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
30 Jul – 6 Aug
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
23 Feb – 2 Mar
Cottage in Clearwater
4.77 out of 5 average rating, 129 reviewsPink Gulfside Cottage, Steps to Beach, Pets OK
16–23 Nov
Cottage in Holmes Beach
4.91 out of 5 average rating, 45 reviewsKiwi Cottage *Heated Pool+Spa+ walk to the Beach!
21–28 Sep
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
11–18 Feb
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
21–28 Aug
Cottage in Indian Rocks Beach
4.82 out of 5 average rating, 62 reviewsTurtle Nest Cottage
12–19 Sep
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
28 Sep – 5 Oct
Pet-friendly cottage rentals
Cottage in Siesta Key
4.89 out of 5 average rating, 142 reviewsSiesta Key Cozy Cottage across from the beach!
28 Oct – 4 Nov
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 241 reviewsVintage Florida Beach Cottage
28 Oct – 4 Nov
Cottage in Tampa
4.97 out of 5 average rating, 265 reviewsHistoric Heights Hideaway *LOW FEES*
22–29 Mar
Cottage in Dunedin
4.99 out of 5 average rating, 268 reviewsWalk to Downtown & Waterfront - Barefoot Parrot 2
29 Jul – 5 Aug
Cottage in Gulfport
4.96 out of 5 average rating, 134 reviewsThe Pelicans Roost / Gulfport
12–19 Aug
Cottage in Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
16–23 Oct
Cottage in Gulfport
4.99 out of 5 average rating, 257 reviewsGulfport Art District - One Block From Beach!
1–8 Oct
Cottage in Indian Rocks Beach
4.99 out of 5 average rating, 155 reviewsCottage w/ Private Patio | 3 Min Walk to the Beach
28 Jul – 4 Aug
Private cottage rentals
Cottage in Bradenton Beach
4.91 out of 5 average rating, 129 reviewsHistoric Beach Cottage with private garden
5–12 Jul
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
4–11 Mar
Cottage in Treasure Island
4.97 out of 5 average rating, 150 reviewsPeacock Beach Cabana beach in 100 steps
31 Jan – 7 Feb
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
24–31 May
Cottage in Sarasota
4.83 out of 5 average rating, 108 reviewsWalk to Beach & St. Armands/Private cottage &grill
25 Nov – 2 Dec
Cottage in Siesta Key
4.88 out of 5 average rating, 215 reviewsSiesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
2–9 Jan
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
22–29 Sep
Cottage in Treasure Island
4.91 out of 5 average rating, 114 reviewsHistoric Holly House on Treasure Island
19–26 Sep
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
€ 75 before taxes and fees
Destinations to explore
- Anna Maria Island Holiday rentals
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- Rentals with outdoor seating Longboat Key
- Family-friendly rentals Longboat Key
- Villa rentals Longboat Key
- Rentals with a patio Longboat Key
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- Rentals with a kayak Longboat Key
- Cabin rentals Longboat Key
- Beachfront rentals Longboat Key
- Rentals with beach access Longboat Key
- Rentals with a hot tub Longboat Key
- Beach house rentals Longboat Key
- Rentals with pools Longboat Key
- Family-friendly rentals Longboat Key
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- Rentals with lake access Longboat Key
- Waterfront rentals Longboat Key
- Rentals with a washing machine and dryer Longboat Key
- Beach apartment rentals Longboat Key
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- Pet-friendly rentals Longboat Key
- Monthly Rentals Longboat Key
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