Vacation rentals in Siesta Key, FL

Best vacation rentals and Airbnb offers in Siesta Key, FL

One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village

Condo, Siesta Key

One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village is a condo in Siesta Key, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village

One Bedroom - Ground Floor Condo - Heated Pool - Siesta Key Village is a condo in Siesta Key, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,192.

From$170/night

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Our House Lake House by Beachside Mgt

Condo, Siesta Key

Our House Lake House by Beachside Mgt is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Our House Lake House by Beachside Mgt

Our House Lake House by Beachside Mgt is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,207.

From$186/night

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Our House at Turtle Gate

Holiday Home, Siesta Key

Our House at Turtle Gate is a holiday home in Siesta Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Our House at Turtle Gate

Our House at Turtle Gate is a holiday home in Siesta Key, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, heated pool, and tennis court.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,419.

From$208/night

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Townhouse with Garage - Across from Siesta Key Beach!

Condo, Siesta Key

Townhouse with Garage - Across from Siesta Key Beach! is a condo in Siesta Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring…

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About Townhouse with Garage - Across from Siesta Key Beach!

Townhouse with Garage - Across from Siesta Key Beach! is a condo in Siesta Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,516.

From$217/night

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Vacation rentals with a pool in Siesta Key, FL

Add a pool to the search when you want an easy place to cool off between outings.

Beach Tree across street from beach

Condo, Siesta Key

Beach Tree across street from beach is a condo in Siesta Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Beach Tree across street from beach

Beach Tree across street from beach is a condo in Siesta Key, with pool access, easy beach access, and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,691.

From$242/night

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Siesta Key Beach Resort and Suites

Villa, Siesta Key

Siesta Key Beach Resort and Suites is a villa in Siesta Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites is a villa in Siesta Key, with pool access and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,298.

From$242/night

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Updated Condo with Beach Access! Shared Pools, BBQ Area! Jamaica Royale Unit 053

Condo, Siesta Key

Updated Condo with Beach Access! Shared Pools, BBQ Area! Jamaica Royale Unit 053 is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers…

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About Updated Condo with Beach Access! Shared Pools, BBQ Area! Jamaica Royale Unit 053

Updated Condo with Beach Access! Shared Pools, BBQ Area! Jamaica Royale Unit 053 is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,809.

From$258/night

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Our House at the Beach E-402 Beach view

Condo, Siesta Key

Our House at the Beach E-402 Beach view is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Our House at the Beach E-402 Beach view

Our House at the Beach E-402 Beach view is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,823.

From$260/night

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Vacation rentals with parking in Siesta Key, FL

Find vacation rentals that make arriving by car easier.

Sarasota Springs Apartment

Apartment, Siesta Key

Sarasota Springs Apartment is a apartment in Siesta Key, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Sarasota Springs Apartment

Sarasota Springs Apartment is a apartment in Siesta Key, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $811.

From$116/night

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Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!

Holiday Home, Siesta Key

Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025! is a holiday home in Siesta Key, with parking and kitchen access. This stay gives travelers a comfortable base for…

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About Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025!

Fall is the best time! To vacation here, Avail ALL Autumn till NYE 2025! is a holiday home in Siesta Key, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $958.

From$137/night

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Homey Comfort Meets Championship Golf–Ground Floor Condo in Stoneybrook Sarasota

Condo, Siesta Key

Homey Comfort Meets Championship Golf–Ground Floor Condo in Stoneybrook Sarasota is a condo in Siesta Key, with pool access and parking. This stay gives travelers a comfortable base for…

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About Homey Comfort Meets Championship Golf–Ground Floor Condo in Stoneybrook Sarasota

Homey Comfort Meets Championship Golf–Ground Floor Condo in Stoneybrook Sarasota is a condo in Siesta Key, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, gym, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $967.

From$138/night

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Private guesthouse near the beach

Guest House, Siesta Key

Private guesthouse near the beach is a guest house in Siesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Private guesthouse near the beach

Private guesthouse near the beach is a guest house in Siesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, gym, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,024.

From$146/night

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Pet-friendly vacation rentals in Siesta Key, FL

Bring your pet along with stays that welcome four-legged travelers.

Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi

Apartment, Siesta Key

Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi is a apartment in Siesta Key, with pet-friendly space. This stay gives travelers a comfortable base for exploring the…

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About Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi

Cozy studio in vibrant Sarasota, steps from Siesta waters, AC, WiFi is a apartment in Siesta Key, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $807.

