Cottage holiday rentals in Longboat Key
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Top-rated cottage rentals in Longboat Key
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 cottage rentals in Longboat Key
Cottage rentals with a hot tub
Cottage in Safety Harbor
4.96 out of 5 average rating, 156 reviewsHarbor Oasis with Hot Tub
5–12 Jun
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
26 Mar – 2 Apr
Cottage in Clearwater
4.77 out of 5 average rating, 123 reviewsCorner Cottage Sleeps 5, Steps to Beach, Pets OK.
19–26 Oct
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
19–26 Nov
Cottage in Palm Harbor
4.84 out of 5 average rating, 49 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
24–31 Jan
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
28 Oct – 4 Nov
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
10–17 Nov
Cottage in Odessa
5.0 out of 5 average rating, 15 reviewsBreathtaking Lakefront Glass Cottage
23–30 Aug
Pet-friendly cottage rentals
Cottage in Palm Harbor
4.78 out of 5 average rating, 167 reviewsCrystal Beach Cottage #1
17–24 Aug
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
15–22 Aug
Cottage in Tampa
4.99 out of 5 average rating, 140 reviewsBay Lake Cottage
11–18 Dec
Cottage in Dunedin
4.96 out of 5 average rating, 304 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
16–23 Sept
Cottage in Tampa
4.97 out of 5 average rating, 265 reviewsHistoric Heights Hideaway *LOW FEES*
18–25 Nov
Cottage in Englewood
4.96 out of 5 average rating, 138 reviewsFamily-Friendly Beach Cottage Manasota Key
22 Feb – 1 Mar
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
31 Aug – 7 Sept
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
12–19 Aug
Private cottage rentals
Cottage in Bradenton Beach
4.91 out of 5 average rating, 129 reviewsHistoric Beach Cottage with private garden
12–19 Oct
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
13–20 Mar
Cottage in Treasure Island
4.97 out of 5 average rating, 150 reviewsPeacock Beach Cabana beach in 100 steps
29 Mar – 5 Apr
Cottage in Madeira Beach
4.8 out of 5 average rating, 163 reviews20% OFF Quaint Madeira Beach Cottage w Heated Pool
13–20 Dec
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
21–28 Dec
Cottage in Sarasota
4.84 out of 5 average rating, 154 reviewsHeated Pool! Beach! Drift Inn Unit B Siesta Key!
24 Sept – 1 Oct
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
22–29 Sept
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
25 Sept – 2 Oct
Quick stats about cottage rentals in Longboat Key
Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with a pool
20 properties have a pool
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
220 reviews
Nightly prices starting at
£64 before taxes and fees
Destinations to explore
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