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 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
15–22 Oct
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 295 reviewsPrivate Heated pool/spa home!
28 Nov – 5 Dec
Cottage in Clearwater
4.77 out of 5 average rating, 167 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
17–24 Dec
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
28 Sep – 5 Oct
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 65 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
26 Dec – 2 Jan
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
2–9 Aug
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Home w/ Pool & Hot Tub
3–10 Nov
Cottage in Largo
5.0 out of 5 average rating, 19 reviewsFamily FUN~Pool, GameRoom+Bikes, Near Beach/Trail
11–18 Jun
Pet-friendly cottage rentals
Cottage in Tampa
4.97 out of 5 average rating, 271 reviewsHistoric Heights Hideaway *LOW FEES*
30 Oct – 6 Nov
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
7–14 Aug
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 156 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
9–16 Nov
Cottage in Dunedin
4.96 out of 5 average rating, 307 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
7–14 Nov
Cottage in Gulfport
4.99 out of 5 average rating, 258 reviewsGulfport Art District - One Block From Beach!
3–10 Dec
Cottage in Gulfport
4.96 out of 5 average rating, 136 reviewsThe Pelicans Roost / Gulfport
5–12 Sep
Cottage in Indian Rocks Beach
4.91 out of 5 average rating, 114 reviewsCoastal Modern 2/2 Coral Sands II at IRB
10–17 Feb
Cottage in St. Petersburg
4.96 out of 5 average rating, 127 reviewsHomey Cottage Close To It All
1–8 Nov
Private cottage rentals
Cottage in Bradenton Beach
4.91 out of 5 average rating, 183 reviewsEbb Tide @ Tides Inn
21–28 Jul
Cottage in Sarasota
4.92 out of 5 average rating, 153 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
10–17 Nov
Cottage in Siesta Key
4.88 out of 5 average rating, 217 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
31 Oct – 7 Nov
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
13–20 Mar
Cottage in Sarasota
4.94 out of 5 average rating, 140 reviewsSea-esta Cottage-cheerful 2bd/1ba w/ free parking
15–22 Jan
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
20–27 Aug
Cottage in Sarasota
4.83 out of 5 average rating, 151 reviewsCharming Beach Cottage
23 Feb – 2 Mar
Cottage in Madeira Beach
4.8 out of 5 average rating, 163 reviewsQuaint Madeira Beach Cottage with Heated Pool
27 Aug – 3 Sep
Quick stats about cottage rentals in Longboat Key
Total rentals
30 properties
Wi-Fi availability
30 properties include access to Wi-Fi
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
$133 NZD before taxes and fees
Destinations to explore
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- Rentals with lake access Longboat Key
- Pet-friendly rentals Longboat Key
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