Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!
Kaia's Sun and Sea Newly remodeled with pool and jacuzzi, just 1-minute walk to Siesta Key beach! Poolside lounging and grilling, sunsets, sandbars, and on reef snorkeling and paddling. Just 4-min walk to shopping dining bars and live music. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love ∙ Front Porch – southwesterly porch on the palms (shared) ∙ Beaches – 1-min walk to award winning beaches, white sand, calm water ∙ Relaxing – private balcony and patio with dining and lounging ∙ Pool – beautiful heated pool with tropical plants just 1-minute walk ∙ Reef Snorkeling – 70-yard walk to Point of Rocks, free snorkel gear provided ∙ The Food –12 restaurants within 0.5 miles, 3 waterfront restaurants within 4 miles ∙ Activities – Boat bike jet-ski & sport-fishing tours, marina and rentals 7-min away ∙ Sunsets –1-minute walk to best sunsets and whatever comes next ∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts ∙ The Memories – access Siesta Key's top attractions and beaches guaranteed fun for all
The Beach Access to two private Siesta Key beaches. With no public parking nearby, this cove is one of Siesta's more exclusive beaches. The white quartz sand, tide pools, and calm, clear water are perfect for relaxing. A livelier scene with food, drinks, and the weekend drum circle is just a short beach walk north. Point of Rocks reef is only 60 yards south.
The Location No car needed. Nestled on a quiet street with no traffic, businesses, or public parking. Walk 4-minutes two 12 bars and restaurants. Walk 7-minutes to Siesta's top eco-adventures boat, bike, jet-ski, and fishing tours. Prefer to relax? Sunbathe at the beach, nap by the pool or enjoy Siesta s top-rated seafood, ice cream, and waterfront dining. Just a short stroll to favorites like Daiquiri Deck, Sniki-Tiki, Crescent Club, and Orange Octopus.
Reef Snorkeling Siesta Key is already paradise now add one of the Gulf Coasts best snorkeling spots! Just 60 yards south, Point of Rocks offers safe, shallow waters filled with tide pools, colorful marine life, and shelling treasures. Most days you'll spot chameleons, sponges, mother-of-pearl shells, conch, and maybe even dolphins or turtles. Ideal for exploring by foot, snorkel, paddleboard, or kayak.
Bedroom Details This unit is two flights up with no one above it. There is a king bedroom, a queen bedroom and a sectional sofa. Need more space? We can get you an additional unit nearby.
Beach Gear Provided We provide beach towels and the resort supplies chairs and umbrellas. If you don't have what you need, just reach out and we can usually get it for you. Correction for Air-b-n-b listings this location doesn't provide "snorkeling gear" but this and anything you need can be rented or purchased nearby.
Household Items Provided We provide bedding, kitchen items, most major and minor appliances, blow dryers, and hangers. Simple soaps and paper products come in starter-supply that will get you through a short stay and anything you need can be purchased nearby.
What to Bring It's a laid-back island so pack as lite as you like. Our fashion is casual, wash and wear, and all units have laundries. Also, anything you forget to bring can be found nearby in good supply and fair prices.
Post Booking Support We understand vacation time is precious and will make sure you get the most out of it. Our number is the only contact information you need. All units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. No check-in restrictions, check-in any day of the week at any time using a private door-code. Never a cleaning requirement at checkout. Free early check-in when possible. No hidden fees or solicitations. Every unit including this one is available for instant booking. We can recommend the best spot for fishing or fresh fish, Michigan or Ohio State games, romantic-dinners marriage-proposals or singles, eco-tourism, family friendly activities, or safe ways to lose your kids when you(they) need alone time.
Travel Insurance If you prefer insured bookings, we also offer travel insurance. Basic Travel Insurance- cost is 7%, covers 30 different issues, coverage begins only after protection has been purchased. CFAR (cancel for any reason) insurance is available in states applicable- cost is approximately 11% (7% basic plus additional 3.8% to add CFAR). Basic and CFAR must be purchased together as CFAR cannot be purchased individually. CFAR covers 60% of the trip cost with no questions asked. Travel insurance must be purchased within 14 days of booking and 30 days before check-in. Claim must be filed two days prior to arrival, available to U.S. citizens only.
Terms Payments are 50% refundable when canceled at least 60 days before arrival. Payments are not refundable when canceled less than 60 days before arrival. Events or gatherings involving outside guests are only allowed with prior approval from the management. Guest agrees to hold the Property Manager and Owner harmless from any liability for injuries while on vacation. Sorry but events involving guests in excess of your unit occupancy limit are not permitted at this location.
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Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Frequently asked questions
Does Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music! have a pool?
Yes, this property has a pool.
How much does it cost to stay at Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!?
As of 31 Mar 2026, prices found for a 1-night stay for 2 adults at Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music! on 23 May 2026 start from AU$623, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
Is Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music! pet-friendly?
No, pets are not allowed at this property.
How much is parking at Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!?
On-site parking is available at the property.
What time is check-in at Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!?
Check-in begins at 3:00 PM.
What time is check-out at Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music!?
Checkout is at 10:00 AM.
Where is Gertrude's Siesta | Pool, Jacuzzi | 1 Min to Beach | 4 Min to Dining & Music! located?
