Search Guest Houses in Longboat Key from CA $141

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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 CA $154
CA $285 total
includes taxes & fees
Nov 9 - Nov 10
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.
The price is CA $171
CA $272 total
includes taxes & fees
Nov 10 - Nov 11
Coolest Downtown Neighborhood - Ebikes

3. 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 CA $159
CA $346 total
includes taxes & fees
Nov 10 - Nov 11
Close to Siesta Key beach with a hot tub and a large garden

4. 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 CA $192
CA $457 total
includes taxes & fees
Dec 2 - Dec 3
Charming Cottage in Pass-A-Grille Beach, Dogs Ok

5. 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 CA $141
CA $381 total
includes taxes & fees
Nov 9 - Nov 10
Siesta key Guest House 5 star on the water Private

6. 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)
"Great location for walking to beach and local restaurants. Prefect size for my family of four."
United States
Melissa G
The price is CA $159
CA $460 total
includes taxes & fees
Nov 11 - Nov 12
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.

Learn more about Longboat Key

Pristine white-sand beaches stretch for miles where dolphins play just offshore during sunset walks. Kayak through mangrove tunnels in the morning, then enjoy fresh grouper at waterfront restaurants where no one minds your flip-flops.

A coastal town with a beach, residential areas, and a marina.

Top reviews in Longboat Key

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