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New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village!

Photo gallery for New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village!

Refined and cozy living room, 4BR Siesta Key
Timeless Florida home, 4BR Siesta Key
Large swimming pool, 4BR Siesta Key.
Large swimming pool, 4BR Siesta Key.
Gertrude - One name, numerous possibilities!

Reviews

9.2 out of 10
Wonderful
4 bedrooms2+ bathroomsSleeps 10

Popular amenities

  • Parking available
  • Air conditioning
  • Pet-friendly
  • Dryer
  • Washer
  • Outdoor space

Explore the area

Map
Siesta Key, FL
  • Siesta Key Beach
    ‪2 min drive‬
  • Crescent Beach
    ‪7 min drive‬
  • Lido Beach
    ‪21 min drive‬
  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪21 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 2

1 King Bed

Bedroom 4

2 Single Beds

Common Space

1 Double Sofa Bed

Full and full trundle

1 Single Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Toilet · Shower only

Bathroom 2

Bathtub or shower · Toilet

Half Bathroom 3

Toilet

Spaces

Deck or patio
Kitchen
Office
Balcony
Separate dining area
Dining area

About this property

New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village!

New Listing! Rudy s Hideaway with a Private Pool near the Siesta Key Beach and Village! Get your comfort quiet and personal space on Siesta Key at this 100% Private 2300sqft property. Perfect for larger groups. Lounge dine and drink while you soak up the sun on Pool Deck. Walk, bike or golf cart to all the islands top attractions. This is a NEW Gertrude Rentals property. Please check our thousands of existing reviews averaging 4.9/5 stars, we are very proud of them!

RUDY S HIDEAWAY AT A GLANCE
- 100% private house with private pool and pool-deck.
- Large 4BR/2.5Bath (sleeps 11)
- Twice the size of some four bedroom units.
- On World famous Siesta Key near the Beach and Village.
- Award Winning Beaches, 20 Bar Restaurants.
- Just 1-mile to Live Music, Daiquiris, Oysters, Stone Crab, Ice Cream, fresh Donuts, craft Beer.
- Clear calm Azure Water pure quartz White Sand.
- Tide Pools Sand Bars for lounging, sleeping, relaxing, or water sports.
- Kayak, bike, paddle-board, scooter, golf cart rentals.
- Perfect house for large gatherings with multiple dining areas inside and out.

The House - 100% private freestanding house with private pool surrounded by tropical plants. Perfect fit for anyone who enjoys the space and privacy of a proper house, but without giving up access to all Siesta Keys top attractions. The sun-room and deck are perfect for enjoying a quiet cup of coffee, good book, cocktail(s), or an al-fresco meal.

The Location - Walk bike or cart in minutes to Siesta Key Beach and a free trolley to every other Siesta Key attraction. Siesta Key Beach is just 1-mile or 3 minutes by golf cart, or 5 by bike, and 15 walking. This beach is shallow clear and calm with white quartz-sand tide-pools perfect for sleeping drinking or playing. Beach amenities include showers, bathrooms, snack bar, volleyball, playgrounds, tennis, pickle and cocktails. You can also go straight from the water to a free trolley taking you 1 mile to lunch or dinner in the Siesta Key Village and back to the sand, all without putting on your shirt and shoes. Siesta boasts dozens of beaches, reefs, and lagoons, eco-activities, and dining including 20 bars and restaurants.

Your Group Will Love it - You aren t planning one vacation, you re planning vacations for every individual in your party. Whether it s solitude or activities, this property will deliver what they need. Conveniently located, your crew can walk bike golf cart to all the islands top attractions. Back at the house, you have multiple private gathering areas for your bonding enjoyment.

Bear Gear - Correction for Air-b-n-b listings. We provide beach towels and beach chairs at every location, umbrellas and carts at most locations, and do not provide snorkeling gear at any locations. Sorry for the confusion. Snorkeling gear can be rented or purchased nearby.

Support Post Booking - I understand vacation time is precious and I will make sure you get the most out of it. My number is the only contact information you need. My units are at the top attractions on the island. Cars are never required, but you will have private parking near the unit. Check-in any day of the week at any time using your private door-code. No requirement ever at checkout. Free early check-in when possible. Never hidden fees or solicitations. Every unit including this one is available for instant booking.

When you book with me you get a fully accessible and knowledgeable owner/host and reliable advice from a G-approved local expert. I 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 need a break. For the less extroverted, every booking comes with an unabashed guidebook detailing the property, all my favorite things to do in the area, and never any advertisements or solicitations. This is the only rental offering of its kind on the key.

Events - Only with prior permission.

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. *If you prefer insured bookings, we recommend providers Generali and Rental Guardian for Trip-Protection coverage.

