List your Property
Siesta Key, Florida, United States of America

Siesta Key rentals with private pools

We found 1,166 rentals with private pools — enter your dates for availability

Explore Siesta Key rentals with private pools

Beachfront Luxury Condo Overlooking Gulf

Sleeps 5 · 2 Bedrooms · 2 Bathrooms
$180 avg/night
(103)

1 Block to the Beach on Siesta Key Vacation Rental Home With Swimming Pool

Sleeps 6 · 3 Bedrooms · 2 Bathrooms
$116 avg/night
(45)

RENOVATED 2BED/2BATH'S ON CRESCENT BEACH

Sleeps 6 · 2 Bedrooms · 2 Bathrooms
$150 avg/night
(89)

Fantastic Beachside Condo, at Surf & Racquet Resort on Siesta Key Beach

Sleeps 6 · 2 Bedrooms
$245 avg/night
(20)

Updated Home, Heated Saltwater Pool/Spa, Sits on a small lake, 6 min Bike Ride to SK Beach & Village

Sleeps 8 · 4 Bedrooms · 2 Bathrooms
$152 avg/night
(10)

2 BEDROOM 2 FULL BATH CONDO

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
$185 avg/night
(31)

Search 1,166 private pool rental

Recent reviews of Siesta Key rentals with private pools
Stayed Jul 2021

Book it! You won’t regret it!

Steve was outstanding from start to finish! Condo was very well stocked with everything you could possibly need! Being just across the street from the beach was perfect! It was the first vacation that none of us was ready to go “home” because it felt...

Kim K.
Kim K.
Stayed Jul 2021

Loved our stay at siesta key

Condo had plenty of room and the extra rollaway bed was great. The kitchen had all the amenities and laundry was conveniently located next to our room. The access to the beach and pool was a short walk and the staff available to setup beach chairs an...

Joy F.
Joy F.
Stayed Jun 2021

Absolutely Perfect

We had the best experience at the House of Sun making this one of our favorite vacations. Donna, the property owner, anticipated everything we could possibly need. She even went above and beyond and brought a crockpot over so my life would be easier....

Heather M.
Heather M.

Toledo

Stayed May 2021

Fantastic!

Gary’s condo is nothing short of amazing. The location is extremely convenient, clean, roomy, and as an extra bonus… you have a view of the ocean! Gary is an amazing host. I emailed him giving him a heads up the tv didn’t work in the bedroom and he w...

Jennifer G.
Jennifer G.
Stayed May 2021

Fantastic Getaway

I can’t say enough good things about my stay at this property. This was our first family vacation since my son was born in January 2020. We rented the larger unit at the same tome as this one so that our whole family could be together but have separa...

Brianna M.
Brianna M.

Mint Hill, North Carolina

Stayed May 2021

Perfect location, house and vacation!

I can’t say enough good things about my stay at this home. This was our first family vacation since my son was born in January 2020. Our great experience started even before arriving at the property. We needed to have my son sleep in a full size crib...

Brianna M.
Brianna M.

Mint Hill, North Carolina

Stayed May 2021

Siesta Key Perfect Location

This was our first trip to Siesta Key and it won’t be our last. This unit was absolutely perfect all the way around. Without knowing anything about the area, we wanted to stay somewhere convenient to not only the village but also the beach and this i...

Michele L.
Michele L.
Stayed Apr 2021

Perfect location!

Condo was perfectly located...grocery store, shops, restaurants and bars right across the street. Sea Shell is right on the beach. Unit is on the first floor, parking space is just steps from the door. Unit overlooks the pool...great if you have kids...

Connie H.
Connie H.
Discover other property types

Houses

View 808 Houses

Condos/Apartments

View 346 Condos/Apartments

Cottages

View 17 Cottages

Villas

View 25 Villas

Bungalows

View 17 Bungalows

Townhouses

View 60 Townhouses

Cabins

View 17 Cabins

Studios

View 32 Studios

Rental Ideas

People also search for

Top Filters