Cottage vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Longboat Key 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
Oct 15 – 22
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 295 reviewsPrivate Heated pool/spa home!
Nov 28 – Dec 5
Cottage in Clearwater
4.77 out of 5 average rating, 167 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
Dec 17 – 24
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
Sep 28 – Oct 5
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 65 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
Dec 26 – Jan 2
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
Aug 2 – 9
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Home w/ Pool & Hot Tub
Nov 3 – 10
Cottage in Largo
5.0 out of 5 average rating, 19 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
Jun 11 – 18
Pet-friendly cottage rentals
Cottage in Tampa
4.97 out of 5 average rating, 271 reviewsHistoric Heights Hideaway *LOW FEES*
Oct 30 – Nov 6
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
Aug 7 – 14
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 156 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
Nov 9 – 16
Cottage in Dunedin
4.96 out of 5 average rating, 307 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
Nov 7 – 14
Cottage in Gulfport
4.99 out of 5 average rating, 258 reviewsGulfport Art District - One Block From Beach!
Dec 3 – 10
Cottage in Gulfport
4.96 out of 5 average rating, 136 reviewsThe Pelicans Roost / Gulfport
Sep 5 – 12
Cottage in Indian Rocks Beach
4.91 out of 5 average rating, 114 reviewsCoastal Modern 2/2 Coral Sands II at IRB
Feb 10 – 17
Cottage in St. Petersburg
4.96 out of 5 average rating, 127 reviewsHomey Cottage Close To It All
Nov 1 – 8
Private cottage rentals
Cottage in Bradenton Beach
4.91 out of 5 average rating, 183 reviewsEbb Tide @ Tides Inn
Jul 21 – 28
Cottage in Sarasota
4.92 out of 5 average rating, 153 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
Nov 10 – 17
Cottage in Siesta Key
4.88 out of 5 average rating, 217 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Oct 31 – Nov 7
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
Mar 13 – 20
Cottage in Sarasota
4.94 out of 5 average rating, 140 reviewsSea-esta Cottage-cheerful 2bd/1ba w/ free parking
Jan 15 – 22
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
Aug 20 – 27
Cottage in Sarasota
4.83 out of 5 average rating, 151 reviewsCharming Beach Cottage
Feb 23 – Mar 2
Cottage in Madeira Beach
4.84 out of 5 average rating, 64 reviewsQuaint Madeira Beach Cottage with Heated Pool
Aug 27 – Sep 3
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
$80 before taxes and fees
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