Condo
Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!
Photo gallery for Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!





Reviews
10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms2 bathroomsSleeps 692.9 sq m
Popular amenities
Explore the area

Siesta Key, FL
- Place, Siesta Key Beach6 min walk
- Place, Siesta Key Marina2 min drive
- Place, Crescent Beach2 min drive
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)30 min drive
Rooms & beds
2 bedrooms (sleeps 6)
Bedroom 1
1 King Bed
Bedroom 2
2 Double Beds
Common Space
1 Double Sofa Bed
2 bathrooms
Bathroom 1
Bathtub or shower · Toilet
Bathroom 2
Bathtub or shower · Toilet
Spaces
Deck or patio
Kitchen
Office
Balcony
Separate dining area
Garden
Dining area
About this property
Gertrude's Siesta | Bayside Unit, Balcony, Private-Beach, Heated Pools, Pickle, Hot-tub, Tennis!
The Bayside Unit
Top floor bayside unit with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love
∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moors
∙ The Balcony – royal palm views from balcony connecting bedrooms and living area
∙ The Grounds – fishing causeway, private bay and beach access, lined by royal palms
∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sands
∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainment
∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balcony
∙ Activities – scooter, golf cart, bike and kayak rentals nearby
∙ 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 – perfect fit for all with resort amenities and trolley to all top attractions
The Beach
Our beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.
The Location
With so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool.
Bedroom Details
This is a 3rd-floor (top) unit with an elevator. This two-bedroom unit has a king bedroom, a bedroom with two fulls, and a sofa in the living room. You can sleep up to 6. If you need more space, I can get an additional unit nearby.
Beach Gear Provided
We provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. 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.
Important Resort Limits
1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional "emergency parking space" is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available.
Household Items Provided
We provide bedding, kitchen items, private laundry, 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.
Top floor bayside unit with 40-foot balcony, tennis/pickleball courts, elevator, private beach and complimentary beach chaises, two heated pools, bay-front lounging area, hot tub, causeway on inter-coastal, boat moors, fitness center, fishing pier, and beautifully manicured grounds stretching from Beach to Bay. Enjoy resort amenities in the heart of Siesta Key. Book a getaway now! - Tollbooth by VRBOCorpMiddlemen, but this property is from GertrudeRentalsSiesta
What Guests Love
∙ Resort Amenities – heated pools, jacuzzi, gym, pickle, tennis, and boat moors
∙ The Balcony – royal palm views from balcony connecting bedrooms and living area
∙ The Grounds – fishing causeway, private bay and beach access, lined by royal palms
∙ Private Beach – 4-min walk to private beach and Siesta Key's widest whitest sands
∙ Restaurants – 2-min walk to free trolley to all Siesta's shopping dining and entertainment
∙ Sunsets –walk 4-min to best sunsets in America or just enjoy from your balcony
∙ Activities – scooter, golf cart, bike and kayak rentals nearby
∙ 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 – perfect fit for all with resort amenities and trolley to all top attractions
The Beach
Our beach is a private Siesta Key beach with the widest whitest sands, free chaise lounges, and umbrella rentals. The water is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing.
The Location
With so many amenities, and all of it free of charge, a 3-night stay here will feel like a two-week getaway. If you get the most from a vacation when you don't have search or worry about anything, this unit is not a plus for you it's a must! Although you could easily take a free trolley 1-mile any direction to dozens of shops and restaurants, you can also satisfy every vacation desire without ever putting on your shoes or leaving this resort. You can swim in pools or in the Gulf, fish the inter-coastal, exercise in the gym, sleep in the sun, explore Siesta Key's best beach, make Sandcastles, and even sightsee all in a safe environment and right on your property. The beach here has the whitest sand on the island, but some of the best moments are watching boats and dolphins pass from the private balcony or nearby bay-front pool.
