun 30 – Jul 7
Cottage in Palmetto
4.97 out of 5 average rating, 70 reviewsCentral Quiet Bright Cottage, near Skyway Bridge.
Apr 24 – May 1
Cottage in St. Petersburg
5.0 out of 5 average rating, 76 reviewsVictoria’s Cottage near Beaches, Downtown & Trail
Jul 2 – 9
Destinations to explore
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- Rentals with a patio Hillsborough County
- Rentals with a washer and dryer Hillsborough County
- Ski-in/ski-out rentals Hillsborough County
- Fitness-friendly rentals Hillsborough County
- Rentals with a home theater Hillsborough County
- Rentals with a fireplace Hillsborough County
- Boutique hotel rentals Hillsborough County
- Bed and breakfasts Hillsborough County
- Rentals with lake access Hillsborough County
- Pet-friendly rentals Hillsborough County
- Private suite rentals Hillsborough County
- Wheelchair accessible rentals Hillsborough County
- Farmstay rentals Hillsborough County
- Rentals with an EV charger Hillsborough County
- Tiny house rentals Hillsborough County
- Rentals with pools Hillsborough County
- Hotel rentals Hillsborough County
- Rentals with outdoor seating Hillsborough County
- Rentals with a hot tub Hillsborough County
- Kid-friendly rentals Hillsborough County
- Waterfront rentals Hillsborough County
- Rentals with beach access Hillsborough County
- Rentals with breakfast Hillsborough County
- Rentals with an accessible height bed Hillsborough County
- Rentals with a fire pit Hillsborough County
- Bungalow rentals Hillsborough County
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- Rentals with a kayak Hillsborough County
- Smoking-friendly rentals Hillsborough County
- House rentals Hillsborough County
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- Townhouse rentals Hillsborough County
- Rentals with an accessible height toilet Hillsborough County
- Rentals with a sauna Hillsborough County
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