Mid Island Vacation Packages 2026 from $682

Your Mid Island Vacation

Take in everything this neighborhood has to offer with a customized Mid Island vacation package. However you imagine yourself spending your days here, you'll find countless opportunities for fun, adventure and relaxation. Want to see the sights during your trip to Mid Island? Be sure to check out nearby attractions such as Lovers Key Beach, Santini Marina Shopping Plaza and Matanzaz Pass Preserve. No matter your travel plans or the size of your budget, booking the ultimate Mid Island vacation is easy with Expedia.

The Latest Mid Island Vacation Packages

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

Landing Fort Myers Near Highland Pines

Daniels Corridor

Save 100% on your flight

$682

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.2/10 Wonderful! (14 reviews)

Very Clean

Reviewed on Sep 9, 2026

The Perry Hotel Naples

Save 100% on your flight

$1,601

per person

Nov 22 - Nov 28

found 2 days ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (1,099 reviews)

The location is unique and has a water taxi to a semi private beach The parking garage is nice and secure The bathroom soaps have a medicinal smell not fond of that

Reviewed on Sep 12, 2026

Mariners Boathouse by Coolvacay

South Island

Save 100% on your flight

$801

per person

Nov 17 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.8/10 Exceptional! (13 reviews)

Very nice place, our 2nd time here and we still love it

Reviewed on Sep 7, 2026

Landing Furnished Apartments - Naples, FL

Save 100% on your flight

$1,264

per person

Dec 2 - Dec 9

found 21 hours ago

Roundtrip flight included

Newark Liberty Intl. Airport (EWR) to Fort Myers (RSW)

9.6/10 Exceptional! (11 reviews)

Landing Apartments Fort Myers near Eastwood Village

Save 100% on your flight

$699

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Fort Myers (RSW)

9.6/10 Exceptional! (30 reviews)

This place is as beautiful as the pictures. Welcome kit has essentials for a short stay. The place is clean and cozy. Highly recommended.

Reviewed on Sep 4, 2026

Where to stay in Mid Island

Find the best Mid Island areas and neighborhoods for the activities you enjoy most. Learn more about Mid Island

Two seashells on a pebbly beach with the ocean in the background.

South Island

2 out of top 10 points of interest in this area

While visiting South Island, you might make a stop by sights like Santini Marina Shopping Plaza and Castle Beach.

A coastal cityscape with a marina, dense housing, and a beach.

TP Hill's

When in TP Hill's, you can plan a visit to Key West Express and Estero Boulevard Beach, some noteworthy sights in the nearby area.

A beach at sunset with a pink and purple sky, people walking, and a lifeguard tower in the distance.

Downtown Fort Myers Beach

1 out of top 10 points of interest in this area

If you're spending some time in Downtown Fort Myers Beach, Lynn Hall Memorial Park and Estero Boulevard Beach are top sights worth seeing.

A coastal town with a beach, buildings, and a road.

Winklers

While Winklers might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Key West Express and Estero Boulevard Beach.

A river with a cityscape in the background.

Laguna Shores

Though Laguna Shores might not have many top sights, you can venture to the surrounding area to see attractions like Lover's Key Beach and Santini Marina Shopping Plaza.

Mid Island Hotel Deals

Flamingo Inn

6090 Estero Blvd Fort Myers Beach FL

$158 nightly

$176 total

Sep 22 - Sep 23

Total with taxes and fees

8/10 Very Good! (1,025 reviews)

"La limpieza es súper excelente,pero saqué la reserva por expidia y pagué un dinero por adelantado y me ponían que cuando llegara a la reserva pagaba el restante y no fue así,tuve que pagar la reserva completa y al hora tengo que hacer el reclamo a expido 😔,por lo demás todo excelente"

Reviewed on Sep 8, 2026

Labor Day, XMas🎄Available- Beach 🏖️ 2min walk🩴

Fort Myers Beach FL

10/10 Exceptional! (139 reviews)

"We have been vacation in FMB since 2017 and this property was by far the cleanest and the communication with Jackie was seamless and prompt. Although the pictures are accurate they do not convey the overall quality of the property. The amount of organization and attention to detail is second to none. ..."

Reviewed on Jul 4, 2026

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5350 Chasing Sunshine: 5BD/4.5BA Pool Home, Steps to Sand!

Fort Myers Beach FL

10/10 Exceptional! (7 reviews)

"Enjoyed our stay! Very convenient and beautiful house. Highly recommend!"

Reviewed on Jul 19, 2026

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See all 741 properties in Mid Island

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.