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The Estates Vacation Packages

The Estates Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG

Holiday Inn Express Hotel & Suites Fort Myers East - The Forum by IHG

2.5 out of 5
The Forum
Price was $508, price is now $391 per person
$391
per person
Dec 7 - Dec 11
found 14 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly hotel in Fort Myers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions JetBlue Park at Fenway South and Calusa Nature Center and Planetarium are located nearby.
Windward Passage Resort

Windward Passage Resort

2 out of 5
Save 100% on your flight
Price was $1,251, price is now $831 per person
$831
per person
Dec 17 - Dec 21
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this beach hotel in Fort Myers Beach. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Key West Express and Lynn Hall Memorial Park are located nearby.
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Save 100% on your flight
Price was $1,371, price is now $1,002 per person
$1,002
per person
Dec 17 - Dec 21
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this luxury hotel in Naples. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Popular attractions Vanderbilt Beach and Barefoot Beach are located nearby.
Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

3 out of 5
Price was $1,805, price is now $1,340 per person
$1,340
per person
Dec 8 - Dec 12
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this cottage in Bonita Springs. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Barefoot Beach and Bonita Springs Public Beach are located nearby.
Spacious Family Retreat Port Charlotte

Spacious Family Retreat Port Charlotte

2 out of 5
Price was $3,306, price is now $2,465 per person
$2,465
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Washington (IAD) to Fort Myers (RSW)
Stay at this hotel in Port Charlotte. Enjoy free WiFi, free parking, and patios. Popular attractions Cultural Center of Charlotte County and Port Charlotte Beach Park are located nearby.
Wiggins Pass Chalet

Wiggins Pass Chalet

4 out of 5
Price was $784, price is now $594 per person
$594
per person
Dec 17 - Dec 21
found 10 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Book a stay at this business-friendly aparthotel in Naples. Enjoy free WiFi, free parking, and free bicycles on site. Our guests praise the helpful staff in our reviews. Popular attractions Barefoot Beach and Vanderbilt Beach are located nearby.
A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave

A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave

3 out of 5
Price was $3,566, price is now $2,717 per person
$2,717
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Stay at this cottage in Naples. Enjoy free parking, patios, and in-room washers/dryers. Popular attractions Fifth Avenue South and Paradise Coast Sports Compex are located nearby.
THE Palmview AND Sandpiper Inns

THE Palmview AND Sandpiper Inns

3.5 out of 5
Mid Island
Price was $841, price is now $652 per person
$652
per person
Dec 8 - Dec 12
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Stay at this motel in Sanibel. Enjoy free WiFi, free parking, and in-room massages. Popular attractions Sanibel Island Southern Beach and Sanibel Island Golf Club are located nearby.

3-4 Night Vacations in The Estates

Price found within the past 48 hours. Click for updated prices.
Resort Harbour Properties

Resort Harbour Properties

3.5 out of 5
Punta Rassa
Price was $938, price is now $743 per person
$743
per person
Dec 5 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

Blue Sunset by Avantstay Pool + Spa + Fire Table Near Beaches + Naples

3 out of 5
Price was $1,805, price is now $1,340 per person
$1,340
per person
Dec 8 - Dec 12
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave

A Peaceful Paradise by Avantstay Screened Pool + Outdoor Kitchen + Fire Table 15 Min to 5th Ave

3 out of 5
Price was $3,566, price is now $2,717 per person
$2,717
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
Punta Rassa
Price was $1,751, price is now $1,375 per person
$1,375
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)

5-7 Night Vacations in The Estates

Price found within the past 48 hours. Click for updated prices.
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

3 out of 5
Save 100% on your flight
Price was $1,073, price is now $709 per person
$709
per person
Dec 6 - Dec 11
found 4 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
Windward Passage Resort

Windward Passage Resort

2 out of 5
Price was $1,077, price is now $847 per person
$847
per person
Dec 9 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
LaPlaya Beach & Golf Resort - A Noble House Resort

LaPlaya Beach & Golf Resort - A Noble House Resort

4.5 out of 5
Vanderbilt Beach
Price was $5,964, price is now $4,365 per person
$4,365
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)
The Perry Hotel Naples

