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 Safety Harbor
4.96 out of 5 average rating, 157 reviewsHarbor Oasis with Hot Tub
Apr 3 – 10
Cottage in Tampa
5.0 out of 5 average rating, 5 reviewsTraveler's Sanctuary
Aug 13 – 20
Cottage in Odessa
5.0 out of 5 average rating, 16 reviewsBreathtaking Lakefront Glass Cottage
Dec 16 – 23
Cottage in Palm Harbor
4.85 out of 5 average rating, 52 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
Dec 1 – 8
Cottage in Largo
5.0 out of 5 average rating, 19 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
Sep 16 – 23
Cottage in Largo
4.95 out of 5 average rating, 59 reviewsHidden Oasis #1, just a few minutes to the beaches
Jan 15 – 22
Cottage in Tampa
4.94 out of 5 average rating, 79 reviewsHot tub, riverfront, Bush Gardens, kajaks, 2floors
Nov 15 – 22
Cottage in Treasure Island
5.0 out of 5 average rating, 29 reviewsCasa Sunset by Agua Salá
Oct 14 – 21
Pet-friendly cottage rentals
Cottage in Dunedin
4.97 out of 5 average rating, 264 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
Aug 1 – 8
Cottage in Tampa
4.74 out of 5 average rating, 125 reviewsEclectic cottage nestled in million $ street
Sep 25 – Oct 2
Cottage in Clearwater
4.84 out of 5 average rating, 118 reviewsBeach Guest Cottage. Gulf Semi Private Area.
Dec 8 – 15
Cottage in Dunedin
4.84 out of 5 average rating, 317 reviewsCozy up in a French Country nest NEAR EVERYTHING
Sep 7 – 14
Cottage in Tampa
4.96 out of 5 average rating, 24 reviewsCarriage House 1893
Dec 13 – 20
Cottage in Ruskin
4.92 out of 5 average rating, 91 reviewsLittle Manatee River Cottage
Dec 21 – 28
Cottage in St. Petersburg
4.96 out of 5 average rating, 95 reviewsArtsy guest house; near downtown w/ private patio
Nov 18 – 25
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 reviews$99/nt Quaint Madeira Beach Cottage w Heated Pool
Oct 24 – 31
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
Aug 28 – Sep 4
Cottage in Madeira Beach
4.96 out of 5 average rating, 135 reviewsBEACHFRONT FAIRWINDS Cottage Lower
Sep 18 – 25
Cottage in Tampa
4.96 out of 5 average rating, 55 reviewsTranquil Guesthouse Hideaway (Near MacDill AFB)
Jul 18 – 25
Cottage in Palmetto
4.97 out of 5 average rating, 70 reviewsCentral Quiet Bright Cottage, near Skyway Bridge.
Aug 1 – 8
Cottage in Gulfport
4.97 out of 5 average rating, 67 reviewsCozy Cottage for Lovers
Aug 13 – 20
Cottage in Dunedin
4.95 out of 5 average rating, 97 reviewsBeachBunkies Cottage 2. Four miles to the beach!
Aug 27 – Sep 3
Cottage in St. Petersburg
5.0 out of 5 average rating, 76 reviewsVictoria’s Cottage near Beaches, Downtown & Trail
Jun 2 – 9
Destinations to explore
- Cottage rentals Orlando
- Cottage rentals Florida
- Cottage rentals Florida
- Cottage rentals Kissimmee
- Fitness-friendly rentals Hillsborough County
- Rentals with pools Hillsborough County
- Tiny house rentals Hillsborough County
- Private suite rentals Hillsborough County
- Wheelchair accessible rentals Hillsborough County
- Waterfront rentals Hillsborough County
- House rentals Hillsborough County
- Rentals with a sauna Hillsborough County
- Rentals with outdoor seating Hillsborough County
- Villa rentals Hillsborough County
- Monthly Rentals Hillsborough County
- Rentals with a washer and dryer Hillsborough County
- Rentals with a hot tub Hillsborough County
- Rentals with a home theater Hillsborough County
- Rentals with an accessible height toilet Hillsborough County
- Smoking-friendly rentals Hillsborough County
- Bungalow rentals Hillsborough County
- Rentals with an EV charger Hillsborough County
- Pet-friendly rentals Hillsborough County
- Rentals with lake access Hillsborough County
- Family-friendly rentals Hillsborough County
- Rentals with a kayak Hillsborough County
- Farmstay rentals Hillsborough County
- Loft rentals Hillsborough County
- Rentals with a patio Hillsborough County
- Hotel rentals Hillsborough County
- Boutique hotel rentals Hillsborough County
- Rentals with breakfast Hillsborough County
- Beachfront rentals Hillsborough County
- Condo rentals Hillsborough County
- Rentals with a fireplace Hillsborough County
- Townhouse rentals Hillsborough County
- Ski-in/ski-out rentals Hillsborough County
- Guesthouse rentals Hillsborough County
- Rentals with a fire pit Hillsborough County
- Rentals with an accessible height bed Hillsborough County
- Bed and breakfasts Hillsborough County
- Apartment rentals Hillsborough County
- Kid-friendly rentals Hillsborough County
- Rentals with beach access Hillsborough County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom