Apartment
Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!
Photo gallery for Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!





Reviews
10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 10
Popular amenities
Explore the area

Siesta Key, FL
- Place, Siesta Key Beach2 min walk
- Place, Siesta Key Beach Playground12 min walk
- Place, Siesta Key Farmers Market12 min walk
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)29 min drive
Rooms & beds
3 bedrooms (sleeps 10)
Bedroom 1
1 King Bed
Bedroom 2
1 King Bed
Bedroom 3
2 Single Bunk Beds
Common Space
2 Double Sofa Beds
2 bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Office
Balcony
Separate dining area
Dining area
About this property
Gertrude's Siesta | Oceanview Penthouse, 12-steps Beach Path, 4-min trolley to Village!
The Oceanview Penthouse 603
Oceanview Penthouse, 12-steps to Siesta Key's best beach access! Stunning views with floor-to-ceiling “movable' glass walls in master bedroom and living area. Just 3-min by trolley or bike (10-min walk) to Siesta Village. Remodeled in 2023. Free bikes and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar below. Perfect for families and couples looking to relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love
∙ Ocean Views – southwest views of Gulf and sunsets through floor-to-ceiling windows
∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or night
∙ It's a Penthouse –no neighbors above or next to you and best views at property
∙ Beaches – 12-steps to access of Americas top beach, white sand and calm clear water
∙ Relaxing – safe easy access to outside attractions and lots of plus-space on site
∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living room
∙ Island Trolley –picks up out front, free of charge to all attractions and welcome's drinks
∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby
∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the back
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts
∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for all
The Beach
Our beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn't easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.
The Home
Ocean view property contains just 3 units and was remodeled in 2022. The penthouse unit has the best views, sun and breezes. It also doesn't share a wall or ceiling with another unit. Floor to ceiling glass walls in master bedroom and living area create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.
Bedroom Details
This ocean view penthouse unit is 3BR and is two staircases from the ground. There is one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. Tempur-pedic rollaway beds are available with advance notice, and although the master bedroom is quite big, setting up by the window in the living room makes it the best sleeping area in the house. You can sleep up to 9 family style. Need more space? Ask about an additional unit nearby.
Beach Gear Provided
We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. 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.
History – There's no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it's still the spot to fall in love or rekindle an old flame.
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.
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.
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.
Oceanview Penthouse, 12-steps to Siesta Key's best beach access! Stunning views with floor-to-ceiling “movable' glass walls in master bedroom and living area. Just 3-min by trolley or bike (10-min walk) to Siesta Village. Remodeled in 2023. Free bikes and paddle boards. Communal lounging, alfresco dining, ping-pong, and Tiki bar below. Perfect for families and couples looking to relax, explore and repeat. Book your getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love
∙ Ocean Views – southwest views of Gulf and sunsets through floor-to-ceiling windows
∙ Gulf Breezes – wall of windows folds for unobstructed ocean breezes day or night
∙ It's a Penthouse –no neighbors above or next to you and best views at property
∙ Beaches – 12-steps to access of Americas top beach, white sand and calm clear water
∙ Relaxing – safe easy access to outside attractions and lots of plus-space on site
∙ Sunsets –walk 30-seconds to best sunsets or just enjoy from your living room
∙ Island Trolley –picks up out front, free of charge to all attractions and welcome's drinks
∙ Activities – free bikes and paddleboards provided, scooter and golf cart rentals nearby
∙ Extra Spaces –ping pong room, alfresco dining-lounging, DIY tiki bar in the back
∙ Exploring - sand dollars, shells, dolphins, occasionally manatees and live conch
∙ The Fun - live music, daiquiris, oysters, stone crab, craft beer, ice cream, fresh donuts
∙ The Memories – walk to all Siesta Key's top attractions and guaranteed fun for all
The Beach
Our beach access is across the street, 12-steps, and is quieter and more private. Although one of the most desirable on the Siesta Key and has no parking available so isn't easy to access from rentals outside the neighborhood. The water here is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. A livelier beach scene with food, drinks and even a weekend drum circle is accessible a 5-to-10-minute walk south on the beach.
The Home
Ocean view property contains just 3 units and was remodeled in 2022. The penthouse unit has the best views, sun and breezes. It also doesn't share a wall or ceiling with another unit. Floor to ceiling glass walls in master bedroom and living area create wide-open southwestern exposures. Glass wall is bifold design and fully opens for maximum ocean or sunset views and refreshing breezes day and night. Common areas include the ping-pong room, tiki bar, alfresco dining, and usually cornhole. Set on the Southern edge of Siesta Village and surrounded by tropical plants. Just 10-second walk to top beaches, and 3-minute golf cart or trolly ride (10-minute walk) to restaurants and the best fresh oysters, seafood, tropical drinks, ice cream, entertainment, and even gourmet donuts on the island.
Bedroom Details
This ocean view penthouse unit is 3BR and is two staircases from the ground. There is one large king bedroom, an ocean view queen bedroom, and a bunkroom with twin-over-full and twin-over-twin-bunks. Tempur-pedic rollaway beds are available with advance notice, and although the master bedroom is quite big, setting up by the window in the living room makes it the best sleeping area in the house. You can sleep up to 9 family style. Need more space? Ask about an additional unit nearby.
