Exclusive Paradise Island Vacation Deals

Paradise Island vacation package deals

Price found within the past 48 hours. Click for updated prices.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,343, price is now $898 per person
$898
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
An outdoor pool, free self parking, and laundry facilities are featured at this aparthotel. WiFi in public areas is free. A terrace, a garden, and a picnic area are also on offer.
Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

3 out of 5
Save 100% on your flight
Price was $2,487, price is now $1,322 per person
$1,322
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
An outdoor pool is featured at this hotel, along with free WiFi in public areas and a safe deposit box.
The Westin Sarasota

The Westin Sarasota

4 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,921, price is now $1,213 per person
$1,213
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Enjoy the 24-hour gym and perks like a free beach shuttle. You'll appreciate the a rooftop terrace, bar/lounge, and laundry facilities.
Azul Resort

Azul Resort

2 out of 5
South Village
Save 100% on your flight
Price was $1,488, price is now $941 per person
$941
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. Staff at the 24-hour front desk can provide around-the-clock assistance.
Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,491, price is now $1,002 per person
$1,002
per person
Dec 19 - Dec 24
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
This hotel features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A poolside bar, a 24-hour front desk, and a garden are also provided.
Cottages at Siesta Key Inn

Cottages at Siesta Key Inn

3 out of 5
South Village
Save 100% on your flight
Price was $1,355, price is now $923 per person
$923
per person
Nov 27 - Dec 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
An outdoor pool is featured at this hotel, along with free self parking. WiFi in public areas is free. A terrace is also provided.

Top Paradise Island hotel deals

Ozello Waterfront Paradise

Ozello Waterfront Paradise

Crystal River FL
This apartment features a garden, laundry facilities, and barbecue grills.
Kitchen
Washer
“ A Fisherman’s Paradise Waterfront Retreat with World-Class Fishing”

“ A Fisherman’s Paradise Waterfront Retreat with World-Class Fishing”

Crystal River FL
Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Three Sisters Springs and Paradise Island are located nearby.
Backwater Bungalow Sleeps 8 Kayaks+ Dock+ Fire Pit

Backwater Bungalow Sleeps 8 Kayaks+ Dock+ Fire Pit

Crystal River FL
This vacation home features laundry facilities.
Kitchen
Washer
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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.