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, 156 reviewsHarbor Oasis with Hot Tub
15–22 Sep
Cottage in Clearwater
4.77 out of 5 average rating, 166 reviewsTiki Cottage Sleeps 6, Pets OK, Steps to Beach
18–25 Sep
Cottage in Indian Rocks Beach
4.96 out of 5 average rating, 293 reviewsPrivate Heated pool/spa home!
19–26 Nov
Cottage in Indian Rocks Beach
4.97 out of 5 average rating, 63 reviewsNEW! Updated Stilt Home STEPS TO BEACH!
14–21 Jan
Cottage in Bradenton
4.95 out of 5 average rating, 82 reviewsCoastal Cottage w/ Pool & Hot Tub
25 Apr – 2 May
Cottage in Largo
4.95 out of 5 average rating, 59 reviewsHidden Oasis #1, just a few minutes to the beaches
20–27 Aug
Cottage in Palm Harbor
4.84 out of 5 average rating, 49 reviewsHappy Camper Cottage | Cozy Oasis with Hot Tub
3–10 Mar
Cottage in Sarasota
4.96 out of 5 average rating, 23 reviewsCharming Coastal Oasis 2 Bed/2 Bath Cottage
1–8 Oct
Pet-friendly cottage rentals
Cottage in Siesta Key
4.89 out of 5 average rating, 143 reviewsSiesta Key Cozy Cottage across from the beach!
28 Aug – 4 Sep
Cottage in Palm Harbor
4.78 out of 5 average rating, 167 reviewsCrystal Beach Cottage #1
29 Jun – 6 Jul
Cottage in Tampa
4.97 out of 5 average rating, 265 reviewsHistoric Heights Hideaway *LOW FEES*
6–13 Jan
Cottage in Indian Rocks Beach
4.89 out of 5 average rating, 242 reviewsVintage Florida Beach Cottage B
20–27 Nov
Cottage in Dunedin
4.96 out of 5 average rating, 304 reviewsWalk to Downtown & Waterfront- Barefoot Parrot 1
5–12 Dec
Cottage in Gulfport
4.96 out of 5 average rating, 135 reviewsThe Pelicans Roost / Gulfport
12–19 Aug
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 Saint Pete Beach
4.86 out of 5 average rating, 155 reviewsSunny Sandy Escape! Steps 2 Famous Beach w/2 Bikes
15–22 Dec
Private cottage rentals
Cottage in Indian Rocks Beach
4.93 out of 5 average rating, 179 reviewsKooky Coconut Cottage, Indian Rocks Beach
19–26 Jan
Cottage in Sarasota
4.92 out of 5 average rating, 152 reviewsCasa El Sueño - 8 min to Siesta Key - Intracoastal
24–31 Oct
Cottage in Largo
4.94 out of 5 average rating, 124 reviewsFall special 3rd night free! “The Sweet”
5–12 Aug
Cottage in Treasure Island
4.97 out of 5 average rating, 150 reviewsPeacock Beach Cabana beach in 100 steps
2–9 Apr
Cottage in Bradenton Beach
4.9 out of 5 average rating, 170 reviewsOhana Gulfside C Historic 1 Bed - 250 ft. to Beach
15–22 Mar
Cottage in Madeira Beach
4.8 out of 5 average rating, 163 reviews20% OFF Quaint Madeira Beach Cottage w Heated Pool
9–16 Dec
Cottage in Sarasota
4.87 out of 5 average rating, 131 reviewsCharming Lido Cottage
22–29 Sep
Cottage in Sarasota
4.83 out of 5 average rating, 108 reviewsWalk to Beach & St. Armands/Private cottage &grill
27 Apr – 4 May
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
$134 NZD before taxes and fees
Destinations to explore
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- Family-friendly rentals Longboat Key
- Rentals with a patio Longboat Key
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