Condo
9.8(42 Reviews)
3 Bedrooms
6 Guests
Oceanfront
Parking
Pool
Ocean View
US $904/Night
7 Nights - US $6,326
Longboat Key, FL Holiday Rentals
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Compare Holiday Rentals, Villas & Resorts in Longboat Key
9.8
Apartment
10.0(2 Reviews)
1 Bedroom
4 Guests
Private Beach- Oceanfront
- Parking
- Pool
US $437/Night
7 Nights - US $3,057
US $1,010/Night
7 Nights - US $7,068
Condo
10.0(14 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $449/Night
7 Nights - US $3,144
Apartment
10.0(2 Reviews)
1 Bedroom
6 Guests
- Private Beach
- Oceanfront
- Parking
- Pool
US $418/Night
7 Nights - US $2,926
Condo
10.0(7 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Pool
- Ocean View
Balcony/Terrace
US $498/Night
7 Nights - US $3,483
Condo
10.0(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $495/Night
7 Nights - US $3,467
Condo
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
View
US $498/Night
7 Nights - US $3,483
Condo
10.0(5 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
Hot Tub- Parking
- Pool
US $404/Night
7 Nights - US $2,825
Luxury Holiday Rentals in Longboat Key
Over 850+ Luxury Holiday Rentals in or Near Longboat Key
Condo
10.0(3 Reviews)
2 Bedrooms
5 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $2,214/Night
7 Nights - US $15,496
Condo
1 Bedroom
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $1,561/Night
7 Nights - US $10,928
House
6 Bedrooms
10 Guests
Private Pool- Oceanfront
- Hot Tub
- Parking
US $1,453/Night
7 Nights - US $10,169
Condo
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,171/Night
7 Nights - US $8,198
Condo
3 Bedrooms
6 Guests
- Oceanfront
- Pool
- Ocean View
- View
US $1,088/Night
7 Nights - US $7,616
Apartment
9.6(19 Reviews)
3 Bedrooms
6 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $988/Night
7 Nights - US $6,914
Condo
9.4(3 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $988/Night
7 Nights - US $6,913
Condo
10.0(4 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $988/Night
7 Nights - US $6,913
Condo
8.8(6 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $963/Night
7 Nights - US $6,738
Top-Rated Holiday Rentals with a Pool in Longboat Key
Over 681+ The Best Private Villas and Holiday Rentals in Longboat Key with a Pool
Condo
10.0(219 Reviews)
1 Bedroom
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $577/Night
7 Nights - US $4,039
Condo
10.0(137 Reviews)
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $312/Night
7 Nights - US $2,182
Condo
10.0(96 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $712/Night
7 Nights - US $4,986
House
10.0(38 Reviews)
4 Bedrooms
8 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $474/Night
7 Nights - US $3,318
New
Condo
10.0(38 Reviews)
2 Bedrooms
4 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $251/Night
7 Nights - US $1,757
Condo
10.0(37 Reviews)
2 Bedrooms
6 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $495/Night
7 Nights - US $3,467
Condo
10.0(26 Reviews)
2 Bedrooms
6 Guests
- Private Pool
- Oceanfront
- Parking
- Pool
US $301/Night
7 Nights - US $2,108
US $492/Night
7 Nights - US $3,444
House
10.0(17 Reviews)
3 Bedrooms
6 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $366/Night
7 Nights - US $2,560
Pet-Friendly Holiday Rentals in Longboat Key
Over 81+ Pet-Friendly Holiday Rentals in or Near Longboat Key
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $381/Night
7 Nights - US $2,668
US $193/Night
7 Nights - US $1,351
House
10.0(1 Review)
2 Bedrooms
4 Guests
- Private Pool
- Parking
- Pool
- Ocean View
US $403/Night
7 Nights - US $2,823
Hotel
9.0(33 Reviews)
- Private Pool
- Private Beach
- Oceanfront
- Hot Tub
US $874/Night
7 Nights - US $6,118
House
8.8(6 Reviews)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $385/Night
7 Nights - US $2,698
Villa
2 Bedrooms
2 Guests
Kitchen
Air Conditioner
Internet
Pet Friendly
US $180/Night
7 Nights - US $1,263
House
10.0(1 Review)
2 Bedrooms
6 Guests
- Parking
- Ocean View
- Balcony/Terrace
- View
US $275/Night
7 Nights - US $1,928
Condo
10.0(1 Review)
2 Bedrooms
5 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $247/Night
7 Nights - US $1,730
Condo
2 Bedrooms
6 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $288/Night
7 Nights - US $2,016
Large Holiday Rentals and Private Villas in Longboat Key
Over 31+ Large Holiday Rentals and Private Villas in or Near Longboat Key
Villa
9.6(4 Reviews)
2 Bedrooms
6 Guests
- Kitchen
- Air Conditioner
- Internet
Child Friendly
US $681/Night
7 Nights - US $4,766
Apartment
9.3(12 Reviews)
34 Bedrooms
114 Guests
- Private Beach
- Oceanfront
- Parking
- Pool
US $254/Night
7 Nights - US $1,778
US $501/Night
7 Nights - US $3,505
US $289/Night
7 Nights - US $2,021
US $850/Night
7 Nights - US $5,948
US $637/Night
7 Nights - US $4,456
Villa
3 Bedrooms
6 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $631/Night
7 Nights - US $4,415
New
Condo
4 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $512/Night
7 Nights - US $3,584
Condo
3 Bedrooms
10 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $506/Night
7 Nights - US $3,543
Wheelchair Accessible Holiday Homes in Longboat Key
Over 362+ Wheelchair Accessible Holiday Homes in or Near Longboat Key
Condo
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
Spa
US $358/Night
7 Nights - US $2,509
US $417/Night
7 Nights - US $2,917