Beach Gear Provided
We provide beach towels, chairs, carts, umbrellas, bikes and paddle boards. 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.
History – There's no public parking in this area so, even though this is a gorgeous beach, it ends up being a little more private than most. When I was a kid growing up on Siesta Key, this beach access was called “Palm Island” and named after the island of the same name right at the end of the street. The island has a small bridge going to it and is literally a “heart shaped” island within the island of Siesta Key. When I was younger this was our lovers lane and, for me, it's still the spot to fall in love or rekindle an old flame.
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.
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.
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.
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi
Air conditioning
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10.0 out of 10, Exceptional, (11 reviews)
House Rules
Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
Pets allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
About the area
Siesta Key
Located in Siesta Key, this apartment is in the city centre and near the beach. St. Armands Circle and Mall at University Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's natural beauty can explore Siesta Key Beach and Crescent Beach. Travelling with kids? Consider Mote Marine Laboratory & Aquarium and St. Boniface Episcopal Church Labyrinth. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Siesta Key, FL
What's nearby
- Siesta Key Beach - 2 min walk - 0.2 km
- Siesta Key Beach Playground - 12 min walk - 1.1 km
- Siesta Key Farmers Market - 12 min walk - 1.1 km
- St. Boniface Episcopal Church Labyrinth - 15 min walk - 1.3 km
- Irma Beach - 3 min drive - 2.5 km
Getting around
Restaurants
- Siesta Beach Pavilion - 8 min walk
- Siesta Key Snack Bar - 8 min walk
- Circle K - 15 min walk
- Gilligan's Island Bar & Grill - 11 min walk
- Sun Garden Cafe - 14 min walk
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window9.8/10
Cleanliness
10/10
Amenities
10/10
Property conditions & facilities
10/10
Check-in
10/10
Communication
10/10
Location
9.8/10
Listing accuracy
Reviews
29 Dec, 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Dec 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Brad C.
8 Aug, 2025
Great stay, great loction
Brad C.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Michael J.
21 Apr, 2025
Across the street from the beach!
Michael J.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Luis C.
21 Nov, 2024
Great place
Luis C.
10/10 Excellent
Regina M.
5 Nov, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location.
Regina M.
Stayed 3 nights in Nov 2023
10/10 Excellent
Ever M.
16 Jul, 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place!
Ever M.
Stayed 3 nights in Jul 2022
10/10 Excellent
Melissa F.
20 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Can't wait to return
Melissa F.
Stayed 4 nights in May 2023
10/10 Excellent
Tracy M.
20 Oct, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Daughters 21st birthday celebration!
Tracy M.
Stayed 3 nights in Oct 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Stacia G.
13 Feb, 2024
wonderful vacay at the Penthouse!
Stacia G.
10/10 Excellent
Gary L.
17 Mar, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Roomy, clean, good location and comfy beds and linens
Gary L.
Stayed 5 nights in Mar 2023
10/10 Excellent
Melissa A.
27 Feb, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Loved everything about this place!
Melissa A.
Stayed 4 nights in Feb 2023
10/10 Excellent
Ashley B.
13 Oct, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great Place and Great Location
Ashley B.
Stayed 4 nights in Oct 2023
10/10 Excellent
Julie C.
2 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent location for the beach
Julie C.
Stayed 3 nights in Apr 2023
10/10 Excellent
Ashley B.
22 May, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Family Vacay
Ashley B.
Stayed 5 nights in May 2024
10/10 Excellent
Ann D.
25 Feb, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
The view ♥️
Ann D.
Stayed 4 nights in Feb 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
maria B.
2 May, 2024
Perfect in every way!
maria B.
10/10 Excellent
DOUGLAS F.
1 Mar, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect stay
DOUGLAS F.
Stayed 3 nights in Feb 2024
10/10 Excellent
kelly f.
8 May, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Perfect location!
kelly f.
Stayed 3 nights in May 2023
10/10 Excellent
Wendy D.
1 Oct, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Very Clean
Wendy D.
Stayed 3 nights in Sep 2023
8/10 Good
Keri W.
30 Dec, 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Holiday Rental
Keri W.
Stayed 4 nights in Dec 2024
10/10 Excellent
Meaghan J.
16 Jan, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Location location location!
Meaghan J.
Stayed 2 nights in Jan 2023
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Scott H.
16 May, 2024
603PH
Scott H.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Michelle B.
19 Mar, 2024
Fabulous location
Michelle B.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Peter C.
8 Mar, 2024
Another Awesome Vacation
Peter C.
10/10 Excellent
Natalie L.
11 Jan, 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Business Strategy Off Site
Natalie L.
Stayed 2 nights in Jan 2023
About the host
Hosted by Gertrude Rentals 888-5SIESTA
Dan Jones, "owner" Gertrude Rentals
Phone: (888) 5-SIESTA
Email: gertrude.rentals@gmail.com
Website: gertruderentals.com
Phone: (888) 5-SIESTA
Email: gertrude.rentals@gmail.com
Website: gertruderentals.com
Languages:
English, French
Premier Host
They consistently provide great experiences for their guests
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