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Check prices for these dates

Next weekend
14 Mar - 16 Mar
In two weeks
21 Mar - 23 Mar
In one month
4 Apr - 6 Apr
In two months
2 May - 4 May

Compare 666 Vacation Homes in Siesta Key with updated reviews, rates, and availability.

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
Fridge, microwave, oven, stovetop

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (86)
"Over all great, just never got a response on if the pool was heated or not"
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.
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, (116)
"We had a great experience staying in the "The GULL" at Siesta Key. It had everything we needed and the location was perfect for the beach and the village! We would definitely return to this property for future vacations! "
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Siesta Key Island Rentals
Outdoor pool

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
The price is AED 2,442
AED 3,520 total
includes taxes & fees
22 Mar - 23 Mar
Siesta Key Island Rentals
Beachside Retreat with Pool and Beach Access
Outdoor dining

Beachside Retreat with Pool and Beach Access

9.0 out of 10, Wonderful, (33)
"See above "
The price is AED 3,252
AED 5,678 total
includes taxes & fees
7 Mar - 8 Mar
Beachside Retreat with Pool and Beach Access
Toes In The Sand | Cottage with Private Pool, Walk to SK Beach and Village 🏝️ 🌅
A heated pool

Toes In The Sand | Cottage with Private Pool, Walk to SK Beach and Village 🏝️ 🌅

2.0 star property
10.0 out of 10, Exceptional, (3)
" Very nice property right near everything. Would highly recommend"
The price is AED 7,139
AED 10,904 total
includes taxes & fees
31 Mar - 1 Apr
Toes In The Sand | Cottage with Private Pool, Walk to SK Beach and Village 🏝️ 🌅
Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!
TV

Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!

9.8 out of 10, Exceptional, (12)
"We really enjoyed our stay at the Hemingway home. The lay out was great and the kitchen was well equipped with cooking necessities. The location was great- however we came 3 weeks post hurricane Milton and the street that the house was/is on- was a destruction zone. There was so much debris on the sides of the road it looked like a war zone. The Hemingway way home was thankfully unscathed but I am pretty sure the surrounding houses were sadly very affected. The only real negative about the...
Hemingway House | Beautiful Traditional Home w/ Spacious Outdoor Dining Area & Private Pool!
Stunning Siesta Key,, . , Walk to to Shell beach, HEATED POOL Discouts
Outdoor pool, a heated pool

Stunning Siesta Key,, . , Walk to to Shell beach, HEATED POOL Discouts

9.8 out of 10, Exceptional, (107)
"A 5 minute drive to Siesta Village makes this house a great option. The home is spacious and well kept. The kids loved the pool & hot tub. "
Stunning Siesta Key,, . , Walk to to Shell beach, HEATED POOL Discouts
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!
Beach nearby

SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!

10.0 out of 10, Exceptional, (23)
"Great place and right near town center. Location Location Location. "
SKV 315 - Pool, Walk to Village, Beach, Restaurants, Bars, Shops!!
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
Beach nearby, sun loungers

Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)

10.0 out of 10, Exceptional, (30)
"Clean home, perfect size, great neighborhood for morning and evening walks. Close to everything!"
Location Location! Two Minutes from Siesta Key Beach (#1 Beach in the U.S.)
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Beach nearby, sun loungers, beach towels

Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows

9.6 out of 10, Exceptional, (92)
"Location is everything and this property has it in spades!!! Steps from the beach with a beach cart, umbrella, chairs and towels ready for our use. Perfect. "
Siesta Key 2 BR 1BA less than 1000 ft from Beach-“GEM”-Barefoot Bungalows
Stunning Gulf Views! Walk to Siesta Key Beach, Private Pool/Spa & Waterfall
Property grounds

Stunning Gulf Views! Walk to Siesta Key Beach, Private Pool/Spa & Waterfall

10.0 out of 10, Exceptional, (43)
"This house was absolutely awesome, and it’s right across the street from the beach with direct access. It’s a quick 5 minute walk into the village which was very nice. The house manager was also fantastic. Great communication and they made sure we had everything we needed. Highly recommend this place! "
Stunning Gulf Views! Walk to Siesta Key Beach, Private Pool/Spa & Waterfall
Siesta Key Village Home < Half Mi to Beach!
Fridge, microwave, stovetop, dishwasher

Siesta Key Village Home < Half Mi to Beach!

