A coastal cityscape with a sunset over the water, featuring several high-rise buildings and palm trees.

Search Guest Houses in Longboat Key

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Our top choices for Longboat Key guest houses

1. ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym
Whitfield Estates
7.4 out of 10, Good, (6 reviews)
"Looking for a couple nights close to Anna Maria Island without being ON the island. Turns out we were here once before and didnt realize it was the same place. Love the "Back Yard" surprises"
United States
Susan B.
The price is AED 400
AED 742 total
includes taxes & fees
3 Dec - 4 Dec
ALL BRAND-NEW Waterfront room-Heated Pool, Tiki Bar, Gym

2. Coolest Downtown Neighborhood - Ebikes

Coolest Downtown Neighborhood - Ebikes
Central Sarasota
9.8 out of 10, Exceptional, (140 reviews)
"Cute place in a great location! Accurate listing, clean, and easy place to relax."
United States
Kathleen R.
Coolest Downtown Neighborhood - Ebikes

3. Siesta key Guest House 5 star on the water Private

Siesta key Guest House 5 star on the water Private
South Sarasota
8.8 out of 10, Excellent, (21 reviews)
"Great location, right on the Phillipi Creek. Host was super friendly and welcoming. "
United States
Scott E.
The price is AED 367
AED 1,032 total
includes taxes & fees
12 Nov - 13 Nov
Siesta key Guest House 5 star on the water Private

4. PaG Studio, Sunsets, Steps 2 Sand

PaG Studio, Sunsets, Steps 2 Sand
Pass-a-Grille
9.2 out of 10, Wonderful, (10 reviews)
"Perfect little space. Clean, comfortable and you just can't beat the location. Lisa was a joy to work with. "
United States
Laura P.
The price is AED 421
AED 1,019 total
includes taxes & fees
15 Nov - 16 Nov
PaG Studio, Sunsets, Steps 2 Sand

5. Charming Cottage in Pass-A-Grille Beach, Dogs Ok

Charming Cottage in Pass-A-Grille Beach, Dogs Ok
Pass-a-Grille
9.6 out of 10, Exceptional, (46 reviews)
"I’ve stayed here twice and I just love it!"
United States
Julie R.
The price is AED 395
AED 1,055 total
includes taxes & fees
15 Nov - 16 Nov
Charming Cottage in Pass-A-Grille Beach, Dogs Ok

6. Close to Siesta Key beach with a hot tub and a large garden

Close to Siesta Key beach with a hot tub and a large garden
Sarasota
9.8 out of 10, Exceptional, (143 reviews)
"The hosts and the property were a joy to be involved with. We really enjoyed our stay."
United States
Dennis B.
The price is AED 436
AED 925 total
includes taxes & fees
20 Nov - 21 Nov
Close to Siesta Key beach with a hot tub and a large garden

7. A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!

A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
Pass-a-Grille
9.6 out of 10, Exceptional, (18 reviews)
"Close to beach very convenient to walk to nearby restaurants!"
United States
Anonymous traveler
The price is AED 442
AED 1,227 total
includes taxes & fees
16 Nov - 17 Nov
A Hidden Gem Steps to Pass-a-Grille Beach-Dog Ok!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Longboat Key Hotel Reviews