The Perry Hotel Naples

4.5 out of 5
Price was $2,775, price is now $2,034 per person
$2,034
per person
Dec 27 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

Cheap Hotel Deals in The Estates

Hilton Marco Island Beach Resort and Spa

Hilton Marco Island Beach Resort and Spa

4 out of 5
560 S Collier Blvd Marco Island FL
Book a stay at this beach resort in Marco Island. Enjoy a full-service spa, a beach locale, and room service. Our guests praise the pool and the restaurant in ...
Opens in a new windowHilton Marco Island Beach Resort and Spa
Hyatt House Naples/5th Avenue

Hyatt House Naples/5th Avenue

3.5 out of 5
1345 5th Avenue South Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and a marina. Our guests praise the breakfast and the pool in our reviews. ...
Opens in a new windowHyatt House Naples/5th Avenue
Bayfront Inn Fifth Avenue

Bayfront Inn Fifth Avenue

3.5 out of 5
1221 5th Ave S Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free WiFi, a marina, and breakfast (surcharge). Our guests praise the restaurant and the helpful ...
Opens in a new windowBayfront Inn Fifth Avenue
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Great Wolf Lodge Naples

Great Wolf Lodge Naples

3 out of 5
3900 City Gate Blvd N. Naples FL
Book a stay at this family-friendly hotel in Naples. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Popular attractions Paradise Coast Sports Compex and ...
Opens in a new windowGreat Wolf Lodge Naples
La Quinta Inn & Suites by Wyndham Naples Downtown

La Quinta Inn & Suites by Wyndham Naples Downtown

3 out of 5
1555 5th Ave S Naples FL
Book a stay at this business-friendly hotel in Naples. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham Naples Downtown
Marco Beach Ocean Suites

Marco Beach Ocean Suites

2 out of 5
480 S Collier Blvd Marco Island FL
Book a stay at this beach resort in Marco Island. Enjoy free WiFi, a beach locale, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowMarco Beach Ocean Suites
JW Marriott Marco Island Beach Resort

JW Marriott Marco Island Beach Resort

4 out of 5
400 S Collier Blvd Marco Island FL
Book a stay at this beach resort in Marco Island. Enjoy 3 outdoor pools, a full-service spa, and 5 restaurants. Our guests praise the helpful staff and the property ...
Opens in a new windowJW Marriott Marco Island Beach Resort

Naples Bay Resort & Marina

4 out of 5
1500 Fifth Ave S Naples FL
Book a stay at this spa hotel in Naples. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in ...
Opens in a new windowNaples Bay Resort & Marina
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.

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Mon, Jan 11 - Fri, Jan 22
PHL
Philadelphia Intl.
RSW
Southwest Florida Intl.
$100 Roundtrip, found 7 hours ago
$100
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Mon, Jan 11 from Philadelphia Intl. to Southwest Florida Intl., returning Fri, Jan 22, priced at $100 found 7 hours ago
Frontier Airlines
Sun, Jan 17 - Thu, Jan 28
DTW
Detroit Metropolitan Wayne County
RSW
Southwest Florida Intl.
$110 Roundtrip, found 5 hours ago
$110
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Sun, Jan 17 from Detroit Metropolitan Wayne County to Southwest Florida Intl., returning Thu, Jan 28, priced at $110 found 5 hours ago
Breeze Airways
Mon, Jan 11 - Fri, Jan 22
TTN
Mercer
RSW
Southwest Florida Intl.
$142 Roundtrip, found 5 hours ago
$142
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Jan 11 from Mercer to Southwest Florida Intl., returning Fri, Jan 22, priced at $142 found 5 hours ago
Frontier Airlines
Mon, Dec 7 - Mon, Dec 21
CLE
Hopkins Intl.
RSW
Southwest Florida Intl.
$148 Roundtrip, found 9 hours ago
$148
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Mon, Dec 7 from Hopkins Intl. to Southwest Florida Intl., returning Mon, Dec 21, priced at $148 found 9 hours ago