From$115/night

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Living the Dream by Beachside Managment

Apartment, Siesta Key

Living the Dream by Beachside Managment is a apartment in Siesta Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring…

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About Living the Dream by Beachside Managment

Living the Dream by Beachside Managment is a apartment in Siesta Key, with pet-friendly space, pool access, and easy beach access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,816.

From$263/night

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Our House at the Beach C-112 Great Location, Spacious, Updated

Holiday Home, Siesta Key

Our House at the Beach C-112 Great Location, Spacious, Updated is a holiday home in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Our House at the Beach C-112 Great Location, Spacious, Updated

Our House at the Beach C-112 Great Location, Spacious, Updated is a holiday home in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,901.

From$272/night

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La Siesta #202. Located directly across from Siesta Key Beach.

Condo, Siesta Key

La Siesta #202. Located directly across from Siesta Key Beach. is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable…

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About La Siesta #202. Located directly across from Siesta Key Beach.

La Siesta #202. Located directly across from Siesta Key Beach. is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,935.

From$276/night

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Vacation rentals with a kitchen in Siesta Key, FL

Compare stays with kitchen access for longer trips and easier meals.

Near Beach! Shared Pool and Tennis Court- Our House at the Beach C-121

Condo, Siesta Key

Near Beach! Shared Pool and Tennis Court- Our House at the Beach C-121 is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a…

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About Near Beach! Shared Pool and Tennis Court- Our House at the Beach C-121

Near Beach! Shared Pool and Tennis Court- Our House at the Beach C-121 is a condo in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,832.

From$262/night

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Our House at the Beach C-120 Corner Townhouse Unit!

Holiday Home, Siesta Key

Our House at the Beach C-120 Corner Townhouse Unit! is a holiday home in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base…

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About Our House at the Beach C-120 Corner Townhouse Unit!

Our House at the Beach C-120 Corner Townhouse Unit! is a holiday home in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,838.

From$263/night

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Across the Street to Siesta Key Beach, Tennis. Pickleball, Park, Heated Pool | Waterfront Balcony!

Condo, Siesta Key

Across the Street to Siesta Key Beach, Tennis. Pickleball, Park, Heated Pool · Waterfront Balcony! is a condo in Siesta Key, with pool access, easy beach access, and outdoor space. This…

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About Across the Street to Siesta Key Beach, Tennis. Pickleball, Park, Heated Pool | Waterfront Balcony!

Across the Street to Siesta Key Beach, Tennis. Pickleball, Park, Heated Pool · Waterfront Balcony! is a condo in Siesta Key, with pool access, easy beach access, and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,839.

From$263/night

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Condo Near Beach with Shared Pool, Tennis - Our House at the Beach C-205

Holiday Home, Siesta Key

Condo Near Beach with Shared Pool, Tennis - Our House at the Beach C-205 is a holiday home in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers…

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About Condo Near Beach with Shared Pool, Tennis - Our House at the Beach C-205

Condo Near Beach with Shared Pool, Tennis - Our House at the Beach C-205 is a holiday home in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,849.

From$264/night

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Family-friendly vacation rentals in Siesta Key, FL

Plan a trip with stays that give families more room to spread out.

5 Mi to Beach: Family Retreat in Sarasota!

Holiday Home, Siesta Key

5 Mi to Beach: Family Retreat in Sarasota! is a holiday home in Siesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring…

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About 5 Mi to Beach: Family Retreat in Sarasota!

5 Mi to Beach: Family Retreat in Sarasota! is a holiday home in Siesta Key, with easy beach access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,098.

From$157/night

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4 Mi to Siesta Key: Family Getaway w/ Balcony

Cottage, Siesta Key

4 Mi to Siesta Key: Family Getaway w/ Balcony is a cottage in Siesta Key, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 4 Mi to Siesta Key: Family Getaway w/ Balcony

4 Mi to Siesta Key: Family Getaway w/ Balcony is a cottage in Siesta Key, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,790.

From$187/night

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Prescott Pearl 3-Bed, 3-Bath

Holiday Home, Siesta Key

Prescott Pearl 3-Bed, 3-Bath is a holiday home in Siesta Key, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Prescott Pearl 3-Bed, 3-Bath

Prescott Pearl 3-Bed, 3-Bath is a holiday home in Siesta Key, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,341.

From$192/night

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Blue Dolphin Cottage steps from the beach

Cottage, Siesta Key

Blue Dolphin Cottage steps from the beach is a cottage in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach is a cottage in Siesta Key, with pool access, easy beach access, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,815.

From$259/night

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