Cottage holiday rentals in Pinellas County
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Top-rated cottage rentals in Pinellas County
Guests agree: These cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Pinellas County cottage rentals
Cottage rentals with a hot tub
Cottage in Clearwater
4.77 out of 5 average rating, 166 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
21–28 Apr
Cottage in Palm Harbor
4.84 out of 5 average rating, 51 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
10–17 Dec
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
21–28 Aug
Cottage in Odessa
5.0 out of 5 average rating, 16 reviewsBreathtaking Lakefront Glass Cottage
26 Aug – 2 Sep
Cottage in Largo
5.0 out of 5 average rating, 19 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
12–19 Jun
Cottage in Largo
4.95 out of 5 average rating, 59 reviewsHidden Oasis #1, just a few minutes to the beaches
19–26 Mar
Cottage in Treasure Island
5.0 out of 5 average rating, 29 reviewsCasa Sunset by Agua Salá
12–19 Oct
Cottage in Indian Rocks Beach
5.0 out of 5 average rating, 24 reviewsBeachy Keen Cottage A only steps to the Beach
23–30 Sep
Pet-friendly cottage rentals
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
9–16 Nov
Cottage in Dunedin
4.97 out of 5 average rating, 264 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 3
1–8 Aug
Cottage in Clearwater
4.84 out of 5 average rating, 118 reviewsBeach Guest Cottage. Gulf Semi Private Area.
7–14 Dec
Cottage in Indian Rocks Beach
4.91 out of 5 average rating, 114 reviewsCoastal Modern 2/2 Coral Sands II at IRB
11–18 Sep
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 242 reviewsVintage Florida Beach Cottage B
1–8 Mar
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
12–19 Nov
Cottage in Indian Rocks Beach
4.68 out of 5 average rating, 186 reviewsBeachy Paradise
26 Mar – 2 Apr
Cottage in Indian Rocks Beach
4.75 out of 5 average rating, 106 reviewsBest location, Steps 2 Beach, BBQ firepit Pets OK
7–14 Jun
Private cottage rentals
Cottage in Dunedin
5.0 out of 5 average rating, 227 reviewsDowntown Dunedin Historic Orange Blossom Cottage 1
12–19 Jul
Cottage in Madeira Beach
4.8 out of 5 average rating, 163 reviews$99/nt Quaint Madeira Beach Cottage w Heated Pool
11–18 Apr
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
28 Aug – 4 Sep
Cottage in Indian Shores
4.86 out of 5 average rating, 161 reviews*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*
18–25 Aug
Cottage in Madeira Beach
4.96 out of 5 average rating, 135 reviewsBEACHFRONT FAIRWINDS Cottage Lower
7–14 Apr
Cottage in St. Petersburg
5.0 out of 5 average rating, 76 reviewsVictoria’s Cottage near Beaches, Downtown & Trail
2–9 Jun
Cottage in Safety Harbor
5.0 out of 5 average rating, 27 reviews"Sweet Harbor Cottage" Walk to Downtown
12–19 Jun
Cottage in Gulfport
4.97 out of 5 average rating, 67 reviewsCozy Cottage for Lovers
10–17 Apr
Destinations to explore
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