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!
USA's #1 Beach, Siesta Key 4BR
Patio-adjacent living room (pool cage has been removed)
Patio-adjacent living room
Open-air book lounge
Design-forward dining room
Design-forward dining room
Design-forward dining room, 4BR Siesta Key
Design-forward dining room
Full kitchen,
Timeless Florida home, 4BR Siesta Key
Timeless Florida home, 4BR Siesta Key
King bedroom,  4BR Siesta Key
King bedroom,  4BR Siesta Key
Sleek rustic-inspired bath
Full bedroom, 4BR Siesta Key
Full bedroom, 4BR Siesta Key
Two twin bedroom
Two twin bedroom
Single Twin bedroom
Single Twin bedroom
Washer/Dryer included
Chic rustic bathroom
Timeless Florida home, 4BR Siesta Key
Timeless Florida home, 4BR Siesta Key
Large swimming pool, 4BR Siesta Key.
Large swimming pool, 4BR Siesta Key.
Large swimming pool, 4BR Siesta Key.
Large swimming pool, 4BR Siesta Key.
Grill comes complete
Warm seating zone around the fire
Worlds Best Sunsets - with siesta key paraglider, Siesta Key 4BR
The Sniki Tiki, Siesta Key 4BR
The Sniki Tiki, Siesta Key 4BR
White Sand Islands, Siesta Key 4BR
White Sand Islands, Siesta Key 4BR
Daiquiri Deck - 100 steps thru private gate, Siesta Key 4BR
SKOB - 100 steps thru private gate, Siesta Key 4BR
Siesta Key - Donuts, Siesta Key 4BR
Nearby Restaurants, Siesta Key 4BR
Nearby Restaurants, Siesta Key 4BR
Nearby Restaurants, Siesta Key 4BR
USA's #1 Beach, Siesta Key 4BR
Siesta Key's White Sand Beach, Siesta Key 4BR
Siesta Key's White Sand Beach, Siesta Key 4BR
The HUB - just 2 min walk, Siesta Key 4BR
Amazing Sandbars, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach - 2 min walk, Siesta Key 4BR
Nearby White Sand Island, Siesta Key 4BR
Nearby Sarasota Bay, Siesta Key 4BR
Siesta Key Beach Bicycling, Siesta Key 4BR
Worlds Best Sunsets - 2 min walk, 3 min carrying margarita, Siesta Key 4BR
World Famous Sunday Drum Circle, Siesta Key 4BR
Siesta Key Snorkeling, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Nearby White Sand Island, Siesta Key 4BR
Siesta Key Paddle Boarding, Siesta Key 4BR
Siesta Key Dolphin Show, Siesta Key 4BR
Siesta Key Drum Circle - 1 mile south on the beach, Siesta Key 4BR
Siesta Key Drum Circle - 1 mile south on the beach, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Dolphin Show, Siesta Key 4BR
Siesta Key Beach - 2 min walk, Siesta Key 4BR
Worlds Best Sunsets - 2 min walk from dinner, Siesta Key 4BR
Siesta Key's Patriot Pier - 2 min walk, Siesta Key 4BR
Siesta Key Dry Sand Bar, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Nearby Lido Kayak tours, Siesta Key 4BR
Nearby Lido Kayak tours, Siesta Key 4BR
Siesta Key Dry Sand Bar, Siesta Key 4BR
Siesta Key Drum Circle, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Osprey Nest and Paddle Boarders, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach Yoga, Siesta Key 4BR
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!
USA's #1 Beach, Siesta Key 4BR
Patio-adjacent living room (pool cage has been removed)
Patio-adjacent living room
Open-air book lounge
Design-forward dining room
Design-forward dining room
Design-forward dining room, 4BR Siesta Key
Design-forward dining room
Full kitchen,
Timeless Florida home, 4BR Siesta Key
Timeless Florida home, 4BR Siesta Key
King bedroom,  4BR Siesta Key
King bedroom,  4BR Siesta Key
Sleek rustic-inspired bath
Full bedroom, 4BR Siesta Key
Full bedroom, 4BR Siesta Key
Two twin bedroom
Two twin bedroom
Single Twin bedroom
Single Twin bedroom
Washer/Dryer included
Chic rustic bathroom
Timeless Florida home, 4BR Siesta Key
Timeless Florida home, 4BR Siesta Key
Large swimming pool, 4BR Siesta Key.
Large swimming pool, 4BR Siesta Key.
Large swimming pool, 4BR Siesta Key.
Large swimming pool, 4BR Siesta Key.
Grill comes complete
Warm seating zone around the fire
Worlds Best Sunsets - with siesta key paraglider, Siesta Key 4BR
The Sniki Tiki, Siesta Key 4BR
The Sniki Tiki, Siesta Key 4BR
White Sand Islands, Siesta Key 4BR
White Sand Islands, Siesta Key 4BR
Daiquiri Deck - 100 steps thru private gate, Siesta Key 4BR
SKOB - 100 steps thru private gate, Siesta Key 4BR
Siesta Key - Donuts, Siesta Key 4BR
Nearby Restaurants, Siesta Key 4BR
Nearby Restaurants, Siesta Key 4BR
Nearby Restaurants, Siesta Key 4BR
USA's #1 Beach, Siesta Key 4BR
Siesta Key's White Sand Beach, Siesta Key 4BR
Siesta Key's White Sand Beach, Siesta Key 4BR
The HUB - just 2 min walk, Siesta Key 4BR
Amazing Sandbars, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach - 2 min walk, Siesta Key 4BR
Nearby White Sand Island, Siesta Key 4BR
Nearby Sarasota Bay, Siesta Key 4BR
Siesta Key Beach Bicycling, Siesta Key 4BR
Worlds Best Sunsets - 2 min walk, 3 min carrying margarita, Siesta Key 4BR
World Famous Sunday Drum Circle, Siesta Key 4BR
Siesta Key Snorkeling, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Nearby White Sand Island, Siesta Key 4BR
Siesta Key Paddle Boarding, Siesta Key 4BR
Siesta Key Dolphin Show, Siesta Key 4BR
Siesta Key Drum Circle - 1 mile south on the beach, Siesta Key 4BR
Siesta Key Drum Circle - 1 mile south on the beach, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Dolphin Show, Siesta Key 4BR
Siesta Key Beach - 2 min walk, Siesta Key 4BR
Worlds Best Sunsets - 2 min walk from dinner, Siesta Key 4BR
Siesta Key's Patriot Pier - 2 min walk, Siesta Key 4BR
Siesta Key Dry Sand Bar, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Nearby Lido Kayak tours, Siesta Key 4BR
Nearby Lido Kayak tours, Siesta Key 4BR
Siesta Key Dry Sand Bar, Siesta Key 4BR
Siesta Key Drum Circle, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Osprey Nest and Paddle Boarders, Siesta Key 4BR
Siesta Key Beach, Siesta Key 4BR
Siesta Key Beach Yoga, Siesta Key 4BR

Description

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 1.4-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 1.4-mile or 7 minutes by golf cart or bike.  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. 

Beach 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. 

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.
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795 Plymouth

  • 4 Beds |
  • 2 Baths |
  • 10 Guests
  • | 2 Pets
5 3 reviews

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