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $275/Night
7 Nights - US $1,923
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $927/Night
7 Nights - US $6,492
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $753/Night
7 Nights - US $5,271
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $255/Night
7 Nights - US $1,788
Condo
10.0(2 Reviews)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $255/Night
7 Nights - US $1,784
US $606/Night
7 Nights - US $4,245
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $597/Night
7 Nights - US $4,179
Longboat Key Private Villas and Holiday Homes Under $200
Over 110+ Longboat Key Private Villas and Holiday Homes Under $200
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Pool
- View
- Kitchen
- Air Conditioner
US $187/Night
7 Nights - US $1,312
US $194/Night
7 Nights - US $1,358
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $172/Night
7 Nights - US $1,203
US $183/Night
7 Nights - US $1,281
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $78/Night
7 Nights - US $547
Condo
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $173/Night
7 Nights - US $1,214
Condo
2 Bedrooms
4 Guests
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $173/Night
7 Nights - US $1,210
Condo
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $172/Night
7 Nights - US $1,203
Condo
2 Bedrooms
4 Guests
- Pool
- Kitchen
- Air Conditioner
- Internet
US $168/Night
7 Nights - US $1,177
Instantly Bookable Holiday Homes in Longboat Key
Over 501+ Instantly Bookable Holiday Homes in or Near Longboat Key
Condo
10.0(5 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $256/Night
7 Nights - US $1,795
Apartment
1 Bedroom
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $426/Night
7 Nights - US $2,980
Condo
10.0(3 Reviews)
2 Bedrooms
6 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $487/Night
7 Nights - US $3,406
Condo
10.0(3 Reviews)
2 Bedrooms
4 Guests
- Oceanfront
- Hot Tub
- Parking
- Pool
US $343/Night
7 Nights - US $2,401
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Oceanfront
- Parking
- Pool
- Ocean View
US $565/Night
7 Nights - US $3,954
US $449/Night
7 Nights - US $3,141
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Hot Tub
- Parking
- Pool
- Ocean View
US $358/Night
7 Nights - US $2,509
Condo
10.0(1 Review)
2 Bedrooms
4 Guests
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $327/Night
7 Nights - US $2,291
Condo
10.0(1 Review)
1 Bedroom
4 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $324/Night
7 Nights - US $2,268
Book a Last Minute Place to Stay in Longboat Key
About Casai's Private Villas and Holiday Rentals in Longboat Key
Discover more than 859 vacation rentals available in Longboat Key. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Longboat Key.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Longboat Key, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Longboat Key. On average, places to stay near Longboat Key offer 838.56 ft², with nightly prices averaging US $413.
With Casai, finding and comparing holiday rentals in Longboat Key is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Other Places to Stay in Longboat Key, FL
There are 859 Longboat Key, FL Holiday Rentals
- Prices for a holiday home in Longboat Key start at US $78
- Top rated vacation home in Longboat Key is Fall sale ready for a luxury 5-floor penthouse 60 ft from water,
- Most popular short term in Longboat Key is Zota Beach Resort
- Cheapest place to stay in Longboat Key is Charming 2BR ground floor condo in Beach Harbor Club on Longboat Key - Sea Ya
- Most expensive holiday rental in Longboat Key is Luxury Beachfront Living - St Regis Waterfront Residency - Longboat Key - Sunset Reflections
Recently Booked Holiday Rentals in Longboat Key
Frequently Asked Questions About Longboat Key?
What are the top holiday rentals in Longboat Key?
With numerous options available in Longboat Key, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Longboat Key:
- Fall sale ready for a luxury 5-floor penthouse 60 ft from water,
- Direct Oceanview: Open Wednesday Night!
- Beautiful, renovated Gulf Front at Sand Cay with private beach on Longboat
- Beach and Boaters Paradise! Heated pool, Fish off the dock, walk to the beach!
- Upscale Beachplace Condo.availability starting in Oct 2026.please inquire
- Unit #210 Sand Cay Beach Resort Pool View
- Exquisite Beachfront Condo with both Sunrise & Sunset Views
- Beachcomber unit 204
- UPDATED GORGEOUS CANAL SOUTH END LBK PROPERTY WALK TO BEACH SHOPPING CLOSE BY
- Beachcomber unit 205
How many holiday rentals have private pools in Longboat Key?
Discover a selection of holiday rentals with private pools near Longboat Key with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
Which holiday homes in Longboat Key are best for families?
If you're searching for a family-friendly holiday home in Longboat Key, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Longboat Key:
How many Casai.nz holiday rentals are available in Longboat Key?
As of 2026, Casai boasts over 859 properties listed in the Longboat Key area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Longboat Key.
Nearby Neighborhood (2)
| Neighborhood | Property Count |
|---|---|
| Bay Isles Vacation Rentals in Sarasota, Florida | 817 |
| Longbeach Village Vacation Rentals in Sarasota, Florida | 2496 |