Bedroom Details
This is a 3rd-floor (top) unit with an elevator. This two-bedroom unit has a king bedroom, a bedroom with two fulls, and a sofa in the living room. You can sleep up to 6. If you need more space, I can get an additional unit nearby.
Beach Gear Provided
We provide beach towels, and the resort provides free chaise loungers and umbrella rentals. If you have any issues just reach out and we will do whatever we can. 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.
Important Resort Limits
1) Expect a special experience where each visitor's peaceful enjoyment is respected. The minimum age for visitors not accompanied by a parent or guardian is 25 years. Stay up as late as you want, but the “quiet neighbor times” begin 10 PM. After 10 PM relocate the party to nearby Siesta Village or the Crescent Beach area. 2) Just one parking space per unit. However, cars are not necessary and an additional "emergency parking space" is available 1 mile away. If any of these limits are not a fit for you, please let me know, I have other properties available.
Household Items Provided
We provide bedding, kitchen items, private laundry, 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.
Add dates for prices
Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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House Rules
Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No 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 condo is near theme parks and on the waterfront. 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, or check out an event or a game at Ed Smith Stadium. 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 - 6 min walk - 0.6 km
- St. Boniface Episcopal Church Labyrinth - 14 min walk - 1.2 km
- Siesta Key Beach Playground - 15 min walk - 1.3 km
- Siesta Key Marina - 2 min drive - 1.8 km
- Crescent Beach - 2 min drive - 2.1 km
Getting around
Restaurants
- Siesta Beach Pavilion - 18 min walk
- McDonald's - 3 min drive
- Siesta Key Snack Bar - 18 min walk
- Captain Curt's Crab & Oyster Bar - 18 min walk
- Dunkin' - 4 min drive
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 window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
16 November 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Nov 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Kevin C.
13 October 2025
Great
Kevin C.
10/10 Excellent
Tracy B.
17 November 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Tracy B.
Stayed 3 nights in Nov 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nova H.
24 November 2024
Great
Nova H.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nicholas B.
3 August 2025
Great
Nicholas B.
10/10 Excellent
Mary S.
6 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Birthdays 2025
Mary S.
Stayed 4 nights in Mar 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
julie c.
1 December 2024
Great
julie c.
10/10 Excellent
Connie D.
21 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Retirement!
Connie D.
Stayed 5 nights in Mar 2025
10/10 Excellent
Steve M.
31 December 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay in siesta key
Steve M.
Stayed 3 nights in Dec 2024
10/10 Excellent
Todd T.
9 February 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
A great condo in a wonderful location!
Todd T.
Stayed 4 nights in Feb 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nova H.
22 November 2024
Perfect Getaway
Nova H.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
barbara d.
12 April 2025
Great time!
barbara d.
10/10 Excellent
Kim T.
16 March 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fulfilled Expectations
Kim T.
Stayed 6 nights in Mar 2025
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nova H.
22 November 2024
Beautiful property!
Nova H.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nova H.
21 November 2024
Favorite Siesta resort so far!
Nova H.
10/10 Excellent
Jason D.
25 November 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Weekend
Jason D.
Stayed 3 nights in Nov 2024
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
jill h.
11 January 2025
Perfect family getaway
jill h.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Adam W.
16 January 2025
Great
Adam W.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Hannan Abdel-Jalil H.
7 July 2025
Great Stay
Hannan Abdel-Jalil H.
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Nicki M.
25 February 2026
⭐️⭐️⭐️⭐️⭐️
Nicki M.
10/10 Excellent
Verified traveller
20 February 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Verified traveller
Stayed 4 nights in Feb 2026
10/10 Excellent
Hiroko D.
30 January 2026
Liked: Cleanliness, check-in, communication, location, listing accuracy
Hiroko D.
Stayed 6 nights in Jan 2026
This review is from a guest who booked and stayed through a partner site and can't be verified.
10/10 Excellent
Kelly R.
30 May 2025
Very clean, great location
Kelly R.
10/10 Excellent
katie r.
10 April 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
katie r.
Stayed 3 nights in Feb 2025
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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