This family-friendly Siesta Key holiday home is located by the sea, within 1 mi (2 km) of Crescent Beach and Siesta Key Beach. Point of Rocks and Siesta Key Marina are also within 15 minutes.
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
This is a perfect location for walks on the beach and easy access to nightly sunsets!! Comfortable beds, plenty of towels and everything you need for the beach! Clean grills next to a heated pool was also a great addition! Would stay again!
Great place, perfect for our quick family getaway.
Tracy P.
Stayed 4 nights in Apr 2025
Response from VrboOwner on 11 May 2025
Thank you for staying with us! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Patrik F.
13 Apr 2025
Great Location, spacious and well equipped condo
we had a great time at Crescent beach Siesta, the Condo was spacious and well equipped. The location close to the beach and near to many good restaurants is perfect. We loved our stay here!
Patrik F.
From a partner site
10/10 Excellent
Richard K.
14 Sept 2025
Great Location
This 2 bed/2 bath condo was perfect for our stay in Siesta Key. Clean/ fully equipped kitchen/ comfortable living room and 2 large bedrooms all complete with TV's. Steps to the beautiful beach….. just so convenient to restaurants and stores as well. Great communication with owner as well. Definitely recommend!!!
Thank you for staying with us! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Gregory C.
22 Nov 2024
Fantastic Trip
Nice condo in a very quiet neighborhood extremely close to the beach. The grandkids really enjoyed the pool and hot tub.
Gregory C.
From a partner site
10/10 Excellent
Loren K.
25 Mar 2025
Great All Around
Everything here was great. Updated, clean, and great location to the beach, restaurants, and convenience stores. The owner was very helpful, answering all my questions quickly. Would stay here again!
Loren K.
From a partner site
10/10 Excellent
David B.
6 Mar 2025
Vaca
The accommodations were very clean and comfortable, the location was very accessible to the beach And an easy walk to the market area and some very good eateries. Just a short trolley ride up the road to some additional great restaurants in the village area. A highly recommended vacation spot.
David B.
From a partner site
10/10 Excellent
Abby P.
25 Mar 2025
Perfect Location for our Spring Break Trip
Our unit was exactly as pictured and described. Dan was great with any questions or concerns we had before and during our stay. We will definitely return and book with Gertrude Rentals!
Abby P.
From a partner site
10/10 Excellent
Brandon C.
16 Dec 2024
Peaceful work trip
Last minute trip to Siesta Key and had another great stay. Visited new restaurants along the Crescent beach area that I'll add to our list of places to continue eat at. Each time we come we find something new!
Loved the area. Very quiet. Hot tub and grill were great to have. Beach chairs and towels for use also. Host was very helpful on a missing kitchen item, replacement was dropped off just a few hours later. Room was spotless. We were able to get in the ocean during our stay, not for the weak of heart though. We will be back.
Bryan W.
Stayed 5 nights in Dec 2025
Response from VrboOwner on 10 Jan 2026
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones
Verified
10/10 Excellent
Leanna
5 Jan 2025
Liked: Cleanliness, amenities, property conditions & facilities, communication
Loved it!
Leanna
Stayed 3 nights in Oct 2024
From a partner site
10/10 Excellent
Joan B.
10 Jan 2025
Great
We thoroughly enjoyed our stay. It was quiet, clean and well maintained. The only thing missing was a kitchen trash can.
This property was clean and comfortable. It had everything you needed to enjoy your stay. The new furniture was comfortable and cute! Communication with the property manager was 5 star!
hillary f.
Stayed 5 nights in Nov 2024
Response from VrboOwner on 20 Dec 2024
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Kade H.
19 Sept 2024
Well needed late summer getaway
Great location. Danny and his team are super friendly and responsive to my needs. Unit was clean and met my needs on a short getaway! Will come back and use Gertrude again.
Kade H.
From a partner site
10/10 Excellent
Amanda H.
13 Mar 2025
Wonderful Stay!
This was our first time to Siesta Key & the Gertrude Rentals team went above & beyond to make our stay so great! Check in was seamless. We had a few questions throughout our stay & always got quick responses. Love that there was no “Check out checklist” as well. We will be back!
Traveled to area to search for apartments for our son moving to Florida. Booked on short notice and everything was great. Great communication. All of our needs met. Great location. Pool and hot tub very nice. Beds super comfortable. Great shower. Definitely would stay again and book for longer stay. Easy access to the beach
Tonya A.
Stayed 3 nights in Dec 2024
Response from VrboOwner on 12 Jan 2025
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me at 8885SIESTA and I’ll take care of you! - Daniel Jones
From a partner site
10/10 Excellent
Brandon C.
19 Sept 2024
Calm and Quiet Location with all the perks
We loved the ability to park our car and never have to drive again. This property was so close to everything. The beach is right out in front and the restaurants we really enjoyed are less than 2 blocks away. Somehow it still keeps its unique calm and quiet character even with being so close to the typically busy and loud areas. We loved the resort style pool and the large bedrooms. When we did have to drive it only took 2 minutes to get across the bridge back into Sarasota! Perfect spot for our vacation.
Thank you for staying with me! We hope you come again soon. If you ever need anything at all, reach out to me and I’ll take care of you! - Daniel Jones