Compare Siesta Key Vacation Rentals

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Siesta Key Rentals

Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
2.62 mi from city center
$147 nightly
The price is $166 total per night
$166 total
Oct 26 - Oct 27
Total with taxes and fees
At Tropical Beach Resorts, guests have access to an outdoor pool, free WiFi in public areas, and coffee in a common area. If you drive, put free parking to good use. A multilingual staff is on hand to assist with luggage storage, securing valuables, and concierge services. Other amenities at this beach aparthotel include a library, free newspapers, and laundry facilities.
Pool
Kitchen
Captiva Beach Resort

Captiva Beach Resort

3 out of 5
6772 Sara Sea Circle, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
2.68 mi from city center
$167 nightly
The price is $187 total per night
$187 total
Oct 26 - Oct 27
Total with taxes and fees
Guests staying at Captiva Beach Resort enjoy access to a private beach, an outdoor pool, and free WiFi in public areas. If you drive, take advantage of free parking. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Other amenities at this beach condo building include laundry facilities, a picnic area, and barbecue grills.
Pool
Kitchen
SeaSpray Resort

SeaSpray Resort

4 out of 5
574 Canal Rd, Siesta Key, FL
Free Cancellation
Reserve now, pay when you stay
0.53 mi from city center
$219 nightly
The price is $247 total per night
$247 total
Oct 26 - Oct 27
Total with taxes and fees
Guests of SeaSpray Resort enjoy features like an outdoor pool, free WiFi in public areas, and laundry facilities. There's free parking if you drive. The 24-hour front desk has staff standing by to help with dry cleaning or laundry, and answer any questions about the accommodations. Additional amenities include a garden, a picnic area, and barbecue grills.
Pool
Pet friendly
The Ringling Beach House

The Ringling Beach House

3.5 out of 5
523 Beach Road, Siesta Key, FL
0.45 mi from city center
Guests of The Ringling Beach House enjoy features like an outdoor pool, free WiFi in public areas, and a library. Free parking is included with your stay. Helpful staff is there to provide concierge services, as well as offer insight about the area. Additional amenities include a terrace, a picnic area, and barbecue grills.
Pool
Kitchen
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
915 Seaside Drive, Siesta Key, FL
Free Cancellation
2.56 mi from city center
$474 nightly
The price is $536 total per night
$536 total
Nov 11 - Nov 12
Total with taxes and fees
At The Residences at Siesta Key Beach by Hyatt Vacation Club, guests enjoy a private beach, an outdoor pool, and a gym. If you decide to drive, there's free valet parking. Front-desk staff can assist with concierge services, dry cleaning/laundry, and securing valuables. Other amenities at this beach aparthotel include free WiFi in public areas, a business center, and a computer station.
Pool
Breakfast included
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

0.22 mi from city center
Guests staying at this vacation home enjoy a water park, a hot tub, and an arcade/game room. This family-friendly vacation home also has laundry facilities.
Pool
Hot Tub
Siesta Key Island Rentals

Siesta Key Island Rentals

3 out of 5
515 Beach Rd, Siesta Key, FL
0.42 mi from city center
$231 nightly
The price is $261 total per night
$261 total
Oct 26 - Oct 27
Total with taxes and fees
At Siesta Key Island Rentals, guests have access to features like laundry facilities. If you decide to drive, there's free parking.
Washer
Dryer
Siesta Palms By the Beach

Siesta Palms By the Beach

3.5 out of 5
1017 Point of Rocks Rd, Siesta Key, FL
2.7 mi from city center
At Siesta Palms By the Beach, guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. There's free parking if you drive. Helpful staff is there to provide luggage storage, as well as offer insight about the area. Additional amenities include a terrace, laundry facilities, and a garden.
Pool
Hot Tub
The Inn On Siesta Key

The Inn On Siesta Key

3.5 out of 5
515 Beach Road, Siesta Key, FL
0.42 mi from city center
Guests of The Inn On Siesta Key enjoy features like an outdoor pool, free WiFi in public areas, and free use of bicycles. If you decide to drive, there's free parking. Front-desk staff can help with concierge services, and provide local restaurant recommendations. Other amenities at this beach cottage include a terrace, laundry facilities, and a garden.
Pool
Kitchen
Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views

0.15 mi from city center
Guests staying at this vacation home enjoy access to a water park, an outdoor pool, and a hot tub. Staff members can help with accommodation requests, and provide concierge services. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Pool
Hot Tub
Private Home Directly on Siesta Key Beach!

Private Home Directly on Siesta Key Beach!

0.6 mi from city center
At this vacation home, guests have access to features like laundry facilities. This beach vacation home also has barbecue grills.
Pool
Kitchen
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

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

0.59 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and laundry facilities.
Pool
Hot Tub
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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.

Siesta Key Large Group Rentals

How to Book Vacation Rentals in Siesta Key



🏠 What is the best price for Siesta Key vacation rentals?

Siesta Key vacation rentals range in price, starting at $166 per night.


🏠 What types of vacation rentals in Siesta Key can I rent?

Orbitz offers a wide range of Siesta Key rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Siesta Key condo rentals.


🏠 Is it free to cancel my Siesta Key vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Siesta Key vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Siesta Key. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Siesta Key?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Siesta Key apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Siesta Key?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Siesta Key package deals will get you even more savings.

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