Property manager

Gertrude Rentals 888-5SIESTA
Premier Host

Languages

English, French

Add dates for prices

Amenities

Pool
Kitchen
Washer
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 3:00 PM
Minimum age to rent: 21
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed
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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, a first aid kit and a deadlock

About the area

Siesta Key

Located in Siesta Key, this holiday home 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 Coconuts Family Entertainment Center. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
Map
Siesta Key, FL

What's nearby

  • Siesta Key Beach - 2 min drive - 1.1 km
  • Shell Beach - 4 min drive - 2.8 km
  • Siesta Key Marina - 6 min drive - 4.5 km
  • Crescent Beach - 7 min drive - 4.5 km
  • Lido Beach - 21 min drive - 17.3 km

Getting around

  • Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 32 min drive

Restaurants

  • ‪Gilligan's Island Bar & Grill - ‬3 min drive
  • ‪Siesta Key Oyster Bar - ‬3 min drive
  • ‪Siesta Key Beach Pavilion - ‬5 min drive
  • ‪Starbucks - ‬10 min drive
  • ‪The Old Salty Dog - ‬18 min walk

Frequently asked questions

Does New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village! have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village! pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village!?

Check-in begins at 3:00 PM.

What time is check-out at New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village!?

Checkout is at 10:00 AM.

Where is New Listing! Rudy's Hideaway - Spacious Tropical with Private Pool. Near Siesta Key Beach/Village! located?

This family-friendly Siesta Key holiday home is located by the sea, within 1 mi (2 km) of Irma Beach and Siesta Key Farmers Market. Siesta Key Beach is 1.7 mi (2.7 km) away.

Reviews

9.2

Wonderful

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 10 out of 13 reviews
Rating 8 - Good. 1 out of 13 reviews
Rating 6 - Okay. 1 out of 13 reviews
Rating 4 - Poor. 1 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

10/10

Cleanliness

9.8/10

Check-in

10/10

Communication

10/10

Location

9.6/10

Listing accuracy

Reviews

8/10 Good

Nate G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quick beach getaway

Will book again
Stayed 6 nights in Mar 2025

10/10 Excellent

Karla C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Siesta Key rental

The home was spacious, had plenty of towels both beach and bath, kitchen utensils and appliances were good. Great pool. The home was clean, nice furniture and décor. We had a great time
Stayed 4 nights in Apr 2025

10/10 Excellent

Cindy T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

great location

Updated and clean. Lot of space. Pool was great. Location was awesome .
Stayed 3 nights in Feb 2025

10/10 Excellent

Chris W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spacious Vacation House with a Great Pool

Nice, Clean house, great and quiet neighborhood only minutes drive to the beach. The pool area was the highlight of the evening for our kids.
Stayed 5 nights in Sep 2024

10/10 Excellent

rebecca g.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property

This house was so nice and really close to the beach. It was amazing for our short stay. We would definitely stay again!
Stayed 3 nights in May 2024

10/10 Excellent

Josh C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Loved this house and the pool!

I lived the location near The Village and the feel of driving thru Canopy Trail to get to the house. Pool and deck with TV and fridges and fire pit was so fun. Definitely would stay here again.
Stayed 5 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Christopher C.

Great

Very nice unit and great customer service. Seemed to be recently renovated and very clean upon entry. Nice pool and the location was tucked away in a very nice neighborhood which kept things on the quiet side. Would definitely consider staying here again and would recommend this place to family and friends.
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

John D.

Great

The room was very nice, warm and accommodating

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property

Was very impressed with the cleanliness of the home. The screened in pool was great as well. Everything was perfect. I honestly could not say one bad thing. Even the checkout was great. We will definitely stay here again.
Stayed 6 nights in Jun 2024
This review comes from a trusted partner site and has not been verified.

6/10 Okay

Kayla M.

Decent House - horrible experiences & no response from owner

We stayed here and the house was super nice but we noticed some things that were instantly just off. There was no side gate on the right hand side and no enclosure over the pool. We were never told about a handy man coming to fix the gate and being only women in the house, that was terrifying. The washer didn't work properly, there was a cockroach, the back door was extremely difficult and complicated to lock, and the lights would shut off if someone used a blow dryer. We were told the owner would reach out and he never did. I selected this based off how he said he cared and would respond quickly. What a lie. Never would rent again from Gertrude rentals.

10/10 Excellent

Jordan S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Stay!

This is a great house in which to experience Siesta Key! Lots of gorgeous expensive homes in the neighborhood we felt safe and welcomed by friendly people. We rented a golf cart and enjoyed short drives to the beach and downtown. The pool was a nice activity and they provided lots of beach towels, kitchen items, and comfortable beach chairs. The AC was super cold and felt great after coming in from the heat. The owner was very nice and had great communication if we needed anything.
Stayed 5 nights in Jul 2024

4/10 Poor

Danielle L.

Stayed 3 nights in Mar 2025

10/10 Excellent

William N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

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Stayed 5 nights in Jun 2024

About the host

Hosted by Gertrude Rentals 888-5SIESTA

Host profile image
Dan Jones, "owner" Gertrude Rentals
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