Mid Island Vacations from $517

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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.
Lehigh Resort Club

Lehigh Resort Club

Joel
Save 100% on your flight
$517
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9/10 Wonderful! (115 reviews)
The Perry Hotel Naples

The Perry Hotel Naples

Save 100% on your flight
$972
per person
Nov 27 - Dec 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
9.6/10 Exceptional! (1,099 reviews)
Tween Waters Island Resort & Spa

Tween Waters Island Resort & Spa

Save 100% on your flight
$2,393,570
per person
Dec 1 - Dec 8
found 22 hours ago
Roundtrip flight included
Boston (BOS) to Fort Myers (RSW)
8.6/10 Excellent! (1,005 reviews)
My husband and I were able to check in right on time. We were given a helpful overview of the property, a map, and list of the numerous amenities (complimentary kayaks, bikes, beach towels, pools and hot tubs, as well as the many restaurants, shops, rentals, and beach services) and opening and closing times said amenities. Prices for amenities and rentals were reasonable in my opinion. The restaurants range in price from reasonable to upscale dining. Our room was exactly as pictured. The entire property including the private beach - which was just across the road - were exceptionally clean. My only complaint was our bed was very firm for our tastes. The Gulf side beach was gorgeous. We saw many shore birds and dolphins. The bay side features a large marina and manatees in the cove. All staff we encountered were very friendly and helpful. We stayed in mid September and it appeared that most of the rooms were filled, but it was still very relaxing, quiet, and uncrowded. The location is excellent. It's easy to find off the main road through the islands and it's only a short drive to the attractions and beaches in both Sanibel and Captiva. Overall I would recommend and would stay here again.

Reviewed on Sep 20, 2026

Mariners Boathouse by Coolvacay

Mariners Boathouse by Coolvacay

South Island
Save 100% on your flight
$869
per person
Nov 27 - Dec 2
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

Windward Passage Resort

Windward Passage Resort

Save 100% on your flight
$835
per person
Oct 31 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Fort Myers (RSW)
8.8/10 Excellent! (11 reviews)
Wonderful view of the ocean

Reviewed on Sep 15, 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

Flamingo Inn

6090 Estero Blvd Fort Myers Beach FL
$155 nightly
$173 total
Sep 30 - Oct 1
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

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

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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Labor Day, XMas🎄Available- Beach 🏖️ 2min walk🩴
5350 Chasing Sunshine: 5BD/4.5BA Pool Home, Steps to Sand!

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

Get rates
5350 Chasing Sunshine: 5BD/4.5BA Pool Home, Steps to Sand!
See all 743 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.

Stay near popular Mid Island attractions

Estero Boulevard Beach

9.0/10 (177 reviews)
Why not spend a lazy afternoon at Estero Boulevard Beach during your trip to Fort Myers Beach?
See properties

Sterling Ave Beach

10.0/10 (2 reviews)
Why not spend a lazy afternoon at Sterling Ave Beach during your trip to Fort Myers Beach?
See properties

Mound House

7.8/10 (28 reviews)
Learn about the local history of Fort Myers Beach with a stop at Mound House. Wander the beautiful beaches and seaside in this family-friendly area.
See properties

Things to do

Fort Myers Beach Sunset and Dolphin Watching Cruise

Fort Myers Beach Sunset and Dolphin Watching Cruise

$63
per adult
100% of travellers recommend
Fort Myers Beach Sunset and Dolphin Watching Cruise
2.5-Hour Guided Group Kayak Tour on Big Hickory Pass

2.5-Hour Guided Group Kayak Tour on Big Hickory Pass

$55
per adult
2.5-Hour Guided Group Kayak Tour on Big Hickory Pass
Copacetic Day Sail

Copacetic Day Sail

$70
per adult
100% of travellers recommend
Copacetic Day Sail
See all activities in Fort Myers Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.