10.0 out of 10, Exceptional, (24)
"Wonderful location. 3 adult siblings stayed with plenty of room. The beach accessories and bikes were a nice added bonus. "
Siesta Key Village Home < Half Mi to Beach!
Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!
Fridge, microwave, oven, stovetop

Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!

9.8 out of 10, Exceptional, (20)
"Just like the pics and great location for beach and village amenities."
Island Escape | Home on Siesta Key w/ Private Heated Pool & Ping Pong Table!
Luxury condo steps away from Siesta Key public beach
Beach nearby

Luxury condo steps away from Siesta Key public beach

9.6 out of 10, Exceptional, (60)
"This is our second time renting this condo and already booked again for next year. Condo and location are perfect!"
Luxury condo steps away from Siesta Key public 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, (96)
"We needed enough rooms and baths for 3 couples. We had more room than we needed. We also enjoyed the short walking distance to the beach."
Luxury Home w/ Heated Pool and Private Beach Access
[escape to paradise] siesta key beach getaway
Fridge, microwave, oven, stovetop

[escape to paradise] siesta key beach getaway

9.8 out of 10, Exceptional, (16)
"Great location to market area and beach. Quiet neighborhood "
The price is AED 1,018
AED 1,848 total
includes taxes & fees
9 Mar - 10 Mar
[escape to paradise] siesta key beach getaway
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
Pool

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.4 out of 10, Exceptional, (6)
"Couldn’t ask for anything more! This was by far the cleanest place I’ve ever stayed! We ran into a little mishap checking in, our gps took us to the location across the street. We couldn’t figure out where exactly the rental was located. I called Alex and he was super quick to respond and guided us to the right location. The rental has everything you could ever need, beach chairs, umbrellas, dishware to laundry soap. The beds were more comfortable than my bed at home. The rental was spacious and...
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING
On the beach, sun loungers, beach towels

5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING

9.8 out of 10, Exceptional, (129)
"This property is exactly as advertised and better. Location is phenomenal. We walked everywhere. The kitchen was well stocked and the furniture very comfortable. The pool area is amazing. "
The price is AED 6,978
AED 12,512 total
includes taxes & fees
12 Mar - 13 Mar
5 STAR SIESTA KEY, 80 STEPS to BEACH, RESORT POOL, 6 BEDROOMS, SPACIOUS LIVING
Tropical Oasis 5 min to Siesta Key, Private Salt Water Pool w Lanai!
Beach nearby, sun loungers

Tropical Oasis 5 min to Siesta Key, Private Salt Water Pool w Lanai!

10.0 out of 10, Exceptional, (57)
"Our stay at was absolutely wonderful! From the moment we arrived, we felt right at home. The property is even more beautiful in person than in the photos. The space was clean, spacious, and thoughtfully decorated. We loved the cozy ambiance and all the little touches that made it feel like a true retreat. The backyard is a lush wonderland of gorgeous trees and plants, and is fully fenced, so great for dogs. The location is fantastic – quiet, yet close enough to all the attractions we wanted to...
Tropical Oasis 5 min to Siesta Key, Private Salt Water Pool w Lanai!
Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Aerial view

Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

10.0 out of 10, Exceptional, (23)
"Sea Crest in Siesta Key Village is a truly magical destination. We've been fortunate to stay regularly over the past few years, and it never fails to impress. The rooms are very charming, updated and stylish very close to the town center with its fantastic restaurants and unique stores to the breathtaking beaches, this place is a paradise on Earth. The welcoming atmosphere and locatio make it a must-visit destination. Highly recommended!"
The price is AED 1,646
AED 3,270 total
includes taxes & fees
5 Mar - 6 Mar
Sea Breeze | Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
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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Other property types in Siesta Key

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4570)
"Great place, doing a great job of recovery after the last storm. Love staying at this end of the island."
The price is AED 877
AED 1,074 total
includes taxes & fees
5 Mar - 6 Mar
Tropical Beach Resorts
The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (293)
"Could be more clean and updated. Great location!"
The price is AED 1,540
AED 2,114 total
includes taxes & fees
6 Mar - 7 Mar
The Ringling Beach House
Captiva Beach Resort
Florida Family Single | Private kitchen | Fridge, microwave, coffee/tea maker, toaster

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1071)
"Great service, nice room, still a little beat up from hurricane. Otherwise would have been all 5s"
The price is AED 1,154
AED 1,428 total
includes taxes & fees
5 Mar - 6 Mar
Captiva Beach Resort
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.