Exclusive Pye Key Vacation Deals
Pye Key vacation package deals
Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Price was $1,453, price is now $557 per person
$557
per person
Jan 30 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This smoke-free motel's marina and 2 outdoor pools are some of the highlights. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area and barbecue grills are also provided.
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,318, price is now $1,019 per person
$1,019
per person
Feb 1 - Feb 4
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
A private beach, a 24-hour gym, and a restaurant are all featured at this boutique hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and get perks like free WiFi.
Hawks Cay Resort
Price was $1,684, price is now $760 per person
$760
per person
Feb 28 - Mar 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This luxury hotel features a private beach, a full-service spa, and a marina. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. There's fun for all ages with a children's club and a children's pool, and families will appreciate the picnic area.
Casablanca Miami Beach
North Beach
Price was $1,287, price is now $611 per person
$611
per person
Feb 8 - Feb 14
found 21 hours ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
An outdoor pool, valet parking, and laundry facilities are featured at this aparthotel. A grocery/convenience store, a communal living room, and express check-out are also on offer.
Flow Miami Hotel
Downtown Miami
Price was $2,374, price is now $1,128 per person
$1,128
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This apartment features an outdoor pool and a 24-hour gym. WiFi in public areas is free. Valet parking and a safe deposit box are also offered on site.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was $22,273, price is now $10,579 per person
$10,579
per person
Feb 26 - Mar 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
This condo resort features 2 restaurants, 3 outdoor pools, and a gym. There's fun for all ages with a children's club and a children's pool, and babysitting is an added bonus. Enjoy the a rooftop terrace and perks like free WiFi.
Top Pye Key hotel deals
Anchors Aweigh: Stunning Oceanfront Views, Dockage, Private Pool, Tiki Hut, Spacious & Dog-Friendly!
Summerland Key FL
This vacation home featured laundry facilities and barbecue grills.
Pool
Kitchen
Sirena Key | Luxury Oceanfront Estate, Pool, Guest Cottage, Dock, 30min to Key West
Summerland Key FL
A hot tub is featured at this vacation home, along with a garden and barbecue grills.
Pool
Hot Tub
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Free Cancellation
Reserve now, pay when you stay
$140 nightly
The price is $158 total per night
$158 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A picnic area, express check-in, and luggage storage are also on offer.
Pool
Pet friendly
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.