Holiday Homes in Siesta Key

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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured Holiday Homes in Siesta Key and around

Our top choices for Siesta Key holiday homes

Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is €231
includes taxes & fees
23 Sept - 24 Sept
Siesta Key Island Rentals
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
On the beach, sun-loungers, beach towels

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

9.6 out of 10, Exceptional, (51)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
The price is €628
includes taxes & fees
22 Sept - 23 Sept
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Beach nearby, sun-loungers, beach towels

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (137)
"The home was cozy. Best feature- so close to the beach! "
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen
On the beach, sun-loungers, beach towels

Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

10.0 out of 10, Exceptional, (122)
"Directly across from public beach, nice clean pool and the pond was perfect! We really enjoyed our stay! The pond has turtles and crabs that are so much fun to watch right from your porch/balcony! We hope to do this trip yearly!"
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen
Private Home Directly on Siesta Key Beach!
On the beach

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (5)
Private Home Directly on Siesta Key Beach!
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
On the beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (22)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
Outdoor pool, a heated pool

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
Outdoor pool, a heated pool

Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

10.0 out of 10, Exceptional, (1)
"We loved this house. We celebrated a cousins 50th birthday and had so much fun. The location is close to all restaurants and beach. The golf cart was so fun to use. The house is nicely stocked with necessary items, pool noodles and toys. There was everything needed for the beach.The most important part was the owners were very responsive to all questions. We look forward to coming and staying here again."
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas
Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!
Beach nearby

Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!

10.0 out of 10, Exceptional, (41)
"We stayed a week with a family of 11.We absolutely loved it something for everyone. Close to anything you need within walking distance. Easy in and easy out. Would stay again. Lots of memories.Owner very responsive to anything you might need."
Gertrude's Siesta | 6 Terraces, Rooftop, Pool, 1-min to Beach and Village!
Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3
Beach nearby, sun-loungers, beach towels

Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3

9.8 out of 10, Exceptional, (102)
"Perfect location for beach access and a short walk to the village. "
Siesta Key 2BR 1Bath unit COZY Barefoot Bungalows 1500 ft from beach access#3
Newly renovated TH in Siesta Key FL - #1 beach in US
Beach

Newly renovated TH in Siesta Key FL - #1 beach in US

6.0 out of 10, (1)
"Property was very dated. Noisy street location for the guest bedroom; master was fine. Property is located in a good condo complex. Private beach not crowded at all. Set in a very lush tropical garden. Not what we expected but adequate for our visit. If the new owner is going to continue to rent he needs to perform some major renovations/updates."
Newly renovated TH in Siesta Key FL - #1 beach in US
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
A heated pool

Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West

9.6 out of 10, Exceptional, (61)
"Great location!"
The price is €581
includes taxes & fees
24 Sept - 25 Sept
Private Pool/Spa in Siesta Key Village, Steps to the Beach! Island Time West
Siesta beach....one and only
Interior

Siesta beach....one and only

9.4 out of 10, Exceptional, (186)
"Great property, clean, friendly, great area, and communication "
The price is €409
includes taxes & fees
22 Oct - 23 Oct
Siesta beach....one and only
Beachside Retreat with Pool and Beach Access
Outdoor dining

Beachside Retreat with Pool and Beach Access

8.8 out of 10, Excellent, (41)
"Great house. no complaints. Thank you. "
Beachside Retreat with Pool and Beach Access
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
Beach nearby

Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach

9.0 out of 10, Wonderful, (55)
"So close to the beach!"
Suite w/ Shared Pool, Free WiFi, Central AC - Steps to the White Sand Beach
Luxury Home w/ Heated Pool and Private Beach Access
Property grounds

Luxury Home w/ Heated Pool and Private Beach Access

9.4 out of 10, Exceptional, (102)
"Beautiful inside and out, plenty of supplied amenities for the beach, great location, easy beach access, plenty of space for everyone to be together and apart when needed. Overall a great stay in a beautiful place! "
Luxury Home w/ Heated Pool and Private Beach Access
Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!
A heated pool

Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!

9.6 out of 10, Exceptional, (79)
"This ended up being a perfect location for our beach vacation! Close to the beach, provided plenty of beach chairs/umbrellas/boogie boards, and close to trolley stops. We had a great time in this VRBO!"
Cozy 3 bedr townhouse beach retreat, only 60 steps to Siesta Key Public Beach!
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Fridge, microwave, oven, stovetop

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (104)
"Beautiful home and perfect location! Our family had a wonderful time in Siesta Key. Highly recommend this property for your next vacay."
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
The Key Canal - Spacious Waterfront Home w/ Rooftop Deck, Walk to Siesta Beach & Village
Exterior

The Key Canal - Spacious Waterfront Home w/ Rooftop Deck, Walk to Siesta Beach & Village

9.8 out of 10, Exceptional, (27)
"This property is great, it has a private pool, is very well outfitted, all of the kitchen items you need and would want and the location is excellent."
The Key Canal - Spacious Waterfront Home w/ Rooftop Deck, Walk to Siesta Beach & Village
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Siesta Key Hotel Reviews

Twin Palms at Siesta

Twin Palms at Siesta

10/10 Excellent
"Excellent stay! The location is perfect, just 3 minutes from the beach. The apartment was practical, beautifully decorated, and had a fully equipped kitchen. We loved it and will definitely be back soon!”"
MELINA 2-night trip
Posted 5 days ago
Twin Palms at Siesta

Find out more about Siesta Key

Find out more about Siesta Key

Siesta Key Holiday Homes information

Number of reviews
992
Accommodation
896 Holiday Homes
Lowest Price
€231
Highest Price
€628

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